Organic compounds

Abstract

There is provided a compound of formula (I) wherein R1 is R5R6CH; wherein R1 comprises 5 to 20 carbon atoms; R5 and R6 are independently selected from H or a hydrocarbon residue, and wherein the hydrocarbon residue optionally comprises one or more groups selected from carboxyl (–C(O)O–), carbonyl (–C(O) –), hydroxy (–OH) and ether (–O–); R2 is selected from the group consisting of hydrogen, methyl or ethyl; Y is selected from the group consisting of –CH2–, –CH=CH–, –O– and R3CH< wherein R3 is selected from the group consisting of H, methyl or ethyl; X is selected from the group consisting of –CH2–, –O–, and R4CH < wherein R4 is selected from the group consisting of H, methyl or ethyl; with the proviso that X and Y can't be –O– at the same time. The compound can be used as fragrance precursor.

Description

[0001] ORGANIC COMPOUNDS

[0002] TECHNICAL FIELD

[0003] The present invention relates to a particular class of compounds capable of releasing fragrant compounds in a controlled manner into the surroundings, so called fragrance precursors. The invention also relates to perfume preparations and consumer products containing said precursors. The invention further relates to methods of making said perfume precursors, perfume preparations and consumer products, as well as the use of said perfume precursors and perfume preparations in consumer products, such as personal care and household care products.

[0004] BACKGROUND

[0005] Perfumed consumer products such as personal care, cleaning or laundry products comprising fragrances are well-known in the art. However, there are several drawbacks. The fragrance material can have high water solubility, resulting in fragrance loss during use, in particular when used in combination with cleaning and laundry products. Some fragrance materials are also interacting with other materials present in the consumer product base, which may result in discoloration of the base over time. This leads to certain fragrances not being used or only used in tiny amounts in certain consumer products, even though they would be very interesting from an olfactory view point.

[0006] There is a longstanding need in the fragrance industry of ingredients which are capable of prolonging or enhancing the perfuming effect for a certain time. It is particularly desirable to obtain long-lasting properties for odoriferous ingredients which are as such possessing a low substantively on substrates such as fabrics and / or hair. In addition, the industry is constantly looking for new olfactory experiences.

[0007] To address this needs, fragrance precursors can be used, which are substances that are essentially odourless themselves, but which, in particular circumstances, are capable of liberating one or more odoriferous molecules.

[0008] There are several classes of known precursors which release fragrant molecules upon activation, such as hydrolysis, temperature change, oxygen, action of light and enzymes. There is still need to provide precursors able to release odoriferous compounds over time which can be easily incorporated into a variety of consumer products.

[0009] 31309 PCT2 It has now surprisingly found that carbonyl enol ethers of formula (I) are capable of liberating odoriferous compounds which are taken in isolation are relatively high water soluble and thus get lost during rinse-off.

[0010] SUMMARY

[0011] In accordance with a first aspect of the present invention there is provided a carbonyl enol ether of formula (I) wherein

[0012] R1is R5R6CH; wherein R1comprises 5 to 20 carbon atoms; R5and R6are independently selected from H or a hydrocarbon residue, and wherein the hydrocarbon residue optionally comprises one or more groups selected from carboxyl (-C(O)O-), carbonyl (-C(O) -), hydroxy (-OH) and ether (-O-);

[0013] R2is selected from the group consisting of hydrogen, methyl or ethyl;

[0014] Y is selected from the group consisting of -CH2-, -CH=CH-, -O- and R3CH< wherein R3is selected from the group consisting of H, methyl or ethyl;

[0015] X is selected from the group consisting of -CH2-, -O-, and R4CH < wherein R4is selected from the group consisting of H, methyl or ethyl; with the proviso that X and Y can’t be -O- at the same time.

[0016] In accordance with a second aspect of the present invention there is provided the compound of formula (I) as precursor for generating a compound of formula (la)

[0017] 31309 PCT2 wherein

[0018] R2is selected from the group consisting of hydrogen, methyl or ethyl;

[0019] Y is selected from the group consisting of -CH2-, -CH=CH-, -O- and R3CH< wherein R3is selected from the group consisting of H, methyl or ethyl;

[0020] X is selected from the group consisting of — CH2-, -O-, and R4CH< wherein R4is selected from the group consisting of H, methyl or ethyl; with the proviso that X and Y can’t be -O- at the same time; and an alcohol R1OH, with R1defined as above.

[0021] In accordance with a third aspect of the present invention there is provided a use of the compound of formula (I) as precursor for generating a compound of formula (la) and alcohol R1OH as described above, or further release aldehydes or ketones.

[0022] In accordance with a fourth aspect of the present invention there is provided a fragrance composition and consumer products comprising said compounds of formula (I).

[0023] In accordance with a fifth aspect of the present invention there is provided a method to release a compound of formula (la) and an alcohol R1OH, or further release aldehydes or ketones.

[0024] In accordance with a sixth aspect of the present invention there are provided methods of making said fragrance precursors, perfume preparations and consumer products.

[0025] In accordance with a seventh aspect of the present invention there is provided the use of said perfume precursors and perfume preparations in consumer products, such as fabric care, personal care and household care products.

[0026] In accordance with an eighth aspect of the present invention there is provided a method to confer, enhance, improve or modify the hedonic properties of a fragrance composition or a consumer product.

[0027] Certain embodiments of any aspect of the present invention may provide one or more of the following advantages:

[0028] • release of odoriferous carbonyl enols,

[0029] • efficient delivery of the odors of odoriferous alcohols in consumer products,

[0030] • stability of fragrance precursors in consumer product bases as well as after their deposition on substrates,

[0031] • none or greatly reduced discoloration effects in consumer product bases,

[0032] • long-lasting effect of the free alcohol and / or aldehyde or ketone

[0033] • increased substantivity, in particular in rinse-off applications, and

[0034] 31309 PCT2 • favourable biodegradation profile of the compounds.

[0035] The details, examples and preferences provided in relation to any particular one or more of the stated aspects of the present invention will be further described herein and apply equally to all aspects of the present invention. Any combination of the embodiments, examples and preferences described herein in all possible variations thereof is encompassed by the present invention unless otherwise indicated herein, or otherwise clearly contradicted by context.

[0036] DETAILED DESCRIPTION

[0037] The present invention is based on the surprising finding that ethers of carbonyl enols can serve as precursors able to release said carbonyl enols and (odoriferous) alcohols, aldehydes or ketones over time. These novel carbonyl enol ether precursors provide a high substantivity of the carbonyl enols.

[0038] There is therefore provided in a first aspect of the present invention a compound of formula (I) wherein

[0039] R1is R5R6CH; wherein R1comprises 5 to 20 carbon atoms; R5and R6are independently selected from H or a hydrocarbon residue, and wherein the hydrocarbon residue optionally comprises one or more groups selected from carboxyl (-C(O)O-), carbonyl (-C(O)-), hydroxy (-OH) and ether (-O-);

[0040] R2is selected from the group consisting of hydrogen, methyl or ethyl;

[0041] Y is selected from the group consisting of -CH2-, -CH=CH-, -O- and R3CH<, wherein R3is selected from the group consisting of H, methyl or ethyl; and

[0042] X is selected from the group consisting of -CH2-, -O-, and R4CH<, wherein R4is selected from the group consisting of hydrogen, methyl or ethyl; with the proviso that X and Y can’t be -O- at the same time; and the proviso that the compound is not (Z)-4-(hex-3-en-1-yloxy)-2,5-dimethylfuran-3(2H)-one, 4-(isopentyloxy)-2,5-dimethylfuran-3(2H)-one, 3-(hexyloxy)-2-methyl-4H-pyran-4-one, 2- methyl-3-(pentyloxy)-4H-pyran-4-one, 3-(heptyloxy)-2-methyl-4H-pyran-4-one, 3- (isopentyloxy)-2-methyl-4H-pyran-4-one, 2-methyl-3-(nonyloxy)-4H-pyran-4-one, 2-methyl-3-

[0043] 31309 PCT2 phenoxy-4H-pyran-4-one, 3-(3-(cyclopenta-1 ,3-dien-1-yl)propoxy)-2-methyl-4H-pyran-4-one, 3- (benzyloxy)-2-methyl-4H-pyran-4-one, 3-(benzyloxy)-2-ethyl-4H-pyran-4-one, 3-(hex-5-en-2- yn-1-yloxy)-2-methyl-4H-pyran-4-one, 2-methyl-3-phenethoxy-4H-pyran-4-one, 3-((3-(furan-2- yl)prop-2-yn-1-yl)oxy)-2-methyl-4H-pyran-4-one, 2-methyl-3-((5-methylhex-5-en-2-yn-1-yl)oxy)- 4H-pyran-4-one, 3-(hex-5-en-2-yn-1-yloxy)-2-methyl-4H-pyran-4-one, (E)-3-(hexa-3,5-dien-1- yloxy)-2-methyl-4H-pyran-4-one, ethyl 4-((2-ethyl-4-oxo-4H-pyran-3-yl)oxy)butanoate, 2- methyl-3-(3-phenylpropoxy)-4H-pyran-4-one, ethyl 3-((2-methyl-4-oxo-4H-pyran-3- yl)oxy)propanoate, 4-((2-ethyl-4-oxo-4H-pyran-3-yl)oxy)butanoic acid, propyl 2-((2-methyl-4- oxo-4H-pyran-3-yl)oxy)acetate, 2-methyl-3-((4-methylbenzyl)oxy)-4H-pyran-4-one, 2-Methyl-3- (3-phenoxypropoxy)-4H-pyran-4-one, 2-methyl-3-((2-methylbenzyl)oxy)-4H-pyran-4-one, 3- (((3E,5E)-hepta-3,5-dien-1-yl)oxy)-2-methyl-4H-pyran-4-one, 2-methyl-3-((5-methylhex-5-en-1- yl)oxy)-4H-pyran-4-one, 5-ethyl-4-methyl-3-(pentyloxy)furan-2(5H)-one.

[0044] Some of the compounds of formula (I) are known per se from a different context, for example as intermediates in different synthesis routes, and are therefore excluded. However, their use as fragrance precursor, discussed later on, is not known.

[0045] In one particular embodiment, there is provided a carbonyl enol ether of formula (I), wherein R1is R5R6CH; wherein R1comprises 5 to 20 carbon atoms; R5and R6are independently selected from H or a hydrocarbon residue, and wherein the hydrocarbon residue optionally comprises one or more groups selected from carboxyl (-C(O)O-), carbonyl (-C(O)-) and hydroxy (-OH).

[0046] In one particular embodiment, there is provided a carbonyl enol ether of formula (I), wherein R1is R5R6CH; wherein R1comprises 5 to 20 carbon atoms; R5and R6are independently selected from H or a hydrocarbon residue, and wherein the hydrocarbon residue optionally comprises one or more carboxyl groups (-C(O)O-).

[0047] In one particular embodiment, there is provided a carbonyl enol ether of formula (I), wherein R1is R5R6CH; wherein R1comprises 5 to 20 carbon atoms; R5and R6are independently selected from H or a hydrocarbon residue.

[0048] In one particular embodiment, there is provided a carbonyl enol ether of formula (I), wherein R1is R5R6CH, wherein R5is H and R6is a hydrocarbon residue comprising 4 to 19 carbon atoms, and wherein the hydrocarbon residue optionally comprises one or more groups selected from carboxyl (-C(O)O-), carbonyl (-C(O)-), hydroxy (-OH) and ether (-O-).

[0049] In one particular embodiment, there is provided a carbonyl enol ether of formula (I), wherein R1is R5R6CH, wherein R5is H and R6is a hydrocarbon residue comprising 4 to 19 carbon atoms, and wherein the hydrocarbon residue optionally comprises one or more groups selected from carboxyl (-C(O)O-), carbonyl (-C(O)-) and hydroxy (-OH).The compound of formula (I) is

[0050] 31309 PCT2 odourless or mainly odourless, and it can release carbonyl enols and (odoriferous) alcohols, aldehydes or ketones over time.

[0051] The released alcohol R1OH can be odourless or contribute more or less to the overall odour perception. A relatively short alcohol part, for example with up to five carbon atoms, supports the substantivity of the compound of formula (I) in application, it impacts the ClogP value of the compound and also its release. Furthermore, it stabilizes the molecule and make it colorless or less colorless, which is desired to avoid discoloration of the consumer product. A relatively long alcohol part, for example with more than five carbon atoms, provides also the described effects, and in addition leads to an odoriferous alcohol R1OH which is released. R1part might further oxidative releases odoriferous aldehydes or ketones under air.

[0052] In one particular embodiment the compound is a compound of formula (I) wherein R1is a hydrocarbon residue comprising up to 20 carbon atoms, for example up to 19 C atoms, for example up to 18 C atoms, for example up to 17 C atoms, for example up to 16 C atoms, for example up to 15 C atoms, for example up to 14 C atoms, for example up to 13 C atoms, for example up to 12 C atoms, for example up to 11 C atoms, for example up to10 C atoms.

[0053] In another particular embodiment the compound is a compound of formula (I) wherein R1is a hydrocarbon residue comprising at least 5 C atoms, for example 6 C atoms, for example 7 C atoms, for example 8 C atoms, for example 9 C atoms, for example 10 C atoms, for example 11 C atoms.

[0054] In another particular embodiment the compound is a compound of formula (I) wherein R1is a hydrocarbon residue comprising up to 20 carbon atoms, for example up to 19 C atoms, for example up to 18 C atoms, for example up to 17 C atoms, for example up to 16 C atoms, for example up to 15 C atoms, for example up to 14 C atoms, for example up to 13 C atoms, for example up to 12 C atoms, for example up to 11 C atoms, for example up to 10 C atoms, and optionally up to three groups (e.g. one or two groups) selected from carboxyl (-C(O)O-), carbonyl (-C(O)-), hydroxy (-OH) and ether (-O-). For example, the compound is a compound of formula (I) wherein R1is a hydrocarbon residue comprising up to 20 carbon atoms and optionally up to three groups (e.g. one or two groups) selected from carboxyl (-C(O)O-), carbonyl (-C(O)-) and hydroxy (-OH).

[0055] In another particular embodiment the compound is a compound of formula (I) wherein R1is a hydrocarbon residue comprising at least 5 C atoms, for example 6 C atoms, for example 7 C atoms, for example 8 C atoms, for example 9 C atoms, for example 10 C atoms, for example 11 C atoms, and optionally up to three groups (for example, one or two groups) selected from carboxyl (-C(O)O-), carbonyl (-C(O)-), hydroxy (-OH) and ether (-O-). For example, the

[0056] 31309 PCT2 compound is a compound of formula (I) wherein R1is a hydrocarbon residue comprising at least 5 C atoms and optionally up to three groups (e.g. one or two groups) selected from carboxyl (- C(O)O-), carbonyl (-C(O)-) and hydroxy (-OH).

[0057] In one particular embodiment the compound of formula (I) is a compound of formula (II) wherein

[0058] R1is R5R6CH; wherein R1comprises 5 to 20 carbon atoms; R5and R6are independently selected from H or a hydrocarbon residue, and wherein the hydrocarbon residue optionally comprises one or more groups selected from carboxyl (-C(O)O-), carbonyl (-C(O)-), hydroxy (-OH) and ether (-O-); and

[0059] R2is methyl or ethyl.

[0060] For example, in the compound of formula (II), R1is R5R6CH, wherein R5is H and R6is a hydrocarbon residue comprising 4 to 19 carbon atoms, and wherein the hydrocarbon residue optionally comprises one or more groups selected from carboxyl (-C(O)O-), carbonyl (-C(O)-) and hydroxy (-OH).

[0061] For example, in the compound of formula (II), R1is R5R6CH, wherein R5is H and R6is a hydrocarbon residue comprising 4 to 19 carbon atoms, and wherein the hydrocarbon residue optionally comprises one or more carboxyl groups (-C(O)O-).

[0062] In one particular embodiment, there is provided a carbonyl enol ether of formula (I), wherein R1is R5R6CH, wherein R5is H and R6is a hydrocarbon residue comprising 4 to 19 carbon atoms.

[0063] The compound of formula (II) is a compound of formula (I) wherein X is -O- and Y is -CH=CH- . The compound of formula (II) is an ether of maltol (wherein R2is methyl) or an ether of ethyl maltol (wherein R2is ethyl).

[0064] For example, the compound of formula (II) is selected from the group consisting of 3-((3,7- dimethylnon-6-en-1-yl)oxy)-2-ethyl-4H-pyran-4-one (Example 4-3), 2-ethyl-3-((2,4,7- trimethyloct-6-en-1-yl)oxy)-4H-pyran-4-one (E4-4), 2-ethyl-3-(((3E,6Z)-nona-3,6-dien-1-yl)oxy)- 4 / 7-pyran-4-one (E4-5), methyl (S,Z)-12-((2-ethyl-4-oxo-4 / 7-pyran-3-yl)oxy)octadec-9-enoate (E4-6), 2-ethyl-3-(tetradec-1-en-4-yloxy)-4 / 7-pyran-4-one (E4-8), 2-ethyl-3-((4,8,12-

[0065] 31309 PCT2 trimethyltrideca-3, 7, 11-trien-1-yl)oxy)-4 / 7-pyran-4-one (E4-9), 3-((4,8-dimethylnona-3,7-dien-1- yl)oxy)-2-ethyl-4H-pyran-4-one (E4-11), (Z)-2-ethyl-3-(non-6-en-1-yloxy)-4H-pyran-4-one (E4- 13), (Z)-2-ethyl-3-(hept-4-en-2-yloxy)-4 / 7-pyran-4-one (E5-6), 2-ethyl-3-(((2E,6Z)-nona-2,6- dien-1-yl)oxy)-4 / 7-pyran-4-one (E5-15), 2-ethyl-3-((4-methyl-6-phenylhex-3-en-1-yl)oxy)-4 / 7- pyran-4-one (E5-19) , 2-ethyl-3-((4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hex-3-en-1- yl)oxy)-4H-pyran-4-one (E7-3).

[0066] In a further particular embodiment the compound of formula (I) is a compound of formula (III) wherein

[0067] R1is R5R6CH; wherein R1comprises 5 to 20 carbon atoms; R5and R6are independently selected from H or a hydrocarbon residue,, and wherein the hydrocarbon residue optionally comprises one or more groups selected from carboxyl (-C(O)O-), carbonyl (-C(O)-), hydroxy (-OH) and ether (-O-);

[0068] R2is methyl or ethyl; and

[0069] R3is methyl or ethyl.

[0070] For example, in the compound of formula (III), R1is R5R6CH, wherein R5is H and R6is a hydrocarbon residue comprising 4 to 19 carbon atoms, and wherein the hydrocarbon residue optionally comprises one or more groups selected from carboxyl (-C(O)O-), carbonyl (-C(O)-) and hydroxy (-OH).

[0071] For example, in the compound of formula (III), R1is R5R6CH, wherein R5is H and R6is a hydrocarbon residue comprising 4 to 19 carbon atoms, and wherein the hydrocarbon residue optionally comprises one or more carboxyl groups (-C(O)O-).

[0072] In one particular embodiment, there is provided a carbonyl enol ether of formula (III), wherein R1is R5R6CH, wherein R5is H and R6is a hydrocarbon residue comprising 4 to 19 carbon atoms.

[0073] The compound of formula (III) is a compound of formula (I) wherein X is -O- and Y is R3CH. The compound of formula (III) is an ether of furaneol (wherein R2is methyl) or an ether of ethyl furaneol (wherein R2is ethyl).

[0074] 31309 PCT2 For example, the compound of formula (III) is selected from the group consisting of 4-((4,8- dimethylnona-3,7-dien-1-yl)oxy)-2,5-dimethylfuran-3(2H)-one (Example 1-1), 4-((3,7- dimethylnon-6-en-1-yl)oxy)-2,5-dimethylfuran-3(2H)-one (E1-2), 2,5-dimethyl-4-((2,4,7- trimethyloct-6-en-1-yl)oxy)furan-3(2H)-one (E1-4), 2,5-dimethyl-4-((1-methyl-2-(5-methylhex-4- en-2-yl)cyclopropyl)methoxy)furan-3(2H)-one (E1-6), 2,5-dimethyl-4-((3-methyl-5-(2,2,3- trimethylcyclopent-3-en-1-yl)pent-4-en-2-yl)oxy)furan-3(2H)-one (E1-8), 4-((3,7-dimethylocta- 2,6-dien-1-yl)oxy)-2,5-dimethylfuran-3(2H)-one (E1-9), 2,5-dimethyl-4-(((2E,6Z)-nona-2,6-dien- 1-yl)oxy)furan-3(2H)-one (E1-13), 4-((2-ethyl-4-(2,2,3-trimethylcyclopent-3-en-1-yl)but-2-en-1- yl)oxy)-2,5-dimethylfuran-3(2H)-one (E1-17), (Z)-4-(hept-4-en-2-yloxy)-2,5-dimethylfuran- 3(2H)-one (E1-21), 2,5-dimethyl-4-((1-phenylbut-3-en-1-yl)oxy)furan-3(2H)-one (E1-25), 4- (dec-1-en-4-yloxy)-2,5-dimethylfuran-3(2H)-one (E1-26), methyl (12S,Z)-12-((2,5-dimethyl-4- oxo-4, 5-dihydrofuran-3-yl)oxy)octadec-9-enoate (E1-32), 2,5-dimethyl-4-(((3E,6Z)-nona-3,6- dien-1-yl)oxy)furan-3(2H)-one (E1-34) , 2,5-dimethyl-4-((4,8, 12-trimethyltrideca-3,7,11-trien-1- yl)oxy)furan-3(2H)-one (E1-36), 4-((4,8-dimethylnona-3,7-dien-1-yl)oxy)-2-ethyl-5-methylfuran- 3(2H)-one (E1-43), (Z)-2,5-dimethyl-4-(non-6-en-1-yloxy)furan-3(2H)-one (E1-45), 4-(((S)-3,7- dimethylnon-6-en-1-yl)oxy)-2,5-dimethylfuran-3(2H)-one (E1-48), 2-ethyl-5-methyl-4-(tetradec- 1-en-4-yloxy)furan-3(2H)-one (E1-49), (Z)-2-ethyl-4-(hex-3-en-1-yloxy)-5-methylfuran-3(2H)- one (E2-2), 2,5-dimethyl-4-((4-methyl-6-phenylhex-3-en-1-yl)oxy)furan-3(2 / 7)-one (E5-20), 2,5- dimethyl-4-(tetradec-1-en-4-yloxy)furan-3(2 / - / )-one (E5-21).

[0075] In a further particular embodiment the compound of formula (I) is a compound of formula (IV) wherein

[0076] R1is R5R6CH; wherein R1comprises 5 to 20 carbon atoms; R5and R6are independently selected from H or a hydrocarbon residue,, and wherein the hydrocarbon residue optionally comprises one or more groups selected from carboxyl (-C(O)O-), carbonyl (-C(O)-), hydroxy (-0H) and ether (-0-);

[0077] R2is methyl or ethyl;

[0078] R3is H, methyl or ethyl; and

[0079] R4is hydrogen or methyl.

[0080] 31309 PCT2 For example, in the compound of formula (IV), R1is R5R6CH, wherein R5is H and R6is a hydrocarbon residue comprising 4 to 19 carbon atoms, and wherein the hydrocarbon residue optionally comprises one or more groups selected from carboxyl (-C(O)O-), carbonyl (-C(O)-) and hydroxy (-OH).

[0081] For example, in the compound of formula (IV), R1is R5R6CH, wherein R5is H and R6is a hydrocarbon residue comprising 4 to 19 carbon atoms, and wherein the hydrocarbon residue optionally comprises one or more carboxyl groups (-C(O)O-).

[0082] In one particular embodiment, there is provided a carbonyl enol ether of formula (IV), wherein R1is R5R6CH, wherein R5is H and R6is a hydrocarbon residue comprising 4 to 19 carbon atoms.

[0083] The compound of formula (IV) is a compound of formula (I) wherein X is R4CH<, Y is - R3CH<- . The compound of formula (IV) is an ether of corylone (wherein R2is Me, R3is H, and R4is hydrogen), an ether of methyl corylone (wherein R2is Me, R3is H, and R4is methyl), an ether of coronol (wherein R2is Me, R3is Me, and R4is hydrogen), an ether of ethylcyclotene (wherein R2is Et, R3is H, and R4is hydrogen).

[0084] For example, the compound of formula (IV) is selected from the group consisting of 2-((3,7- dimethylnon-6-en-1-yl)oxy)-3-methylcyclopent-2-en-1-one (Example 6-1), 3-methyl-2-((3- methyl-5-(2,2,3-trimethylcyclopent-3-en-1-yl)pent-4-en-2-yl)oxy)cyclopent-2-en-1-one (E6-2), 3-methyl-2-((1-methyl-2-(5-methylhex-4-en-2-yl)cyclopropyl)methoxy)cyclopent-2-en-1-one (E6-3), (Z)-2-(hept-4-en-2-yloxy)-3-methylcyclopent-2-en-1-one (E6-4), -methyl-2-(tetradec-1- en-4-yloxy)cyclopent-2-en-1-one (E6-5).

[0085] In a further particular embodiment the compound of formula (I) is a compound of formula (V) wherein

[0086] R1is R5R6CH; wherein R1comprises 5 to 20 carbon atoms; R5and R6are independently selected from H or a hydrocarbon residue,, and wherein the hydrocarbon residue optionally comprises one or more groups selected from carboxyl (-C(O)O-), carbonyl (-C(O)-), hydroxy (-OH) and ether (-O-);

[0087] R2is hydrogen or methyl; and

[0088] R4is hydrogen, methyl or ethyl.

[0089] 31309 PCT2 For example, in the compound of formula (V), R1is R5R6CH, wherein R5is H and R6is a hydrocarbon residue comprising 4 to 19 carbon atoms, and wherein the hydrocarbon residue optionally comprises one or more groups selected from carboxyl (-C(O)O-), carbonyl (-C(O)-) and hydroxy (-OH).

[0090] For example, in the compound of formula (V), R1is R5R6CH, wherein R5is H and R6is a hydrocarbon residue comprising 4 to 19 carbon atoms, and wherein the hydrocarbon residue optionally comprises one or more carboxyl groups (-C(O)O-).

[0091] In one particular embodiment, there is provided a carbonyl enol ether of formula (V), wherein R1is R5R6CH, wherein R5is H and R6is a hydrocarbon residue comprising 4 to 19 carbon atoms.

[0092] The compound of formula (V) is a compound of formula (I) wherein X is R4CH< and Y is -O-. The compound of formula (V) is an ether of caramel lactone (wherein R4= R2= methyl) or an ether of furonol (wherein R4= R2= hydrogen) or an ether of emoxyfurone (wherein R4= Et and R2= Me).

[0093] For example, the compound of formula (V) is selected from the group consisting of (Z)-4,5- dimethyl-3-(non-6-en-1-yloxy)furan-2(5H)-one (Example 3-2), 3-(((S)-3,7-dimethylnon-6-en-1- yl)oxy)-4,5-dimethylfuran-2(5H)-one (E3-3), 3-(hex-3-en-1-yloxy)-4,5-dimethylfuran-2(5H)-one (E3-4).

[0094] It should be understood that compounds of formula (II), (III), (IV) and (V) are all compounds of formula (I).

[0095] In another particular embodiment the compound is a compound of formula (I) wherein R1is the residue of an alcohol R1OH. The alcohol R1OH (or R5R6CH-OH) can be odourless or odoriferous.

[0096] Compounds of formula (I) (and therefore also the compounds of formula (II), (III), (IV) and (V)) releasing a carbonyl enol (preferably odoriferous carbonyl enol) of formula (la) wherein R2, X and Y have the same meaning as given for the compound of formula (I) and an alcohol R1OH.

[0097] 31309 PCT2 Examples of alcohols (R1OH) are:

[0098] R1OH wherein R1is a C5 to C20 alkyl, optionally substituted with one or more groups selected from carboxyl (-C(O)O-), carbonyl (-C(O)-), hydroxy (-OH) and ether (-O-), R1OH being for example selected from but not limited to the group consisting of amyl alcohol; hexyl alcohol; 2-hexyl alcohol; heptyl alcohol; octyl alcohol; nonyl alcohol; decyl alcohol, for example dodecan- 1-ol; undecyl alcohol; lauryl alcohol; myristic alcohol; 3,5,5-trimethyl-hexanol; 3, 4, 5,6,6- pentamethylheptan-2-ol; 2,5,7-trimethyl-octan-3-ol; 3,7-dimethyloctanol; 7-methoxy-3, 7- dimethyl-octan-2-ol; 5-ethyl-2-nonanol; 6,8-dimethyl-2-nonanol; 2-methyl-undecanol; 2,6- dimethyl-heptan-2-ol; 3-oxobutan-2-ol;

[0099] R1OH wherein R1is a C5 to C20 alkenyl (linear or branched) comprising one, two or three double bonds, optionally substituted with one or more groups selected from carboxyl (- C(O)O-), carbonyl (-C(O)-), hydroxy (-OH) and ether (-O-), R1OH being for example selected from but not limited to the group consisting of: 3-methyl-but-2-en-1-ol; 3-methylbut-3-en-1-ol; 3- methyl-1-pentanol; cis-3-hexenol; cis-4-hexenol; 3,7-dimethyloct-6-en-1-ol (citronellol); 3,7- dimethylocta-2,6-dien-1-ol (geraniol); oct-1-en-3-ol; 2-cis-3,7-dimethyl-2,6-octadien-1-ol; 6- ethyl-3-methyl-5-octen-1-ol; 3,7-dimethyl-oct-3,6-dienol; non-6-en-1-ol; 2,2,8-trimethyl-7(8)- nonene-3-ol; nona-2,6-dien-1-ol; 4-methyl-3-decen-5-ol; dec-9-en-1-ol; dec-1-en-4-ol; 10- undecen-1-ol; 3,7,11-trimethyldodeca-2,6,10-trien-1-ol (farnesol); 2,6-dimethyl-oct-7-en-2-ol;

[0100] 3.7-dimethyl-octa-1 ,6-dien-3-ol; 3,7-dimethylnon-6-en-1-ol; methyl-12-hydroxyoctadec-9- enoate (e.g. methyl (E)-12-hydroxyoctadec-9-enoate); (E)-9-hydroxy-5,9-dimethyldec-4-enal;

[0101] 4.8-dimethylnona-3,7-dien-1-ol; 2,4,7-trimethyloct-6-en-1-ol, 2,4,7-trimethylocta-2,6-dien-1-ol, hept-4-en-2-ol; 3,7-dimethylnona-2,6-dien-1-ol; 2-methylpent-2-en-1-ol; octa-2, 7-dien-1-ol; 6,10-dimethylundeca-5,9-dien-2-ol; 4,8,12-trimethyltrideca-3,7,11-trien-1-ol; tetradec-1-en-4-ol; 4-methylpent-3-en-1-ol; pent-3-en-1-ol; hex-3-en-1-ol; nona-3,6-dien-1-ol; 3-oxobutan-2-ol; 2- methylundecan-1-ol; hept-4-en-2-ol; 5,9-dimethyldeca-3,8-dien-1-ol; 4,6-dimethylhepta-3,6- dien-1-ol; 4,6-dimethylhepta-3,5-dien-1-ol; 4-methylhept-3-en-1-ol; 6-methylhept-3-en-1-ol; hept-3-en-1-ol; 4-methyldec-3-en-1-ol; 4-methylhepta-3,6-dien-1-ol; 4-methylhepta-3,5-dien-1- ol; dec-3-en-1-ol; 5-methylhex-3-en-1-ol; but-3-en-1-ol; 4-methylnon-3-en-1-ol; 4-methyloct-3- en-1-ol; 4-methyldodec-3-en-1-ol;

[0102] R1OH wherein R1is a C5 to C20 hydrocarbon residue comprising a cyclic residue, the hydrocarbon residue optionally comprising one, two or three double bonds, and optionally comprising one or more groups selected from carboxyl (-C(O)O-), carbonyl (-C(O)-), hydroxy (- OH) and ether (-O-), R1OH being for example selected from but not limited to the group consisting of: decahydro-2-naphthalenol; borneol; cedrenol; fenchyl alcohol; menthol; 2-(1 ,1- dimethylethyl)cyclohexanol; 3-(1 ,1-dimethylethyl)cyclohexanol; 4-(1 , 1- dimethylethyl)cyclohexanol; 4-isopropyl-cyclohexanol; 6,6-dimethyl-bicyclo[3.1.1 ]hept-2-ene- 31309 PCT2 methanol; p-menth-8-en-3-ol; 3,3,5-trimethyl-cyclohexanol; 2,4,6-trimethyl-3-cyclohexenyl- methanol; 4-(1-methylethyl)-cyclohexyl-methanol; 4-(1,1-dimethylethyl)-cyclohexanol; 5-(2,2,3- trimethyl-3-cyclopentenyl)-3-methylpentan-2-ol; 3-methyl-5-(2,2,3-trimethylcyclopent-3- enyl)pent-4-en-2-ol; 2-ethyl-4-(2,2,3-trimethylcyclopent-3-enyl)but-2-en-1-ol; 4-(5,5,6- trimethylbicyclo[2.2.1]hept-2-yl)-cyclohexanol; 2-(2-methylpropyl)-4-hydroxy-4-methyl- tetrahydropyran; 2-cyclohexyl-propanol; 2-(1,1-dimethylethyl)-4-methyl-cyclohexanol; 1-(4- isopropyl-cyclohexyl)-ethanol; 1-(4-isopropyl-cyclohexyl)-methanol; 2-(1,1,5,5-tetramethyl-

[0103] 1.3.4.5.6.7-hexahydro-2H-2,4a-methanonaphthalen-8-yl)propan-1-ol; 2-(1,1,5,5-tetramethyl- 1,3,4,5,6,8a-hexahydro-2H-2,4a-methanonaphthalen-8-yl)propan-1-ol; (1-methyl-2-(5- methylhex-4-en-2-yl)cyclopropyl)methanol; cyclopent-2-en-1-ol; 2-(2,2,3-trimethylcyclopent-3- en-1-yl)ethan-1-ol; cyclopent-3-en-1-ol, cyclohex-3-en-1-ol; 4-(2,6,6-trimethylcyclohex-1-en-1- yl)but-3-en-2-ol; 4-(2,6,6-trimethylcyclohex-1-en-1-yl)butan-2-ol; 2-methyl-4-(2,6,6- trimethylcyclohex-1-en-1-yl)but-2-en-1-ol; 2-methyl-4-(2,2,3-trimethylcyclopent-3-en-1-yl)but-2- en-1-ol; 4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hex-3-en-1-ol;

[0104] R1OH wherein R1is a C5 to C20 hydrocarbon residue comprising an aromatic or heteroaromatic ring, the hydrocarbon residue optionally comprising one, two or three double bonds, and optionally comprising one or more groups selected from carboxyl (-C(O)O-), carbonyl (-C(O)-), hydroxy (-OH) and ether (-O-), R1OH being for example selected from but not limited to the group consisting of: benzylalcohol; 1-phenyl-ethanol; 2-phenyl-ethanol; 2- methyl-3-phenyl-3-propenol; 2-phenyl-propanol; 3-phenyl-propanol; 4-phenyl-2-butanol; 4- phenylbutan-1-ol; 2-methyl-5-phenyl-pentanol; 2-methyl-4-phenyl-pentanol; 3-methyl-5-phenyl- pentanol; 2-(2-methylphenyl)-ethanol; 4-(1-methylethyl)-benzene-methanol; 4-(4- hydroxyphenyl)-butan-2-one; 2-phenoxy-ethanol; 4-(1-methylethyl)-2-hydroxy-1-methyl benzene; 2-methoxy-4-methyl-phenol; 4-methyl-phenol; 4-phenylbut-3-en-1-ol; 1-phenylbut-3- en-1-ol; 1-(4-methoxyphenyl)propan-1-ol; anisic alcohol; p-tolyl alcohol; cinnamic alcohol; vanillin; ethyl vanillin; eugenol; isoeugenol; thymol; furan-2-ylmethanol; 1-(naphthalen-2- yl)ethan-1-ol; 3-(4-isobutyl-2-methylphenyl)propan-1-ol; 3-methyl-5-phenylpentan-1-ol; 4- methyl-6-phenylhex-3-en- 1 -ol .

[0105] The alcohol R1OH can bear one or more of the structural features mentioned above, and therefore can belong to one or more than one of the groups listed above, which should not be regarded as limiting.

[0106] In one example, R1OH is selected from the group consisting of (1-methyl-2-(5-methylhex-4-en- 2-yl)cyclopropyl)methanol (rosyfolia); tetradec- 1-en-4-ol; 2,4,7-trimethyloct-6-en-1-ol (pomelol);

[0107] 3.7-dimethylnon-6-en-1-ol (rosabloom); 4,8-dimethylnona-3,7-dien-1-ol (homogeraniol); 3,7- dimethyloct-6-en-1-ol (citronellol); (4-isopropylcyclohexyl)methanol (mayol); 3-methyl-5-(2,2,3- trimethylcyclopent-3-en-1-yl)pent-4-en-2-ol (ebanol); 3,7-dimethylocta-2,6-dien-1-ol (geraniol);

[0108] 31309 PCT2 2,6-nonadienol; dec-9-en-1-ol (rosalva); 2-ethyl-4-(2,2,3-tnmethylcyclopent-3-en-1-yl)but-2-en- 1-ol (radjanol); (Z)-hept-4-en-2-ol; 1-phenylbut-3-en-1-ol; dec-1-en-4-ol; methyl (R,Z)-12- hydroxyoctadec-9-enoate (Methyl ricinoleate); (E,Z)-3,6-nonadien-1-ol; 4,8, 12-trimethyltrideca- 3,7,11-trien-1-ol (homofarnesol); nonenol-cis-6; (S)-3,7-dimethylnon-6-en-1-ol (rosabloom); 3- cis-hexanol; 3-hydroxybutan-2-one; 3-methyl-5-phenylpentan-1-ol (mefrosol); 4-methyl-6- phenylhex-3-en-1-ol; 4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hex-3-en-1-ol.

[0109] Carbonyl enols are sometimes difficult to use in consumer products because they might cause some colouring issues in some media, such as detergent bases. In addition, they are relative high water soluble and thus might get lost during rinse-off of a consumer product comprising them. Furthermore, some of them are unstable and thus are difficult to store over a longer period. For example, maltol [3-hydroxy-2-methylpyran-4-one] / ethyl maltol [2-ethyl-3-hydroxy-4H-pyran- 4-one] should preferably be stored in a cool, dry place in a tightly sealed container. Furaneol should be stored under nitrogen in the refrigerate in a tightly sealed container.

[0110] However, said carbonyl enols possess interesting odor profiles. For example, maltol is describe as sweet caramel cotton candy jam fruity baked bread; ethyl maltol possess a sweet caramel jam strawberry cotton candy odor profile, and furaneol is described as sweet cotton candy caramel strawberry sugar like.

[0111] Thus there is provided in a second aspect of the present invention the compound of formula (I) as precursor which is capable of realising a carbonyl enol of formula (la) wherein

[0112] R2is selected from the group consisting of hydrogen, methyl or ethyl;

[0113] Y is selected from the group consisting of -CH2-, -CH=CH-, -O- and RaCH< wherein R3 is selected from the group consisting of H, methyl or ethyl;

[0114] X is selected from the group consisting of -CH2-, -O-, and R4CH< wherein R4 is selected from the group consisting of H, methyl or ethyl; with the proviso that X and Y can’t be -O- at the same time.

[0115] 31309 PCT2 In one particular embodiment the released carbonyl enol of formula (la) is a compound of formula (Ila) wherein

[0116] R2is methyl or ethyl.

[0117] For example, the released carbonyl enol of formula (Ila) is maltol (wherein R2is methyl) or an ethyl maltol (wherein R2is ethyl). It is released from the compound of formula (II), which is an ether of maltol (wherein R2is methyl) or an ether of ethyl maltol (wherein R2is ethyl).

[0118] In one particular embodiment the released carbonyl enol of formula (la) is a compound of formula (Illa) wherein

[0119] R2is methyl or ethyl; and

[0120] R3is methyl or ethyl.

[0121] For example, the released carbonyl enol of formula (Illa) is furaneol (wherein R2is methyl, and R3is methyl) or ethyl furaneol (wherein R2is ethyl, and R3is methyl). It is released from the compound of formula (III), which is an ether of furaneol (wherein R2is methyl, and R3is methyl) or an ether of ethyl furaneol (wherein R2is ethyl, and R3is methyl).

[0122] In one particular embodiment the released carbonyl enol of formula (la) is a compound of formula (IVa)

[0123] 31309 PCT2 wherein R2is methyl or ethyl; R3is H, methyl or ethyl; and R4is hydrogen or methyl.

[0124] For example, the released carbonyl enol of formula (IVa) is corylone (wherein R4is hydrogen) or methyl corylone (wherein R4is methyl). It is released from the compound of formula (IV), which is an ether of corylone (wherein R2is Me, R3is H, and R4is hydrogen), an ether of methyl corylone (wherein R2is Me, R3is H, and R4is methyl), an ether of coronol (wherein R2is Me, R3is Me, and R4is hydrogen), an ether of ethylcyclotene (wherein R2is Et, R3is H, and R4is hydrogen).

[0125] In one particular embodiment the released carbonyl enol of formula (la) is a compound of formula (Va) wherein

[0126] R2is hydrogen or methyl; and

[0127] R4is hydrogen, methyl or ethyl.

[0128] For example, the released carbonyl enol of formula (Va) is caramel lactone (wherein R4= R2= methyl) or furonol (wherein R4= R2= hydrogen) or emoxyfurone (wherein R2=Me, R4=Et). It is released from the compound of formula (V), which is an ether of caramel lactone (wherein R4= R2= methyl) or an ether of furonol (wherein R4= R2= hydrogen) or an ether of emoxyfurone (wherein R2=Me, R4=Et).

[0129] 31309 PCT2 It should be understood that compounds of formula (Ila), (Illa), (IVa) and (Va) are all compounds of formula (la).

[0130] By the use of the compound of formula (I) (which encompasses compounds of formula (II), (III), (IV) and (V)) instead of the carbonyl enol (compound of formula (la)) as such, it is possible to provide the odor of the carbonyl enol over prolonged time. Furthermore, it is possible to incorporate the precursor into different consumer products without discoloration issues which might occur when carbonyl enols are used directly. In addition, compounds of formula (I) release the fragrant alcohols R1OH gradually in low concentrations. This is in particular advantageous if R1OH is a very powerful fragrant alcohol, the concentration of which needs to be well controlled to avoid overdosing.

[0131] In a particular example, the substantivity of the carbonyl enol can be increased by the use of the precursor in rinse-off applications, as the precursor is less water soluble than the corresponding carbonyl enol.

[0132] The compounds of formula (I) described above release carbonyl enols of formula (II) and a fragrant alcohol R1OH upon exposure to ambient air or humidity over a long period of time (e.g. several days such as 2-7 days or even longer).

[0133] Exposure of the precursor compound to ambient air means exposure to molecular oxygen which might be responsible for the cleavage of the compound of formula (I) and the release of the compound of formula (II). The concentration of oxygen in the air is sufficient for cleaving the compound of formula (I) so that the cleavage products can be detected in the ambient air, e.g. by olfaction or GC-MS analysis of headspace samples.

[0134] Exposure of the precursor compound to humidity means exposure to water which might be responsible for the cleavage of the compound of formula (I) and the release of the compound of formula (II). Already traces of water are sufficient to allow for cleavage of the compound of formula (I).

[0135] The compounds of formula (I) are very stable when not exposed to ambient air and / or humidity. Thus the compounds of formula (I) may find use in a broad range of consumer products in which a prolonged and defined release of fragrant compounds is desired.

[0136] The compound of formula (I) may be used alone, or in combination with known odorant molecules selected from the extensive range of natural products, and synthetic molecules currently available, such as essential oils, alcohols, aldehydes and ketones, ethers and acetals, esters and lactones, macrocycles and heterocycles, and / or in admixture with one or more ingredients or excipients conventionally used in conjunction with odorants in

[0137] 31309 PCT2 fragrance compositions, for example, carrier materials, and other auxiliary agents commonly used in the art.

[0138] For example, the compound of formula (I) may be used in combination with the free fragrant alcohol of formula (II). Such a combination ensures a continuous perception of the fragrant alcohol with time.

[0139] In a further aspect, the compound of formula (I) may be used in combination with other fragrance precursors, either with further compounds of formula (I) or with precursors possessing a different chemical structure. A combination of precursors allows releasing a perfume accord.

[0140] In a further aspect, there is provided a fragrance composition comprising at least one compound of formula (I). For example, the fragrance composition is further comprising one or more known odorant molecules or fragrance precursors, and / or one or more ingredients or excipients conventionally used in conjunction with odorants in fragrance compositions.

[0141] As used herein, "carrier material" means a material which is practically neutral from an odourant point of view, i.e. a material that does not significantly alter the organoleptic properties of odorants.

[0142] The term "auxiliary agent" refers to ingredients that might be employed in a fragrance composition for reasons not specifically related to the olfactory performance of said composition. For example, an auxiliary agent may be an ingredient that acts as an aid to processing a fragrance ingredient or ingredients, or a composition containing said ingredient(s), or it may improve handling or storage of a fragrance ingredient or composition containing same. It might also be an ingredient that provides additional benefits such as imparting color or texture. It might also be an ingredient that imparts light resistance or chemical stability to one or more ingredients contained in a perfume composition. A detailed description of the nature and type of adjuvants commonly used in perfume compositions containing same cannot be exhaustive, but it has to be mentioned that said ingredients are well known to a person skilled in the art.

[0143] As used herein, "fragrance composition" means any composition comprising the compound of formula (I) and a base material, e.g. a diluent conventionally used in conjunction with odourants, such as diethyl phthalate (DEP), dipropylene glycol (DPG), isopropyl myristate (IPM), pentane-1 ,2-diol, triethyl citrate (TEC) and alcohol (e.g. ethanol). Optionally, the composition may comprise an anti-oxidant adjuvant. Said anti-oxidant may be selected from Tinogard® TT (BASF), Tinogard® Q (BASF), Tocopherol (including its isomers, CAS 59-02-

[0144] 31309 PCT2 9; 364-49-8; 18920-62-2; 121854-78-2), 2,6-bis(1 , 1 -dimethylethyl)-4-methylphenol (BHT, CAS 128-37-0) and related phenols, hydroquinones (CAS 121-31-9).

[0145] The following non limiting list comprises examples of known odourant molecules, which may be combined with the compound of formula (I) in a fragrance composition:

[0146] • Essential oils and extracts, e.g. castoreum, costus root oil, oak moss absolute, geranium oil, tree moss absolute, basil oil, fruit oils, such as bergamot oil and mandarine oil, myrtle oil, palmarose oil, patchouli oil, petitgrain oil, jasmine oil, rose oil, sandalwood oil, wormwood oil, lavender oil and / or ylang-ylang oil;

[0147] • Alcohols, e.g. cinnamic alcohol ((E)-3-phenylprop-2-en-1-ol); cis-3-hexenol ((Z)- hex-3-en-1-ol); Citronellol (3,7-dimethyloct-6-en-1-ol); dihydro myrcenol (2,6- dimethyloct-7-en-2-ol); Ebanol™ ((E)-3-methyl-5-(2,2,3-trimethylcyclopent-3-en-1- yl)pent-4-en-2-ol); eugenol (4-allyl-2-methoxyphenol); ethyl linalool ((E)-3,7- dimethylnona-1 ,6-dien-3-ol); farnesol ((2E,6Z)-3,7,11-trimethyldodeca-2,6,10-trien- 1-ol); geraniol ((E)-3,7-dimethylocta-2,6-dien-1-ol); Super Muguet™ ((E)-6-ethyl-3- methyloct-6-en-1-ol); linalool (3,7-dimethylocta-1 ,6-dien-3-ol); menthol (2-isopropyl- 5-methylcyclohexanol); Nerol (3,7-dimethyl-2,6-octadien-1-ol); phenyl ethyl alcohol (2-phenylethanol); Rhodinol™ (3,7-dimethyloct-6-en-1-ol); Sandalore™ (3-methyl- 5-(2,2,3-trimethylcyclopent-3-en-1-yl)pentan-2-ol); terpineol (2-(4-methylcyclohex- 3-en-1-yl)propan-2-ol); or Timberol™ (1-(2,2,6-trimethylcyclohexyl)hexan-3-ol);

[0148] 2.4.7-trimethylocta-2,6-dien-1-ol, and / or [1-methyl-2(5-methylhex-4-en-2- yl)cyclopropyl]-methanol;

[0149] • Aldehydes and ketones, e.g. anisaldehyde (4-methoxybenzaldehyde); alpha amyl cinnamic aldehyde (2-benzylideneheptanal); Georgywood™ (1 -(1 ,2,8, 8-tetramethyl- 1 ,2,3,4,5,6,7,8-octahydronaphthalen-2-yl)ethanone); Hydroxycitronellal (7-hydroxy-

[0150] 3.7-dimethyloctanal); Iso E Super® (1-(2,3,8,8-tetramethyl-1 ,2,3,4,5,6,7,8- octahydronaphthalen-2-yl)ethanone); Isoraldeine® ((E)-3-methyl-4-(2,6,6- trimethylcyclohex-2-en-1-yl)but-3-en-2-one); Hedione® (methyl 3-oxo-2- pentylcyclopentaneacetate); Nympheal (3-(4-isobutyl-2-methylphenyl)propanal); Mahonial (5,9-dimethyl-9-hydroxy-decen-4-al); maltol; methyl cedryl ketone; methylionone; verbenone; and / or vanillin;

[0151] • Ether and acetals, e.g. Ambrox® (3a,6,6,9a-tetramethyl-2,4,5,5a,7,8,9,9b- octahydro-1 / 7-benzo[e][1]benzofuran); geranyl methyl ether ((2E)-1-methoxy-3,7- dimethylocta-2,6-diene); rose oxide (4-methyl-2-(2-methylprop-1-en-1- yl)tetrahydro-2 / 7-pyran); and / or Spirambrene® (2',2',3,7,7- pentamethylspiro[bicyclo[4.1.0]heptane-2,5'-[1 ,3]dioxane]);

[0152] 31309 PCT2 • Esters and lactones, e.g. benzyl acetate; cedryl acetate ((1 S,6F?,8aF?)-1 ,4,4,6- tetramethyloctahydro-1 / 7-5,8a-methanoazulen-6-yl acetate); y-decalactone (6- pentyltetrahydro-2 / 7-pyran-2-one); Helvetolide® (2-(1-(3,3- dimethylcyclohexyl)ethoxy)-2-methylpropyl propionate); y-undecalactone (5- heptyloxolan-2-one); and I or vetiveryl acetate ((4,8-dimethyl-2-propan-2-ylidene- 3,3a,4,5,6,8a-hexahydro-1 / 7-azulen-6-yl) acetate

[0153] • Macrocycles, e.g. Ambrettolide ((Z)-oxacycloheptadec-10-en-2-one); ethylene brassylate (1 ,4-dioxacycloheptadecane-5, 17-dione); and I or Exaltolide® (16- oxacyclohexadecan-1-one); and

[0154] • Heterocycles, e.g. isobutylquinoline (2-isobutylquinoline).

[0155] Overall, the compounds of formula (I) can be used alone, as a mixture thereof, or in combination with other fragrance ingredients and / or precursors thereof. Such other fragrance ingredients are also described, for example, in "Perfume and Flavor Chemicals", S. Arctander, Ed., Vol. I & II, Allured Publishing Corporation, Carol Stream, USA, 2003 and include fragrance compounds of natural or synthetic origin and essential oils.

[0156] In a further aspect, there is provided a consumer product comprising at least one compound of formula (I) and a consumer product base.

[0157] The consumer product for example is selected from fine fragrance, personal care products (body care products, hair care products, cosmetic products), fabric care products, for example liquid detergents or fabric softeners, home care products and air care products. As used herein, "consumer product base" means a composition for use as a consumer product to fulfill specific actions, such as cleaning, softening, and caring or the like.

[0158] Personal care products to which the compound of formula (I) can be added include for example all kinds of body care products. Especially interesting products are hair care products, for example shampoos, conditioners and hairsprays, and skin care products, like lotions or creams. Furthermore, the compound of formula (I) may be added to soaps, bath and shower gels and deodorants. The compound of formula (I) can be added to cosmetic products.

[0159] Home care products to which the compound of formula (I) can be added include all kinds of detergents, window cleaners, hard surface cleaners, all-purpose cleaners and furniture polishes. Preferably, the products are liquids, e.g. fabric detergent or conditioner compositions.

[0160] For example, the compounds of formula (I) can act as fragrance precursors in consumer products which further comprise enzymes.

[0161] 31309 PCT2 The compound according to formula (I) may be used in a broad range of perfumed consumer products, e.g. in any field of fine and functional perfumery, such as perfumes, air care products, household products, laundry products, body care products and cosmetics. The compound can be employed in widely varying amounts, depending upon the specific consumer product and on the nature and quantity of other odourant ingredients. The proportion of the formula (I) is typically from 0.0001 to 5 weight% of the consumer product. In one embodiment, the compound of formula (I) may be employed in a fabric softener in an amount from 0.001 to 0.3 weight % (e.g. 0.01 to 0.1 including 0.05 weight%). In another embodiment, the compound of formula (I) may be used in fine perfumery but also in consumer products like shampoo, fabric softener or fabric detergents, in amounts from 0.001 to 30 weight% (e.g. up to about 10 or up to 20 weight%), more preferably between 0.01 and 5 weight%. However, these values are given only by way of example, since the experienced perfumer may also achieve effects or may create novel accords with lower or higher concentrations.

[0162] In one embodiment there is provided a consumer product comprising an acceptable amount of the compound of formula (I). For example, the fragranced consumer product may comprise 0.000001 weight% to 90 weight% (including 0.00001 weight %; 0.0001 weight%, 0.001 weight%, 0.01 weight%, 0.05 weight%, 0.1 weight%, 0.5 weight%, 1 weight%, 5 weight%, 8 weight%, 10 weight%, 15 weight%, 20 weight%, 25 weight%, 30 weight%, 50 weight%, 60 weight%, 65 weight%) of the compound of formula (I) based on the total amount of the consumer product.

[0163] The compound of formula (I) may be employed in a consumer product base simply by directly mixing the compound of the present invention, or a fragrance composition comprising the compound of formula (I), with the consumer product base, or it may, in an earlier step, be entrapped with an entrapment material, for example, polymers, capsules, microcapsules and nanocapsules, liposomes, film formers, absorbents such as carbon or zeolites, cyclic oligosaccharides and mixtures thereof, and then mixed with the consumer product base. The consumer base might further contain entrapment material able to release other fragrant compounds.

[0164] Thus, the invention additionally provides a method of manufacturing a consumer product, comprising the incorporation of a compound of formula (I) either by directly admixing it to the consumer product base or by admixing a fragrance composition comprising the compound of formula (I), which may then be mixed with a consumer product base, using conventional techniques and methods. Through the addition of an acceptable amount of the compound of the present invention as hereinabove described, the odour notes of an applied consumer product will be improved, conferred, enhanced, or modified.

[0165] 31309 PCT2 As used herein, ‘consumer product base’ means a composition for use as a consumer product to fulfil specific actions, such as cleaning, softening, and caring or the like.

[0166] In a further aspect of the present invention, there is provided a method to release a a fragrant alcohol of formula (II), wherein a compound of formula (I) according to claim 1 is exposed to ambient air and / or humidity.

[0167] The compounds of the current invention can be prepared by methods known to the person skilled in the art of organic synthesis. For the purpose of illustration, descriptions of general methods are provided in the following. In all cases, isolation and purification of the product is effected according to suitable workup and purification methods known to the person skilled in the art.

[0168] For example, the compound of formula (I) is obtained from a carbonyl enol and an alcohol in the presence of triphenylphosphane and Diisopropyl azodicarboxylate (DIAD). In other examples, the compound of formula (I) is obtained by the reaction of a carbonyl enol with an R1-halogenide, for example with a chloride or bromide.

[0169] The invention is now further described with reference to the following non-limiting examples. These examples are for the purpose of illustration only and it is understood that variations and modifications can be made by one skilled in the art.

[0170] EXAMPLES

[0171] All reactions were performed under argon using solvents and reagents from commercial suppliers without further purification. Solvents for extraction and chromatography were technical grade and used without further purification. Flash chromatography was performed using Tsingdao Haiyang Chemical silica gel (200 - 300 mesh) and Santai Technologies silica flash columns. Unless otherwise noted, a mixture of heptane: MTBE was used as eluent. NMR spectra were recorded with AW 300 MHz and AW 400 MHz Bruker spectrometer instrument. The chemical shifts for1H NMR spectra was reported in 5 (ppm) referenced to the residual proton signal of the deuterated solvent; coupling constants were expressed in Hertz (Hz).13C NMR spectra were referenced to the carbon signals of the deuterated solvent. The following abbreviations are used: s = singlet, d = doublet, t = triplet, q = quartet, m = multiplet, dd = double doublet, bs = broad singlet. GC / MS spectral data were obtained from an Agilent 6890 N and MSD 5975 using a column HP-5 MS, 30 m, 0.25 mm, 0.25 pm. i-one

[0172] 31309 PCT2 To the suspension of furaneol (4-hydroxy-2,5-dimethylfuran-3(2H)-one) (1.5 g, 11.9 mmol), 4,8- dimethylnona-3,7-dien-1-ol (2.0 g, 11.9 mmol) and triphenylphosphane (3.4 g, 13.1 mmol) in THF (50 mL), diisopropyl diazene- 1 ,2-dicarboxylate (2.6 g, 13.1 mmol) was added dropwise at r.t. The mixture was stirred overnight at rt. The solvent was removed and the crude oil was purified with silica gel chromatography (heptane:MTBE=10: 1) to give 4-((4,8-dimethylnona-3,7- dien-1-yl)oxy)-2,5-dimethylfuran-3(2H)-one (1.6 g, 47% yield) as a light yellow liquid.

[0173] 1H NMR (400 MHz, CDCh, mixture of isomers) 5 5.15 - 4.95 (m, 2H), 4.38 - 4.27 (m, 1 H), 4.03 - 3.85 (m, 2H), 2.27 (q, J = 6.8 Hz, 2H), 2.10 (s, 3H), 2.05 - 1.86 (m, 4H), 1.68 - 1.50 (m, 9H), 1.35 (d, J = 7.3 Hz, 3H) ppm.13C NMR (101 MHz, CDCh, mixture of isomers) 5 198.3, 198.3, 178.3, 178.3, 137.8, 137.7, 135.4, 135.4, 131.6, 131.3, 124.1, 124.1 , 120.3, 119.4, 80.3, 71.6, 71.4, 39.7, 32.0, 28.7, 28.6, 26.6, 26.5, 25.6, 23.4, 17.6, 17.6, 16.4, 16.1 , 13.4 ppm. GC / MS (El): m / z (%): 278 (1) [l\ZT, 150 (8), 128 (25), 95 (18), 81 (18), 69 (100).

[0174] Odour description (1% solution in EtOH on paper blotter, 24 h): sweet, gourmand, burnt sugar, caramel, fruity apple.

[0175] Biodegradable: readily biodegradable

[0176] Example 1-2: 4-((3,7-dimethylnon-6-en-1-yl)oxy)-2,5-dimethylfuran-3(2H)-one

[0177] According to the procedure of example 1-1 , 4-((3,7-dimethylnon-6-en-1-yl)oxy)-2,5- dimethylfuran-3(2H)-one was obtained from 4-hydroxy-2,5-dimethylfuran-3(2H)-one (15.1 g, 117.4 mmol) and 3,7-dimethylnon-6-en-1-ol (20.0 g, 117.4 mmol) as a light yellow liquid (8.3 g, 24% yield).

[0178] 1H NMR (400 MHz, CDCh, mixture of isomers): 5 5.03 - 5.12 (m, 1 H), 4.40 (q, J = 7.2 Hz, 1 H), 3.97 - 4.11 (m, 2H), 2.18 (s, 3H), 1.93 - 2.07 (m, 4H), 1.75 - 0.77 (m, 17H) ppm.13C NMR (400 MHz, CDCh, mixture of isomers) 5 198.5, 178.3, 137.0, 136.8, 135.6, 124.3, 123.1 , 80.3, 70.4, 37.5, 37.2, 36.8, 32.3, 29.3, 29.2, 29.2, 25.3, 25.0, 24.7, 22.9, 19.5, 19.5, 16.5, 16.5, 15.9, 13.5, 12.8, 12.8 ppm. GC / MS (El): m / z (%): 280 (7) [ / W+], 152 (9), 128 (92), 123 (30), 111 (28), 95 (11), 55 (100).

[0179] Odour description (1% solution in EtOH on paper blotter, 24 h): floral, rosy, sweet, maltol, caramel.

[0180] Biodegradable: readily biodegradable. i-one

[0181] According to the procedure of example 1-1 , 4-((3,7-dimethyloct-6-en-1-yl)oxy)-2,5- dimethylfuran-3(2H)-one was obtained from 4-hydroxy-2,5-dimethylfuran-3(2H)-one (4.9 g, 38.4 mmol) and 3,7-dimethyloct-6-en-1-ol (6.0 g, 38.4 mmol) as a light yellow liquid (5.6 g, 53% yield).1H NMR (400 MHz, CDCh, mixture of isomers): 5 5.15 - 5.09 (m, 1 H), 4.40 (q, J = 7.1 Hz, 1 H), 4.12 - 3.97 (m, 2H), 2.18 (s, 3H), 2.08 - 1.90 (m, 2H), 1.76 - 1.54 (m, 8H), 1.52 - 1.12 (m, 6H),

[0182] 31309 PCT2 0.92 (d, J = 6.5 Hz, 3H) ppm.13C NMR (400 MHz, CDCh, mixture of isomers) 5 198.5, 178.3, 135.6, 131.2, 124.7, 80.3, 70.4, 70.3, 37.1 , 36.8, 29.2, 29.2, 25.7, 25.4, 19.4, 17.6, 16.5, 16.5,

[0183] 13.5 ppm. GC / MS (El): m / z (%): 266 (10) [ / W+], 251 (1), 138 (12), 128 (100), 85 (34), 69 (98). Odour description (1% solution in EtOH on paper blotter, 24 h): gourmand, burnt, caramel, fruity.

[0184] Biodegradable: inherently biodegradable. i-one

[0185] According to the procedure of example 1-1, 2,5-dimethyl-4-((2,4,7-trimethyloct-6-en-1- yl)oxy)furan-3(2H)-one was obtained from 4-hydroxy-2,5-dimethylfuran-3(2H)-one (0.8 g, 6.5 mmol) and 2,4,7-trimethyloct-6-en-1-ol (1.1 g, 6.5 mmol) as a light yellow liquid (0.2 g, 11 % yield).

[0186] 1H NMR (400 MHz, CDCh, mixture of isomers): 55.11 - 5.05 (m, 1 H), 4.32 (q, J = 7.0 Hz, 1 H), 3.88 - 3.62 (m, 2H), 2.12 (s, 3H), 1.96 - 1.01 (m, 15H), 0.99 - 0.71 (m, 6H).13C NMR (400 MHz, CDCh, mixture of isomers) 5 198.4, 178.0, 177.9, 135.9, 135.9, 132.1 , 123.2, 123.1, 80.3, 77.8, 77.8, 77.1, 77.0, 40.7, 40.7, 40.2, 36.2, 35.0, 35.0, 31.2, 30.9, 30.8, 25.8, 20.2, 19.2, 17.8, 17.6, 16.5, 16.4, 13.5, 13.5 ppm. GC / MS (El): m / z (%): 280 (6) [ / Vf], 152 (11), 128 (98), 109 (25), 97 (29), 83 (45), 69 (100), 55 (65).

[0187] Odour description (1% solution in EtOH on paper blotter, 24 h): sweet, rosy.

[0188] Example 1-5: 2,5-dimethyl-4-((2,4,7-trimethylocta-2,6-dien-1-yl)oxy)furan-3(2 / 7)-one

[0189] According to the procedure of example 1-1, 2,5-dimethyl-4-((2,4,7-trimethylocta-2,6-dien-1- yl)oxy)furan-3(2 / - / )-one was obtained from 4-hydroxy-2,5-dimethylfuran-3(2 / 7)-one (2.3 g, 17.8 mmol) and 2,4,7-trimethylocta-2,6-dien-1-ol (3.0 g, 17.8 mmol) as a light yellow liquid (2.0 g, 39% yield).

[0190] 1H NMR (400 MHz, CDCh, mixture of isomers): 5 = 5.28 - 5.22 (m, 1 H), 5.08 - 5.00 (m, 1 H), 4.34 - 4.45 (m, 3H), 2.38 - 2.41 (m, 1 H), 2.16 (s, 3H), 2.03 - 1.82 (m, 2H), 1.74 - 1.65 (m, 6H), 1.58 (s, 3H), 1.42 (d, J = 7.3 Hz, 3H), 0.91 (d, J = 6.8 Hz, 3H).13C NMR (400 MHz, CDCh, mixture of isomers) 5 198.5, 178.6, 178.6, 137.5, 137.3, 134.7, 134.6, 132.3, 132.3, 129.5, 129.4, 122.6, 122.6, 80.3, 80.2, 77.6, 77.4, 35.4, 32.9, 25.8, 20.3, 20.2, 17.8, 16.5, 16.5, 14.2, 13.6 ppm. GC / MS (El): m / z (%): 278 (1) [ / Vf], 209 (2), 150 (20), 128 (100), 95 (22), 85 (22), 69 (85).

[0191] Odour description (1% solution in EtOH on paper blotter, 24 h): sweet, rosy.

[0192] 31309 PCT2 According to the procedure of example 1-1, 2,5-dimethyl-4-((1-methyl-2-(5-methylhex-4-en-2- yl)cyclopropyl)methoxy)furan-3(2H)-one was obtained from 4-hydroxy-2,5-dimethylfuran-3(2H)- one (9.1 g, 71.3 mmol) and (1-methyl-2-(5-methylhex-4-en-2-yl)cyclopropyl)methanol (13.0 g, 71.3 mmol) as a light yellow liquid (7.4 g, 35% yield).

[0193] 1H NMR (400 MHz, CDCh, mixture of isomers) 5 5.50 - 5.22 (m, 1 H), 4.72 - 4.40 (m, 1 H), 4.08 - 3.64 (m, 2H), 2.39 (s, 3H), 2.33 - 1 .99 (m, 2H), 1.90 (s, 3H), 1.78 (s, 3H), 1.66 - 1.54 (m, 3H), 1.38 (s, 3H), 1.28 - 1.18 (m, 1 H), 1.18 - 1.01 (m, 3H), 0.85 - 0.58 (m, 2H), 0.34 - 0.10 (m, 1 H) ppm.13C NMR (400 MHz, CDCh, mixture of isomers) 5198.4, 198.4, 177.8, 135.9, 135.9, 135.7, 132.0, 131.8, 123.0, 123.0, 81.0, 80.9, 80.7, 80.6, 80.2, 80.2, 35.8, 35.7, 35.5, 34.7, 34.2, 29.1 , 29.1 , 28.9, 25.8, 20.1 , 20.1 , 20.4, 19.9, 19.8, 17.8, 16.5, 16.5, 16.5, 16.4, 16.0, 15.8, 15.8, 13.5 ppm. GC / MS (El): m / z (%): 292 (1) [ / Vf], 223 (2), 164 (15), 149 (9), 128 (80), 109 (55), 95 (41), 81 (26), 69 (100), 55 (29).

[0194] Odour description (1% solution in EtOH on paper blotter, 24 h): sweet, furaneol, rosy, rosyfolia, terpenic, sandalwood.

[0195] Example 1-7: 4-((4-isopropylcyclohexyl)methoxy)-2,5-dimethylfuran-3(2H)-one

[0196] According to the procedure of example 1-1 , 4-((4-isopropylcyclohexyl)methoxy)-2,5- dimethylfuran-3(2H)-one was obtained from 4-hydroxy-2,5-dimethylfuran-3(2H)-one (2.5 g, 19.2 mmol) and (4-isopropylcyclohexyl)methanol (3.0 g, 19.2 mmol) as a light yellow liquid (0.6 g, 11% yield).

[0197] 1H NMR (400 MHz, CDCh, mixture of isomers) 5 4.39 (q, J = 7.1 Hz, 1 H), 4.00 - 3.89 (m, 1 H), 3.85 - 3.75 (m, 1 H), 2.19 (s, 3H), 1.96 - 0.91 (m, 14H), 0.86 (d, J = 6.8 Hz, 6H) ppm.13C NMR (101 MHz, CDCh, mixture of isomers) 5 198.5, 198.5, 178.1 , 178.0, 136.0, 135.9, 80.3, 77.6, 74.5, 44.1 , 42.9, 38.4, 34.8, 32.9, 30.5, 29.8, 29.7, 29.1 , 25.9, 20.3, 19.8, 16.5, 13.5 ppm. GC / MS (El): m / z (%): 266 (10) [ / W+], 138 (7), 128(100), 123 (4), 95 (20), 83 (24), 69 (8), 55 (25). Odour description (1% solution in EtOH on paper blotter, 24 h): sweet, floral.

[0198] :-3-en-1-yl)pent-4-en-2-

[0199] According to the procedure of example 1-1 , 2,5-dimethyl-4-((3-methyl-5-(2,2,3- trimethylcyclopent-3-en-1-yl)pent-4-en-2-yl)oxy)furan-3(2H)-one was obtained from 4-hydroxy- 2,5-dimethylfuran-3(2H)-one (21.5 g, 168 mmol) and 3-methyl-5-(2,2,3-trimethylcyclopent-3-en- 1-yl)pent-4-en-2-ol (35.0 g, 168 mmol) as a light yellow liquid (12.5 g, 14% yield).

[0200] 1H NMR (400 MHz, CDCh, mixture of isomers): 55.60 - 5.34 (m, 2H), 5.25 - 5.18 (m, 1 H), 4.46 - 4.05 (m, 2H), 2.48 - 1.98 (m, 7H), 1.64 - 1.55 (m, 3H), 1.46 - 1.40 (m, 3H), 1.18 - 1.05 (m, 6H), 0.99 - 0.91 (m, 3H), 0.85 - 0.69 (m, 3H) ppm. GC / MS (El): m / z (%): 318 (1) [ / Vf], 191 (28), 175 (17), 155 (17), 121 (43), 109 (100), 91 (30), 83 (65).

[0201] 31309 PCT2 Odour description (1% solution in EtOH on paper blotter, 24 h): sweet, burnt sugar, furaneol, woody, sandalwood.

[0202] Example 1-9: 4-((3,7-dimethylocta-2,6-dien-1-yl)oxy)-2,5-dimethylfuran-3(2H)-one

[0203] According to the procedure of example 1-1 , 4-((3,7-dimethylocta-2,6-dien-1-yl)oxy)-2,5- dimethylfuran-3(2H)-one was obtained from 4-hydroxy-2,5-dimethylfuran-3(2H)-one (5.8 g, 45.4 mmol) and 3,7-dimethylocta-2,6-dien-1-ol (7.0 g, 45.4 mmol) as a light yellow liquid (7.5 g, 61 % yield).

[0204] 1H NMR (400 MHz, CDCh): 55.37 (t, J = 7.1 Hz, 1 H), 5.10 - 5.04 (m, 1 H), 4.65 - 4.49 (m, 2H), 4.46 - 4.33 (m, 1 H), 2.17 (s, 3H), 2.13 - 1.97 (m, 4H), 1.72 - 1.57 (m, 9H), 1.43 (d, J = 7.3 Hz, 3H) ppm.13C NMR (400 MHz, CDCh) 5 198.7, 179.1 , 142.7, 134.9, 131.8, 123.7, 119.7, 80.3, 67.9, 39.6, 26.3, 25.7, 17.7, 16.5, 16.4, 13.6 ppm. GC / MS (El): m / z (%): 264 (1) [ / W+], 136 (23), 128 (75), 93 (30), 85 (28), 81 (32), 69 (100).

[0205] Odour description (1% solution in EtOH on paper blotter, 24 h): sweet, furaneol, floral, rosy.

[0206] Example 1-10: 4-((4-isopropylcyclohexyl)oxy)-2,5-dimethylfuran-3(2H)-one

[0207] According to the procedure of example 1-1, 4-((4-isopropylcyclohexyl)oxy)-2,5-dimethylfuran- 3(2H)-one was obtained from 4-hydroxy-2,5-dimethylfuran-3(2H)-one (1.8 g, 14.1 mmol) and 4- isopropylcyclohexan-1-ol (2.0 g, 14.1 mmol) as a light yellow liquid (0.4 g, 13% yield).

[0208] 1H NMR (400 MHz, CDCh, mixture of isomers): 54.62 - 3.93 (m, 2H), 2.25 - 2.15 (m, 3H), 2.12 - 1.69 (m, 4H), 1.52 - 0.96 (m, 9H), 0.93 - 0.80 (m, 6H) ppm.13C NMR (101 MHz, CDCh, mixture of isomers) 5 198.9, 198.8, 179.3, 178.6, 134.2, 134.1, 80.3, 80.3, 79.7, 74.8, 43.2, 43.1, 32.7, 32.7, 32.4, 32.3, 30.2, 30.0, 27.6, 27.5, 23.8, 19.9, 19.8, 16.6, 13.7, 13.6 ppm. GC / MS (El): m / z (%): 252 (2) [ / Vf], 128 (100), 124 (5), 109 (8), 85 (34), 69 (27), 55 (21).

[0209] Odour description (1% solution in EtOH on paper blotter, 24 h): sweet

[0210] Example 1-11 : 4-(cyclopent-2-en-1-yloxy)-2,5-dimethylfuran-3(2H)-one

[0211] According to the procedure of example 1-1 , 4-(cyclopent-2-en-1-yloxy)-2,5-dimethylfuran-3(2H)- one was obtained from 4-hydroxy-2,5-dimethylfuran-3(2H)-one (4.6 g, 35.7 mmol) and cyclopent-2-en-1-ol (3.0 g, 35.7 mmol) as a light yellow liquid (2.5 g, 37% yield).

[0212] 1H NMR (400 MHz, CDCh, mixture of isomers): 56.12 - 6.07 (m, 1 H), 5.90 - 5.83 (m, 1 H), 5.40 - 5.30 (s, 1 H), 4.45 - 4.39 (m, 1 H), 2.60 - 2.41 (m, 1 H), 2.36 - 2.24 (m, 1 H), 2.21 - 2.06 (m, 4H), 1.93 - 1.94 (m, 1 H), 1.44 (d, J = 7.1 Hz, 3H) ppm.13C NMR (101 MHz, CDCh, mixture of isomers): 5 198.7, 198.7, 179.3, 179.2, 137.3, 134.8, 130.4, 130.3, 86.7, 86.6, 80.3, 30.7, 16.6, 13.6 ppm. GC / MS (El): m / z (%): 194 (1) [ / Vf], 128 (100), 85 (67), 67 (88).

[0213] Odour description (1% solution in EtOH on paper blotter, 24 h): sweet

[0214] 31309 PCT2 1-12: 2,5-dimethyl-4-(2-(1 ,1 ,5,5-tetramethyl-1 ,3,4,5,6,8a-hexahydro-2H-2,4a- i-8-' i-one

[0215] According to the procedure of example 1-1 , 2,5-dimethyl-4-(2-(1 ,1 ,5,5-tetramethyl-1 ,3,4,5,6,8a- hexahydro-2H-2,4a-methanonaphthalen-8-yl)propoxy)furan-3(2H)-one was obtained from 4- hydroxy-2,5-dimethylfuran-3(2H)-one (5.0 g, 39.0 mmol) and 2-(1 , 1 ,5,5-tetramethyl- 1 ,3,4,5,6,8a-hexahydro-2H-2,4a-methanonaphthalen-8-yl)propan-1-ol (Ambermax™) (11.3 g, 42.9 mmol) as a light yellow liquid (2.6 g, 18% yield).

[0216] 13C NMR (101 MHz, CDCh, mixture of isomers) 198.3, 177.9, 177.8, 177.7, 147.6, 139.6, 139.5, 135.8, 135.8, 135.8, 124.9, 122.6, 122.6, 80.3, 78.5, 78.4, 74.8, 56.9, 55.1 , 55.1 , 55.0, 51.0, 49.4, 42.7, 39.4, 37.7, 36.3, 36.2, 35.5, 33.9, 33.7, 33.7, 32.6, 31.2, 29.1 , 27.2, 27.2, 26.6, 26.3, 26.2, 25.0, 24.7, 24.2, 24.1 , 23.7, 22.5, 21.1 , 21.1 , 16.5, 16.4, 16.3, 16.3, 15.9, 13.6 ppm. GC / MS (El): m / z (%): 372 (1) [l\ZT, 245 (100), 229 (4), 203 (11), 189 (55), 175 (15), 161 (18), 147 (20), 133 (21), 119 (28), 69 (22).

[0217] Odour description (1% solution in EtOH on paper blotter, 24 h): woody, ambery, ambermax, sweet, caramel, burnt sugar, maltol, furaneol.

[0218] Example 1-13: 2,5-dimethyl-4-(((2E,6Z)-nona-2,6-dien-1-yl)oxy)furan-3(2H)-one

[0219] According to the procedure of example 1-1 , 2,5-dimethyl-4-(((2E,6Z)-nona-2,6-dien-1- yl)oxy)furan-3(2H)-one was obtained from 4-hydroxy-2,5-dimethylfuran-3(2H)-one (2.7 g, 21.4 mmol) and (2E,6Z)-nona-2,6-dien-1-ol (3.0 g, 21 .4 mmol) as a light pink liquid (3.0 g, 54% yield).1H NMR (400 MHz, CDCh) 6 5.80 - 5.55 (m, 2H), 5.45 - 5.24 (m, 2H), 4.53 - 4.30 (m, 3H), 2.25 - 1.95 (m, 9H), 1.42 (d, J= 7.0 Hz, 3H), 0.95 (t, J = 7.3 Hz, 3H) ppm.13C NMR (101 MHz, CDCh) 5 198.5, 178.9, 136.3, 134.8, 132.3, 127.9, 125.5, 80.3, 72.2, 32.4, 26.5, 20.5, 16.5, 14.3, 13.6 ppm. GC / MS (El): m / z (%): 250 (1) [ / W+], 128 (100), 122 (18), 93 (15), 85 (47), 69 (32).

[0220] Odour description (1% solution in EtOH on paper blotter, 24 h): aldehydic, fatty, oily, paint, violet, green, caramel, furaneol.

[0221] Biodegradation: inherently biodegradable. -one

[0222] According to the procedure of example 1-1 , 4-(dec-9-en-1-yloxy)-2,5-dimethylfuran-3(2H)-one was obtained from 4-hydroxy-2,5-dimethylfuran-3(2H)-one (2.5 g, 19.2 mmol) and dec-9-en-1- ol (3.0 g, 19.2 mmol) as a light pink liquid (3.2 g, 60% yield).

[0223] 1H NMR (400 MHz, CDCh) 55.90 - 5.74 (m, 1 H), 5.05 - 4.87 (m, 2H), 4.40 (q, J = 7.0 Hz, 1 H), 4.07 - 3.91 (m, 2H), 2.19 (s, 3H), 2.04 (q, J = 6.7 Hz, 2H), 1.70 - 1.59 (m, 2H), 1.51 - 1.25 (m, 13H) ppm.13C NMR (101 MHz, CDCh) 6 = 198.5, 178.3, 139.2, 135.6, 114.1 , 80.3, 72.1, 33.8,

[0224] 31309 PCT2 29.8, 29.4, 29.3, 29.0, 28.9, 25.7, 16.5, 13.5 ppm. GC / MS (El): m / z (%): 266 (19) [ / Vf], 128 (100), 110 (1), 85 (39), 72 (18), 55 (22).

[0225] Odour description (1% solution in EtOH on paper blotter, 24 h): caramel, furaneol, aldehydic, metallic, vibrant, green.

[0226] Biodegradation: inherently biodegradable. i-one

[0227] According to the procedure of example 1-1 , 2,5-dimethyl-4-(4-phenylbutoxy)furan-3(2H)-one was obtained from 4-hydroxy-2,5-dimethylfuran-3(2 / 7)-one (2.6 g, 20.0 mmol) and 4- phenylbutan-1-ol (3.0 g, 20.0 mmol) as a light yellow liquid (3.0 g, 56% yield).

[0228] 1H NMR (400 MHz, CDCI3) 5 7.37 - 7.23 (m, 2H), 7.22 - 7.14 (m, 3H), 4.38 (q, J = 6.8 Hz, 1 H), 4.10 - 3.91 (m, 2H), 2.65 (t, J = 6.6 Hz, 2H), 2.16 (s, 3H), 1.85 - 1.65 (m, 4H), 1.42 (d, J = 7.1 Hz, 3H) ppm.13C NMR (101 MHz, CDCI3) 5 198.4, 178.2, 142.2, 135.5, 128.4, 128.3, 125.7, 80.3, 71.7, 35.5, 29.4, 27.6, 16.5, 13.5 ppm. GC / MS (El): m / z (%): 260 (5) [ / W+], 128 (58), 117 (12), 104 (11), 91 (100), 85 (21).

[0229] Odour description (1% solution in EtOH on paper blotter, 24 h): sweet.

[0230] According to the procedure of example 1-1, (Z)-4,4'-(but-2-ene-1 ,4-diylbis(oxy))bis(2,5- dimethylfuran-3(2H)-one) was obtained from 4-hydroxy-2,5-dimethylfuran-3(2 / 7)-one (10.1 g, 79.0 mmol) and (Z)-but-2-ene-1 ,4-diol (3.5 g, 39.4 mmol) as a light yellow liquid (2.6 g, 20% yield).

[0231] 1H NMR (400 MHz, CDCI3) 56.09 - 5.45 (m, 2H), 4.90 - 4.48 (m, 4H), 4.41 (q, J = 7.1 Hz, 2H), 2.56 - 1.96 (m, 6H), 1.42 (t, J = 6.3 Hz, 6H) ppm.13C NMR (101 MHz, CDCI3) 5 198.3, 178.8, 134.9, 129.8, 129.4, 80.4, 66.8, 13.6 ppm. GC / MS (El): m / z (%): 308 (18) [ / Vf], 181 (80), 163 (10), 141 (21), 128 (100), 81 (38), 55 (35).

[0232] Odour description (1% solution in EtOH on paper blotter, 24 h): sweet, burnt sugar, caramel, toffee apple, brown, straw. 1-17: 4-((2-ethyl-4-(2,2,3-trimethylcyclopent-3-en-1-yl)but-2-en-1-yl)oxy)-2,5- i-one

[0233] According to the procedure of example 1-1, 4-((2-ethyl-4-(2,2,3-trimethylcyclopent-3-en-1- yl)but-2-en-1-yl)oxy)-2,5-dimethylfuran-3(2H)-one was obtained from 4-hydroxy-2,5- dimethylfuran-3(2H)-one (3.1 g, 24.0 mmol) and 2-ethyl-4-(2,2,3-trimethylcyclopent-3-en-1- yl)but-2-en-1-ol (5.0 g, 24.0 mmol) as a light yellow liquid (3.5 g, 44% yield).

[0234] 1H NMR (400 MHz, CDCI3, mixture of isomers) 5 5.42 (t, J = 7.2 Hz, 1 H), 5.21 (s, 1 H), 4.53 - 4.33 (m, 3H), 2.26 - 1.72 (m, 10H), 1.60 (d, J = 1.3 Hz, 3H), 1.42 (d, J = 7.1 Hz, 3H), 1.03 (t, J

[0235] 31309 PCT2 = 7.6 Hz, 3H), 1.00 - 0.96 (m, 3H), 0.79 (s, 3H) ppm.13C NMR (101 MHz, CDCh, mixture of isomers) 6 198.5, 178.5, 178.4, 148.5, 136.9, 134.8, 130.6, 121.6, 80.3, 75.0, 50.4, 50.4, 46.8, 35.6, 35.5, 28.0, 28.0, 25.9, 21.0, 21.0, 19.7, 19.7, 16.5, 13.6, 12.9, 12.6 ppm. GC / MS (El): m / z (%): 318 (1) [ / Vf], 191 (64), 175 (16), 161 (14), 148 (7), 135 (46), 129 (50), 121 (100), 108 (68), 93 (50), 79 (58).

[0236] Odour description (1% solution in EtOH on paper blotter, 24 h): gourmand woody. i-one

[0237] According to the procedure of example 1-1, 2,5-dimethyl-4-((2-methylundecyl)oxy)furan-3(2H)- one was obtained from 4-hydroxy-2,5-dimethylfuran-3(2 / - / )-one (3.4 g, 26.8 mmol) and 2- methylundecan-1-ol (5.0 g, 26.8 mmol) as a light yellow liquid (2.5 g, 31% yield).

[0238] 1H NMR (400 MHz, CDCh, mixture of isomers) 54.39 (q, J = 7.1 Hz, 1 H), 3.94 - 3.70 (m, 2H), 2.19 (d, J = 0.6 Hz, 3H), 1.98 - 1.66 (m, 1 H), 1.47 - 1.18 (m, 18H), 1.18 - 0.97 (m, 1 H), 0.96 (d, J = 6.7 Hz, 3H), 0.88 (t, J = 6.8 Hz, 3H) ppm.13C NMR (101 MHz, CDCh, mixture of isomers) 5 198.4, 178.0, 135.9, 135.9, 80.3, 77.2, 33.6, 33.2, 31.9, 29.9, 29.6, 29.6, 29.3, 26.9, 22.7, 16.7, 16.7, 16.5, 14.1 , 13.5 ppm. GC / MS (El): m / z (%): 296 (4) [ / Vf], 128 (100), 85 (26), 72 (13), 57 (14).

[0239] Odour description (1 % solution in EtOH on paper blotter, 24 h): sweet, maltol, fresh, aldehydic. Biodegradation: inherently biodegradable. i-one

[0240] According to the procedure of example 1-1, 2,5-dimethyl-4-((3-methylbut-3-en-1-yl)oxy)furan- 3(2H)-one was obtained from 4-hydroxy-2,5-dimethylfuran-3(2H)-one (3.7 g, 29.0 mmol) and 3- methylbut-3-en-1-ol (2.5 g, 29.0 mmol) as a light pink liquid (3.1 g, 53% yield).

[0241] 1H NMR (400 MHz, CDCh) 54.86 - 4.76 (m, 2H), 4.44 - 4.36 (m, 1 H), 4.23 - 4.01 (m, 2H), 2.37 (t, J = 6.8 Hz, 2H), 2.18 (d, J = 0.8 Hz, 3H), 1.78 (s, 3H), 1.43 (d, J = 7.1 Hz, 3H) ppm.13C NMR (101 MHz, CDCh) 5 198.4, 178.5, 142.0, 135.4, 112.0, 80.3, 69.8, 37.9, 22.5, 16.5, 13.5 ppm. GC / MS (El): m / z (%): 196 (9) [ / Vf], 128 (100), 85 (61), 74 (23), 69 (28), 57 (19), 56 (7).

[0242] Odour description (1% solution in EtOH on paper blotter, 24 h): caramel, burnt, sugar, maltol.

[0243] Example 1-20: 4-(furan-2-ylmethoxy)-2,5-dimethylfuran-3(2H)-one

[0244] According to the procedure of example 1-1 , 4-(furan-2-ylmethoxy)-2,5-dimethylfuran-3(2H)-one was obtained from 4-hydroxy-2,5-dimethylfuran-3(2 / 7)-one (4.6 g, 35.7 mmol) and furan-2- ylmethanol (3.5 g, 35.7 mmol) as a light yellow liquid (1.6 g, 21% yield).

[0245] 1H NMR (400 MHz, CDCh) 5 7.47 - 7.35 (m, 1 H), 6.36 - 6.27 (m, 2H), 5.09 - 4.89 (m, 2H), 4.40 (q, J = 7.1 Hz, 1 H), 1.95 (s, 3H), 1.42 (d, J = 7.3 Hz, 3H) ppm.13C NMR (101 MHz, CDCh) 5

[0246] 31309 PCT2 198.4, 180.1 , 150.6, 143.4, 134.0, 111.1 , 110.5, 80.5, 64.6, 16.5, 13.1 ppm. GC / MS (El): m / z (%): 208 (3) [ / W+], 81 (100), 53 (17).

[0247] Odour description (1% solution in EtOH on paper blotter, 24 h): sweet, caramel, burnt sugar, maltol.

[0248] 1-21 : (Z)-4-(hept-4-en-2-yloxy)-2,5-dimethylfuran-3(2H)-one

[0249] According to the procedure of example 1-1 , (Z)-4-(hept-4-en-2-yloxy)-2,5-dimethylfuran-3(2H)- one was obtained from 4-hydroxy-2,5-dimethylfuran-3(2H)-one (4.6 g, 35.9 mmol) and (Z)-hept-

[0250] 4-en-2-ol (4.1 g, 35.9 mmol) as a colorless liquid (3.4 g, 41% yield).

[0251] 1H NMR (400 MHz, CDCI3) 55.60 - 5.21 (m, 2H), 4.48 - 4.31 (m, 2H), 2.46 - 2.20 (m, 2H), 2.18

[0252] (s, 3H), 2.05 (q, J = 7.4 Hz, 2H), 1 .43 (d, J = 7.3 Hz, 3H), 1.20 (t, J = 6.0 Hz, 3H), 0.96 (t, J =

[0253] 7.5 Hz, 3H) ppm.13C NMR (101 MHz, CDCI3) 5198.6, 179.0, 179.0, 134.3, 134.3, 134.0, 134.0,

[0254] 124.0, 124.0, 80.3, 76.6, 76.6, 34.2, 34.1 , 20.7, 19.9, 19.8, 16.6, 16.6, 14.1 , 13.6 ppm. GC / MS

[0255] (El): m / z (%): 224 (5) [l\ZT, 181 (3), 155 (4), 128 (85), 96 (25), 85 (41), 81 (43), 55 (100).

[0256] Odour description (1% solution in EtOH on paper blotter, 24 h): caramel, burnt, sugar, maltol, bread crust.

[0257] Example 1-22: 2,5-dimethyl-4-(2-(2,2,3-trimethylcyclopent-3-en-1-yl)ethoxy)furan-3(2H)-one

[0258] According to the procedure of example 1-1, 2,5-dimethyl-4-(2-(2,2,3-trimethylcyclopent-3-en-1- yl)ethoxy)furan-3(2H)-one was obtained from 4-hydroxy-2,5-dimethylfuran-3(2H)-one (4.2 g,

[0259] 32.4 mmol) and 2-(2,2,3-trimethylcyclopent-3-en-1-yl)ethan-1-ol (5.0 g, 32.4 mmol) as a light yellow liquid (4.6 g, 52% yield).

[0260] 1H NMR (400 MHz, CDCI3, mixture of isomers) 55.25 - 2.19 (m, 1 H), 4.41 (q, J = 7.1 Hz, 1 H), 4.17 - 3.90 (m, 2H), 2.39 - 2.24 (m, 1 H), 2.20 (s, 3H), 1.94 - 1.82 (m, 3H), 1.69 - 1.51 (m, 4H), 1.44 (d, J = 7.1 Hz, 3H), 0.99 (s, 3H), 0.81 - 0.72 (m, 3H) ppm.13C NMR (101 MHz, CDCI3, mixture of isomers) 5 198.5, 178.2, 148.5, 148.5, 135.6, 121.6, 121.6, 80.3, 71.6, 46.8, 46.6, 35.4, 30.3, 25.7, 19.7, 16.5, 16.5, 13.6, 12.6 ppm. GC / MS (El): m / z (%): 264 (2) [ / W+], 137 (100), 128 (25), 121 (26), 109 (16), 95 (64), 81 (96), 67 (24), 57 (17).

[0261] Odour description (1% solution in EtOH on paper blotter, 24 h): sweet, caramel, burnt sugar, maltol. i-one

[0262] According to the procedure of example 1-1, 2,5-dimethyl-4-((3-methylbut-2-en-1-yl)oxy)furan- 3(2H)-one was obtained from 4-hydroxy-2,5-dimethylfuran-3(2H)-one (4.5 g, 34.8 mmol) and 3- methylbut-2-en-1-ol (3.0 g, 34.8 mmol) as a colorless liquid (3.6 g, 52% yield).

[0263] 1H NMR (400 MHz, CDCI3) 5 5.44 - 5.30 (m, 1 H), 4.58 - 4.46 (m, 2H), 4.45 - 4.34 (m, 1 H), 2.17 (s, 3H), 1.76 (s, 3H), 1.71 - 1.66 (m, 3H), 1.43 (d, J = 7.1 Hz, 3H) ppm.13C NMR (101 MHz,

[0264] 31309 PCT2 CDCI3) 6 198.7, 179.0, 139.4, 135.0, 119.9, 80.3, 67.9, 25.8, 18.0, 16.5, 13.5 ppm. GC / MS (El): m / z (%): 196 (1) [ / Vf], 128 (100), 85 (54), 72 (12), 69 (49), 57 (17).

[0265] Odour description (1% solution in EtOH on paper blotter, 24 h): caramel, burnt, licorice.

[0266] Example 1-24: 4-((3,7-dimethylnona-2,6-dien-1-yl)oxy)-2,5-dimethylfuran-3(2H)-one

[0267] According to the procedure of example 1-1 , 4-((3,7-dimethylnona-2,6-dien-1-yl)oxy)-2,5- dimethylfuran-3(2H)-one was obtained from 4-hydroxy-2,5-dimethylfuran-3(2 / 7)-one (4.6 g, 35.7 mmol) and 3,7-dimethylnona-2,6-dien-1-ol (6.0 g, 35.7 mmol) as a light yellow liquid (5.5 g, 54% yield).

[0268] 1H NMR (400 MHz, CDCh, mixture of isomers) 55.42 - 5.34 (m, 1 H), 5.12 - 4.97 (m, 1 H), 4.61 - 4.49 (m, 2H), 4.43 - 4.36 (m, 1 H), 2.17 (s, 3H), 2.13 - 1.92 (m, 6H), 1.82 - 1.55 (m, 6H), 1.43 - 1.42 (m, 3H), 1.02 - 0.92 (m, 3H) ppm.13C NMR (101 MHz, CDCh, mixture of isomers) 5 198.7, 198.6, 179.1 , 142.8, 142.7, 142.6, 142.5, 137.6, 137.4, 135.1, 135.0, 123.3, 123.2, 122.2, 122.0, 120.7, 120.7, 119.6, 119.6, 80.3, 67.9, 67.8, 39.9, 39.7, 32.4, 32.3, 32.3, 32.1 , 26.6, 26.4, 26.2, 25.9, 24.8, 24.7, 23.6, 22.9, 22.9, 16.5, 16.5, 16.5, 15.9, 15.9, 13.6, 12.8, 12.7 ppm. GC / MS (El): m / z (%): 278 (1) [ / Vf], 150 (32), 128 (100), 121 (21), 109 (5), 93 (39), 83 (67), 68 (27), 55 (85).

[0269] Odour description (1% solution in EtOH on paper blotter, 24 h): sweet, caramel.

[0270] Example 1-25: 2,5-dimethyl-4-((1-phenylbut-3-en-1-yl)oxy)furan-3(2H)-one

[0271] According to the procedure of example 1-1, 2,5-dimethyl-4-((1-phenylbut-3-en-1-yl)oxy)furan- 3(2H)-one was obtained from 4-hydroxy-2,5-dimethylfuran-3(2H)-one(0.9 g, 1.0 mmol) and 1- phenylbut-3-en-1-ol (1.0 g, 6.8 mmol) as a light yellow liquid (0.3 g, 17% yield).

[0272] 1H NMR (400 MHz, CDCh, mixture of isomers) 5 7.36 - 7.21 (m, 5H), 5.92 - 5.72 (m, 1 H), 5.49 - 5.32 (m, 1 H), 5.17 - 5.00 (m, 2H), 4.37 - 4.18 (m, 1 H), 2.90 - 2.51 (m, 2H), 1.97 - 1.92 (m, 3H), 1.40 - 1.22 (m, 3H) ppm.13C NMR (101 MHz, CDCh, mixture of isomers) 5 198.4, 198.3, 179.1 , 178.8, 140.5, 140.3, 134.1 , 134.0, 133.9, 128.3, 128.3, 128.2, 128.2, 127.4, 127.3, 117.5, 117.5, 81.2, 81.2, 80.2, 80.1 , 41.2, 40.7, 16.7, 16.2, 13.6. GC / MS (El): m / z (%): 258 (1) [ / Vf], 130 (100), 115 (25), 103 (9), 91 (50), 85 (6), 77 (11).

[0273] Odour description (1% solution in EtOH on paper blotter, 24 h): sweet, caramel, green, aldehydic. -one

[0274] According to the procedure of example 1-1 , 4-(dec-1-en-4-yloxy)-2,5-dimethylfuran-3(2H)-one was obtained from 4-hydroxy-2,5-dimethylfuran-3(2H)-one (1.2 g, 9.6 mmol) and dec-1-en-4-ol (1.5 g, 9.6 mmol) as a light yellow liquid (0.35 g, 14% yield).

[0275] 31309 PCT21H NMR (400 MHz, CDCh, mixture of isomers) 55.89 - 5.75 (m, 1 H), 5.16 - 5.07 (m, 1 H), 4.47 - 4.29 (m, 2H), 2.38 - 2.28 (m, 2H), 2.17 (s, 3H), 1.63 - 1.21 (m, 14H), 0.91 - 0.85 (m, 3H) ppm.13C NMR (101 MHz, CDCh, mixture of isomers) 5 198.4, 178.5, 178.5, 134.5, 134.4, 134.2, 117.2, 117.1, 80.2, 79.5, 79.5, 38.6, 38.5, 33.8, 33.8, 31.8, 31.8, 29.4, 25.1 , 25.0, 22.6, 22.6,

[0276] 16.6, 16.5, 14.1 , 13.7 ppm. GC / MS (El): m / z (%): 266 (2) [ / Vf], 138 (3), 128 (100), 85 (35), 72 (16), 55 (17).

[0277] Odour description (1 % solution in EtOH on paper blotter, 24 h): fatty, waxy, floral, sweet, caramel.

[0278] Example 1-27: 2,5-dimethyl-4-((3,7,11-trimethyldodeca-2,6,10-trien-1-yl)oxy)furan-3(2H)-one

[0279] According to the procedure of example 1-1 , 2,5-dimethyl-4-((3,7,11-trimethyldodeca-2,6,10- trien-1-yl)oxy)furan-3(2H)-one was obtained from 4-hydroxy-2,5-dimethylfuran-3(2H)-one(1 .7 g, 13.5 mmol) and 3,7,11-trimethyldodeca-2, 6,10-trien-1-ol (3.0 g, 13.5 mmol) as a light yellow liquid (3.0 g, 65% yield).

[0280] 1H NMR (400 MHz, CDCh, mixture of isomers) 5 5.46 - 5.35 (m, 1 H), 5.17 - 5.06 (m, 2H), 4.62 - 4.47 (m, 2H), 4.39 (q, J = 7.2 Hz, 1 H), 2.20 - 2.15 (m, 3H), 2.14 - 1.93 (m, 8H), 1.73 - 1.56 (m, 12H), 1.43 (d, J = 7.1 Hz, 3H) ppm. 13C NMR (101 MHz, CDCI3, mixture of isomers) 5 198.7, 179.0, 142.8, 142.7, 135.6, 135.4, 135.0 131.6, 131.3, 124.4, 124.3, 124.2, 123.6, 120.6, 119.7,

[0281] 119.6, 80.3, 67.9, 67.8, 39.9, 39.7, 39.6, 31.9, 26.7, 26.5, 26.3, 26.1 , 25.8, 25.7, 23.5, 23.3, 17.7,

[0282] 17.6, 16.5, 16.5, 16.4, 16.0, 13.6 ppm. GC / MS (El): m / z (%): 332 (1) [l\ZT, 204 (10), 189 (4), 161 (6), 128 (61), 93 (35), 80 (44), 69 (100).

[0283] Odour description (1% solution in EtOH on paper blotter, 24 h): fresh, aldehydic, floral, sweet, caramel.

[0284] Biodegradable: inherently biodegradable.

[0285] According to the procedure of example 1-1, 4,4'-(hexane-1 ,6-diylbis(oxy))bis(2,5-dimethylfuran- 3(2H)-one) was obtained from 4-hydroxy-2,5-dimethylfuran-3(2H)-one(4.0 g, 31.2 mmol) and hexane-1 ,6-diol (1.8 g, 15.6 mmol) as a light yellow liquid (1.0 g, 20% yield).

[0286] 1H NMR (400 MHz, CDCh) 54.40 (q, J = 7.2 Hz, 2H), 4.08 - 3.92 (m, 4H), 2.19 (s, 6H), 1.72 - 1.61 (m, 4H), 1.49 - 1.39 (m, 10H) ppm.13C NMR (101 MHz, CDCh) 5 198.4, 178.3, 135.5, 80.3, 71.8, 29.7, 25.5, 16.4, 13.4. GC / MS (El): m / z (%): 338 (21) [ / W+], 211 (75), 167 (3), 141 (9), 129 (98), 83 (68), 55 (100).

[0287] Odour description (1% solution in EtOH on paper blotter, 24 h): sweet, caramel, maltol, furaneol. i-one

[0288] 31309 PCT2 According to the procedure of example 1-1 , 2,5-dimethyl-4-((2-methylpent-2-en-1-yl)oxy)furan- 3(2H)-one_was obtained from 4-hydroxy-2,5-dimethylfuran-3(2H)-one(3.8 g, 30.0 mmol) and 2- methylpent-2-en-1-ol (3.0 g, 30.0 mmol) as a colorless liquid (4.0 g, 62% yield).

[0289] 1H NMR (400 MHz, CDCh) 6 5.42 (t, J = 7.1 Hz, 1 H), 4.48 - 4.31 (m, 3H), 2.17 (s, 3H), 2.03 (q, J = 7.4 Hz, 2H), 1.71 (s, 3H), 1.42 (d, J = 7.3 Hz, 3H), 0.94 (t, J = 7.5 Hz, 3H) ppm.13C NMR (101 MHz, CDCh) 6 198.5, 178.5, 134.8, 132.8, 130.4, 80.2, 77.5, 21.0, 16.6, 13.8, 13.5 ppm. GC / MS (El): m / z (%): 210 (1) [ / Vf], 128 (100), 85 (79), 72 (25), 67 (30), 55 (95).

[0290] Odour description (1% solution in EtOH on paper blotter, 24 h): sweet, caramel, green, fatty, aldehydic.

[0291] Example 1-30: 2,5-dimethyl-4-(octa-2,7-dien-1-yloxy)furan-3(2H)-one

[0292] According to the procedure of example 1-1 , 2,5-dimethyl-4-(octa-2,7-dien-1-yloxy)furan-3(2H)- one was obtained from 4-hydroxy-2,5-dimethylfuran-3(2H)-one(5.1 g, 39.6 mmol) and octa-2, 7- dien-1-ol (5.0 g, 39.6 mmol) as a colorless liquid (3.3 g, 35% yield).

[0293] 1H NMR (400 MHz, CDCh, mixture of isomers) 5 5.85 - 5.53 (m, 3H), 5.05 - 4.92 (m, 2H), 4.63 - 4.34 (m, 3H), 2.20 - 2.15 (m, 3H), 2.08 - 2.00 (m, 4H), 1.53 - 1.39 (m, 5H) ppm.13C NMR (101 MHz, CDCh, mixture of isomers) 5 198.5, 178.9, 138.4, 136.7, 135.1 , 134.7, 125.5, 125.1, 114.7, 114.7, 80.3, 72.1, 66.9, 33.2, 33.1 , 31.6, 28.7, 28.1 , 26.9, 16.5, 16.5, 13.6 ppm. GC / MS (El): m / z (%): 236 (1) [l\ZT, 128 (100), 108 (6), 93 (8), 85 (50), 79 (9), 72 (13), 67 (52).

[0294] Odour description (1 % solution in EtOH on paper blotter, 24 h): green, fatty, plastic, straw, sweet, caramel.

[0295] Example 1-31 : 4-(cyclohex-3-en-1-yloxy)-2,5-dimethylfuran-3(2H)-one

[0296] According to the procedure of example 1-1 , 4-(cyclohex-3-en-1-yloxy)-2,5-dimethylfuran-3(2H)- one was obtained from 4-hydroxy-2,5-dimethylfuran-3(2H)-one (4.0 g, 31.2 mmol) and cyclohex- 3-en-1-ol (1.8 g, 18.4 mmol) as a light yellow liquid (0.4 g, 10% yield).

[0297] 1H NMR (400 MHz, CDCh, mixture of isomers) 5 5.74 - 5.49 (m, 2H), 4.55 - 4.36 (m, 2H), 2.44 - 1.87 (m, 8H), 1.79 - 1.65 (m, 1 H), 1.44 (d, J = 7.1 Hz, 3H) ppm.13C NMR (101 MHz, CDCh, mixture of isomers) 5 198.7, 179.3, 179.3, 134.1 , 126.9, 126.8, 123.6, 123.5, 80.3, 75.4, 75.4, 31.4, 31 .3, 28.0, 27.9, 23.4, 23.3, 16.6, 13.5 ppm. GC / MS (El): m / z (%): 208 (11) [ / W+], 129 (100), 111 (3), 101 (5), 85 (49), 79 (78), 72 (11), 57 (20), 53 (29).

[0298] Odour description (1% solution in EtOH on paper blotter, 24 h): sweet, caramel, maltol, furaneol.

[0299] 1-32: methyl (12S,Z)-12-((2,5-dimethyl-4-oxo-4,5-dihydrofuran-3-yl)oxy)octadec-9- enoate

[0300] According to the procedure of example 1-1 , methyl (12S,Z)-12-((2,5-dimethyl-4-oxo-4,5- dihydrofuran-3-yl)oxy)octadec-9-enoate was obtained from 4-hydroxy-2,5-dimethylfuran-3(2H)-

[0301] 31309 PCT2 one(3.0 g, 23.0 mmol) and methyl (R,Z)-12-hydroxyoctadec-9-enoate (6.0 g, 19.2 mmol) as a light yellow liquid (1.5 g, 18% yield).

[0302] 1H NMR (400 MHz, CDCh, mixture of isomers) 5 5.55 - 5.28 (m, 2H), 4.43 - 4.25 (m, 2H), 3.67 (s, 3H), 2.36 - 2.22 (m, 4H), 2.17 (s, 3H), 2.03 - 1.95 (m, 2H), 1.66 - 1.16 (m, 23H), 0.94 - 0.83 (m, 3H) ppm.13C NMR (101 MHz, CDCh, mixture of isomers) 5 198.4, 198.4, 178.5, 174.3, 134.5, 134.5, 132.2, 132.1 , 124.8, 124.6, 80.2, 80.1 , 80.0, 51.4, 34.1, 33.9, 33.9, 31.9, 31.8, 31.8, 29.5, 29.4, 29.2, 29.1 , 29.1 , 27.4, 25.2, 25.1 , 24.9, 22.6, 16.7, 16.5, 14.1 , 13.6 ppm. GC / MS (El): m / z (%): 422 (1) [ / Vf], 391 (3), 294 (15), 263 (7), 245 (4), 128 (100), 95 (17), 85 (23), 55 (30).

[0303] Odour description (1% solution in EtOH on paper blotter, 24 h): sweet, burnt sugar.

[0304] Example 1-33: 4-(dodecyloxy)-2,5-dimethylfuran-3(2H)-one

[0305] According to the procedure of example 1-1, 4-(dodecyloxy)-2,5-dimethylfuran-3(2H)-one was obtained from 4-hydroxy-2,5-dimethylfuran-3(2H)-one (3.8 g, 29.5 mmol) and dodecan-1-ol (5.0 g, 26.8 mmol) as a colorless liquid (1.1 g, 14% yield).

[0306] 1H NMR (400 MHz, CDCh) 6 = 4.47 - 4.32 (m, 1 H), 4.07 - 3.91 (m, 2H), 2.19 (s, 3H), 1.72 - 1.59 (m, 3H), 1.51 - 1.15 (m, 20H), 0.88 (t, J = 6.8 Hz, 3H) ppm.13C NMR (101 MHz, CDCh) 6 = 198.5, 178.3, 135.6, 80.3, 72.1 , 31.9, 29.8, 29.6, 29.6, 29.5, 29.4, 29.4, 25.7, 22.7, 16.5, 14.1 , 13.5 ppm. GC / MS (El): m / z (%): 296 (10) [ / W+], 128 (100), 85 (25), 72 (13), 57 (10).

[0307] Odour description (1% solution in EtOH on paper blotter, 24 h): sweet, burnt sugar, aldehydic.

[0308] Example 1-34: 2,5-dimethyl-4-(((3E,6Z)-nona-3,6-dien-1-yl)oxy)furan-3(2H)-one

[0309] According to the procedure of example 1-1 , 2,5-dimethyl-4-(((3E,6Z)-nona-3,6-dien-1- yl)oxy)furan-3(2H)-one was obtained from 4-hydroxy-2,5-dimethylfuran-3(2H)-one (5.0 g, 39.2 mmol) and (3E, 6Z)-nona-3,6-dien-1-ol (5.0 g, 35.7 mmol) as a colorless liquid (2.5 g, 28% yield).1H NMR (400 MHz, CDCh) 55.63 - 5.23 (m, 4H), 4.40 (q, J = 7.1 Hz, 1 H), 4.12 - 3.95 (m, 2H), 2.75 (br t, J = 6.3 Hz, 2H), 2.34 (q, J = 6.6 Hz, 2H), 2.17 (s, 3H), 2.10 - 1.95 (m, 2H), 1.43 (d, J = 7.1 Hz, 3H), 0.96 (t, J = 7.6 Hz, 3H) ppm.13C NMR (101 MHz, CDCh) 6 198.3, 178.4, 135.3, 132.4, 131.2, 126.5, 125.8, 80.3, 71.3, 33.0, 30.3, 20.4, 16.5, 14.2, 13.5 ppm. GC / MS (El): m / z (%): 250 (3) [ / W+], 207 (3), 128 (72), 122 (55), (57), 81 (100), 67 (60), 55 (45).

[0310] Odour description (1% solution in EtOH on paper blotter, 24 h): sweet, caramel, maltol, green. Biodegradation: readily biodegradable. i-one

[0311] According to the procedure of example 1-1 , 4-((6,10-dimethylundeca-5,9-dien-2-yl)oxy)-2,5- dimethylfuran-3(2H)-one was obtained from 4-hydroxy-2,5-dimethylfuran-3(2H)-one (0.6 g, 4.7

[0312] 31309 PCT2 mmol) and 6, 10-dimethylundeca-5,9-dien-2-ol (1.0 g, 5.1 mmol) as a colorless liquid (0.3 g, 21% yield).

[0313] 1H NMR (400 MHz, CDCh, mixture of isomers) 55.19 - 5.04 (m, 2H), 4.46 - 3.87 (m, 2H), 2.23 - 1.92 (m, 9H), 1.73 - 1.40 (m, 14H), 1.24 - 1.13 (m, 3H) ppm.13C NMR (101 MHz, CDCh, mixture of isomers) 5 = 198.6, 178.9, 135.6, 135.4, 134.3, 131.5, 131.3, 124.6, 124.5, 124.3, 124.2, 123.8, 123.7, 80.2, 76.7, 76.6, 39.7, 37.0, 36.9, 36.8, 36.6, 31.9, 26.6, 26.5, 25.7, 25.6,

[0314] 23.8, 23.8, 23.7, 23.7, 23.3, 20.1 , 20.0, 17.6, 17.6, 16.6, 16.5, 15.9, 13.5 ppm. GC / MS (El) m / z (%): 306 (1) [IVT], 178 (10), 163 (3), 135 (7), 128 (34), 109 (23), 81 (30), 69 (100).

[0315] Odour description (1% solution in EtOH on paper blotter, 24 h): sweet, caramel, maltol.

[0316] Example 1-36: 2,5-dimethyl-4-((4,8,12-trimethyltrideca-3,7,11-trien-1-yl)oxy)furan-3(2H)-one

[0317] According to the procedure of example 1-1 , 2,5-dimethyl-4-((4,8,12-trimethyltrideca-3,7,11- trien-1-yl)oxy)furan-3(2H)-one was obtained from 4-hydroxy-2,5-dimethylfuran-3(2H)-one(6.5 g, 50.8 mmol) and 4,8, 12-trimethyltrideca-3,7, 11-trien-1 -ol (10.0 g, 42.3 mmol) as a colorless liquid (3.8 g, 26% yield).

[0318] 1H NMR (400 MHz, CDCh, mixture of isomers) 5 5.23 - 4.98 (m, 3H), 4.43 - 4.36 (m, 1 H), 4.09 - 3.87 (m, 2H), 2.38 - 2.32 (m, 3H), 2.18 (s, 3H), 2.15 - 1.89 (m, 8H), 1.74 - 1.53 (m, 12H), 1.43 (d, J = 7.1 Hz, 3H).13C NMR (101 MHz, CDCh, mixture of isomers) 5 198.4, 178.4, 137.9,

[0319] 137.8, 135.4, 135.3, 135.1 , 131.2, 124.3, 124.0, 123.9, 120.2, 119.4, 80.3, 71.4, 39.7, 28.7, 26.7, 26.5, 25.6, 17.6, 16.5, 16.2, 15.9, 13.4 ppm. GC / MS (El): m / z (%): 346 (1) [ / W+], 163 (2), 149 (6), 128 (31), 81 (59).

[0320] Odour description (1 % solution in EtOH on paper blotter, 24 h): sweet gourmand, caramel, maltol.

[0321] Biodegradation: readily biodegradable. -one

[0322] According to the procedure of example 1-1 , 4-(1-(4-methoxyphenyl)propoxy)-2,5-dimethylfuran- 3(2H)-one was obtained from 4-hydroxy-2,5-dimethylfuran-3(2H)-one (2.3 g, 18.1 mmol) and 1- (4-methoxyphenyl)propan-1-ol (3.0 g, 18.1 mmol) as a light yellow liquid (0.6 g, 12% yield).

[0323] 1H NMR (400 MHz, CDCh, mixture of isomers) 57.20 (d, J = 8.6 Hz, 2H), 6.84 (d, J = 8.6 Hz, 2H), 5.15 (d, J = 7.1 Hz, 1 H), 4.27 (d, J = 7.1 Hz, 1 H), 3.95 - 3.69 (m, 3H), 2.08 (d, J = 7.1 Hz, 1 H), 1.90 (t, J = 9.1 Hz, 3H), 1.86 - 1.65 (m, 1 H), 1.31 (d, J = 7.1 Hz, 3H), 0.91 (d, J = 7.2 Hz, 3H) ppm.13C NMR (101 MHz, CDCh, mixture of isomers) 5 198.7, 198.5, 179.2, 178.8, 159.4, 159.3, 134.1 , 134.0, 132.9, 132.6, 128.7, 128.5, 113.5, 83.2, 83.1 , 80.1 , 80.0, 55.1 , 29.5, 29.0,

[0324] 16.8, 16.2, 13.4, 10.2, 10.1 ppm. GC / MS (El): m / z (%): 276 (1) [IVT], 149 (100), 134 (4), 121 (55), 109 (9), 77 (6), 65 (4).

[0325] Odour description (1% solution in EtOH on paper blotter, 24 h): sweet, maltol, furaneol.

[0326] 31309 PCT2 1-38: 2,5-dimethyl-4-((4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-yl)oxy)furan-

[0327] -one

[0328] According to the procedure of example 1-1, 2,5-dimethyl-4-((4-(2,6,6-trimethylcyclohex-1-en-1- yl)but-3-en-2-yl)oxy)furan-3(2H)-one was obtained from 4-hydroxy-2,5-dimethylfuran-3(2H)- one(4.0 g, 30.9 mmol) and 4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-ol (6.0 g, 30.9 mmol) as a light yellow liquid (1.3 g, 13% yield).

[0329] 1H NMR (400 MHz, CDCh, mixture of isomers) 56.03 - 5.92 (m, 1 H), 5.33 - 5.20 (m, 1 H), 5.06 - 4.85 (m, 1 H), 4.47 - 4.30 (m, 1 H), 2.14 (s, 3H), 2.00 - 1.93 (m, 2H), 1.67 - 1.53 (m, 5H), 1.47 - 1.36 (m, 8H), 0.97 - 0.86 (m, 6H) ppm.13C NMR (101 MHz, CDCh, mixture of isomers) 5 198.7, 198.6, 179.4, 179.0, 136.6, 136.6, 134.3, 134.2, 134.2, 134.1, 131.7, 131.3, 129.2, 129.0, 80.3, 80.2, 77.9, 77.8, 39.3, 39.2, 33.8, 33.8, 32.6, 32.6, 28.6, 28.6, 28.6, 28.5, 21.7, 21.6, 21.3, 21.2, 19.2, 19.2, 16.6, 16.3, 13.6, 13.6 ppm. GC / MS (El): m / z (%): 304 (1) [IVT], 177 (100), 161 (10), 147 (9), 135 (10).

[0330] Odour description (1% solution in EtOH on paper blotter, 24 h): sweet, caramel, maltol. Biodegradation: readily biodegradable.

[0331] 1-39: 2,5-dimethyl-4-((2-methyl-4-(2,6,6-trimethylcvclohex-1-en-1-yl)but-2-en-1- i-one

[0332] According to the procedure of example 1-1 , 2,5-dimethyl-4-((2-methyl-4-(2,6,6- trimethylcyclohex-1-en-1-yl)but-2-en-1-yl)oxy)furan-3(2H)-one was obtained from 4-hydroxy-

[0333] 2,5-dimethylfuran-3(2H)-one (1.6 g, 12.5 mmol) and 2-methyl-4-(2,6,6-trimethylcyclohex-1-en- 1-yl)but-2-en-1-ol (2.6 g, 12.5 mmol) as a colorless liquid (2.3 g, 56% yield).

[0334] 1H NMR (400 MHz, CDCh) 5 5.29 - 5.21 (m, 1 H), 4.46 - 4.29 (m, 3H), 2.71 (br d, J = 6.1 Hz, 2H), 2.15 (s, 3H), 1.90 (br t, J = 6.2 Hz, 2H), 1.76 (s, 3H), 1.61 - 1.32 (m, 10H), 0.94 (d, J = 3.5 Hz, 6H) ppm.13C NMR (101 MHz, CDCh) 5 198.5, 178.5, 135.9, 134.6, 132.4, 129.4, 128.0, 80.2, 77.3, 39.7, 34.9, 32.8, 28.2, 28.2, 27.2, 19.6, 19.5, 16.5, 14.1 , 13.5 ppm. GC / MS (El): m / z (%): 318 (1) [ / W+], 190 (78), 175 (30), 161 (8), 149 (11), 135 (41), 121 (63), 108 (66), 95 (100), 82 (32), 69 (59), 55 (35).

[0335] Odour description (1% solution in EtOH on paper blotter, 24 h): sweet, caramel, maltol. i-one

[0336] According to the procedure of example 1-1 , 4-(cyclopent-3-en-1-yloxy)-2,5-dimethylfuran-3(2H)- one was obtained from 4-hydroxy-2,5-dimethylfuran-3(2H)-one (5.0 g, 39.2 mmol) and cyclopent-3-en-1-ol (3.0 g, 35.7 mmol) as a light pink liquid (2.0 g, 29% yield).

[0337] 1H NMR (400 MHz, CDCh) 55.78 - 5.57 (m, 2H), 5.18 - 5.07 (m, 1 H), 4.49 - 4.33 (m, 1 H), 2.68 - 2.37 (m, 4H), 2.14 (s, 3H), 1.52 - 1.33 (m, 3H) ppm. GC / MS (El): m / z (%): 194 (3) [ / W+], 128 (95), 111 (2), 101 (3), 85 (100), 72 (34), 67 (91), 57 (45).

[0338] 31309 PCT2 Odour description (1% solution in EtOH on paper blotter, 24 h): sweet.

[0339] According to the procedure of example 1-1, 2,5-dimethyl-4-((4-(2,6,6-trimethylcyclohex-1-en-1- yl)butan-2-yl)oxy)furan-3(2H)-one was obtained from 4-hydroxy-2,5-dimethylfuran-3(2H)- one(3.3 g, 25.5 mmol) and 4-(2,6,6-trimethylcyclohex-1-en-1-yl)butan-2-ol (5.0 g, 25.5 mmol) as a light yellow liquid (3.5 g, 43% yield).

[0340] 1H NMR (400 MHz, CDCh, mixture of isomers) 5 = 4.43 - 4.34 (m, 2H), 2.24 - 1.86 (m, 7H), 1.75 - 1.37 (m, 11 H), 1.25 - 1.17 (m, 3H), 1.04 - 0.95 (m, 6H) ppm.13C NMR (101 MHz, CDCh, mixture of isomers) 5 = 198.5, 178.7, 178.6, 136.8, 136.8, 134.5, 134.3, 127.0, 127.0, 80.2, 77.3, 77.1 , 39.8, 37.2, 35.0, 32.7, 28.6, 24.3, 20.1 , 20.0, 19.8, 19.5, 16.6, 16.6, 13.6, 13.6 ppm. GC / MS (El): m / z (%): 306 (10) [ / Vf], 178 (64), 163 (56), 149 (9), 137 (74), 129 (54), 123 (75), 109 (64), 95 (100), 81 (59), 68 (32), 55 (36).

[0341] Odour description (1% solution in EtOH on paper blotter, 24 h): sweet, gourmand. -one

[0342] According to the procedure of example 1-1, 2,5-dimethyl-4-((4-phenylbut-3-en-1-yl)oxy)furan- 3(2H)-one was obtained from 4-hydroxy-2,5-dimethylfuran-3(2H)-one (2.9 g, 22.2 mmol) and 4- phenylbut-3-en-1-ol (3.3 g, 22.2 mmol) as a colorless liquid (2.0 g, 35% yield).

[0343] 1H NMR (400 MHz, CDCh) 57.53 - 7.10 (m, 5H), 6.56 - 6.12 (m, 2H), 4.51 - 3.99 (m, 4H), 2.64 - 2.51 (m, 1 H), 2.20 - 2.11 (m, 3H), 1.47 - 1.38 (m, 3H) ppm.13C NMR (101 MHz, CDCh) 5 198.5, 178.7, 137.4, 135.4, 132.2, 128.5, 127.2, 126.1 , 126.0, 80.5, 71.0, 33.6, 16.5, 13.6 ppm. GC / MS (El): m / z (%): 258 (1) [ / Vf], 131 (100), 115 (27), 101 (6), 91 (54), 83 (18).

[0344] Odour description (1% solution in EtOH on paper blotter, 24 h): sweet, gourmand. i-one and 4-

[0345] According to the procedure of example 1-1 , the mixture of ((4,8-dimethylnona-3,7-dien-1-yl)oxy)- 2-ethyl-5-methylfuran-3(2H)-one and 4-((4,8-dimethylnona-3,7-dien-1-yl)oxy)-5-ethyl-2- methylfuran-3(2H)-one was obtained from homofuronol (mixture of 2-ethyl-4-hydroxy-5- methylfuran-3(2H)-one and 5-ethyl-4-hydroxy-2-methylfuran-3(2H)-one via NMR analysis) (1.3 g, 8.9 mmol) and 4,8-dimethylnona-3,7-dien-1-ol (1.5 g, 8.9 mmol) as a light yellow liquid (1.5 g, 56% yield).

[0346] 13C NMR (101 MHz, CDCh, mixture of isomer) 5198.7, 197.6, 197.6, 182.5, 178.8, 178.8, 137.8, 137.7, 136.2, 136.2, 134.4, 131.6, 131.4, 124.1, 124.1 , 120.3, 119.4, 119.4, 84.8, 80.2, 71.7,

[0347] 31309 PCT2 71.6, 71.5, 71.4, 39.7, 32.0, 28.7, 28.6, 26.6, 26.5, 25.6, 24.5, 23.4, 20.8, 17.6, 17.6, 16.1 , 13.3, 8.4 ppm. GC / MS (El): m / z (%): 292 (1) [M+], 207 (1), 142 (20), 114 (4), 95 (21), 69 (100). Odour description (1% solution in EtOH on paper blotter, 24 h): sweet, burnt sugar, caramel. Biodegradation: readily biodegradable.

[0348] 1-44: 2,5-dimethyl-4-((2-methyl-4-(2,2,3-trimethylcvclopent-3-en-1-yl)but-2-en-1- i-one

[0349] According to the procedure of example 1-1 , 2,5-dimethyl-4-((2-methyl-4-(2,2,3- trimethylcyclopent-3-en-1-yl)but-2-en-1-yl)oxy)furan-3(2H)-one was obtained from 4-hydroxy- 2,5-dimethylfuran-3(2H)-one(6.0 g, 46.8 mmol) and 2-methyl-4-(2,2,3-trimethylcyclopent-3-en- 1-yl)but-2-en-1-ol (9.1 g, 46.8 mmol) as a colorless liquid (7.5 g, 50% yield).

[0350] 1H NMR (400 MHz, CDCI3) <55.45 (t, J = 7.3 Hz, 1 H), 5.25 - 5.16 (m, 1 H), 4.52 - 4.31 (m, 3H), 2.29 - 1.89 (m, 6H), 1.85 - 1.55 (m, 8H), 1.50 - 1 .33 (m, 3H), 1.03 - 0.90 (m, 3H), 0.79 (s, 3H) ppm.13C NMR (101 MHz, CDCI3) 5 198.5, 178.5, 178.4, 148.5, 134.8, 131.0, 130.8, 121.6, 80.3, 77.5, 50.2, 50.2, 46.7, 35.6, 35.5, 28.4, 28.4, 25.9, 19.7, 19.7, 16.5, 14.1, 14.1 , 13.5, 12.6 ppm. GC / MS (El): m / z (%): 304 (1) [ / Vf], 177 (61), 161 (20), 129 (31), 107 (57), 93 (45), 79 (44), 69 (31), 55 (25).

[0351] Odour description (1 % solution in EtOH on paper blotter, 24 h): woody, sandalwood, warm, powdery, gourmand, caramel, homofuronol, maltol. i-one

[0352] According to the procedure of example 1-1 , (Z)-2,5-dimethyl-4-(non-6-en-1-yloxy)furan-3(2H)- one was obtained from 4-hydroxy-2,5-dimethylfuran-3(2H)-one(5.0 g, 38.7 mmol) and (Z)-non- 6-en-1-ol (5.0 g, 35.2 mmol) as a colorless liquid (2.1 g, 24% yield).

[0353] 1H NMR (400 MHz, CDCI3) 5 5.44 - 5.26 (m, 2H), 4.40 (q, J = 7.1 Hz, 1 H), 4.07 - 3.91 (m, 2H), 2.19 (s, 3H), 2.09 - 1.94 (m, 4H), 1.72 - 1.57 (m, 2H), 1.46 - 1.31 (m, 7H), 0.95 (t, J = 7.6 Hz, 3H) ppm.13C NMR (101 MHz, CDCI3) 5 198.5, 178.3, 135.6, 131.8, 128.9, 80.3, 72.0, 29.7, 29.5, 27.0, 25.4, 20.5, 16.5, 14.4, 13.5 ppm. GC / MS (El): m / z (%): 252 (8) [ / Vf], 209 (2), 128 (100), 85 (62), 69 (47), 55 (44).

[0354] Odour description (1 % solution in EtOH on paper blotter, 24 h): green, melon, watermelon, gourmand, caramel, maltol.

[0355] Biodegradation: readily biodegradable.

[0356] 2-ethyl-5-methyl-4-((3-methylbut-3-en-1-yl)oxy)furan-3(2H)-one and 5-ethyl-2- -one

[0357] According to the procedure of example 1-1 , mixture of 2-ethyl-5-methyl-4-((3-methylbut-3-en-1- yl)oxy)furan-3(2H)-one and 5-ethyl-2-methyl-4-((3-methylbut-3-en-1-yl)oxy)furan-3(2H)-one

[0358] 31309 PCT2 (ratio: 3:1) was obtained from homofuronol (mixture of 2-ethyl-4-hydroxy-5-methylfuran-3(2H)- one and 5-ethyl-4-hydroxy-2-methylfuran-3(2H)-one via NMR analysis) (5.0 g, 35.2 mmol) and

[0359] 3-methylbut-3-en-1-ol (3.3 g, 38.7 mmol) as a colorless wine liquid (5.1 g, 69% yield).

[0360] 2-ethyl-5-methyl-4-((3-methylbut-3-en-1-yl)oxy)furan-3(2H)-one:1H NMR (400 MHz, CDCh) 5 197.6, 178.9, 141.9, 136.1 , 112.0, 84.8, 69.7, 37.8, 24.5, 22.4, 13.4, 8.4 ppm. 5-ethyl-2-methyl-

[0361] 4-((3-methylbut-3-en-1-yl)oxy)furan-3(2H)-one:1H NMR (400 MHz, CDCh) 5 198.7, 182.5, 141.9, 134.4, 111.9, 80.2, 69.8, 37.8, 22.5, 20.8, 16.5, 10.1 ppm.

[0362] Odour description (1% solution in EtOH on paper blotter, 24 h): gourmand, maltol, caramel. -one

[0363] According to the procedure of example 1-1, 2,5-dimethyl-4-(1-(naphthalen-2-yl)ethoxy)furan- 3(2H)-one was obtained from 4-hydroxy-2,5-dimethylfuran-3(2H)-one (3.7 g, 29.0 mmol) and 1- (naphthalen-2-yl)ethan-1-ol (5.0 g, 29.0 mmol) as a colorless liquid (1.4 g, 17% yield).

[0364] 1H NMR (400 MHz, CDCh, mixture of isomers) 5 7.92 - 7.65 (m, 4H), 7.61 - 7.34 (m, 3H), 5.84 - 5.52 (m, 1 H), 4.48 - 4.07 (m, 1 H), 1 .96 (d, J = 14.6 Hz, 3H), 1.69 (t, J = 5.2 Hz, 3H), 1 .40 - 1.16 (m, 3H) ppm.13C NMR (101 MHz, CDCh, mixture of isomers) 5 198.7, 198.6, 179.4, 178.8, 139.6, 139.2, 134.2, 134.1 , 133.2, 133.2, 133.1 , 133.0, 128.3, 128.3, 128.0, 127.7, 126.2, 126.1 , 124.1 , 80.3, 80.2, 78.1 , 78.0, 22.8, 22.2, 16.7, 16.3, 13.6, 13.6 ppm. GC / MS (El): m / z (%): 282 (1) [ / W+], 155 (100), 141 (1), 128 (14), 115 (7), 101 (1), 77 (2).

[0365] Odour description (1% solution in EtOH on paper blotter, 24 h): floral, oranger, sweet, maltol. i-one

[0366] According to the procedure of example 1-1 , 4-(((S)-3,7-dimethylnon-6-en-1-yl)oxy)-2,5- dimethylfuran-3(2H)-one was obtained from 4-hydroxy-2,5-dimethylfuran-3(2H)-one (2.0 g, 15.6 mmol) and (S)-3,7-dimethylnon-6-en-1-ol (2.9 g, 17.2 mmol) as a light pink liquid (2.6 g, 59% yield).

[0367] 1H NMR (400 MHz, CDCh, mixture of isomers) 55.07 - 4.88 (m, 1 H), 4.41 - 4.24 (m, 1 H), 4.06 - 3.87 (m, 2H), 2.10 (s, 3H), 2.01 - 1.82 (m, 4H), 1.70 - 1.25 (m, 11 H), 0.97 - 0.80 (m, 6H) ppm.13C NMR (101 MHz, CDCh, mixture of isomers) 5 198.3, 178.1 , 136.9, 136.6, 135.5, 124.2, 123.0, 80.2, 70.3, 70.2, 37.4, 37.1 , 36.7, 32.3, 29.3, 29.2, 29.1 , 25.2, 24.9, 24.6, 22.8, 19.4, 16.5, 16.4, 15.8, 13.4, 12.8, 12.7 ppm. GC / MS (El): m / z (%): 280 (11) [ / W+], 265 (1), 152 (9), 128 (100), 83 (55), 69 (20), 55 (95).

[0368] Odour description (1% solution in EtOH on paper blotter, 24 h): gourmand, maltol, floral, rosy. Biodegradation: readily biodegradable.

[0369] )le 1-49: 2-ethyl-5-methyl-4-(tetradec-1-en-4-yloxy)furan-3(2H)-one and 5-ethyl-2- l-4-(tetradec-1-en-4- i-one

[0370] 31309 PCT2 According to the procedure of example 1-1, the mixture of 2-ethyl-5-methyl-4-(tetradec-1-en-4- yloxy)furan-3(2H)-one and 5-ethyl-2-methyl-4-(tetradec-1-en-4-yloxy)furan-3(2H)-one (ratio = 3:1) was obtained from tetradec- 1-en-4-ol (8.0 g, 37.7 mmol) and homofuronol (mixture of 2- ethyl-4-hydroxy-5-methylfuran-3(2H)-one and 5-ethyl-4-hydroxy-2-methylfuran-3(2H)-one via NMR analysis) (6.4 g, 45.2 mmol) as a light pink liquid (5.1 g, 40% yield).

[0371] 1H NMR (400 MHz, CDCI3, mixture of isomers) 55.88 - 5.78 (m, 1 H), 5.16 - 4.99 (m, 2H), 4.40

[0372] - 4.28 (m, 2H), 2.65 - 2.47 (m, 1 H), 2.32 - 2.29 (m, 2H), 2.17 (s, 2H), 1.98 - 1.93 (m, 1 H), 1.83

[0373] - 1.64 (m, 1 H), 1.59 - 1.48 (m, 2H), 1.45 - 1.34 (m, 3H), 1.38 - 1.28 (m, 12H), 1.20 (t, J = 7.6 Hz, 2H), 0.98 (t, J= 7.4 Hz, 2H), 0.88 (t, J= 6.8 Hz, 3H) ppm.13C NMR (101 MHz, CDCh, mixture of isomers) 5197.7, 178.9, 135.3, 134.3, 134.2, 133.4, 117.2, 117.1 , 84.7, 80.1 , 79.5, 79.4, 79.3, 38.4, 38.4, 33.7, 33.7, 31.9, 29.7, 29.7, 29.6, 29.5, 29.3, 25.1 , 25.0, 24.6, 24.5, 22.6, 20.8, 16.7, 16.6, 14.1 , 13.6, 10.0, 8.5 ppm.

[0374] Odour description (1 % solution in EtOH on paper blotter, 24 h): gourmand, caramel, maltol, furaneol, aldehydic, metallic, fatty, mandarin aldehyde.

[0375] Biodegradable: readily biodegradable.

[0376] Example 2-1 : (Z)-4-(hex-3-en-1-yloxy)-2,5-dimethylfuran-3(2H)-one

[0377] To a solution of 4-hydroxy-2,5-dimethylfuran-3(2H)-one (5.0 g, 39.0 mmol) and potassium carbonate (8.1 g, 58.5 mmol) in DMF (50 mL) was added (Z)-1-bromohex-3-ene (8.3 g, 50.7 mmol) at rt and stirred at 100 °C for 3 h. The mixture was then stirred at rt. overnight. The suspension was filtered and the solvent was removed. The result crude oil was purified via silica gel chromatography to give (Z)-4-(hex-3-en-1-yloxy)-2,5-dimethylfuran-3(2H)-one (3.1 g, 38% yield) as a light yellow liquid.

[0378] 1H NMR (400 MHz, CDCI3): 5 5.50 - 5.17 (m, 2H), 4.39 - 4.27 (m, 1 H), 4.03 - 3.86 (m, 2H), 2.38 - 1.91 (m, 7H), 1.35 (d, J = 7.3 Hz, 3H), 0.89 (t, J = 7.4 Hz, 3H) ppm.13C NMR (101 MHz, CDCI3) 5 198.4, 178.5, 135.4, 134.1 , 124.1 , 80.3, 71.3, 27.9, 20.6, 16.4, 14.1 , 13.5 ppm. GC / MS (El): m / z (%): 210 (5) [M ], 167 (3), 141 (1), 128 (100), 111 (1), 85 (56), 55 (68).

[0379] Odour description (1% solution in EtOH on paper blotter, 24 h): strong, gourmand, caramel, licorice, burnt sugar. i-one and (Z)-5-ethyl-4-

[0380] 3-en-1-yloxy)-2-methylfuran-3(2H)-one

[0381] According to the procedure of example 2-1 , the compound (mixture of (Z)-2-ethyl-4-(hex-3-en- 1-yloxy)-5-methylfuran-3(2H)-one and (Z)-5-ethyl-4-(hex-3-en-1-yloxy)-2-methylfuran-3(2H)- one, ratio =3: 1) was obtained from homofuronol (mixture of 2-ethyl-4-hydroxy-5-methylfuran- 3(2H)-one and 5-ethyl-4-hydroxy-2-methylfuran-3(2H)-one via NMR analysis) (6.5 g, 46.0 mmol) and (Z)-1-bromohex-3-ene (5.0 g, 30.7 mmol) as a light pink liquid (2.0 g, 30% yield).

[0382] 31309 PCT2 (Z)-2-ethyl-4-(hex-3-en-1-yloxy)-5-methylfuran-3(2H)-one:13C NMR (400 MHz, CDCh) 6 197.7, 178.9, 136.2, 134.2, 124.1 , 84.9, 71.4, 27.9, 24.5, 20.7, 14.2, 13.4, 8.5 ppm. (Z)-5-ethyl-4-(hex- 3-en-1-yloxy)-2-methylfuran-3(2H)-one:13C NMR (101 MHz, CDCI3) 5 (ppm) = 198.8, 182.5, 134.7, 134.5, 124.4, 80.3, 71.4, 33.1 , 25.6, 20.9, 16.6, 13.7, 10.1 ppm.

[0383] Odour description (1% solution in EtOH on paper blotter, 24 h): sweet, maltol. i-one

[0384] According to the procedure of example 2-1 , the compound 2,5-dimethyl-4-((4-methylpent-3-en- 1-yl)oxy)furan-3(2H)-one was obtained from 4-hydroxy-2,5-dimethylfuran-3(2H)-one(3.5 g, 27.6 mmol) and 5-bromo-2-methylpent-2-ene (3.0 g, 18.4 mmol) as a light yellow liquid (2.5 g, 64% yield).

[0385] 1H NMR (400 MHz, CDCh) 5 5.22 - 5.07 (m, 1 H), 4.46 - 4.37 (m, 1 H), 4.07 - 3.89 (m, 2H), 2.34 (q, J = 7.0 Hz, 2H), 2.18 (d, J = 0.8 Hz, 3H), 1.71 (d, J = 0.9 Hz, 3H), 1.66 - 1.60 (m, 3H), 1.43 (d, J = 7.3 Hz, 3H) ppm.13C NMR (101 MHz, CDCh) 5 198.4, 178.4, 135.4, 134.1, 119.7, 80.3, 77.2, 71.5, 28.8, 25.7, 17.8, 16.5, 13.5 ppm. GC / MS (El): m / z (%): 210 (1) [ / W+], 128 (59), 83 (80), 72 (15), 67 (28), 55 (100).

[0386] Odour description (1% solution in EtOH on paper blotter, 24 h): green, fatty, floral, muguet. i-one

[0387] According to the procedure of example 2-1 , 2,5-dimethyl-4-(pent-3-en-1-yloxy)furan-3(2H)-one was obtained from 4-hydroxy-2,5-dimethylfuran-3(2H)-one (1.9 g, 14.8 mmol) and 5-bromopent- 2-ene (2.0 g, 13.4 mmol) as a light yellow liquid (1.2 g, 46% yield).

[0388] 1H NMR (400 MHz, CDCh, mixture of E / Z isomers) 55.64 - 5.31 (m, 2H), 4.46 - 4.33 (m, 1 H), 4.09 - 3.93 (m, 2H), 2.47 - 2.28 (m, 2H), 2.18 (s, 3H), 1.73 - 1.57 (m, 3H), 1.48 - 1.38 (m, 3H) ppm.13C NMR (101 MHz, CDCh, mixture of E / Z isomers) 5 198.4, 198.4, 178.5, 178.5, 135.4, 127.5, 126.7, 126.4, 125.7, 80.3, 71.4, 71.2, 33.1 , 27.7, 18.0, 16.5, 13.5, 13.5, 12.9 ppm. GC / MS (El): m / z (%): 196 (4) [l\ZT, 167 (1), 153 (3), 128 (100), 111 (1), 85 (73), 69 (48).

[0389] Odour description (1% solution in EtOH on paper blotter, 24 h): maltol, caramel, burnt sugar. 2-ethyl-5-methyl-4-(pent-3-en-1-yloxy)furan-3(2H)-one and 5-ethyl-2-methyl-4-

[0390] :-3-en-1- i-one

[0391] According to the procedure of example 2-1 , the compound (mixture of 2-ethyl-5-methyl-4-(pent- 3-en-1-yloxy)furan-3(2H)-one and 5-ethyl-2-methyl-4-(pent-3-en-1-yloxy)furan-3(2H)-one, ratio=3:1) was obtained from homofuronol (mixture of 5-ethyl-4-hydroxy-2-methylfuran-3(2H)- one and 2-ethyl-4-hydroxy-5-methylfuran-3(2H)-one) (1 .6 g, 11.1 mmol) and 5-bromopent-2-ene (1.5 g, 10.1 mmol) as a light yellow liquid (1.2 g, 57% yield).

[0392] 31309 PCT2 13C NMR (101 MHz, CDCI3, mixture of isomers) 6 198.7, 197.6, 197.6, 182.5, 178.9, 136.2, 134.4, 127.5, 127.5, 126.7, 126.3, 125.7, 84.8, 80.2, 71.5, 71.4, 71.1, 33.1 , 27.7, 24.5, 20.8, 17.9, 16.5, 13.4, 13.4, 12.8, 10.1 , 8.4 ppm.

[0393] Odour description (1% solution in EtOH on paper blotter, 24 h): sweet, gourmand, burnt sugar, caramel. i-one

[0394] According to the procedure of example 1-1 , 3-((3,7-dimethyloct-6-en-1-yl)oxy)-4,5- dimethylfuran-2(5H)-one was obtained from 3-hydroxy-4,5-dimethylfuran-2(5H)-one (caramel lactone) (1.0 g, 7.8 mmol) and 3,7-dimethyloct-6-en-1-ol (1.3 g, 8.6 mmol) as a colorless liquid (1.0 g, 48% yield).

[0395] 1H NMR (400 MHz, CDCI3) 65.11 - 4.91 (m, 1 H), 4.82 - 4.61 (m, 1 H), 4.37 - 3.85 (m, 2H), 2.02 - 1.86 (m, 2H), 1.86 - 1.79 (m, 3H), 1.72 - 1.48 (m, 8H), 1.46 - 1.04 (m, 6H), 0.86 (d, J = 6.6 Hz, 3H) ppm.13C NMR (101 MHz, CDCI3) 6 167.5, 140.1 , 139.1, 130.3, 123.6, 75.7, 68.3, 36.1, 35.8, 28.2, 24.7, 24.4, 18.4, 17.6, 16.6, 8.7ppm. GC / MS (El): m / z (%): 266 (1) [ / W+], 251 (1), 139 (19), 128 (31), 95 (33), 83 (100), 69 (95), 55 (52).

[0396] Odour description (1% solution in EtOH on paper blotter, 24 h): gourmand, maltol, green. -one

[0397] According to the procedure of example 1-1 , (Z)-4,5-dimethyl-3-(non-6-en-1-yloxy)furan-2(5H)- one was obtained from 3-hydroxy-4,5-dimethylfuran-2(5H)-one (4.0 g, 31.2 mmol) and (Z)-non- 6-en-1-ol (5.8 g, 40.6 mmol) as a colorless liquid (6.4 g, 81% yield).

[0398] 1H NMR (400 MHz, CDCI3) 6 5.54 - 5.20 (m, 2H), 4.91 - 4.54 (m, 1 H), 4.29 - 4.06 (m, 2H), 2.15 - 1.97 (m, 4H), 1.90 (d, J = 1.0 Hz, 3H), 1.79 - 1.59 (m, 2H), 1.52 - 1.35 (m, 7H), 0.95 (t, J = 7.5 Hz, 3H) ppm.13C NMR (101 MHz, CDCI3) 6 = 168.5, 141.0, 140.0, 131.8, 128.8, 76.7, 70.9, 29.7, 29.4, 26.9, 25.3, 20.5, 18.6, 14.3, 9.7 ppm. GC / MS (El): m / z (%): 252(11) [ / Vf], 207 (33), 128 (25), 95 (32), 83 (100), 69 (66), 55 (77).

[0399] Odour description (1% solution in EtOH on paper blotter, 24 h): powdery gourmand, maltol. i-one

[0400] According to the procedure of example 1-1 , 3-(((S)-3,7-dimethylnon-6-en-1-yl)oxy)-4,5- dimethylfuran-2(5H)-one was obtained from 3-hydroxy-4,5-dimethylfuran-2(5H)-one (2.0 g, 15.6 mmol) and (S)-3,7-dimethylnon-6-en-1-ol (2.9 g, 17.2 mmol) as a colorless liquid (3.12 g, 71% yield).

[0401] 1H NMR (400 MHz, CDCI3) 65.23 - 4.95 (m, 1 H), 4.88 - 4.69 (m, 1 H), 4.36 - 4.11 (m, 2H), 2.11 - 1.93 (m, 4H), 1.90 (d, J = 1.0 Hz, 3H), 1.74 - 1.59 (m, 5H), 1.54 - 1.21 (m, 6H), 1.02 - 0.88 (m, 6H) ppm.13C NMR (101 MHz, CDCI3) 6 = 168.5, 141.0, 140.0, 137.0, 136.8, 124.2, 123.0,

[0402] 31309 PCT2 76.7, 69.3, 37.4, 37.1 , 36.8, 32.3, 29.3, 29.2, 25.2, 25.0, 24.7, 22.8, 19.5, 19.4, 18.6, 15.8, 12.9,

[0403] 12.8, 9.7 ppm.

[0404] Odour description (1% solution in EtOH on paper blotter, 24 h): powdery, licorice, fenugreek, straw, gourmand citrus. i-one

[0405] According to the procedure of example 2-1 , 3-(hex-3-en-1-yloxy)-4,5-dimethylfuran-2(5 / - / )-one was obtained from 3-hydroxy-4,5-dimethylfuran-2(5H)-one (2.4 g, 18.4 mmol) and 1-bromohex- 3-ene (2.0 g, 12.3 mmol) as a colorless liquid (1.5 g, 58% yield).

[0406] 1H NMR (400 MHz, CDCI3) 55.72 - 5.25 (m, 2H), 4.92 - 4.58 (m, 1 H), 4.29 - 4.06 (m, 2H), 2.57 - 2.25 (m, 2H), 2.15 - 1.96 (m, 2H), 1.93 - 1.67 (m, 3H), 1.54 - 1.24 (m, 3H), 1.08 - 0.86 (m, 3H) ppm.13C NMR (101 MHz, CDCI3) 5 168.4, 141.3, 139.8, 134.9, 134.3, 124.1, 123.8, 76.7, 70.2, 33.1 , 27.9, 25.6, 20.6, 18.5, 14.2, 13.6, 9.6 ppm. GC / MS (El): m / z (%): 210(1) [ / W+], 165 (5), 128 (22), 83 (100), 67 (30), 55 (85).

[0407] Odour description (1% solution in EtOH on paper blotter, 24 h): sweet rosy

[0408] Example 4-1 : (Z)-2-ethyl-3-(hex-3-en-1-yloxy)-4 / 7-pyran-4-one

[0409] According to the procedure of example 1-1 , (Z)-2-ethyl-3-(hex-3-en-1-yloxy)-4 / 7-pyran-4-one was obtained from 2-ethyl-3-hydroxy-4 / 7-pyran-4-one (8.0 g, 57.1 mmol) and (Z)-hex-3-en-1-ol (8.6 g, 86.0 mmol) as a light yellow liquid (4.2 g, 33% yield).

[0410] 1H NMR (300 MHz, CDCI3) 5 7.59 (d, J = 5.6 Hz, 1 H), 6.27 (d, J = 5.6 Hz, 1 H), 5.55 - 5.18 (m, 2H), 4.00 (t, J = 6.8 Hz, 2H), 2.63 (q, J = 7.5 Hz, 2H), 2.40 - 2.37 (m, 2H), 2.02 - 1.98 (m, 2H), 1.16 - 1.12 (m, 3H), 0.89 (t, J = 7.5 Hz, 3H) ppm.13C NMR (75 MHz, CDCI3) 5 175.2, 163.2, 153.4, 143.9, 134.0, 124.3, 116.9, 71.8, 28.0, 21.9, 20.5, 14.1 , 11.2 ppm. GC / MS (El): m / z (%): 222 (1) [ / W+], 193 (6), 167 (2), 153 (7), 140 (100), 123 (11), 55 (31).

[0411] Odour description (1% solution in EtOH on paper blotter, 24 h): caramel, maltol, green.

[0412] Example 4-2: 3-((3,7-dimethyloct-6-en-1-yl)oxy)-2-ethyl-4 / 7-pyran-4-one

[0413] According to the procedure of example 1-1 , 3-((3,7-dimethyloct-6-en-1-yl)oxy)-2-ethyl-4 / 7- pyran-4-one was obtained from 2-ethyl-3-hydroxy-4 / 7-pyran-4-one (8.0 g, 57.1 mmol) and 3,7- dimethyloct-6-en-1-ol (11.6 g, 74.2 mmol) as a light yellow liquid (7.0 g, 44% yield).

[0414] 1H NMR (300 MHz, CDCI3) 67.69 (d, J = 5.6 Hz, 1 H), 6.33 (d, J = 5.6 Hz, 1 H), 5.16 - 5.00 (m, 1 H), 4.20 - 3.95 (m, 2H), 2.71 (q, J = 7.6 Hz, 2H), 2.11 - 1.87 (m, 2H), 1.84 - 1.72 (m, 1 H), 1.71 - 1.57 (m, 6H), 1.57 - 1.46 (m, 1 H), 1.44 - 1.13 (m, 6H), 0.94 (d, J = 6.4 Hz, 3H) ppm.13C NMR (75 MHz, CDCh) 6 175.1, 162.9, 153.4, 144.0, 130.9, 124.5, 116.9, 70.6, 37.0, 36.9, 29.1 , 25.5, 25.3, 21.6, 19.3, 17.4, 11.2 ppm. GC / MS (El): m / z (%): 278 (10) [ / W+], 249 (8), 209 (1), 167 (24), 140 (100), 123 (19), 95 (13), 69 (35).

[0415] 31309 PCT2 Odour description (1% solution in EtOH on paper blotter, 24 h): sweet, maltol, citrus.

[0416] Example 4-3: 3-((3,7-dimethylnon-6-en-1-yl)oxy)-2-ethyl-4H-pyran-4-one

[0417] According to the procedure of example 1-1 , 3-((3,7-dimethylnon-6-en-1-yl)oxy)-2-methyl-4 / 7- pyran-4-one was obtained from 2-ethyl-3-hydroxy-4 / 7-pyran-4-one (2.5 g, 17.6 mmol) and 3,7- dimethylnon-6-en-1-ol (3.0 g, 17.6 mmol) as a light yellow liquid (2.0 g, 37% yield).

[0418] 1H NMR (400 MHz, CDCh, mixture of isomers) 5 7.64 (d, J = 5.6 Hz, 1 H), 6.34 (d, J = 5.6 Hz, 1 H), 5.20 - 4.98 (m, 1 H), 4.12 - 4.08 (m, 2H), 2.71 (q, J = 7.6 Hz, 2H), 2.02 - 1.98 (m, 3H), 1.85 - 1.73 (m, 1 H), 1.70 - 1.59 (m, 3H), 1.54 - 1.50 (m, 1 H), 1.38 - 1.13 (m, 7H), 1.04 - 0.90 (m, 5H), 0.87 - 0.83 (m, 1 H) ppm.13C NMR (101 MHz, CDCh, mixture of isomers) 5 175.3, 163.2, 153.4, 144.1 , 136.9, 136.7, 124.3, 123.0, 117.0, 71.0, 70.9, 70.8, 37.5, 37.4, 37.3, 37.2, 37.1, 37.0, 36.9, 36.8, 34.3, 32.3, 29.7, 29.6, 29.5, 29.4, 29.3, 29.2, 25.3, 25.0, 24.7, 24.3, 22.8, 21.8, 19.6, 19.5, 19.4, 19.3, 19.2, 19.1 , 15.8, 12.8, 12.7, 11.4, 11.3 ppm. GC / MS (El): m / z (%): 292 (9) [ / W+], 263 (8), 181 (3), 167 (29), 140 (100), 123 (41), 55 (46).

[0419] Odor description (1% solution in EtOH on paper blotter, 24 h): waxy, rosy, tetrahydro geraniol.

[0420] Example 4-4: 2-ethyl-3-((2,4,7-trimethyloct-6-en-1-yl)oxy)-4H-pyran-4-one

[0421] According to the procedure of example 1-1 , 2-ethyl-3-((2,4,7-trimethyloct-6-en-1-yl)oxy)-4H- pyran-4-onewas obtained from 2-ethyl-3-hydroxy-4 / 7-pyran-4-one (0.6 g, 4.1 mmol) and 2,4,7- trimethyloct-6-en-1-ol (0.7 g, 4.1 mmol) as a pink liquid (0.4 g, 32% yield).

[0422] 1H NMR (400 MHz, CDCh, mixture of isomers) 5 7.63 (d, J = 5.6 Hz, 1 H), 6.33 (d, J = 5.6 Hz, 1 H), 5.12 (d, J = 7.0 Hz, 1 H), 4.14 - 3.64 (m, 2H), 2.71 (q, J = 7.Q Hz, 2H), 2.09 - 1.90 (m, 2H), 1.79 - 1.76 (m, 1 H), 1.70 (s, 3H), 1.59 (s, 3H), 1.48 - 1.41 (m, 1 H), 1.34 - 1.17 (m, 4H), 1.08 - 0.95 (m, 4H), 0.89-0.85 (m, 3H) ppm.13C NMR (101 MHz, CDCh, mixture of isomers) 5 175.3,

[0423] 162.9, 162.9, 153.3, 144.4, 132.0, 123.2, 123.1 , 117.1 , 78.3, 77.6, 40.8, 40.3, 36.2, 35.0, 31.4,

[0424] 30.9, 30.7, 25.8, 21.8, 20.2, 19.1, 17.8, 17.7, 16.5, 11 .3 ppm. GC / MS (El): m / z (%): 292 (6) [ / Vf], 263 (4), 181 (4), 167 (5), 153 (6), 140 (100), 69 (64), 55 (44).

[0425] Odour description (1% solution in EtOH on paper blotter, 24 h): caramel, citrus.

[0426] Example 4-5: 2-ethyl-3-(((3E,6Z)-nona-3,6-dien-1-yl)oxy)-4 / 7-pyran-4-one

[0427] According to the procedure of example 1-1, 2-ethyl-3-(((3E,6Z)-nona-3,6-dien-1-yl)oxy)-4 / 7- pyran-4-one was obtained from 2-ethyl-3-hydroxy-4 / 7-pyran-4-one (5.5 g, 39.2 mmol) and (3E,6Z)-nona-3,6-dien-1-ol (5.0 g, 35.7 mmol) as a light yellow liquid (1.8 g, 19% yield).

[0428] 1H NMR (400 MHz, CDCh) 57.64 (d, J = 5.6 Hz, 1 H), 6.33 (d, J = 5.6 Hz, 1 H), 5.63 - 5.24 (m, 4H), 4.09 (t, J = 6.8 Hz, 2H), 2.78 - 2.63 (m, 4H), 2.41 (q, J = 6.8 Hz, 2H), 2.11 - 1.94 (m, 2H), 1.21 (t, J = 7.5 Hz, 3H), 0.96 (t, J = 7.5 Hz, 3H) ppm.13C NMR (101 MHz, CDCh) 5 175.3, 163.2, 153.4, 143.9, 132.3, 131.2, 126.5, 126.0, 117.0, 71.9, 33.2, 30.3, 21.7, 20.4, 14.2, 11.2 ppm.

[0429] 31309 PCT2 Odour description (1% solution in EtOH on paper blotter, 24 h): green, crushed leaf, apple skin, lawn, green fruit, hexenol, sweet, burnt sugar, maltol.

[0430] Example 4-6: methyl (S,Z)-12-((2-ethyl-4-oxo-4 / 7-pyran-3-yl)oxy)octadec-9-enoate

[0431] According to the procedure of example 1-1, methyl (S,Z)-12-((2-ethyl-4-oxo-4 / 7-pyran-3- yl)oxy)octadec-9-enoate was obtained from 2-ethyl-3-hydroxy-4 / 7-pyran-4-one (5.0 g, 35.7 mmol) and methyl (R,Z)-12-hydroxyoctadec-9-enoate (14.5 g, 46.4 mmol) as a light yellow liquid (6.3 g, 41 % yield).

[0432] 1H NMR (400 MHz, CDCI3) 5 7.63 (d, J = 5.6 Hz, 1 H), 6.30 (d, J = 5.6 Hz, 1 H), 5.54 - 5.31 (m, 2H), 4.66 (p, J = 5.9 Hz, 1 H), 3.67 (s, 3H), 2.84 - 2.57 (m, 2H), 2.40 - 2.21 (m, 4H), 2.06 - 1.91 (m, 2H), 1.67 - 1.50 (m, 4H), 1.46 - 1.23 (m, 16H), 1.20 (t, J = 7.6 Hz, 3H), 0.87 (t, J = 6.6 Hz, 3H) ppm.13C NMR (101 MHz, CDCI3) 5 175.3, 174.3, 162.8, 153.1 , 142.5, 132.0, 124.7, 116.9,

[0433] 79.4, 51.4, 34.0, 33.7, 31.8, 31.5, 29.5, 29.4, 29.2, 29.1 , 29.1 , 27.4, 25.1 , 24.9, 22.6, 21.7, 14.0, 10.9 ppm.

[0434] Odour description (1% solution in EtOH on paper blotter, 24 h): sweet, maltol.

[0435] Biodegradable: inherently biodegradable

[0436] Example 4-7: 2-ethyl-3-((3-methylbut-3-en-1-yl)oxy)-4 / 7-pyran-4-one

[0437] According to the procedure of example 1-1, 2-ethyl-3-((3-methylbut-3-en-1-yl)oxy)-4 / 7-pyran-4- one was obtained from 2-ethyl-3-hydroxy-4 / 7-pyran-4-one (6.0 g, 42.8 mmol) and 3-methylbut- 3-en-1-ol (4.43 g, 51.4 mmol) as a light yellow liquid (5.1 g, 57% yield).

[0438] 1H NMR (400 MHz, CDCI3) 57.76 - 7.56 (m, 1 H), 6.41 - 6.27 (m, 1 H), 4.82 (d, J = 8.1 Hz, 2H), 4.28 - 4.11 (m, 2H), 2.77 - 2.63 (m, 2H), 2.48 - 2.38 (m, 2H), 1.79 (s, 3H), 1.26 - 1.14 (m, 3H) ppm.13C NMR (101 MHz, CDCI3) 5 175.2, 163.2, 153.5, 143.9, 142.0, 117.0, 111.9, 70.4, 38.0,

[0439] 22.5, 21.7, 11.2 ppm.

[0440] Odour description (1% solution in EtOH on paper blotter, 24 h): maltol, caramel, burnt sugar, green, metallic.

[0441] Example 4-8: 2-ethyl-3-(tetradec-1-en-4-yloxy)-4 / 7-pyran-4-one

[0442] According to the procedure of example 1-1, 2-ethyl-3-(tetradec-1-en-4-yloxy)-4 / 7-pyran-4-one was obtained from 2-ethyl-3-hydroxy-4 / 7-pyran-4-one (2.0 g, 14.3 mmol) and tetradec- 1-en-4-ol (3.3 g, 15.7 mmol) as a colorless liquid (0.9 g, 18% yield).

[0443] 1H NMR (400 MHz, CDCI3) 5 7.63 (d, J = 5.6 Hz, 1 H), 6.30 (d, J = 5.6 Hz, 1 H), 5.94 - 5.75 (m, 1 H), 5.14 - 4.98 (m, 2H), 4.78 - 4.56 (m, 1 H), 2.79 - 2.60 (m, 2H), 2.39 - 2.31 (m, 2H), 1.61 - 1.52 (m, 2H), 1.44 - 1.35 (m, 2H), 1.33 - 1.18 (m, 17H), 0.92 - 0.84 (m, 3H) ppm.13C NMR (101 MHz, CDCI3) 5 175.3, 162.8, 153.1 , 142.5, 134.3, 117.1, 116.9, 78.9, 38.3, 33.6, 31.9, 29.8,

[0444] 29.6, 29.5, 29.3, 25.0, 22.6, 21.7, 14.1 , 10.9 ppm.

[0445] Odour description (1% solution in EtOH on paper blotter, 24 h): gourmand, caramel, maltol, fatty, green aldehydic, citrus, mandarin.

[0446] 31309 PCT2 Example 4-9: 2-ethyl-3-((4,8,12-trimethyltrideca-3,7,11-trien-1-yl)oxy)-4 / 7-pyran-4-one

[0447] According to the procedure of example 1-1, 2-ethyl-3-((4,8,12-trimethyltrideca-3,7,11-trien-1- yl)oxy)-4 / 7-pyran-4-one was obtained from 2-ethyl-3-hydroxy-4 / 7-pyran-4-one (6.0 g, 42.8 mmol) and 4,8, 12-trimethyltrideca-3,7, 11 -trien-1-ol (3.3 g, 15.7 mmol) as a colorless liquid (3.3 g, 22 % yield).

[0448] 1H NMR (400 MHz, CDCh, mixture of isomers) 5 7.64 (d, J = 5.6 Hz, 1 H), 6.34 (d, J = 5.6 Hz, 1 H), 5.30 - 4.93 (m, 3H), 4.17 - 3.82 (m, 2H), 2.71 (q, J = 7.6 Hz, 2H), 2.43 (q, J = 7.0 Hz, 2H), 2.14 - 1.93 (m, 8H), 1.73 - 1.54 (m, 12H), 1.22 (t, J = 7.6 Hz, 3H) ppm.13C NMR (101 MHz, CDCh, mixture of isomers) 5 175.3, 163.2, 153.4, 144.0, 137.9, 137.8, 135.3, 135.0, 131.2, 124.3, 124.0, 123.9, 120.5, 119.6, 117.0, 72.1 , 39.7, 39.1 , 32.0, 28.8, 28.7, 26.7, 26.7, 26.5, 26.4, 25.6, 23.4, 21.7, 17.6, 16.2, 15.9, 11.3 ppm.

[0449] Odour description (1% solution in EtOH on paper blotter, 24 h): sweet, burnt sugar, caramel

[0450] Example 4-10: 2-methyl-3-(((3E,6Z)-nona-3,6-dien-1-yl)oxy)-4H-pyran-4-one

[0451] According to the procedure of example 1-1, 2-methyl-3-(((3E,6Z)-nona-3,6-dien-1-yl)oxy)-4H- pyran-4-one was obtained from (3E,6Z)-nona-3,6-dien-1-ol (5.0 g, 35.7 mmol) and 3-hydroxy- 2-methyl-4H-pyran-4-one (5.0 g, 39.2 mmol) as a light yellow liquid (3.9 g, 44% yield).

[0452] 1H NMR (400 MHz, CDCh) 57.61 (d, J = 5.6 Hz, 1 H), 6.33 (d, J = 5.6 Hz, 1 H), 5.63 - 5.20 (m, 4H), 4.17 - 4.02 (m, 2H), 2.75 (t, J = 6.3 Hz, 2H), 2.41 (q, J = 6.6 Hz, 2H), 2.30 (s, 3H), 2.04 (m, 2H), 1.05 - 0.83 (m, 3H) ppm.13C NMR (101 MHz, CDCh) 6 175.0, 159.0, 153.3, 144.7, 132.3, 131.2, 126.5, 126.0, 117.1 , 71.7, 33.2, 30.3, 20.4, 14.7, 14.2 ppm.

[0453] GC / MS (El): m / z (%): 248 (1) [ / Vf], 233 (1), 179 (1), 153 (1), 139 (10), 126 (100), 93 (24), 79 (25).

[0454] Odour description (1% solution in EtOH on paper blotter, 24 h): green, crushed leaf, apple skin, lawn, green fruit, hexenol.

[0455] Example 4-11 : (E)-3-((4,8-dimethylnona-3,7-dien-1-yl)oxy)-2-ethyl-4H-pyran-4-one

[0456] According to the procedure of example 1-1, (E)-3-((4,8-dimethylnona-3,7-dien-1-yl)oxy)-2-ethyl- 4H-pyran-4-one was obtained from (E)-4,8-dimethylnona-3,7-dien-1-ol (5.0 g, 29.7 mmol) and 2-ethyl-3-hydroxy-4H-pyran-4-one (4.2 g, 29.7 mmol) as a light yellow liquid (6.1 g, 71% yield).1H NMR (400 MHz, CDCh) 6 7.58 (d, J = 5.6 Hz, 1 H), 6.26 (d, J = 5.6 Hz, 1 H), 5.13 - 5.06 (m, 2H), 3.97 (t, J = 7.0 Hz, 2H), 2.63 (q, J = 7.6 Hz, 2H), 2.34 (q, J = 6.9 Hz, 2H), 2.05 - 1.84 (m, 4H), 1.71 - 1.50 (m, 9H), 1.14 (t, J = 7.6 Hz, 3H) ppm.13C NMR (101 MHz, CDCh) 6 175.3, 163.2, 153.4, 144.0, 144.0, 137.8, 137.7, 131.6, 131.4, 124.1 , 124.1 , 120.5, 119.6, 117.0, 72.2, 72.0, 39.7, 32.0, 28.8, 28.7, 26.6, 26.4, 25.6, 23.4, 21.7, 17.6, 17.5, 16.1, 11.3 ppm.

[0457] GC / MS (El): m / z (%): 290 (1) [ / Vf], 261 (1), 207 (1), 193 (2), 153 (10), 141 (100), 123 (9), 107 (20), 81 (24), 69 (87).

[0458] Odour description (1% solution in EtOH on paper blotter, 24 h): sweet, caramel, maltol.

[0459] 31309 PCT2 Biodegradable: readily biodegradable l-3-(pent-3-en-1-yloxy)-4H-pyran-4-one

[0460] According to the procedure of example 2-1 , 2-methyl-3-(pent-3-en-1-yloxy)-4H-pyran-4-one was obtained from 5-bromopent-2-ene (E / Z isomers, 2.5 g, 16.8 mmol) and 3-hydroxy-2-methyl-4H- pyran-4-one (2.3 g, 18.5 mmol) as a colorless liquid (1.5 g, 46 % yield).

[0461] 1H NMR (400 MHz, CDCh) 57.56 (d, J = 5.6 Hz, 1 H), 6.31 - 6.15 (m, 1 H), 5.57 - 5.22 (m, 2H), 4.09 - 3.89 (m, 2H), 2.44 - 2.27 (m, 2H), 2.23 (d, J = 3.4 Hz, 3H), 1.72 - 1.42 (m, 3H) ppm.13C NMR (101 MHz, CDCh) 6 175.0, 159.0, 153.3, 144.6, 127.5, 126.8, 126.3, 125.9, 117.0, 71.7, 71.5, 33.2, 27.8, 17.9, 14.6, 12.8 ppm. GC / MS (El): m / z (%): 194 (1) [IVT , 179 (1), 139 (10), 126 (100), 110 (4), 97 (7), 69 (20).

[0462] Odour description (1% solution in EtOH on paper blotter, 24 h): balsamic, myrrh, octenol, anisic, licorice, minty.

[0463] Example 4-13: (Z)-2-ethyl-3-(non-6-en-1-yloxy)-4H-pyran-4-one

[0464] According to the procedure of example 1-1 , (Z)-2-ethyl-3-(non-6-en-1-yloxy)-4H-pyran-4-one was obtained from (Z)-non-6-en-1-ol (5.0 g, 35.2 mmol) and 2-ethyl-3-hydroxy-4H-pyran-4-one (5.4 g, 38.7 mmol) as a light yellow liquid (0.9 g, 9% yield).

[0465] 1H NMR (400 MHz, CDCh) 6 7.64 (d, J = 5.6 Hz, 1 H), 6.34 (d, J = 5.6 Hz, 1 H), 5.48 - 5.21 (m, 2H), 4.04 (t, J = 6.8 Hz, 2H), 2.71 (q, J = 7.6 Hz, 2H), 2.10 - 1.96 (m, 4H), 1.72 (d, J = 7.0 Hz, 2H), 1.47 - 1.32 (m, 4H), 1.23 (t, J = 7.6 Hz, 3H), 0.95 (t, J = 7.5 Hz, 3H) ppm.13C NMR (101 MHz, CDCh) 6 175.3, 163.2, 153.4, 144.1 , 131.7, 128.9, 117.0, 72.5, 29.9, 29.5, 26.9, 25.4, 21.7, 20.5, 14.3, 11.3 ppm.

[0466] Odour description (1% solution in EtOH on paper blotter, 24 h): sweet, green. non-6-en-1-yl)oxy)-2-ethyl-4H-pyran-4-one

[0467] According to the procedure of example 1-1 , (S)-3-((3,7-dimethylnon-6-en-1-yl)oxy)-2-ethyl-4H- pyran-4-one_was obtained from 2-ethyl-3-hydroxy-4H-pyran-4-one (2.0 g, 14.3 mmol) and (S)- 3,7-dimethylnon-6-en-1-ol (2.6 g, 15.7 mmol) as a colorless liquid (1.9 g, 46% yield).

[0468] 1H NMR (400 MHz, CDCh, mixture of isomers) 6 7.65 - 7.42 (m, 1 H), 6.26 (d, J = 5.6 Hz, 1 H), 5.18 - 4.73 (m, 1 H), 4.16 - 3.90 (m, 2H), 2.63 (q, J = 7.6 Hz, 2H), 2.06 - 1.83 (m, 4H), 1.78 - 1.65 (m, 1 H), 1.62 - 1.50 (m, 4H), 1.25 - 1.02 (m, 6H), 0.94 - 0.82 (m, 6H) ppm.13C NMR (101 MHz, CDCh. mixture of isomers) 6 175.3, 163.1 , 153.4, 144.1 , 136.9, 136.7, 124.2, 123.0, 117.0, 70.9, 70.8, 37.4, 37.2, 37.0, 32.3, 29.4, 29.3, 25.2, 25.0, 24.7, 22.8, 21.7, 19.5, 19.4, 15.8, 12.8, 12.7, 11.3 ppm. GC / MS (El): m / z (%): 292(13) [IVT , 263 (11), 167 (13), 140 (100), 123 (45), 81 (20), 67 (11), 55 (42).

[0469] Odour description (1% solution in EtOH on paper blotter, 24 h): powdery, sweet, floral.

[0470] Example 5-1 : 2-ethyl-3-(1-(naphthalen-2-yl)ethoxy)-4 / 7-pyran-4-one

[0471] 31309 PCT2 According to the procedure of example 2-1, 2-ethyl-3-(1-(naphthalen-2-yl)ethoxy)-4 / 7-pyran-4- one was obtained from 2-ethyl-3-hydroxy-4 / 7-pyran-4-one (6.0 g, 42.8 mmol) and 2-(1- chloroethyl)naphthalene (10.6 g, 55.7 mmol) as a light yellow liquid (11.5 g, 91% yield).

[0472] 1H NMR (300 MHz, CDCI3) 6 7.81 - 7.77 (m, 4H), 7.55 - 7.50 (m, 4H), 6.31 (d, J = 5.4 Hz, 1 H), 5.90 (q, J = 6.4 Hz, 1 H), 2.54 - 2.51 (m, 2H), 1.74 (d, J = 6.4 Hz, 3H), 0.88 (t, J = 7.5 Hz, 3H) ppm.13C NMR (75 MHz, CDCI3) 6 175.7, 163.5, 153.3, 142.3, 139.1 , 133.2, 133.0, 128.2, 128.0, 127.6, 126.5, 126.1 , 126.0, 124.5, 116.8, 78.1 , 22.1 , 21.7, 10.8 ppm. GC / MS (El): m / z (%): 294 (1) [ / W+], 207 (1), 155 (100), 139 (3), 128 (11).

[0473] Odour description (1% solution in EtOH on paper blotter, 24 h): powdery, maltol.

[0474] Example 5-2: 2-ethyl-3-((3-oxobutan-2-yl)oxy)-4 / 7-pyran-4-one

[0475] According to the procedure of example 2-1, 2-ethyl-3-((3-oxobutan-2-yl)oxy)-4 / 7-pyran-4-one was obtained from 2-ethyl-3-hydroxy-4 / 7-pyran-4-one (6.0 g, 42.8 mmol) and 3-chlorobutan-2- one (5.9 g, 55.7 mmol) as a light yellow liquid (5.3 g, 59% yield).

[0476] 1H NMR (300 MHz, CDCI3) 6 7.65 (d, J = 5.5 Hz, 1 H), 6.22 (d, J = 5.5 Hz, 1 H), 4.92 (q, J = 6.9 Hz, 1 H), 2.71 (q, J = 7.5 Hz, 2H), 2.20 (s, 3H), 1.30 (d, J = 6.9 Hz, 3H), 1.16 (t, J = 7.5 Hz, 3H) ppm.13C NMR (75 MHz, CDCI3) 207.7, 174.5, 162.6, 153.7, 142.3, 116.6, 80.8, 25.6, 21.6, 17.1, 10.8 ppm. GC / MS (El): m / z (%): 210 (14) [ / W+], 167 (100), 153 (10), 139 (96), 123 (73), 111 (7), 97 (11), 71 (23).

[0477] Odour description (1% solution in EtOH on paper blotter, 24 h): powdery, maltol, sweet.

[0478] Example 5-3: 2-ethyl-3-((2-methylundecyl)oxy)-4 / 7-pyran-4-one

[0479] According to the procedure of example 2-1, 2-ethyl-3-((2-methylundecyl)oxy)-4 / 7-pyran-4-one was obtained from 2-ethyl-3-hydroxy-4 / 7-pyran-4-one (7.0 g, 50.0 mmol) and 1-bromo-2- methylundecane (14.9 g, 59.9 mmol) as a light yellow liquid (9.5 g, 61% yield).

[0480] 1H NMR (300 MHz, CDCI3) 6 7.59 (d, J = 5.6 Hz, 1 H), 6.22 (d, J = 5.6 Hz, 1 H), 3.98 - 3.53 (m, 2H), 2.61 (q, J = 7.5 Hz, 2H), 1.79 - 1.75 (m, 1 H), 1.54 - 1.35 (m, 1 H), 1.35 - 1.03 (m, 18H), 0.92 (d, J = 6.7Hz, 3H), 0.78 (t, J = 6.7 Hz, 3H) ppm.13C NMR (75 MHz, CDCI3) 6 175.0, 162.6, 153.3, 144.2, 116.9, 77.6, 33.7, 33.1 , 31.7, 29.7, 29.5, 29.4, 29.2, 26.7, 22.5, 21.6, 16.7, 13.9, 11.1 ppm. GC / MS (El): m / z (%): 308 (4) [l\ZT, 279 (11), 181 (2), 153 (5), 140 (100), 123 (9), 111 (2), 97 (4).

[0481] Odor description (1% solution in EtOH on paper blotter, 24 h): balsamic, acidic, olibanum, floral, aldehydic, caramel, maltol. -4 / 7-pyran-4-one

[0482] According to the procedure of example 2-1, 2-ethyl-3-(3-(4-isobutyl-2-methylphenyl)propoxy)- 4 / 7-pyran-4-one was obtained from 2-ethyl-3-hydroxy-4 / 7-pyran-4-one (4.0 g, 28.5 mmol) and 1-

[0483] 31309 PCT2 (3-bromopropyl)-4-isobutyl-2-methylbenzene (9.2 g, 34.3 mmol) as a light yellow liquid (6.8 g, 73% yield).

[0484] 1H NMR (300 MHz, CDCI3) 6 7.59 (d, J = 5.6 Hz, 1 H), 7.06 (d, J = 7.4 Hz, 1 H), 6.89 (m, 2H),

[0485] 6.28 (d, J = 5.6 Hz, 1 H), 4.12 (t, J = 6.4 Hz, 2H), 2.75 - 2.65 (m, 4H), 2.39 (d, J = 7.1 Hz, 2H),

[0486] 2.28 (s, 3H), 2.06 - 1.91 (m, 2H), 1.85 - 1.51 (m, 1 H), 1.20 (t, J = 7.6 Hz, 3H), 0.89 (d, J = 6.6 Hz, 6H) ppm.13C NMR (75 MHz, CDCI3) 6 175.0, 162.9, 153.6, 144.1 , 139.1 , 137.0, 135.3, 131.0, 128.4, 126.6, 116.9, 72.0, 45.0, 30.6, 30.1 , 29.2, 22.4, 21.8, 19.2, 11.3 ppm. GC / MS (El): m / z (%): 328 (10) [ / Vf], 299 (37), 188 (31), 167 (13), 145 (100), 140 (21), 131 (50), 123 (6), 105 (14), 91 (12).

[0487] Odor description (1% solution in EtOH on paper blotter, 24 h): floral, muguet, maltol

[0488] Example 5-5: 2-ethyl-3-((3-methyl-5-phenylpentyl)oxy)-4 / 7-pyran-4-one

[0489] According to the procedure of example 2-1 , 2-ethyl-3-((3-methyl-5-phenylpentyl)oxy)-4 / 7-pyran- 4-one was obtained from 2-ethyl-3-hydroxy-4 / 7-pyran-4-one (4.0 g, 28.5 mmol) and (5-bromo- 3-methylpentyl)benzene (8.3 g, 34.3 mmol) as a colorless liquid (7.0 g, 82% yield).

[0490] 1H NMR (300 MHz, CDCI3) <57.60 (d, J = 5.6 Hz, 1 H), 7.38 - 7.05 (m, 5H), 6.30 (d, J = 5.6 Hz, 1 H), 4.24 - 3.94 (m, 2H), 2.77 - 2.47 (m, 4H), 1.95 - 1.41 (m, 5H), 1.19 (t, J = 7.6 Hz, 3H), 1.00 (d, J = 6.2 Hz, 3H) ppm.13C NMR (75 MHz, CDCI3) 6 175.2, 163.1 , 153.5, 144.1 , 142.7, 128.3, 128.2, 125.6, 117.0, 70.6, 39.0, 37.0, 33.3, 29.3, 21.7, 19.5, 11.3 ppm. GC / MS (El): m / z (%): 300 (17) [ / Vf], 271 (14), 209 (1), 167 (34), 140 (100), 123 (14), 91 (91).

[0491] Odour description (1% solution in EtOH on paper blotter, 24 h): floral, maltol.

[0492] Example 5-6: (Z)-2-ethyl-3-(hept-4-en-2-yloxy)-4 / 7-pyran-4-one

[0493] According to the procedure of example 2-1 , (Z)-2-ethyl-3-(hept-4-en-2-yloxy)-4 / 7-pyran-4-one was obtained from 2-ethyl-3-hydroxy-4 / 7-pyran-4-one (4.0 g, 28.5 mmol) and (Z)-6-bromohept- 3-ene (6.1 g, 34.3 mmol) as a light pink liquid (5.1 g, 76% yield).

[0494] 1H NMR (300 MHz, CDCI3) 6 7.58 (d, J = 5.5 Hz, 1 H), 6.24 (d, J = 5.5 Hz, 1 H), 5.40-5.37 (m, 2H), 4.64 - 4.60 (m, 1 H), 2.66 - 2.64 (m, 2H), 2.42 - 2.26 (m, 1 H), 2.23 - 2.21 (m, 1 H), 2.00 - 1.97 (m, 2H), 1.14 (t, J = 6.8 Hz, 6H), 1.01 - 0.83 (t, J = 7.2 Hz, 3H) ppm.13C NMR (75 MHz, CDCh) 6 175.4, 163.1 , 153.3, 142.4, 133.9, 124.0, 116.8, 76.1, 34.2, 21.7, 20.6, 19.5, 14.0, 10.9 ppm. GC / MS (El): m / z (%): 236 (1) [ / Vf], 207 (6), 167 (26), 140 (100), 96 (22), 81 (49), 55 (81). Odour description (1% solution in EtOH on paper blotter, 24 h): green, maltol

[0495] Example 5-7: (Z)-3-(hex-3-en-1-yloxy)-2-methyl-4 / 7-pyran-4-one

[0496] According to the procedure of example 2-1 , (Z)-3-(hex-3-en-1-yloxy)-2-methyl-4H-pyran-4-one was obtained from 3-hydroxy-2-methyl-4H-pyran-4-one (4.0 g, 31 .7 mmol) and (Z)-1-bromo hex- 3-ene (6.2 g, 38.1 mmol) as a light yellow liquid (3.0 g, 45% yield).

[0497] 31309 PCT21H NMR (300 MHz, CDCI3) <57.57 (d, J = 5.6 Hz, 1 H), 6.25 (d, J = 5.6 Hz, 1 H), 5.60 - 5.14 (m, 2H), 4.00 (t, J = 6.8 Hz, 2H), 2.49 - 2.31 (m, 2H), 2.23 (s, 3H), 2.12 - 1.84 (m, 2H), 0.88 (t, J = 7.5 Hz, 3H) ppm.13C NMR (75 MHz, CDCI3) 6 174.9, 158.9, 153.3, 144.6, 134.0, 124.3, 117.0, 71.6, 28.0, 20.5, 14.6, 14.1 ppm. GC / MS (El): m / z (%): 208 (1) [ / Vf], 193 (1), 139 (8), 126 (100), 67 (17), 55 (27).

[0498] Odor description (1% solution in EtOH on paper blotter, 24 h): green, floral, maltol.

[0499] Example 5-8: (Z)-3-(hept-4-en-2-yloxy)-2-methyl-4 / 7-pyran-4-one

[0500] According to the procedure of example 2-1 , (Z)-3-(hept-4-en-2-yloxy)-2-methyl-4 / 7-pyran-4-one was obtained from 3-hydroxy-2-methyl-4 / 7-pyran-4-one (15.0 g, 119.0 mmol) and (Z)-Q- bromohept-3-ene (25.3 g, 143.0 mmol) as a light yellow liquid (1.7 g, 6.5% yield).

[0501] 1H NMR (400 MHz, CDCI3) 6 7.55 (d, J = 5.5 Hz, 1 H), 6.25 (d, J = 5.5 Hz, 1 H), 5.50 - 5.26 (m, 2H), 4.61-4.59 (m, 1 H), 2.45 - 2.31 (m, 1 H), 2.30 - 2.18 (m, 4H), 2.04 - 1.94 (m, 2H), 1.12 (d, J = 7.8 Hz, 3H), 0.89 (t, J = 7.5 Hz, 3H) ppm.13C NMR (101 MHz, CDCI3) 6 175.2, 159.2, 153.2, 143.3, 134.0, 124.0, 116.9, 76.4, 34.2, 20.6, 19.5, 15.0, 14.0 ppm. GC / MS (El): m / z (%): 222 (1) [ / Vf], 207 (1), 153 (31), 127 (100), 96 (24), 81 (43), 55 (66).

[0502] Odor description (1 % solution in EtOH on paper blotter, 24 h): powdery, caramel, sugary, burnt.

[0503] Example 5-9: 2-ethyl-3-phenethoxy-4 / 7-pyran-4-one

[0504] According to the procedure of example 2-1 , 2-ethyl-3-phenethoxy-4 / 7-pyran-4-one was obtained from 2-ethyl-3-hydroxy-4 / 7-pyran-4-one (4.0 g, 28.5 mmol) and (2-bromoethyl)benzene (6.3 g, 34.3 mmol) as a light yellow liquid (3.8 g, 55% yield).

[0505] 1H NMR (300 MHz, CDCI3) 6 7.60 (d, J = 5.6 Hz, 1 H), 7.45 - 7.10 (m, 5H), 6.31 (d, J = 5.6 Hz, 1 H), 4.29 (t, J = 6.9 Hz, 2H), 3.03 (t, J = 6.8 Hz, 2H), 2.41 (q, J = 7.6 Hz, 2H), 1.05 (t, J = 7.6 Hz, 3H) ppm.13C NMR (75 MHz, CDCI3) 6 175.2, 163.4, 153.6, 143.9, 138.4, 128.9, 128.3, 126.3, 116.9, 72.9, 36.5, 21.6, 11.2 ppm. GC / MS (El): m / z (%): 244 (1) [ / Vf], 167 (1), 153 (6), 140 (100), 123 (13), 105 (63), 77 (22).

[0506] Odor description (1% solution in EtOH on paper blotter, 24 h): rosy, powdery, gourmand. i-4 / 7-pyran-4-one

[0507] According to the procedure of example 2-1 , 2-methyl-3-((3-methyl-5-phenylpentyl)oxy)-4 / 7- pyran-4-one was obtained from 3-hydroxy-2-methyl-4 / 7-pyran-4-one (4.0 g, 31.7 mmol) and (5- bromo-3-methylpentyl)benzene (9.2 g, 38.1 mmol) as a light yellow liquid (4.0 g, 44% yield).

[0508] 1H NMR (300 MHz, CDCI3) 6 7.49 (d, J = 5.6 Hz, 1 H), 7.28 - 7.05 (m, 5H), 6.23 (d, J = 5.6 Hz, 1 H), 4.13 - 3.90 (m, 2H), 2.81 - 2.38 (m, 2H), 2.17 (s, 3H), 1.77 - 1.33 (m, 5H), 0.91 (d, J = 6.2 Hz, 3H) ppm.13C NMR (75 MHz, CDCI3) 6 175.0, 158.9, 153.3, 144.8, 142.7, 128.3, 128.3, 125.6, 117.1 , 70.4, 39.0, 37.0, 33.3, 29.3, 19.5, 14.6 ppm. GC / MS (El): m / z (%): 286 (13) [ / W+], 195 (2), 167 (12), 153 (16), 126 (100), 91 (94), 65 (12).

[0509] 31309 PCT2 Odour description (1% solution in EtOH on paper blotter, 24 h): gourmand, floral.

[0510] Example 5-11 : 2-methyl-3-(2-((2S,4aR)-1 ,1 ,5,5-tetramethyl-1 ,3,4,5,6,7-hexahydro-2 / 7-2,4a- methanonaphthalen-8-yl)propoxy)-4 / 7-pyran-4-one and 2-methyl-3-(2-((2S,4aS)-1 , 1 ,5,5- tetramethyl-1 ,3,4,5,6,8a-hexahydro-2 / 7-2,4a-methanonaphthalen-8-yl)propoxy)-4 / 7-pyran-4- one

[0511] According to the procedure of example 2-1 , a mixture of ambermax maltol ether (2-methyl-3-(2- ((2S,4aR)-1 ,1 ,5,5-tetramethyl-1 ,3,4,5,6,7-hexahydro-2 / 7-2,4a-methanonaphthalen-8- yl)propoxy)-4 / 7-pyran-4-one and 2-methyl-3-(2-((2S,4aS)-1 , 1 ,5,5-tetramethyl-1 ,3,4,5,6,8a- hexahydro-2 / 7-2,4a-methanonaphthalen-8-yl)propoxy)-4 / 7-pyran-4-one) was obtained from 3- hydroxy-2-methyl-4 / 7-pyran-4-one (3.0 g, 23.8 mmol) and a mixture of (2S,4aR)-8-(1- bromopropan-2-yl)-1,1 ,5,5-tetramethyl-1 ,3,4,5,6,7-hexahydro-2 / 7-2,4a-methanonaphthalene and (2S,4aS)-8-(1-bromopropan-2-yl)-1 ,1 ,5,5-tetramethyl-1 ,3,4,5,6,8a-hexahydro-2 / 7-2,4a- methanonaphthalene (10.1 g, 30.9 mmol) as a light yellow liquid (1.8 g, 20.6% yield).

[0512] 1H NMR (300 MHz, CDCI3) 5 7.60 (d, J = 5.6 Hz, 1 H), 6.31 (d, J = 5.6 Hz, 1 H), 5.49 - 5.38 (m, 1 H), 4.04 - 3.88 (m, 1 H), 3.61 (t, J = 8.6 Hz, 1 H), 2.67 - 2.63 (m, 1 H), 2.32 (s, 3H), 2.09 (s, 1 H), 1.98 - 1.82 (m, 1 H), 1.75 (s, 1 H), 1.72 - 1.31 (m, 4H), 1.28 - 1.19 (m, 5H), 1.12 (s, 4H), 1.05 (s, 3H), 0.89 (s, 3H), 0.79 (s, 3H) ppm.13C NMR (75 MHz, CDCI3) 5 174.8, 158.5, 153.1 , 145.0, 139.4, 122.6, 117.1 , 78.4, 54.9, 54.8, 50.9, 39.3, 37.6, 36.6, 36.1 , 33.5, 32.5, 26.6, 24.6, 24.0, 23.7, 22.4, 16.4, 14.7 ppm. GC / MS (El): m / z (%): 370 (1) [ / W+], 244 (79), 229 (63), 201 (100), 173 (28), 145 (70), 126 (40), 105 (36).

[0513] Odour description (1% solution in EtOH on paper blotter, 24 h): woody, ambery, gourmand.

[0514] Example 5-12: 2-ethyl-3-(2-((2S,4aR)-1 ,1 ,5,5-tetramethyl-1 ,3,4,5,6,7-hexahydro-2 / 7-2,4a- methanonaphthalen-8-yl)propoxy)-4 / 7-pyran-4-one and 2-ethyl-3-(2-((2S,4aS)-1 , 1 ,5,5- tetramethyl-1 ,3,4,5,6,8a-hexahydro-2 / 7-2,4a-methanonaphthalen-8-yl)propoxy)-4 / 7-pyran-4- one

[0515] According to the procedure of example 2-1 , ambermax ethyl maltol ether was obtained from 2- ethyl-3-hydroxy-4 / 7-pyran-4-one (3.0 g, 21.4 mmol) and a mixture of (2S,4aR)-8-(1- bromopropan-2-yl)-1,1 ,5,5-tetramethyl-1 ,3,4,5,6,7-hexahydro-2 / 7-2,4a-methanonaphthalene and (2S,4aS)-8-(1-bromopropan-2-yl)-1 ,1 ,5,5-tetramethyl-1 ,3,4,5,6,8a-hexahydro-2 / 7-2,4a- methanonaphthalene (9.1 g, 27.8 mmol) as a light yellow liquid (3.3 g, 40 % yield).

[0516] 1H NMR (300 MHz, CDCI3) 5 7.63 (d, J = 5.6 Hz, 1 H), 6.31 (d, J = 5.6 Hz, 1 H), 5.51 - 5.35 (m, 1 H), 3.99-3.91 (m, 1 H), 3.61 (t, J = 7.3 Hz, 1 H), 2.79 - 2.57 (m, 3H), 2.11 (s, 1 H), 1.97 - 1.84 (m, 1 H), 1.75 (s, 1 H), 1.69 - 1.66 (m, 1 H), 1.57 - 1.53 (m, 1 H), 1.42 - 1.38 (m, 2H), 1.32 - 1.18 (m, 8H), 1.17 - 1.13 (m, 4H), 1.07 (s, 3H), 0.89 (s, 3H), 0.80 (s, 3H) ppm.13C NMR (75 MHz, CDCI3) 6 175.1, 162.8, 153.2, 144.2, 139.4, 122.6, 117.0, 78.6, 54.9, 54.9, 50.9, 39.3, 37.6, 36.6,

[0517] 31309 PCT2 36.1 , 33.5, 32.5, 26.6, 24.7, 24.0, 23.7, 22.4, 21.7, 16.4, 11.3 ppm. GC / MS (El): m / z (%): 384 (1) [ / Vf], 281 (1), 244 (71), 229 (57), 215 (25), 201 (100), 187 (11), 173 (24), 159 (29), 145 (68), 119 (44), 105 (49).

[0518] Odor description (1% solution in EtOH on paper blotter, 24 h): woody, ambery, ambermax, powdery, maltol.

[0519] Example 5-13: 3-(dec-9-en-1-yloxy)-2-methyl-4 / 7-pyran-4-one

[0520] According to the procedure of example 2-1 , 3-(dec-9-en-1-yloxy)-2-methyl-4 / 7-pyran-4-one was obtained from 3-hydroxy-2-methyl-4 / 7-pyran-4-one (3.0 g, 23.8 mmol) and 10-bromodec-1-ene (7.8 g, 35.7 mmol) as a light yellow liquid (3.1 g, 49% yield).

[0521] 1H NMR (300 MHz, CDCI3) 5 7.Q5 (d, J = 5.6 Hz, 1 H), 6.33 (d, J = 5.6 Hz, 1 H), 5.84-5.76 (m, 1 H), 5.08 - 4.82 (m, 2H), 4.04 (t, J = 6.7 Hz, 2H), 2.32 (s, 3H), 2.15 - 1.95 (m, 2H), 1.80 - 1.62 (m, 2H), 1.36-1.32 (m, 10H) ppm.13C NMR (75 MHz, CDCI3) 6 174.9, 158.8, 153.3, 144.8, 139.0, 117.0, 114.0, 72.2, 33.7, 29.9, 29.3, 29.2, 28.9, 28.8, 25.7, 14.6 ppm. GC / MS (El): m / z (%): 264 (5) [ / W+], 249 (11), 223 (1), 167 (2), 153 (8), 139 (15), 126 (100), 110 (12), 55 (25).

[0522] Odor description (1% solution in EtOH on paper blotter, 24 h): gourmand, floral.

[0523] Example 5-14: 3-(dec-9-en-1-yloxy)-2-ethyl-4 / 7-pyran-4-one

[0524] According to the procedure of example 2-1 , 3-(dec-9-en-1-yloxy)-2-ethyl-4 / 7-pyran-4-one was obtained from 2-ethyl-3-hydroxy-4 / 7-pyran-4-one (3.0 g, 21.4 mmol) and 10-bromodec-1-ene (7.0 g, 32.1 mmol) as a light yellow liquid (5.0 g, 84% yield).

[0525] 1H NMR (300 MHz, CDCI3) 5 7.66 (d, J = 5.6 Hz, 1 H), 6.33 (d, J = 5.6 Hz, 1 H), 5.83 - 5.77 (m, 1 H), 5.12 - 4.79 (m, 2H), 4.04 (t, J = 6.7 Hz, 2H), 2.71 (q, J = 7.6 Hz, 2H), 2.04 (dd, J = 13.4, 6.6 Hz, 2H), 1.87 - 1.61 (m, 2H), 1.38-1.33 (m, 10H), 1.23 (t, J = 7.Q Hz, 3H) ppm.13C NMR (75 MHz, CDCI3) 5 175.3, 163.1 , 153.4, 144.1 , 139.0, 116.9, 114.1, 72.5, 33.7, 29.9, 29.4, 29.3, 29.0, 28.8, 25.7, 21.7, 11.3 ppm. GC / MS (El): m / z (%): 278 (9) [ / Vf], 249 (28), 167 (7), 153 (13), 140 (100), 123 (19), 55 (24).

[0526] Odour description (1% solution in EtOH on paper blotter, 24 h): gourmand, floral.

[0527] Example 5-15: 2-ethyl-3-(((2E,6Z)-nona-2,6-dien-1-yl)oxy)-4 / 7-pyran-4-one

[0528] According to the procedure of example 2-1, 2-ethyl-3-(((2E,6Z)-nona-2,6-dien-1-yl)oxy)-4 / 7- pyran-4-one was obtained from 2-ethyl-3-hydroxy-4 / 7-pyran-4-one (2.5 g, 17.8 mmol) and (2E,6Z)-1-bromonona-2,6-diene (4.4 g, 21.4 mmol) as a light yellow liquid (1.0 g, 21% yield).

[0529] 1H NMR (300 MHz, CDCI3) 67.66 (d, J = 5.6 Hz, 1 H), 6.34 (d, J = 5.6 Hz, 1 H), 5.84 - 5.55 (m, 2H), 5.47 - 5.21 (m, 2H), 4.56 (d, J = 5.9 Hz, 2H), 2.70 (q, J = 7.6 Hz, 2H), 2.16 - 2.07 (m, 4H), 2.03 - 2.00 (m, 2H), 1.21 (t, J = 7.5 Hz, 3H), 0.94 (t, J = 7.5 Hz, 3H) ppm.13C NMR (75 MHz, CDCh) 6 175.2, 163.6, 153.4, 143.1 , 136.2, 132.1 , 127.9, 125.5, 116.9, 72.5, 32.3, 26.4, 21.8,

[0530] 31309 PCT2 20.5, 14.2, 11.1 ppm. GC / MS (El): m / z (%): 262 (2) [ / Vf], 233 (7), 193 (11), 179 (2), 140 (100), 123 (12), 81 (31), 67 (27).

[0531] Odour description (1% solution in EtOH on paper blotter, 24 h): gourmand, green.

[0532] Example 5-16: 2-methyl-3-((2-methylundecyl)oxy)-4 / 7-pyran-4-one

[0533] According to the procedure of example 2-1 , 2-methyl-3-((2-methylundecyl)oxy)-4 / 7-pyran-4-one was obtained from 3-hydroxy-2-methyl-4 / 7-pyran-4-one (2.0 g, 15.9 mmol) and 1-bromo-2- methylundecane (4.7 g, 19.0 mmol) as a light yellow liquid (3.0 g, 64% yield).

[0534] 1H NMR (400 MHz, CDCh) 57.62 (d, J = 5.6 Hz, 1 H), 6.32 (d, J = 5.6 Hz, 1H), 3.94 (dd, J = 9.0, 5.8Hz, 1 H), 3.81 (dd, J = 9.0, 5.8 Hz, 1 H), 2.32 (s, 3H), 1.89-1.87 (m, 1 H), 1.51 - 1.47 (m, 1 H), 1.37 - 1.14 (m, 15H), 1.01 (d, J = 6.8 Hz, 3H), 0.88 (t, J = 6.8 Hz, 3H) ppm.13C NMR (101 MHz, CDCh) 6 175.0, 158.6, 153.2, 145.1 , 117.1 , 77.4, 33.8, 33.2, 31.8, 29.9, 29.6, 29.5, 29.3, 26.8, 22.6, 16.8, 14.6, 14.0 ppm. GC / MS (El): m / z (%): 294 (3) [ / Vf], 279 (4), 167 (3), 139 (7), 126 (100), 69 (11).

[0535] Odor description (1 % solution in EtOH on paper blotter, 24 h): aldehdic, metallic, C 12 MNA, sweet, maltol.

[0536] Example 5-17: 2-ethyl-3-((4-methylpent-3-en-1-yl)oxy)-4 / 7-pyran-4-one

[0537] According to the procedure of example 2-1 , 2-ethyl-3-((4-methylpent-3-en-1-yl)oxy)-4 / 7-pyran- 4-one was obtained from 2-ethyl-3-hydroxy-4 / 7-pyran-4-one (3.9 g, 27.6 mmol) and 5-bromo-2- methylpent-2-ene (3.0g, 18.4 mmol) as a colorless liquid (2.0 g, 48% yield).

[0538] 1H NMR (400 MHz, CDCh) 6 7.58 (d, J = 5.6 Hz, 1 H), 6.26 (d, J = 5.6 Hz, 1 H), 5.10 (t, J = 7.1 Hz, 1 H), 3.97 (t, J = 7.1 Hz, 2H), 2.63 (q, J = 7.6 Hz, 2H), 2.33 (q, J = 6.9 Hz, 2H), 1.63 (s, 3H), 1.56 (s, 3H), 1.14 (t, J = 7.6 Hz, 3H) ppm.13C NMR (101 MHz, CDCh) 6 174.3, 162.2, 152.4, 143.0, 133.1 , 118.9, 116.0, 71.1 , 27.9, 24.7, 20.7, 16.8, 10.3 ppm.

[0539] Odour description (1% solution in EtOH on paper blotter, 24 h): sweet, caramel, maltol.

[0540] Example 5-18: 2-ethyl-3-(pent-3-en-1-yloxy)-4 / 7-pyran-4-one

[0541] According to the procedure of example 2-1 , 2-ethyl-3-(pent-3-en-1-yloxy)-4 / 7-pyran-4-one was obtained from 2-ethyl-3-hydroxy-4 / 7-pyran-4-one (2.1 g, 14.8 mmol) and 5-bromopent-2-ene (2.0 g, 13.4 mmol) as a light yellow liquid (1.3 g, 46% yield).

[0542] 1H NMR (400 MHz, CDCh, mixture of Z / E isomers) 57.68 (d, J = 5.6 Hz, 2H), 6.34 (d, J = 5.6 Hz, 2H), 5.66 - 5.33 (m, 4H), 4.20 - 3.93 (m, 4H), 2.71 (m, 4H), 2.49 - 2.30 (m, 4H), 1.66 (m, 6H), 1.29 - 1.13 (m, 6H) ppm.13C NMR (101 MHz, CDCh, mixture of Z / E isomers) 5 175.2, 163.2, 153.5, 144.0, 143.9, 127.5, 126.8, 126.3, 125.8, 116.9, 72.0, 71.7, 33.2, 27.8, 21.7, 17.9, 12.8, 11.2, 11.2 ppm.

[0543] Odour description (1% solution in EtOH on paper blotter, 24 h): sweet, maltol.

[0544] 31309 PCT2 Example 5-19: 2-ethyl-3-((4-methyl-6-phenylhex-3-en-1-yl)oxy)-4 / 7-pyran-4-one

[0545] According to the procedure of example 2-1 , 2-ethyl-3-((4-methyl-6-phenylhex-3-en-1-yl)oxy)- 4 / 7-pyran-4-one was obtained from 2-ethyl-3-hydroxy-4 / 7-pyran-4-one (3.0 g, 21.4 mmol) and (6-bromo-3-methylhex-3-en-1-yl)benzene (5.4 g, 21.4 mmol) as a light yellow liquid (4.1 g, 61 % yield).

[0546] 1H NMR (400 MHz, CDCh, mixture of Z / E isomers) <57.65 - 7.58 (m, 1 H), 7.31 - 7.21 (m, 2H), 7.20 - 7.11 (m, 3H), 6.35 - 6.26 (m, 1 H), 5.27 - 5.14 (m, 1 H), 4.11 - 3.89 (m, 2H), 2.78 - 2.57 (m, 4H), 2.49 - 2.22 (m, 4H), 1.78 - 1.66 (m, 3H), 1.27 - 1.12 (m, 3H) ppm.13C NMR (101 MHz, CDCh, mixture of Z / E isomers) <5 175.3, 175.3, 163.3, 163.2, 153.5, 153.4, 144.1 , 142.3, 142.4, 137.1 , 137.1 , 128.3, 128.4, 128.3, 128.3, 125.8, 125.7, 121.3, 120.2, 117.0, 72.1 , 72.0, 41.7, 34.7, 34.3, 34.1 , 28.9, 28.7, 23.5, 21.8, 16.4, 11.4, 11.3 ppm.

[0547] Odour description (1% solution in EtOH on paper blotter, 24 h): caramel, maltol, fruity, raspberry. Biodegradation: inherently biodegradable.

[0548] Example 5-20: 2,5-dimethyl-4-((4-methyl-6-phenylhex-3-en-1-yl)oxy)furan-3(2 / 7)-one

[0549] According to the procedure of example 2-1 , 2,5-dimethyl-4-((4-methyl-6-phenylhex-3-en-1- yl)oxy)furan-3(2 / - / )-one was obtained from 4-hydroxy-2,5-dimethylfuran-3(2 / 7)-one (3.0 g, 23.4 mmol) and (6-bromo-3-methylhex-3-en-1-yl)benzene (6.5 g, 25.8 mmol) as a light yellow liquid (2.1 g, 30 % yield).

[0550] 1H NMR (400 MHz, CDCh, mixture of Z / E isomers) 57.32 - 6.92 (m, 5H), 5.01 (brs, 1 H), 4.43 - 4.20 (m, 1 H), 4.06 - 3.68 (m, 2H), 2.77 - 2.49 (m, 2H), 2.38 - 1.97 (m, 7H), 1.79 - 1.54 (m, 3H), 1.43 - 1.26 (m, 3H) ppm.13C NMR (101 MHz, CDCh, mixture of Z / E isomers) 5 198.4, 178.4,

[0551] 142.3, 142.1 , 137.2, 137.0, 135.4, 128.4, 128.3, 128.2, 125.3, 125.4, 121.0, 120.0, 80.3, 71.5,

[0552] 71.3, 41.6, 34.6, 34.3, 34.1 , 28.7, 28.5, 23.5, 16.5, 16.3, 13.5 ppm.

[0553] Odour description (1% solution in EtOH on paper blotter, 24 h): caramel, licorice Biodegradable: readily biodegradable.

[0554] Example 5-21 : 2,5-dimethyl-4-(tetradec-1-en-4-yloxy)furan-3(2 / 7)-one

[0555] According to the procedure of example 1-1 , 2,5-dimethyl-4-(tetradec-1-en-4-yloxy)furan-3(2 / 7)- one was obtained from 2-ethyl-3-hydroxy-4 / 7-pyran-4-one (5.8 g, 45.2 mmol) and 3- tetradec-1- en-4-ol (8.0 g, 37.7 mmol) as a light pink liquid (4.7 g, 39 % yield).

[0556] 1H NMR (400 MHz, CDCh, mixture of isomers) 5 5.94 - 5.71 (m, 1 H), 5.19 - 4.97 (m, 2H), 4.47 - 4.27 (m, 2H), 2.40 - 2.22 (m, 2H), 2.16 (s, 3H), 1.64 - 1.47 (m, 2H), 1.45 - 1.35 (m, 5H), 1.31 - 1.21 (m, 14H), 0.93 - 0.81 (m, 3H) ppm.13C NMR (101 MHz, CDCh, mixture of isomers) 5 198.4, 178.5, 134.5, 134.4, 134.2, 117.2, 117.1 , 80.2, 79.5, 79.4, 38.6, 38.5, 33.8, 33.7, 31.9, 29.7, 29.6, 29.5, 29.5, 29.3, 25.1 , 25.0, 22.7, 16.6, 16.5, 14.1 , 13.6 ppm.

[0557] Odour description (1% solution in EtOH on paper blotter, 24 h): fruity, caramel, aldehydic, metallic, fatty, mandarin aldehyde.

[0558] 31309 PCT2 Biodegradable: readily biodegradable. t-2-en-1-one

[0559] According to the procedure of example 1-1 , 2-((3,7-dimethylnon-6-en-1-yl)oxy)-3- methylcyclopent-2-en-1-one was obtained from 3,7-dimethylnon-6-en-1-ol (5g, 29.4 mmol) and 2-hydroxy-3-methylcyclopent-2-en-1-one (3.29 g, 29.4 mmol) as a colorless liquid (4.7 g, 39 % yield).

[0560] 1H NMR (400 MHz, CDCI3, mixture of isomers) 55.04 - 5.12 (m, 1 H), 4.10 - 4.21 (m, 2H), 2.40 - 2.45 (m, 2H), 2.33 - 2.37 (m, 2H), 1.89 - 2.07 (m, 7H), 1.66 - 1.75 (m, 3H), 1.60 (s, 1 H), 1.25 - 1.48 (m, 2H), 1.11 - 1.23 (m, 1 H), 0.82 - 1.02 (m, 6H) ppm.13C NMR (101 MHz, CDCI3, mixture of isomers) 5 203.4, 154.9, 152.2, 137.0, 136.7, 124.3, 123.1 , 68.8, 68.8, 37.5, 37.2, 37.1 , 33.0, 32.3, 29.3, 29.2, 27.2, 25.3, 25.0, 24.7, 22.9, 19.5, 19.5, 15.9, 14.9, 12.8, 12.8 ppm.

[0561] Odour description (1% solution in EtOH on paper blotter, 24 h): waxy, rosy, tetrahydro geraniol.

[0562] 3-methyl-2-((3-methyl-5-(2,2,3-trimethylcvclopent-3-en-1-yl)pent-4-en-2- -en-1-one

[0563] According to the procedure of example 1-1, 3-methyl-2-((3-methyl-5-(2,2,3-trimethylcyclopent- 3-en-1-yl)pent-4-en-2-yl)oxy)cyclopent-2-en-1-one was obtained from 2-hydroxy-3- methylcyclopent-2-en-1-one (4.5 g, 40.1 mmol) and -3-methyl-5-(2,2,3-trimethylcyclopent-3-en- 1-yl)pent-4-en-2-ol (8.4 g, 40.1 mmol) as a colorless liquid (2.7 g, 22 % yield).

[0564] 1H NMR (400 MHz, CDCI3, mixture of isomers) 55.58 - 5.33 (m, 2H), 5.25 - 5.17 (m, 1 H), 4.75 - 4.41 (m, 1 H), 2.48 - 2.30 (m, 6H), 2.28 - 2.02 (m, 2H), 1.97 (s, 3H), 1.65 - 1.55 (m, 3H), 1.15 - 1.03 (m, 6H), 0.98 - 0.90 (m, 3H), 0.82 - 0.69 (m, 3H) ppm.13C NMR (101 MHz, CDCI3, mixture of isomers) 5 203.4, 155.4, 155.4, 155.2, 151.3, 151.2, 148.1, 132.5, 132.3, 132.2, 131.7, 131.6, 131.5, 121.5, 78.5, 78.3, 77.9, 54.3, 54.3, 54.2, 48.1 , 48.0, 42.7, 42.1 , 41.8, 41.6, 35.5, 35.4, 33.1 , 27.2, 25.4, 25.4, 20.5, 17.8, 17.3, 16.9, 16.6, 16.5, 15.2, 15.1 , 15.0, 14.9, 12.7 ppm.

[0565] Odour description (1% solution in EtOH on paper blotter, 24 h): woody, sandalwood, green, fenugreek. 3-methyl-2-((1-methyl-2-(5-methylhex-4-en-2-yl)cyclopropyl)methoxy)cyclopent-

[0566] 2-en-1-one

[0567] According to the procedure of example 1-1 , 3-methyl-2-((1-methyl-2-(5-methylhex-4-en-2- yl)cyclopropyl)methoxy)cyclopent-2-en-1-one was obtained from (1-methyl-2-(5-methylhex-4- en-2-yl)cyclopropyl)methanol (5.0 g, 27.4 mmol) and 2-hydroxy-3-methylcyclopent-2-en-1-one (3.1 g, 27.4mmol) as a light yellow liquid (4.8 g, 63% yield).

[0568] 1H NMR (400 MHz, CDCh, mixture of isomers) 55.16 (m, 1 H), 3.99 - 3.78 (m, 2H), 2.45 - 2.39 (m, 2H), 2.36 - 2.28 (m, 2H), 2.13 - 1.81 (m, 5H), 1.73 - 1.66 (m, 3H), 1.59 (s, 3H), 1.18 (d, J

[0569] 31309 PCT2 = 2.9 Hz, 3H), 1.10 - 0.99 (m, 1 H), 0.95 (d, J = 6.5 Hz, 2H), 0.90 (d, J = 6.6 Hz, 1 H), 0.61 - 0.38 (m, 2H), 0.07 - 0.10 (m, 1 H) ppm.13C NMR (101 MHz, CDCh, mixture of isomers) 5 203.4, 203.4, 154.5, 154.4, 152.3, 152.3, 131.9, 131.7, 123.1 , 123.0, 79.2, 79.1 , 35.6, 35.5, 34.7, 34.3, 33.1 , 33.0, 29.2, 29.1 , 27.1 , 25.8, 21.0, 20.2, 20.0, 19.8, 17.7, 16.3, 15.9, 15.7, 15.5, 14.9 ppm. Odour description (1% solution in EtOH on paper blotter, 24 h): burnt sugar, floral.

[0570] (Z)-2-(hept-4-en-2-yloxy)-3-methylcyclopent-2-en-1-one and (Z)-2-(hept-4-en-2- :-2-en-1-one

[0571] According to the procedure of example 1-1 , the mixture of (Z)-2-(hept-4-en-2-yloxy)-3- methylcyclopent-2-en-1-one and (Z)-2-(hept-4-en-2-yloxy)-5-methylcyclopent-2-en-1-one was obtained from 3-methylcyclopentane- 1 ,2-dione (5.0 g, 44.6 mmol) and (Z)-hept-4-en-2-ol (5.6 g,

[0572] 49.1 mmol) as a colorless liquid (4.3 g, 46% yield).

[0573] 1H NMR (400 MHz, CDCh) 56.29 (s, 1 H), 5.59 - 5.24 (m, 2H), 4.70 - 4.43 (m, 1 H), 2.48 - 2.42 (m, 2H), 2.38 - 2.31 (m, 2H), 2.27 - 2.20 (m, 1 H), 2.10 - 2.01 (m, 2H), 1.97 (s, 2H), 1.29 (d, J =

[0574] 6.1 Hz, 1 H), 1.21 - 1.18 (m, 3H), 1.00 - 0.93 (m, 3H) ppm.13C NMR (101 MHz, CDCh) 5205.8, 203.4, 156.0, 154.3, 151.1 , 134.3, 133.7, 126.2, 124.1 , 123.5, 75.6, 74.8, 38.4, 38.4, 34.4, 33.3, 33.2, 32.9, 31.2, 27.1 , 20.6, 20.6, 20.0, 18.8, 18.8, 16.4, 14.9, 14.0 ppm.

[0575] Odour description (1% solution in EtOH on paper blotter, 24 h): burnt sugar, green.

[0576] Example 6-5: 3-methyl-2-(tetradec-1-en-4-yloxy)cyclopent-2-en-1-one

[0577] According to the procedure of example 1-1 , 3-methyl-2-(tetradec-1-en-4-yloxy)cyclopent-2-en- 1-one was obtained from tetradec- 1-en-4-ol ( 4.0 g, 18.8 mmol) and 2-hydroxy-3- methylcyclopent-2-en-1-one (2.5 g, 22.6 mmol) as a colorless liquid (2.8 g, 49% yield).

[0578] 1H NMR (400 MHz, CDCh) 55.93 - 5.72 (m, 1 H), 5.05 (t, J = 12.6 Hz, 2H), 4.69 - 4.64 (m, 1 H), 2.47 - 2.32 (m, 4H), 2.29 (t, J = 6.0 Hz, 2H), 1.96 (s, 3H), 1.61 - 1.49 (m, 2H), 1.47 - 1.40 (m, 2H), 1.28 - 1.23 (m, 14H), 0.88 (t, J = 6.1 Hz, 3H) ppm.13C NMR (101 MHz, CDCh) 5 203.3, 155.3, 151.2, 134.4, 116.9, 77.7, 38.9, 34.1 , 33.0, 31.9, 29.7, 29.6, 29.6, 29.5, 29.3, 27.1 , 25.0, 22.6, 15.0, 14.1 ppm.

[0579] Odour description (1 % solution in EtOH on paper blotter, 24 h): aldehydic, green, fatty, citrus, powdery gourmand, caramel, maltol.

[0580] Example 7-1 : 3-((5,9-dimethyldeca-3,8-dien-1-yl)oxy)-2-ethyl-4H-pyran-4-one

[0581] According to the procedure of example 1-1 , 3-((5,9-dimethyldeca-3,8-dien-1-yl)oxy)-2-ethyl-4H- pyran-4-one was obtained from 2-ethyl-3-hydroxy-4H-pyran-4-one (2.0 g, 14.3 mmol) and 5,9- dimethyldeca-3,8-dien-1-ol (2.60 g, 14.3 mmol) as a yellow liquid (1.4 g, 32% yield).

[0582] 1H NMR (500 MHz, CDCh) 5 7.63 (d, J = 5.8 Hz, 1 H), 6.33 (d, J = 5.5 Hz, 1 H), 5.44 - 5.35 (m, 2H), 5.09 - 5.02 (m, 1 H), 4.12 - 4.02 (m, 2H), 2.75 - 2.65 (m, 2H), 2.46 - 2.34 (m, 2H), 2.13 - 2.02 (m, 1 H), 1.98 - 1.85 (m, 2H), 1.67 (d, J = 0.9 Hz, 3H), 1.57 (s, 3H), 1.30 - 1.23 (m, 2H), 1.21 (t, J = 7.6 Hz, 3H), 0.95 (d, J = 6.7 Hz, 3H) ppm.

[0583] 31309 PCT213C NMR (126 MHz, CDCh) 5 175.3, 163.3, 153.4, 144.0, 139.0, 131.2, 124.7, 123.9, 117.0, 72.2, 37.1 , 36.3, 33.3, 25.8, 25.7, 21.8, 20.6, 17.7, 11.3 ppm.

[0584] Odour description (1% solution in EtOH on paper blotter, 24 h): powdery gourmand (burnt sugar, maltol, caramel).

[0585] Example 7-2: 2-ethyl-3-((6-methylhept-3-en-1-yl)oxy)-4H-pyran-4-one

[0586] According to the procedure of example 1-1 , 2-ethyl-3-((6-methylhept-3-en-1-yl)oxy)-4H-pyran- 4-one was obtained from 2-ethyl-3-hydroxy-4H-pyran-4-one (2.0 g, 14.3 mmol) and 6- methylhept-3-en-1-ol (1.83 g, 14.3 mmol) as a yellow liquid (2.03 g, 57% yield).

[0587] 1H NMR (500 MHz, CDCh, mixture of E / Z isomers) 5 7.63 (d, J = 5.8 Hz, 1 H), 6.33 (d, J = 5.8 Hz, 1 H), 5.58 - 5.46 (m, 1 H), 5.45 - 5.36 (m, 1 H), 4.09 - 3.99 (m, 2H), 2.72 - 2.66 (m, 2H), 2.47 - 2.35 (m, 2H), 1.89 - 1.66 (m, 2H), 1.64 - 1 .50 (m, 1 H), 1.20 (t, J = 7.6 Hz, 3H), 0.90 - 0.84 (m, 6H) ppm.

[0588] 13C NMR (126 MHz, CDCh, mixture of E / Z isomers) 5 175.3, 163.3, 153.4, 144.0, 131.9, 126.7, 117.0, 72.8, 72.1 , 42.0, 33.3, 28.3, 27.8, 22.5, 22.2, 21.9, 21.7, 11.3 ppm.

[0589] Odour description (1% solution in EtOH on paper blotter, 24 h): powdery gourmand(chocolate, bitter dark chocolate) slightly green aldehydic.

[0590] Example 7-3: 2-ethyl-3-((4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hex-3-en-1-yl)oxy)-4H- pyran-4-one

[0591] According to the procedure of example 1-1, 2-ethyl-3-((4-methyl-6-(2,6,6-trimethylcyclohex-1- en-1-yl)hex-3-en-1-yl)oxy)-4H-pyran-4-one was obtained from 2-ethyl-3-hydroxy-4H-pyran-4- one (1.5 g, 10.7 mmol) and 4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hex-3-en-1-ol (2.53 g, 10.7 mmol) as a slightly yellow solid (2.57 g, 67% yield).

[0592] 1H NMR (500 MHz, CDCh) 57.62 (d, J = 5.8 Hz, 1 H), 6.33 (d, J = 5.5 Hz, 1 H), 5.14 (dt, J = 0.9, 7.0 Hz, 1 H), 4.11 - 4.00 (m, 2H), 2.74 - 2.64 (m, 2H), 2.47 - 2.37 (m, 2H), 2.09 - 1.97 (m, 4H), 1.91 - 1.88 (m, 2H), 1.74 (d, J = 1.2 Hz, 3H), 1.62 (s, 3H), 1.59 - 1.52 (m, 2H), 1.44 - 1.37 (m, 2H), 1.20 (t, J = 7.6 Hz, 3H), 0.99 (s, 6H) ppm.

[0593] 13C NMR (126 MHz, CDCh) 5 175.3, 163.2, 153.3, 143.9, 138.6, 136.9, 127.2, 119.9, 117.0, 72.2, 39.8, 34.9, 32.7, 32.7, 28.8, 28.6, 27.2, 23.3, 21.9, 21.7, 19.8, 19.5, 11.3 ppm.

[0594] Odour description (1 % solution in EtOH on paper blotter, 24 h): powdery gourmand(chocolate) fruity(raspberry). :-3-en- 1 -yl)oxy)-4H-pyran-4-one

[0595] According to the procedure of example 1-1 , 2-ethyl-3-((5-methylhex-3-en-1-yl)oxy)-4H-pyran-4- one was obtained from 2-ethyl-3-hydroxy-4H-pyran-4-one (2.0 g, 14.3 mmol) and 5-methylhex- 3-en-1-ol (1.63 g, 14.3 mmol) as a yellow oil (1.44 g, 40% yield).

[0596] 31309 PCT21H NMR (500 MHz, CDCI3) 5 7.62 (d, J = 5.8 Hz, 1 H), 6.32 (d, J = 5.5 Hz, 1 H), 5.53 - 5.47 (m, 1 H), 5.40 - 5.34 (m, 1 H), 4.12 - 4.01 (m, 2H), 2.68 (q, J = 7.6 Hz, 2H), 2.43 - 2.31 (m, 2H), 2.29 - 2.17 (m, 1 H), 1.21 - 1.17 (m, 3H), 0.94 (d, J = 6.7 Hz, 6H) ppm.

[0597] 13C NMR (126 MHz, CDCI3) 5 175.3, 163.2, 153.4, 143.9, 140.2, 122.5, 117.0, 72.1 , 33.1 , 31.0, 22.4, 21.7, 11.2 ppm.

[0598] Odour description (1% solution in EtOH on paper blotter, 24 h): powdery gourmand(sugary, sweet, caramel, chocolate, bread crust) slightly green aldehydic.

[0599] Example 7-5: 3-(but-3-en-1-yloxy)-2-ethyl-4H-pyran-4-one

[0600] According to the procedure of example 2-1, 3-(but-3-en-1-yloxy)-2-ethyl-4H-pyran-4-one was obtained from 2-ethyl-3-hydroxy-4H-pyran-4-one (2.0 g, 14.3 mmol) and 4-bromobut-1-ene (2.0 g, 14.3 mmol) as a colorless oil (1.04 g, 38% yield).

[0601] 1H NMR (400 MHz, CDCI3) 5 7.62 (d, J = 5.6 Hz, 1 H), 6.31 (d, J = 5.6 Hz, 1 H), 5.90 - 5.80 (m, 1 H), 5.16 - 5.09 (m, 1 H), 5.08 - 5.04 (m, 1 H), 4.12 - 4.09 (m, 2H), 2.68 (q, J = 7.6 Hz, 2H), 2.48 - 2.42 (m, 2H), 1.19 (t, J = 7.6 Hz, 3H) ppm.

[0602] 13C NMR (101 MHz, CDCI3) 5 175.2, 163.3, 153.4, 143.9, 134.5, 117.0, 116.9, 71.4, 34.4, 21.7, 11.2 ppm.

[0603] Odour description (1% solution in EtOH on paper blotter, 24 h): powdery gourmand (maltol).

[0604] Example 7-6: 2-ethyl-3-((4-methylhept-3-en-1-yl)oxy)-4H-pyran-4-one

[0605] According to the procedure of example 2-1 , 2-ethyl-3-((4-methylhept-3-en-1-yl)oxy)-4H-pyran- 4-one was obtained from 2-ethyl-3-hydroxy-4H-pyran-4-one (2.0 g, 14.3 mmol) and 1-bromo-4- methylhept-3-ene (2.73 g, 14.3 mmol) as a slightly yellow oil (1.62 g, 45% yield, E / mixture 4:1).

[0606] 1H NMR (400 MHz, CDCI3, mixture of isomers) 57.62 (d, J = 5.6 Hz, 1 H), 6.31 (d, J = 5.6 Hz, 1 H), 5.17 - 5.13 (m, 1 H), 4.05 - 4.00 (m, 2H), 2.71 - 2.65 (m, 2H), 2.43 - 2.37 (m, 2H), 2.02 - 1.91 (m, 2H), 1.67 - 1.56 (m, 3H), 1.43 - 1.36 (m, 2H), 1.19 (t, J = 7.6 Hz, 3H), 0.89 - 0.82 (m, 3H) ppm.

[0607] 13C NMR (101 MHz, CDCh, mixture of isomers) 5 175.3, 163.2, 153.3, 144.0, 137.8, 120.3, 119.5, 117.0, 72.3, 72.1 , 41.7, 33.8, 28.8, 28.7, 23.3, 21.7, 21.0, 20.9, 16.0, 13.9, 13.7, 11.3 ppm.

[0608] Odour description (1% solution in EtOH on paper blotter, 24 h): powdery gourmand (maltol, candy floss) slightly green aldehydic (damp). ;-3-en- 1 -yl)oxy)-4H-pyran-4-one

[0609] 31309 PCT2 According to the procedure of example 2-1 , 2-ethyl-3-((4-methyldec-3-en-1-yl)oxy)-4H-pyran-4- one was obtained from 2-ethyl-3-hydroxy-4H-pyran-4-one (2.13 g, 15.2 mmol) and 1-bromo-4- methyldec-3-ene (6.21 g, 15.2 mmol) as a yellow oil (2.96 g, 67% yield, EZZ mixture 9:1).

[0610] 1H NMR (400 MHz, CDCh, mixture of isomers) 57.62 (d, J = 5.6 Hz, 1 H), 6.32 (d, J = 5.6 Hz, 1 H), 5.17 - 5.13 (m, 1 H), 4.05 - 4.01 (m, 2H), 2.69 (q, J = 7.6 Hz, 2H), 2.40 (dq, J = 0.7, 7.1 Hz, 2H), 2.03 - 1.93 (m, 2H), 1.60 (s, 3H), 1.40 - 1.22 (m, 8H), 1.20 (t, J = 7.6 Hz, 3H), 0.88 - 0.84 (m, 3H) ppm.

[0611] 13C NMR (101 MHz, CDCh, mixture of isomers) 5 175.3, 163.3, 153.4, 144.0, 138.4, 138.2, 120.1 , 119.3, 117.0, 72.3, 72.1 , 39.7, 31.9, 31.8, 31.8, 29.2, 29.0, 28.8, 28.7, 27.9, 27.8, 23.4, 22.6, 22.6, 21.7, 16.1 , 14.1 , 11.3 ppm.

[0612] Odour description (1% solution in EtOH on paper blotter, 24 h): powdery gourmand (maltol, candy floss).

[0613] 7-8: Mixture of 2-ethyl-3-((4- i-3,6-dien-1-yl)oxy)-4H-pyran-4-one and 2- ethyl-3-((4-methylhepta-3,5-dien-1-yl)oxy)-4H-pyran-4-one

[0614] According to the procedure of example 2-1 , a mixture of 2-ethyl-3-((4-methylhepta-3,6-dien-1- yl)oxy)-4H-pyran-4-one (major, 80%, E / Z mixture) and 2-ethyl-3-((4-methylhepta-3,5-dien-1- yl)oxy)-4H-pyran-4-one (minor, 20%, E / Z mixture) was obtained from 2-ethyl-3-hydroxy-4H- pyran-4-one (2.14 g, 15.2 mmol) and 7-bromo-4-methylhepta-1 ,4-diene (5.44 g, 15.2 mmol, 53% purity, prepared according to a modified procedure of W02023067040 by reacting 1- cyclopropylethan-1-one and allylmagnesium bromide) as a yellow oil (2.09 g, 5% yield, complex mixture of isomers).

[0615] 1H NMR (400 MHz, CDCh, mixture of isomers, major) 57.62 (d, J = 5.6 Hz, 1 H), 6.31 (d, J = 5.6 Hz, 1 H), 5.83 - 5.65 (m, 1 H), 5.29 - 5.14 (m, 1 H), 5.10 - 4.94 (m, 2H), 4.11 - 3.98 (m, 2H), 2.87 - 2.62 (m, 3H), 2.57 - 2.38 (m, 2H), 1.94 - 1.57 (m, 4H), 1.26 - 1.12 (m, 3H) ppm.

[0616] 13C NMR (101 MHz, CDCh, peak list for complex mixture) 5 175.3, 163.2, 163.2, 153.4, 144.0, 144.0, 136.6, 136.2, 135.7, 135.7, 135.6, 134.2, 128.2, 125.9, 124.8, 123.2, 122.7, 121.3, 120.8, 117.0, 115.7, 115.2, 113.1 , 77.2, 72.2, 72.1 , 71.9, 71.9, 71.7, 44.0, 36.5, 29.0, 28.9, 28.7, 28.4, 28.2, 23.4, 21.7, 20.6, 18.6, 18.2, 18.1 , 16.2, 12.5, 11.3 ppm.

[0617] Odour description (1% solution in EtOH on paper blotter, 24 h): powdery gourmand (maltol). non-3-en-1-yl)oxy)-4H-pyran-4-one

[0618] According to the procedure of example 2-1 , 2-ethyl-3-((4-methylnon-3-en-1-yl)oxy)-4H-pyran-4- one was obtained from 2-ethyl-3-hydroxy-4H-pyran-4-one (2.00 g, 14.3 mmol) and 1-bromo-4- methylnon-3-ene (3.13 g, 14.3 mmol) as a yellow oil (1.3 g, 33% yield, E / Z mixture 9:1).

[0619] 31309 PCT21H NMR (400 MHz, CDCh, mixture of isomers) 57.62 (d, J = 5.6 Hz, 1 H), 6.32 (d, J = 5.6 Hz, 1 H), 5.17 - 5.13 (m, 1 H), 4.05 - 4.00 (m, 2H), 2.69 (q, J = 7.6 Hz, 2H), 2.40 (dq, J = 0.7, 7.1 Hz, 2H), 2.04 - 1.93 (m, 2H), 1.68 - 1.59 (m, 3H), 1.38 - 1.18 (m, 9H), 0.88 - 0.84 (m, 3H) ppm.

[0620] 13C NMR (101 MHz, CDCh, mixture of isomers) 5 175.3, 163.3, 153.4, 144.0, 138.3, 138.1, 120.1 , 119.3, 117.0, 72.3, 72.1 , 39.6, 31.8, 31.7, 31.5, 28.8, 28.7, 27.6, 27.5, 23.4, 22.5, 22.5, 21.7, 16.1 , 14.0, 11.3 ppm.

[0621] Odour description (1% solution in EtOH on paper blotter, 24 h): powdery gourmand(maltol).

[0622] Example 7-10: 2-ethyl-3-((4-methyloct-3-en-1-yl)oxy)-4H-pyran-4-one

[0623] According to the procedure of example 2-1 , 2-ethyl-3-((4-methyloct-3-en-1-yl)oxy)-4H-pyran-4- one was obtained from 2-ethyl-3-hydroxy-4H-pyran-4-one (3.31 g, 23.6 mmol) and 1-bromo-4- methyloct-3-ene (6.21 g, 23.6 mmol, 78% purity) as a yellow oil (1.2 g, 19% yield, E / Z mixture 9:1).

[0624] 1H NMR (400 MHz, CDCh, mixture of isomers) 57.62 (d, J = 5.6 Hz, 1 H), 6.31 (d, J = 5.6 Hz, 1 H), 5.17 - 5.13 (m, 1 H), 4.05 - 4.00 (m, 2H), 2.71 - 2.65 (m, 1 H), 2.68 (d, J = 7.6 Hz, 1 H), 2.43 - 2.36 (m, 2H), 2.03 - 1.94 (m, 2H), 1.69 - 1.56 (m, 3H), 1.38 - 1.17 (m, 7H), 0.90 - 0.84 (m, 3H) ppm.

[0625] 13C NMR (101 MHz, CDCh, mixture of isomers) 5 175.3, 163.2, 153.4, 144.0, 144.0, 138.3, 138.1 , 120.1 , 119.3, 117.0, 72.3, 72.1 , 39.3, 31.6, 30.2, 30.0, 28.8, 28.7, 23.4, 22.6, 22.3, 21.7, 16.0, 14.0, 14.0, 11.3 ppm.

[0626] Odour description (1% solution in EtOH on paper blotter, 24 h): powdery gourmand(maltol). , i-3,6-dien-1-yl)oxy)-2-ethyl-4H-pyran-4-one and

[0627] 3-((4,6-dimethylhepta-3,5-dien-1-yl)oxy)-2-ethyl-4H-pyran-4-one

[0628] According to the procedure of example 2-1 , a mixture of 3-((4,6-dimethylhepta-3,6-dien-1- yl)oxy)-2-ethyl-4H-pyran-4-one and 3-((4,6-dimethylhepta-3,5-dien-1-yl)oxy)-2-ethyl-4H-pyran-

[0629] 4-one was obtained from 2-ethyl-3-hydroxy-4H-pyran-4-one (2.51 g, 17.9 mmol) and 7-chloro- 2,4-dimethylhepta-1 ,4-diene (2.84 g, 17.9 mmol, prepared according to a modified procedure of W02023067040 by reacting 1-cyclopropylethan-1-one and 2-methallylmagnesium chloride) as a yellow oil (0.34 g, 7% yield, complex mixture of isomers).

[0630] 13C NMR (101 MHz, CDCh, complex mixture of isomers, peak list) 5 175.3, 163.2, 153.4, 153.4, 144.0, 144.0, 143.8, 143.1 , 135.7, 135.5, 135.4, 133.8, 132.4, 128.6, 124.2, 123.7, 122.4, 122.0, 121.7, 119.9, 117.0, 117.0, 111.7, 111.1 , 72.1 , 72.1 , 71.9, 71.8, 48.6, 40.4, 30.0, 29.1 , 29.0, 28.9, 26.6, 25.6, 24.0, 23.4, 22.2, 21.7, 21.7, 19.4, 19.4, 17.7, 17.2, 15.6, 11.3 ppm.

[0631] Odour description (1% solution in EtOH on paper blotter, 24 h): powdery gourmand(maltol).

[0632] 7-12: 3-(dec-3-en-1- i-2- I-4H-I i-4-one

[0633] 31309 PCT2 According to the procedure of example 2-1 , 3-(dec-3-en-1-yloxy)-2-ethyl-4H-pyran-4-one was obtained from 2-ethyl-3-hydroxy-4H-pyran-4-one (3.33 g, 23.5 mmol) and 1-bromodec-3-ene (7.58 g, 23.5 mmol, 68% purity) as a brown oil (1.74 g, 27% yield).

[0634] 1H NMR (400 MHz, CDCh) 5 7.62 (d, J = 5.6 Hz, 1 H), 6.32 (d, J = 5.6 Hz, 1 H), 5.56 - 5.37 (m, 2H), 4.06 (t, J = 6.8 Hz, 2H), 2.69 (q, J = 7.6 Hz, 2H), 2.47 - 2.35 (m, 2H), 2.10 - 1.93 (m, 2H), 1.43 - 1.16 (m, 11 H), 0.89 - 0.83 (m, 3H) ppm.

[0635] 13C NMR (101 MHz, CDCh) 5 175.3, 163.2, 153.4, 144.0, 133.2, 125.5, 117.0, 72.1 , 33.2, 32.6, 31.7, 29.3, 28.8, 22.6, 21.7, 14.0, 11.2 ppm.

[0636] Odour description (1% solution in EtOH on paper blotter, 24 h): fatty aldehydic, powdery gourmand.

[0637] Example 7-13: 2-ethyl-3-(hept-3-en-1-yloxy)-4H-pyran-4-one

[0638] According to the procedure of example 2-1 , 2-ethyl-3-(hept-3-en-1-yloxy)-4H-pyran-4-one was obtained from 2-ethyl-3-hydroxy-4H-pyran-4-one (5.09 g, 36.3 mmol) and 1-bromohept-3-ene (7.56 g, 36.3 mmol, 85% purity) as a brown oil (2.18 g, 25% yield).

[0639] 1H NMR (400 MHz, CDCh) 5 7.62 (d, J = 5.6 Hz, 1 H), 6.31 (d, J = 5.6 Hz, 1 H), 5.56 - 5.38 (m, 2H), 4.06 (t, J = 6.8 Hz, 2H), 2.69 (q, J = 7.6 Hz, 2H), 2.47 - 2.36 (m, 2H), 2.05 - 1.84 (m, 2H), 1.40 - 1.30 (m, 2H), 1.22 - 1.17 (m, 3H), 0.89 - 0.84 (m, 3H) ppm.

[0640] 13C NMR (101 MHz, CDCh) 5 175.3, 163.2, 153.4, 144.0, 133.0, 125.7, 117.0, 72.1 , 34.7, 33.2, 22.5, 21.7, 13.6, 11.2 ppm.

[0641] Odour description (1% solution in EtOH on paper blotter, 24 h): green aldehydic, powdery gourmand(maltol).

[0642] Example 7-14: 2-ethyl-3-((4-methyldodec-3-en-1-yl)oxy)-4H-pyran-4-one

[0643] According to the procedure of example 2-1 , 2-ethyl-3-((4-methyldodec-3-en-1-yl)oxy)-4H-pyran- 4-one was obtained from 2-ethyl-3-hydroxy-4H-pyran-4-one (1.3 g, 9.2 mmol) and 1-bromo-4- methyldodec-3-ene (2.4 g, 9.2 mmol) as a brown oil (0.74 g, 26% yield, EfZ 85:15).

[0644] 1H NMR (400 MHz, CDCh, mixture of isomers) 57.62 (d, J = 5.6 Hz, 1 H), 6.32 (d, J = 5.6 Hz, 1 H), 5.15 (dt, J = 1.2, 7.1 Hz, 1 H), 4.06 - 4.01 (m, 2H), 2.69 (q, J = 7.6 Hz, 2H), 2.43 - 2.37 (m, 2H), 2.04 - 1.92 (m, 2H), 1.70 - 1.56 (m, 3H), 1.39 - 1.18 (m, 15H), 0.88 - 0.84 (m, 3H) ppm.

[0645] 13C NMR (101 MHz, CDCh, mixture of isomers) 5 175.3, 163.2, 163.2, 153.3, 144.0, 138.3, 138.2, 120.1 , 119.3, 117.0, 72.3, 72.1 , 39.7, 31.9, 31.9, 31.8, 30.0, 29.6, 29.5, 29.5, 29.3, 29.3, 29.3, 28.8, 28.7, 28.0, 27.9, 23.4, 22.6, 21.7, 16.1 , 14.1 , 11.3 ppm.

[0646] Odour description (1% solution in EtOH on paper blotter, 24 h): powdery gourmand(maltol). is of released volatiles

[0647] A solution of the compound of formula (I) (100 .g, 1.0 mg / mL solution in MTBE) was evenly applied through a displacement pipette to a cut paper smelling strip (1 cm x 8 cm). The

[0648] 31309 PCT2 paper strip was left to dry (1 h at room temperature), then folded in the middle and inserted in “V”-shape into a 20 mL headspace vial. The vial was closed with a septum screwcap and placed in a cabinet equipped with a fluorescent daylight imitation lamp and mirrored walls for 24 h (temperature 27-28°C).

[0649] Extraction and analysis of the released organic volatiles was effected in automated mode on a Trace 1310 gas chromatograph equipped with a TriPlus RSH autosampler (Thermo Fisher Scientific), coupled to a ISQ LT mass spectrometer (Thermo Fisher Scientific). The extraction of the organic volatiles from the headspace with SPME (solid phase microextraction) was carried out during 1 h at 40°C using a 50 / 30pm divinylbenzene / carboxen / polydimethylsiloxane SPME fibre (DVB / CAR / PDMS, Supelco P / N 57298-U), and subsequently desorbed in splitless mode at 250°C for 1 min. GC-MS analysis (gas chromatography with mass spectrometric detection) was carried out with a VF-WAXms capillary column (Agilent, 30m length, 0.25mm I.D., 0.25pm film thickness). Helium was used as a carrier gas with a constant flow rate of 1ml / min. The GC oven temperature was programmed from 35°C with 2-min hold to 250°C at 5°C / min with a 10- min final temperature hold. The mass spectrometer was operated at 70 eV in El mode over a m / z range of 33-350, scanned at 0.2 s intervals and with a temperature of transfer line and ion source of 230 °C and 220°C, respectively. The main sensorially active volatiles released from the compounds of formula (I) are reported in Table 4 (indicated are relative peak area %; in bold: main odor vector).

[0650] Table 4:

[0651] It should be noted that the indicated relative peak area % values are not related to molar release rates. The relative amount of each volatile in the gas phase depends mainly on volatility.

[0652] The results illustrate that compounds of the present invention are capable of releasing a variety of odorants in the gourmand-sugary as well as in floral and citrus odour directions under ambient conditions.

[0653] Example 9: Application in liquid detergent

[0654] 31309 PCT2 9a) Colour stability

[0655] In order to illustrate the superior colour stability of compounds of the current invention, free furaneol (sample A) and 4-(((S)-3,7-dimethylnon-6-en-1-yl)oxy)-2,5-dimethylfuran-3(2H)- one (Example 1-48 of the current invention, sample B) were incorporated each at 0.2% by weight into unperfumed liquid detergent base by magnetic stirring at room temperature for 24 h. After 3 days at room temperature, the above prepared samples were visually inspected in comparison to an unperfumed base sample (sample C), as shown in Figure 1. Sample (A) containing furaneol showed strong dark yellow coloration, whereas the sample (B) containing the compound of the current invention was optically identical to the unperfumed base (C), showing no coloration.

[0656] The example shows that the ether of the present invention has colour stability and is not causing discoloration in an application like a liquid detergent. It also shows that free furaneol cannot be used in liquid detergent as the coloration after only 3 days of storage at room temperature is not acceptable.

[0657] 9b) Washtest and sensory evaluation

[0658] A 40°C machine wash cycle was performed using 55 g of the above prepared liquid detergent samples A and B and odour-neutral cotton / elastan mixed fabric T-shirts. The wet and line-dried fabric (1 day) was assessed by a panel of 4-6 experts with regard to odour intensity and quality. The odour intensity was recorded on an intensity scale of 0 (odourless) to 5 (extremely strong). As can be seen from the table below, virtually no odour was released from the fabric washed with the colored furaneol containing detergent base, whereas the fabric washed with the color-neutral detergent base containing 4-(((S)-3,7- dimethylnon-6-en-1-yl)oxy)-2,5-dimethylfuran-3(2H)-one exhibited an attractive floral, rosy, green and culinary scent.

[0659] The experiment demonstrates that Example 1-48, a representative of the compound of the present invention, which is stable in the base, imparts an attractive scent on dry fabric.

[0660] 9c) Improved stability in comparison to a counterexample

[0661] In order to further illustrate the superior stability of compounds of the current invention, a counterexample, the furaneol ester 2,5-dimethyl-4-oxo-4,5-dihydrofuran-3-yl 2-(2,2,3-

[0662] 31309 PCT2 trimethylcyclopent-3-en-1-yl)acetate (sample A) and 4-((3,7-dimethylnon-6-en-1-yl)oxy)- 2,5-dimethylfuran-3(2H)-one (Example 1-2 of the current invention, sample B) were incorporated each at 0.2% by weight into unperfumed liquid detergent base by magnetic stirring at room temperature for 24 h. Then the samples were stored for 1 month at 37°C. The above prepared samples were visually inspected in comparison to an unperfumed base sample (sample C). Sample (A) containing a furaneol ester showed yellow coloration and a thick precipitate, whereas the sample (B) containing the compound of the current invention was optically identical to the unperfumed base (C), showing no coloration and no precipitate.

[0663] This demonstrates that a compound of the present invention is stable in liquid detergent, whereas a comparable ester imparted coloration and precipitate and would thus not be usable in liquid detergent as fragrance precursor.

[0664] Counterexample 1 : 2,5-dimethyl-4-oxo-4,5-dihydrofuran-3-yl 2-(2,2,3-trimethylcyclopent-3-en- 1-yl)acetate

[0665] The mixture of 4-hydroxy-2,5-dimethylfuran-3(2H)-one (11.2 g, 87 mmol), 2-(2,2,3- trimethylcyclopent-3-en-1-yl)acetic acid (16.2 g, 96 mmol), dicyclohexylmethanediimine (21.6 g, 105 mmol), and DMAP (2.1 g, 17 mmol) in DCM (400 ml) was stirred at rt. for18 h and the mixture was concentrated. The residue was filtered with a short silica gel pad and washed with ethyl acetate. The solvent was removed and the residue was purified by flash chromatography (heptane: MTBE=90: 10) to give 2,5-dimethyl-4-oxo-4,5-dihydrofuran-3-yl 2-(2,2,3- trimethylcyclopent-3-en-1-yl)acetate (8.1g, 33% yield).

[0666] 1H NMR (400 MHz, CDCh) 65.27 - 5.22(m, 1 H), 4.59 - 4.54 (m, 1 H), 2.69 - 2.64 (m, 1 H), 2.54 - 2.41 (m, 2H), 2.37 - 2.27 (m, 1 H), 2.17 (s, 3H), 2.08 - 1.90 (m, 1 H), 1.66 - 1.59(m, 3H), 1.50 (d, J = 7.0 Hz, 3H), 1.04 (s, 3H), 0.82 (s, 3H) ppm.13C NMR (101 MHz, CDCh) 6 195.8, 179.9, 170.5, 147.8, 129.1 , 121.5, 81.3, 46.9, 46.3, 35.4, 34.7, 25.6, 19.9, 16.3, 14.1 , 12.6 ppm.

[0667] Odour description (1% solution in EtOH on paper blotter, 24 h): sweet, fruity, gourmand, sugar.

[0668] Example 10: Perfumery accord

[0669] 31309 PCT2

[0670] The reference accord described above is a floral fruity accord. For example, it can be used in HDLD (heavy duty liquid detergent) at 0.6 % by weight.

[0671] 31309 PCT2 If 50 parts by weight of DPG is replaced by (S)-3,7-dimethylnon-6-en-1-yl)oxy)-2,5- dimethylfuran-3(2H)-one (compound of example Example 1-48) and incorporated in the HDLD base, the performance on dry fabric after the wash cycle and 1 day and 3 days dry, is stronger, more gourmand and fresh floral (rosy) in comparison to the reference without said compound.

[0672] 31309 PCT2

Claims

Claims1. Use of a compound of formula (I)whereinR1is R5R6CH; wherein R1comprises 5 to 20 carbon atoms; R5and R6are independently selected from H or a hydrocarbon residue, and wherein the hydrocarbon residue optionally comprises one or more groups selected from carboxyl (-C(O)O-), carbonyl (- C(O) -), hydroxy (-OH) and ether (-O-);R2is selected from the group consisting of hydrogen, methyl or ethyl;Y is selected from the group consisting of -CH2-, -CH=CH-, -O- and R3CH< wherein R3is selected from the group consisting of H, methyl or ethyl;X is selected from the group consisting of -CH2-, -O-, and R4CH < wherein R4is selected from the group consisting of H, methyl or ethyl; with the proviso that X and Y can’t be -O- at the same time, as precursor for generating i) a compound of formula (la)whereinR2is selected from the group consisting of hydrogen, methyl or ethyl;Y is selected from the group consisting of -CH2-, -CH=CH-, -O- and R3CH< wherein R3is selected from the group consisting of H, methyl or ethyl;X is selected from the group consisting of -CH2-, -O-, and R4CH < wherein R4is selected from the group consisting of H, methyl or ethyl; with the proviso that X and Y can’t be -O- at the same time; and31309 PCT2ii) an alcohol R1OH, wherein R1is R5R6CH; wherein R1comprises 5 to 20 carbon atoms; R5and R6are independently selected from H or a hydrocarbon residue, and wherein the hydrocarbon residue optionally comprises one or more groups selected from carboxyl (-C(O)O-), carbonyl (-C(O) -), hydroxy (-OH) and ether (-O-).

2. A compound of formula (I)whereinR1is R5R6CH; wherein R1comprises 5 to 20 carbon atoms; R5and R6are independently selected from H or a hydrocarbon residue, and wherein the hydrocarbon residue optionally comprises one or more groups selected from carboxyl (-C(O)O-), carbonyl (- C(O) -), hydroxy (-OH) and ether (-O-);R2is selected from the group consisting of hydrogen, methyl or ethyl;Y is selected from the group consisting of -CH2-, -CH=CH-, -O- and R3CH< wherein R3is selected from the group consisting of H, methyl or ethyl;X is selected from the group consisting of -CH2-, -O-, and R4CH < wherein R4is selected from the group consisting of H, methyl or ethyl; with the proviso that X and Y can’t be -O- at the same time, and the proviso that the compound is not (Z)-4-(hex-3-en-1-yloxy)-2,5-dimethylfuran- 3(2H)-one, 4-(isopentyloxy)-2,5-dimethylfuran-3(2H)-one, 3-(hexyloxy)-2-methyl-4H- pyran-4-one, 2-methyl-3-(pentyloxy)-4H-pyran-4-one, 3-(heptyloxy)-2-methyl-4H-pyran- 4-one, 3-(isopentyloxy)-2-methyl-4H-pyran-4-one, 2-methyl-3-(nonyloxy)-4H-pyran-4- one, 2-methyl-3-phenoxy-4H-pyran-4-one, 3-(3-(cyclopenta-1 ,3-dien-1-yl)propoxy)-2- methyl-4H-pyran-4-one, 3-(benzyloxy)-2-methyl-4H-pyran-4-one, 3-(benzyloxy)-2-ethyl- 4H-pyran-4-one, 3-(hex-5-en-2-yn-1-yloxy)-2-methyl-4H-pyran-4-one, 2-methyl-3- phenethoxy-4H-pyran-4-one, 3-((3-(furan-2-yl)prop-2-yn-1-yl)oxy)-2-methyl-4H-pyran-4- one, 2-methyl-3-((5-methylhex-5-en-2-yn-1-yl)oxy)-4H-pyran-4-one, 3-(hex-5-en-2-yn-1- yloxy)-2-methyl-4H-pyran-4-one, (E)-3-(hexa-3,5-dien-1-yloxy)-2-methyl-4H-pyran-4- one, ethyl 4-((2-ethyl-4-oxo-4H-pyran-3-yl)oxy)butanoate, 2-methyl-3-(3- phenylpropoxy)-4H-pyran-4-one, ethyl 3-((2-methyl-4-oxo-4H-pyran-3- yl)oxy)propanoate, 4-((2-ethyl-4-oxo-4H-pyran-3-yl)oxy)butanoic acid, propyl 2-((2-31309 PCT2methyl-4-oxo-4H-pyran-3-yl)oxy)acetate, 2-methyl-3-((4-methylbenzyl)oxy)-4H-pyran-4- one, 2-Methyl-3-(3-phenoxypropoxy)-4H-pyran-4-one, 2-methyl-3-((2- methylbenzyl)oxy)-4H-pyran-4-one, 3-(((3E,5E)-hepta-3,5-dien-1-yl)oxy)-2-methyl-4H- pyran-4-one, 2-methyl-3-((5-methylhex-5-en-1-yl)oxy)-4H-pyran-4-one, 5-ethyl-4- methyl-3-(pentyloxy)furan-2(5H)-one..

3. A compound of formula (I)whereinR1is R5R6CH; wherein R1comprises 5 to 20 carbon atoms; R5and R6are independently selected from H or a hydrocarbon residue, and wherein the hydrocarbon residue optionally comprises one or more groups selected from carboxyl (-C(O)O-), carbonyl (- C(O) -), hydroxy (-OH) and ether (-O-);R2is selected from the group consisting of hydrogen, methyl or ethyl;Y is selected from the group consisting of -CH2-, -CH=CH-, -O- and R3CH< wherein R3is selected from the group consisting of H, methyl or ethyl;X is selected from the group consisting of -CH2-, -O-, and R4CH < wherein R4is selected from the group consisting of H, methyl or ethyl; with the proviso that X and Y can’t be -O- at the same time, as precursor for generating a compound of formula (la)and an alcohol R1OH.31309 PCT24. A fragrance composition comprising at least one compound of formula (I) as defined in claim 1 and at least one further fragrance compound.

5. A consumer product comprising at least one compound of formula (I) according claim 1 and a consumer product base.

6. A method to release a compound of formula (la)whereinR2is selected from the group consisting of hydrogen, methyl or ethyl;Y is selected from the group consisting of -CH2-, -CH=CH-, -O- and R3CH< wherein R3is selected from the group consisting of H, methyl or ethyl;X is selected from the group consisting of -CH2-, -O-, and R4CH < wherein R4is selected from the group consisting of H, methyl or ethyl; with the proviso that X and Y can’t be -O- at the same time; and an alcohol R1OH, wherein R1is R5R6CH; wherein R1comprises 5 to 20 carbon atoms; R5and R6are independently selected from H or a hydrocarbon residue, and wherein the hydrocarbon residue optionally comprises one or more groups selected from carboxyl (- C(O)O-), carbonyl (-C(O) -), hydroxy (-OH) and ether (-O-), wherein a compound of formula (I) as defined in claim 1 is exposed to ambient air and / or humidity.

7. A method of manufacturing a consumer product, comprising the steps of a) provision of a compound of formula (I) as defined in claim 1 , or a fragrance composition according to claim 4; and b) admixing it to a consumer product base.

8. Use of a compound of formula (I) as defined in claim 1 or a fragrance composition according to claim 4 in consumer products.31309 PCT29. A method to confer, enhance, improve or modify the hedonic properties of a fragrance composition or a consumer product, which method comprises adding to said composition or consumer product at least one compound of formula (I) as defined in claim 1.31309 PCT2

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