Bio-based methyl dihydrojasmonate, bio-based cyclopentanone, methods for their preparation, and uses thereof

Abstract

The present invention relates to novel bio-based methyl dihydrojasmonate and cyclopentanone. The present invention further relates to processes for their preparation and uses of such compounds.

Description

[Technical field]

[0001] This application claims priority to PCT / CN2022 / 075273, filed January 31, 2022, the entire contents of which are incorporated herein by reference for all purposes.

[0002] The present invention relates to bio-based methyl dihydrojasmonate, bio-based cyclopentanone, their preparation methods and uses. [Background technology]

[0003] Methyl dihydrojasmonate (CAS 24851-98-7) is an aroma compound that, in racemic mixture, has a floral and citrus odor. It is used in the perfume and food industries. Methyl dihydrojasmonate is utilized as a synthetic equivalent of methyl jasmonate, a naturally occurring component of jasmine. Industrially, methyl dihydrojasmonate can be produced from adipic acid as a precursor for the preparation of cyclopentanone. Cyclopentanone can then be functionalized by aldol condensation with pentanal followed by Michael addition of dimethyl malonate.

[0004] Synthetic flavours tend to be less popular with consumers than naturally derived flavours, which has led to increased interest in other sources of methyl dihydrojasmonate, as well as specific routes using natural raw materials that can be classified as either natural or biosourced according to existing legislation. Summary of the Invention

[0005] In a first aspect, the present invention relates to methyl dihydrojasmonate having a biobased carbon content of 30% or more or having 5 or more biobased carbon atoms.

[0006] In another aspect, the present invention relates to a method for preparing methyl dihydrojasmonate from bio-based furfuryl alcohol having a bio-based carbon content of 50% or more.

[0007] The present invention further relates to a biobased cyclopentanone having a biobased carbon content of 50% or more.

[0008] In another aspect, the present invention relates to a biobased cyclopentanone having at least two biobased carbon atoms.

[0009] In another aspect, the present invention relates to a method for preparing cyclopentanone from bio-based furfuryl alcohol having a bio-based carbon content of 50% or more.

[0010] The present invention further relates to the use of cyclopentanone or methyl dihydrojasmonate according to the invention as flavouring or fragrance, in particular in perfumes, cosmetics and pharmaceuticals.

[0011] Finally, the present invention also relates to a composition containing methyl dihydrojasmonate and / or cyclopentanone according to the invention, preferably selected from the group consisting of food, beverages, cosmetic preparations, pharmaceutical preparations, fragrances. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0012] The terms used herein have meanings that are accepted and known to those of ordinary skill in the art; however, for convenience and completeness, specific terms and their meanings are set forth below.

[0013] The articles "a", "an" and "the" are used to refer to one or to more than one (i.e. to at least one) of the grammatical object of the article.

[0014] The term "and / or" includes not only the meaning "and", "or" but also all other possible combinations of the elements connected to this term.

[0015] Throughout this specification, including the claims, the term "including one" should be understood to mean the same as the term "including at least one" unless otherwise specified, and "between" should be understood to be inclusive. In the continuation of the description, it is specified that the endpoints are included in the range of values ​​given, unless otherwise specified.

[0016] The term "comprising" should be understood to equally include "consisting of" or "consisting essentially of".

[0017] It should be noted that in specifying a numerical range, such as a concentration, conversion, or selectivity range, any particular upper limit can be associated with any particular lower limit.

[0018] Unless otherwise specified, percentage contents are by weight.

[0019] As used herein, the terms "bio-based material", "bio-sourced material" or "natural material" refer to products that are composed entirely or predominantly of biological products or renewable agricultural materials (such as plants, animals, and marine materials) or forestry materials.

[0020] In the present invention, the expression "bio-based carbon" refers to carbon of renewable origin, such as agricultural, plant, animal, fungal, microbial, marine, or forestry materials that live in a natural environment in equilibrium with the atmosphere. The bio-based carbon content is typically evaluated by carbon-14 dating (also called carbon dating or radiocarbon dating). Furthermore, in the present invention, the "bio-based carbon content" refers to the molar ratio of bio-based carbon to the total carbon of a compound or product. The bio-based carbon content can be preferably measured by a method consisting of measuring the decay process of 14C (carbon-14) in decays per minute per gram of carbon (or dpm / gC) by liquid scintillation counting, preferably according to the standard test method ASTM D6866-16. The said American standard test ASTM D6866 is considered to be equivalent to ISO standard 16620-2. According to said standard ASTM D6866, the test method can preferably utilize AMS (Accelerator Mass Spectrometry) together with IRMS (Isotope Ratio Mass Spectrometry) techniques to quantify the biobased content of a given product.

[0021] In the present invention, the expression "δ 13 "C" refers to the average isotopic variation of carbon-13. The average isotopic variation of 13C is measured by isotope ratio mass spectrometry using the PDB as the international standard. The isotopic fingerprint of a compound provides information about the origin of said compound, especially natural or fossil.

[0022] Methyl dihydrojasmonate The present invention relates to methyl dihydrojasmonate having a biobased carbon content of 30% or more, preferably 35% or more, more preferably 38% or more. Typically, the methyl dihydrojasmonate according to the present invention has a biobased carbon content of 105% or less, preferably 100% or less, more preferably less than 100%.

[0023] According to another aspect, the number of bio-based carbon atoms in the methyl dihydrojasmonate according to the present invention is at least 2, preferably at least 5, more preferably at least 7. In a particular embodiment, all carbon atoms in the methyl dihydrojasmonate according to the present invention are bio-based.

[0024] The present invention further relates to a composition comprising or consisting essentially of methyl dihydrojasmonate having a biobased carbon content of 30% or more, preferably 35% or more, and more preferably 38% or more.

[0025] Said methyl dihydrojasmonate may constitute the main compound of the composition according to the invention. Thus, said methyl dihydrojasmonate may be present in more than 50%, preferably more than 70%, more preferably more than 80% by weight of the total composition. In a more preferred embodiment of the invention, said methyl dihydrojasmonate may be present in more than 90%, preferably more than 95%, more preferably more than 96%, more preferably more than 99%, most preferably more than 99.5% by weight of the total composition. Impurities may be present in an amount of 1 ppm to 5000 ppm, preferably 1 ppm to 500 ppm, more preferably 1 ppm to 50 ppm, most preferably 1 ppm to 20 ppm by weight of the total composition.

[0026] Therefore, in a particular embodiment of the present invention, impurities may be present in an amount of 1 ppm to 100 ppm, preferably 1 ppm to 50 ppm, and more preferably 1 ppm to 10 ppm, based on the total weight of methyl dihydrojasmonate.

[0027] Advantageously, the methyl dihydrojasmonate of the present invention has a purity of more than 90%, preferably more than 95%, more preferably more than 96%, even more preferably more than 99%, even more preferably more than 99.5% and most preferably more than 99.9%.

[0028] It is well known to those skilled in the art that the sensory properties of flavoring substances may depend on the presence and amount of some impurities. Therefore, the preparation method is important for the taste of the final compound. Advantageously, it has been found that the methyl dihydrojasmonate of the present invention exhibits satisfactory sensory properties. It is noteworthy that the sensory profile of the methyl dihydrojasmonate of the present invention is comparable to that of fossil-derived methyl dihydrojasmonate, especially those synthesized from adipic acid, cyclopentene, or dicyclopentadiene.

[0029] Cyclopentanone The present invention relates to cyclopentanone having a biobased carbon content of at least 50%, preferably at least 70%. Typically, the cyclopentanone according to the present invention has a biobased carbon content of at most 105%, preferably at most 100%, more preferably less than 100%.

[0030] According to another aspect, the number of bio-based carbon atoms in the cyclopentanone according to the present invention is greater than or equal to 2, preferably greater than or equal to 3, more preferably greater than or equal to 4. In a particular embodiment, all carbon atoms in the cyclopentanone according to the present invention are bio-based.

[0031] The present invention further relates to compositions comprising, or consisting essentially of, cyclopentanone having a biobased carbon content of 50% or more, preferably 70% or more.

[0032] The bio-based cyclopentanone of the present invention preferably has an average isotope content of -25 to -8‰, preferably -24‰ to -9‰, more preferably -15‰ to -9‰. 13 C deviation may be indicated.

[0033] Said cyclopentanone may constitute the main compound of the composition according to the invention. Thus, said cyclopentanone may be present in more than 50%, preferably more than 70%, more preferably more than 80% by weight of the total composition. In a more preferred embodiment of the invention, said cyclopentanone may be present in more than 90%, preferably more than 95%, more preferably more than 96%, more preferably more than 99%, most preferably more than 99.5% by weight of the total composition. Impurities may be present in an amount of 1 ppm to 5000 ppm, preferably 1 ppm to 500 ppm, more preferably 1 ppm to 50 ppm, most preferably 1 ppm to 20 ppm by weight of the total composition.

[0034] Therefore, in a particular embodiment of the present invention, impurities may be present in an amount of 1 ppm to 100 ppm, preferably 1 ppm to 50 ppm, and more preferably 1 ppm to 10 ppm, based on the total weight of cyclopentanone.

[0035] Advantageously, the cyclopentanone of the present invention has a purity of more than 90%, preferably more than 95%, more preferably more than 96%, even more preferably more than 99%, even more preferably more than 99.5% and most preferably more than 99.9%.

[0036] According to a particular embodiment of the present invention, the cyclopentanone has a purity of 90% to 99.5% and contains at least one compound selected from cyclopentanol and tetrahydrofurfuryl alcohol.

[0037] The present invention further comprises: - 90% to 99.5% by weight, preferably 92% to 98% by weight, more preferably 94% to 96% by weight, most preferably about 95% by weight of cyclopentanone, 0.5% to 10% by weight, preferably 2% to 8% by weight, more preferably 4% to 6% by weight, and most preferably about 5% by weight of at least one compound selected from cyclopentanol and tetrahydrofurfuryl alcohol; Preferably, the composition of the present invention comprises cyclopentanone, wherein the cyclopentanone has a biobased carbon content of 50% or more, or the number of biobased carbon atoms is 2 or more.

[0038] Preferably, the composition of the invention comprises cyclopentanone, the cyclopentanone having a biobased carbon content of 70% or more and / or the number of carbon atoms of biobased origin is 3 or more, preferably 4 or more. Preferably, the composition of the invention comprises cyclopentanone, the cyclopentanone having an average isotopic ratio of -25‰ to -8‰, more preferably -24‰ to -9‰, more preferably -15‰ to -9‰. 13 C indicates deviation.

[0039] It is well known to those skilled in the art that the sensory properties of flavoring substances may depend on the presence and amount of some impurities. Therefore, the preparation method is important for the taste of the final compound. Advantageously, it has been found that the cyclopentanones of the present invention exhibit satisfactory properties, in particular for use in the preparation of flavors and / or fragrances, in particular methyl dihydrojasmonate, and in electronics, in particular as a solvent for semiconductor manufacturing.

[0040] Manufacturing method In another aspect, the present invention relates to a method for preparing methyl dihydrojasmonate and / or cyclopentanone and / or the composition according to the present invention from furfuryl alcohol having a bio-based carbon content of 50% or more. The furfuryl alcohol used in the preparation of methyl dihydrojasmonate and / or cyclopentanone according to the present invention is bio-based furfuryl alcohol.

[0041] Furfuryl alcohol having a biobased carbon content of more than 50% is hereinafter also referred to as "bio-based furfuryl alcohol". The bio-based furfuryl alcohol according to the present invention may have a bio-based carbon content of more than 70%, preferably more than 85%, more preferably more than 90%, more preferably more than 95%, more preferably more than 98%, more preferably more than 99%. Bio-based furfuryl alcohol is a commercial product. Typically, the bio-based furfuryl alcohol according to the present invention may have a bio-based carbon content of 105% or less, preferably 103% or less, more preferably 100% or less. Being of natural origin, the raw furfuryl alcohol may contain some impurities. The impurities may be specific to the origin of the compound. Typically, the content of each impurity in the bio-based furfuryl alcohol may be contained in a range of 0.005-0.1%, more preferably 0.01-0.08%.

[0042] It may be obtained naturally from naturally occurring substrates such as furfural by various methods, such as hydrogenation. For example, furfural can be obtained by decomposing wood hemicellulose into xylose, and then dehydrating the xylose into furfural. Current commercial processes usually start with biomass waste, such as wood or corn stover. Being of natural origin, raw furfural may contain some impurities. Said impurities may be specific to the origin of the compound. Typically, the content of each impurity in bio-based furfural may be contained in 0.005-0.1%, more preferably 0.01-0.08%.

[0043] The bio-based furfuryl alcohol used in the present invention preferably has an average isotope content of -25 to -12‰, more preferably -24 to -14‰. 13 C deviation may be indicated.

[0044] According to another particular embodiment, the bio-based furfuryl alcohol used in the present invention may exhibit an average isotopic deviation of -15‰ to -8‰, preferably -13‰ to -9‰.

[0045] Pentanal The pentanal may be a bio-based pentanal or a non-bio-based pentanal.

[0046] According to a preferred embodiment of the present invention, the pentanals, hereinafter also referred to as "bio-based pentanals", have a bio-based carbon content of more than 50%. The bio-based pentanals according to the present invention may have a bio-based carbon content of more than 60%, preferably between 75% and 105%, more preferably between 90% and 103%, more preferably between 95% and 100%, more preferably between 98% and 100%, more preferably between 99% and 100%.

[0047] The pentanals may be of fossil origin. According to certain embodiments, the pentanals may be upcycled, for example, the pentanals may be obtained from waste or by-products of plastics manufacturing.

[0048] Being of natural origin, untreated pentanal may contain impurities. The impurities may be specific to the origin of the compound. Typically, the content of each impurity in bio-based pentanal may be comprised between 0.005 and 0.1%, more preferably between 0.01 and 0.08%.

[0049] Dimethyl malonate The dimethyl malonate may be bio-based or non-bio-based dimethyl malonate.

[0050] According to a preferred embodiment of the present invention, the dimethyl malonate has a biobased carbon content of more than 50%, hereinafter also referred to as "biobased dimethyl malonate". The biobased dimethyl malonate according to the present invention may have a biobased carbon content of more than 60%, preferably between 75% and 105%, more preferably between 90% and 103%, more preferably between 95% and 100%, more preferably between 98% and 100%, more preferably between 99% and 100%.

[0051] Dimethyl malonate is obtained from malonic acid, preferably with an average isotope of -22 to -17‰. 13 C indicates deviation.

[0052] Bio-based dimethyl malonate can be obtained by fermenting glucose to produce malonic acid (see, for example, WO 2021 / 042058), followed by esterification with methanol, preferably bio-based methanol.

[0053] Step (a) - Hydrogenation According to the invention, the process for preparing cyclopentanone or the composition of the invention comprises the steps of: - (a) hydrogenating the bio-based furfuryl alcohol; Includes.

[0054] According to the present invention, a method for preparing methyl dihydrojasmonate comprises the steps of: - (a) hydrogenating the bio-based furfuryl alcohol; Includes.

[0055] After step (a), bio-based cyclopentanone or a composition comprising bio-based cyclopentanone is obtained.

[0056] Step (a) is a hydrogenation step. Step (a) can be carried out according to the conditions described in Appl. Catal. B: Environ. 2014, 154-155, 294.

[0057] Step (a) may produce some impurities, namely cyclopentanol and / or tetrahydrofurfuryl alcohol.

[0058] Step (a) is usually carried out in an aqueous solvent, and preferably step (a) is carried out in water.

[0059] The aqueous solvent may be a mixture of water and a water-soluble organic solvent, preferably the water-soluble organic solvent is selected from alcohol and ethyl acetate, more preferably selected from the group consisting of ethanol, isopropanol, and ethyl acetate.

[0060] Usually, the concentration of furfuryl alcohol in the aqueous solvent is less than 30% by weight, preferably less than 20%, more preferably less than 10%, and even more preferably less than 8% by weight.

[0061] Usually, step (a) is carried out at a pH of 2-6, preferably 3-5.

[0062] Usually, step (a) is carried out in a H2 atmosphere, preferably at a pressure of 5 to 50 bar, more preferably 10 to 40 bar, and even more preferably 20 to 30 bar.

[0063] Usually, step (a) is carried out at a temperature of 120°C to 200°C, preferably at a temperature of 150°C to 180°C.

[0064] The hydrogenation reaction (step (a)) is usually catalysed, preferably the catalyst is a metal catalyst, the metal preferably being selected from Cu, Pd, Pt, Ni, Au, Rh, Ru. The catalyst may preferably be a nickel-based catalyst, preferably Raney Nickel.

[0065] Usually, the amount of catalyst is 20% by weight or less, preferably 10% by weight or less, more preferably 1% by weight or less. Usually, the amount of catalyst is 0.001% by weight or more, preferably 0.01% by weight or less, more preferably 0.1% by weight or less.

[0066] Advantageously, furfuryl alcohol is first hydrogenated to form a compound of formula (I), which is then hydrolyzed to form a compound of formula (II). Compound of formula (II) is then hydrogenated under the same reaction conditions to form cyclopentanone. This one-pot process is shown in the scheme below. [ka]

[0067] After the hydrogenation reaction, the resulting bio-based cyclopentanone can be separated from the reaction mixture by standard separation techniques.

[0068] After step (a), - from 1% to 10% by weight, preferably from 1.5% to 5% by weight, more preferably from 2% to 4% by weight of cyclopentanone, - 0.01% to 1% by weight, preferably 0.05% to 0.5% by weight, of cyclopentanol, and - 0.001% to 0.5% by weight, preferably 0.01% to 0.1% by weight, of tetrahydrofurfuryl alcohol 1. An aqueous composition comprising:

[0069] The composition obtained after step (a) can be purified by azeotropic distillation of a composition containing water, cyclopentanone, and cyclopentanol. The distilled azeotrope is then further purified by decantation. The organic phase is then further distilled to obtain purified cyclopentanone.

[0070] The distillation can be carried out at atmospheric pressure or under reduced pressure, however, preferably the distillation is carried out under reduced pressure. The use of reduced pressure prevents decomposition of the cyclopentanone.

[0071] Alternatively, the reaction mixture obtained after the hydrogenation step (a) may be used in its existing form, for example in step (b).

[0072] Step (b) - Aldol reaction According to the present invention, a method for preparing methyl dihydrojasmonate comprises the steps of: - reacting the bio-based cyclopentanone with pentanal (b); Further includes.

[0073] Preferably, step (b) is carried out after step (a). The pentanal may be bio-based pentanal or fossil-derived pentanal, such as upcycled pentanal. According to a particular embodiment, the pentanal may be obtained from a fatty acid, such as myristic acid or lauric acid.

[0074] Step (b) is an aldol condensation. Step (b) can be carried out according to the conditions described in U.S. Pat. No. 4,260,830 or U.S. Pat. No. 3,158,644.

[0075] Step (b) is usually carried out in the presence of a base, preferably NaOH. The amount of pentanal is usually 0.5 to 1.2 equivalents. Step (b) is usually carried out in water.

[0076] Step (b) may be carried out at ambient temperature.

[0077] After dehydration and isomerization of the carbon-carbon double bond, the compound of formula (III) is obtained. [ka]

[0078] According to the present invention, the compound of formula (III) may have a biobased carbon content of 50% or more, preferably 70% or more. Typically, the compound of formula (III) according to the present invention has a biobased carbon content of 105% or less, preferably 100% or less, more preferably less than 100%.

[0079] According to another aspect, the number of carbon atoms of bio-based origin in the compound of formula (III) according to the present invention is at least 2, preferably at least 3, more preferably at least 4, preferably at least 5. In a particular embodiment, all carbon atoms in the compound of formula (III) according to the present invention are bio-based.

[0080] Step (c) - Michael Addition According to the present invention, a method for preparing methyl dihydrojasmonate comprises the steps of: - step (c) of reacting the compound of formula (III) with dimethyl malonate. Further includes.

[0081] Preferably, step (c) is carried out after step (b), preferably after steps (a) and (b). Dimethyl malonate may be bio-based or fossil-derived dimethyl malonate. Bio-based dimethyl malonate can be obtained by fermentation of glucose (see, for example, WO 2021 / 042058) followed by esterification with bio-based methanol.

[0082] Step (c) is a Michael addition. Step (c) can be carried out according to the conditions described in U.S. Pat. No. 4,260,830.

[0083] Step (c) is usually carried out in the presence of a base, preferably NaOH. The amount of dimethyl malonate is usually 1.0 to 1.5 equivalents. Step (c) is usually carried out in a solvent containing an alcohol, preferably a solvent containing methanol.

[0084] Step (c) may be carried out at a temperature from -10°C to ambient temperature.

[0085] After decarboxylation, methyl dihydrojasmonate is obtained.

[0086] Usually, a mixture of diastereoisomers is obtained (cis and trans), each diastereoisomer being obtained as a racemic mixture.

[0087] According to the present invention, the obtained methyl dihydrojasmonate may have a biobased carbon content of 30% or more, preferably 35% or more, more preferably 38% or more. Typically, the methyl dihydrojasmonate according to the present invention has a biobased carbon content of 105% or less, preferably 100% or less, more preferably less than 100%.

[0088] According to another aspect, the number of bio-based carbon atoms of the methyl dihydrojasmonate according to the present invention is at least 2, preferably at least 3, more preferably at least 4, preferably at least 5. In a particular embodiment, all carbon atoms of the methyl dihydrojasmonate according to the present invention are bio-based.

[0089] In another aspect of the invention, methyl dihydrojasmonate and / or cyclopentanone and / or compositions obtained by the above disclosed methods are subject of the present invention. These compounds differ from those already known in the art by the fact that they are prepared in part or in whole from raw materials derived from natural or renewable sources.

[0090] This specificity of methyl dihydrojasmonate and / or cyclopentanone and / or the composition may be used to measure the biobased carbon content and / or average isotope ratio. 13 C deviation can be determined.

[0091] The methyl dihydrojasmonate and / or cyclopentanone and / or composition of the present invention can be advantageously used as a flavor or fragrance or as a solvent for the production of semiconductors. Preferably, the methyl dihydrojasmonate and / or cyclopentanone and / or composition of the present invention can be used in industry, such as the food, pharmaceutical or cosmetic industry, in particular for example in the production of fragrances.

[0092] Another object of the present invention relates to a composition containing the methyl dihydrojasmonate and / or cyclopentanone and / or composition of the present invention, preferably selected from the group consisting of food, beverages, cosmetic preparations, pharmaceutical preparations, and fragrances. The disclosures of all patent applications and publications cited herein are hereby incorporated by reference to the extent that they provide exemplary, procedural or other details complementary to those set forth herein. In the event that the disclosures of any of the patents, patent applications and publications incorporated herein by reference conflict with the present specification to the extent that a term may become unclear, the present specification shall control.

[0093] Each and every claim is incorporated into this specification as an embodiment of the present invention. Accordingly, the claims are a further description and in addition to the preferred embodiments of the present invention.

[0094] While preferred embodiments of the present invention have been shown and described, modifications thereof can be made by one skilled in the art without departing from the spirit or teachings of the present invention. The embodiments described herein are illustrative only and not limiting. Many variations and modifications of the system and method are possible and are within the scope of the present invention.

[0095] Accordingly, the scope of protection is not limited by the description set forth above, but is only limited by the scope of the following claims, that scope including all equivalents of the subject matter of the claims.

[0096] To the extent that the disclosures of any patents, patent applications, and publications incorporated herein by reference conflict with the statements in this application to the extent that any term may be unclear, the statements in this application shall control. EXAMPLES

[0097] Example 1: Preparation of bio-based cyclopentanone 3 g of bio-based furfuryl alcohol (100% bio-based carbon content) was hydrogenated in 60 mL of water in the presence of nickel catalyst (30 mg) at a hydrogen pressure of 30 bar and a temperature of 160°C.

[0098] After stirring for 3-4 hours, the reaction mixture is analyzed. Bio-based cyclopentanone is obtained, showing a bio-based carbon content of 100%. Conversion is 100%.

[0099] Example 2: Preparation of bio-based methyl dihydrojasmonate. The bio-based cyclopentanone of Example 1 (100% bio-based carbon content) is reacted with pentanal to produce the compound of formula (III).

[0100] The compound of formula (III) is then reacted with 100% biobased dimethyl malonate, which has a biobased carbon content of 100%.

[0101] Methyl dihydrojasmonate was obtained, showing a biobased carbon content of 62%.

Claims

1. Methyl dihydrojasmonate having a biobased carbon content of 30% or greater and / or having two or more carbon atoms of biobased origin.

2. 2. The methyl dihydrojasmonate of claim 1, having a biobased carbon content of 35% or more, preferably 38% or more, and / or having a number of carbon atoms of biobased origin of 5 or more, preferably 7 or more.

3. Cyclopentanone having a biobased carbon content of 50% or greater, or having two or more carbon atoms of biobased origin.

4. 4. The cyclopentanone of claim 3, having a biobased carbon content of 70% or more and / or having a number of carbon atoms of biobased origin of 3 or more, preferably 4 or more.

5. Average isotopes of -25 to -8‰, more preferably -24 to -9‰ １３ 4. The cyclopentanone of claim 3, exhibiting a C deviation.

6. 90% to 99.5% by weight, preferably 92% to 98% by weight, more preferably 94% to 96% by weight, and most preferably about 95% by weight of cyclopentanone; 0.5% to 10% by weight, preferably 2% to 8% by weight, more preferably 4% to 6% by weight, and most preferably about 5% by weight of at least one compound selected from cyclopentanol and tetrahydrofurfuryl alcohol; A composition comprising:

7. 7. The composition of claim 6, wherein the cyclopentanone has a biobased carbon content of 50% or greater, or the number of biobased carbon atoms is 2 or greater.

8. 8. The composition of claim 7, wherein the cyclopentanone has a biobased carbon content of 70% or more and / or the number of carbon atoms of biobased origin is 3 or more, preferably 4 or more.

9. Cyclopentanone has an average isotope of -25 to -8‰, more preferably -24 to -9‰ １３ The composition of claim 6, exhibiting a C deviation.

10. A method for preparing methyl dihydrojasmonate as defined in claim 1, cyclopentanone as defined in claim 3, or a composition as defined in claim 6 from biobased furfuryl alcohol having a biobased carbon content of 50% or more.

11. 11. A method for preparing methyl dihydrojasmonate or cyclopentanone or the composition of claim 10, comprising step (a) in which bio-based furfuryl alcohol is hydrogenated.

12. 11. The method for preparing methyl dihydrojasmonate according to claim 10, further comprising step (b) wherein bio-based cyclopentanone is reacted with pentanal to form the compound of formula (III).

13. 11. The process for preparing methyl dihydrojasmonate according to claim 10, further comprising a step (c) in which the compound of formula (III) is reacted with dimethyl malonate.

14. Use of cyclopentanone as defined in claim 3 or a composition as defined in claim 6 for the preparation of flavors and / or fragrances or in electronic devices, or use of methyl dihydrojasmonate as defined in claim 1 as a flavor or fragrance, in particular in perfumes, cosmetics, pharmaceuticals.

15. A composition comprising methyl dihydrojasmonate as defined in claim 1 and / or cyclopentanone as defined in claim 3 and / or a composition as defined in claim 6, preferably selected from the group consisting of foods, beverages, cosmetic preparations, pharmaceutical preparations and fragrances.