Novel furan compounds and their use in fragrance formulations

Abstract

The present invention relates to a novel furan compound, 2,2,6,6,7,8,8-heptamethyl-3,3a,4,5,5a,6,7,8-octahydro-2H-indeno[4,5-b]furan, and its use as a fragrance ingredient.

Description

Technical Field

[0001] Status of Related Applications This application claims priority to U.S. Provisional Patent Application No. 63 / 256,146, filed Oct. 15, 2021, the entire contents of which are hereby incorporated by reference herein as if fully set forth.

[0002] Field of the Invention The present invention relates to novel chemical substances and their use in imparting enhanced synergistic odor properties to certain fragrance formulations.

Background Art

[0003] In the fragrance industry, there is a constant need to provide novel chemical substances so that perfumers and others can create novel fragrances for perfumes, colognes, and personal care products. Those skilled in the art understand what differences in the chemical structure of molecules can bring meaningful differences in odor, fragrance notes, and molecular characteristics. They are diverse, and since there is a constant need to discover and use novel chemical substances for the development of novel fragrances, perfumers are applying novel compounds in creating novel fragrances.

Summary of the Invention

Problems to be Solved by the Invention

[0004] The present invention provides an unexpected and advantageous use of novel furan compounds and their enhancement, improvement, or modification of the fragrance of perfumes, colognes, eau de toilettes, fabric care products, personal products, and other like items.

Means for Solving the Problems

[0005] More specifically, the present invention provides Formula I shown below:

Chemical Formula

[0006] Another embodiment of the present invention relates to a fragrance formulation comprising a compound of formula I.

[0007] Another embodiment of the present invention relates to a fragrance formulation comprising the compound of formula I and 2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan.

[0008] Another embodiment of the present invention relates to a fragrance formulation comprising about 0.1% by weight or more of the compound of formula I and about 85 to about 99% by weight of 2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan.

[0009] Another embodiment of the present invention relates to a method for improving, enhancing, or modifying another fragrance formulation, comprising the step of adding the fragrance formulation described above to the other fragrance formulation.

[0010] Another embodiment of the present invention relates to a fragrance product comprising the fragrance formulation described above.

[0011] The above-mentioned and other embodiments of the present invention will become apparent by reading the following specification. [Modes for carrying out the invention]

[0012] The present invention relates to a novel fragrance compound, 2,2,6,6,7,8,8-heptamethyl-3,3a,4,5,5a,6,7,8-octahydro-2H-indeno[4,5-b]furan (Formula I), and its use in perfume formulations, particularly in perfume formulations containing 2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan. The novel fragrance compound of the present invention provides a synergistic effect that unexpectedly and advantageously increases the intensity and complexity of the scent of perfume formulations containing 2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan.

[0013] Since the compounds of the present invention contain a chiral center, those skilled in the art will recognize that multiple stereoisomers of the claimed compound are provided. The compound of formula I contains a chiral center at positions 3a, 5a and 7, and the individual isomers are, for example, (3aS,5aS,7R)-2,2,6,6,7,8,8-heptamethyl-3,3a,4,5,5a,6,7,8-octahydro-2H-indeno[4,5-b]furan, (3aR,5aS,7R)-2,2,6,6,7,8,8-heptamethyl-3,3a,4,5,5a,6,7,8-o Octahydro-2H-indeno[4,5-b]furan, (3aS,5aS,7S)-2,2,6,6,7,8,8-heptamethyl-3,3a,4,5,5a,6,7,8-octahydro-2H-indeno[4,5-b]furan, (3aR,5aS,7S)-2,2,6,6,7,8,8-heptamethyl-3,3a,4,5,5a,6,7,8-octahydro-2H-indeno[ 4,5-b]furan, (3aS,5aR,7R)-2,2,6,6,7,8,8-heptamethyl-3,3a,4,5,5a,6,7,8-octahydro-2H-indeno[4,5-b]furan, (3aR,5aR,7R)-2,2,6,6,7,8,8-heptamethyl-3,3a,4,5,5a,6,7,8-octahydro-2H-indeno[4,5-b]furan, (3a (S,5aR,7S)-2,2,6,6,7,8,8-heptamethyl-3,3a,4,5,5a,6,7,8-octahydro-2H-indeno[4,5-b]furan, (3aR,5aR,7S)-2,2,6,6,7,8,8-heptamethyl-3,3a,4,5,5a,6,7,8-octahydro-2H-indeno[4,5-b]furan, or any mixture thereof.

[0014] Formula II shown below: [ka] Formula II The 2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan, represented by , contains chiral centers at positions 3a, 5a, 7, 8a, and 8b.

[0015] The compound of formula II can be any individual isomer or any mixture thereof, for example, (3aR,5aR,7R,8aR,8bS)-2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan, (3aR,5aR,7S,8aR,8bS)-2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan, (3aR,5aR,8aR,8bS)-2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan (structure 1), (3aS,5aR,7R ,8aR,8bS)-2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan, (3aS,5aR,7S,8aR,8bS)-2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan, (3aS,5aR,8aR,8bS)-2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan (structure 2), (3aS,5aR,7R,8aS,8bS)-2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b] Furan, (3aS,5aR,7S,8aS,8bS)-2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan, (3aS,5aR,8aS,8bS)-2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan (structure 3), (3aS,5aR,7R,8aR,8bR)-2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan, (3aS,5aR,7S,8aR,8bR)-2,2,6,6,7,8,8-heptamethyldecahydro -2H-indeno[4,5-b]furan, (3aS,5aR,8aR,8bR)-2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan (structure 4), (3aS,5aR,7R,8aS,8bR)-2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan, (3aS,5aR,7S,8aS,8bR)-2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan and (3aS,5aR,8aS,8bR)-2,2,6,6,7,8Examples include, but are not limited to, 8-heptamethyldecahydro-2H-indeno[4,5-b]furan (structure 5).

[0016] The compounds of the present invention as described herein are intended to include not only individual isomers that can be separated using techniques known to those skilled in the art, but also mixtures of isomers. Preferred techniques include high-performance liquid chromatography, known as HPLC, particularly silica gel chromatography, and gas chromatography trapping, known as GC trapping. However, commercially available products of this type are mostly provided as mixtures.

[0017] 2,2,6,6,7,8,8-heptamethyl-3,3a,4,5,5a,6,7,8-octahydro-2H-indeno[4,5-b]furan (Formula I) can be used alone, in combination with 2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan (Formula II), or in further combination with additional fragrance compositions, solvents, auxiliaries, or other similar substances.

[0018] The present invention relates to an unexpected advantageous increase in the smell intensity and complexity of a fragrance formulation containing a compound of formula II, provided by a compound of formula I. In a preferred embodiment, the fragrance formulation contains a compound of formula I in an amount of about 0.1% by weight or more and a compound of formula II in an amount of about 85 to about 99% by weight. In a more preferred embodiment, the fragrance formulation contains a compound of formula I in an amount of about 0.1 to about 1% by weight and a compound of formula II in an amount of about 85 to about 99% by weight. In an even more preferred embodiment, the fragrance formulation contains a compound of formula I in an amount of about 0.1 to about 1% by weight, a compound of formula II of structure 1 in an amount of about 65 to about 90% by weight, a compound of formula II of structure 2 in an amount of about 0.1 to about 15% by weight, and a compound of formula II of structure 3 in an amount of about 1 to about 20% by weight. The fragrance formulation in this even more preferred embodiment has been shown to provide an unexpectedly excellent desirable synergistic effect on fragrance properties. Optionally, additional isomers of formula II, such as, but not limited to, (3aS,5aR,8aR,8bR)-2,2,6,6,7,8,8-heptamethyldecahydro-2H-inden[4,5-b]furan (structure 4) and / or (3aS,5aR,8aS,8bR)-2,2,6,6,7,8,8-heptamethyldecahydro-2H-inden[4,5-b]furan (structure 5), etc., can also be included in the fragrance formulation in amounts of about 0 to about 5% by weight, respectively. Thus, the present invention has led to the surprising and unexpected discovery that a synergistic effect is achieved by combining the compounds of formula I and formula II at specific mixing levels in a fragrance formulation.

[0019] The properties and types of other usable ingredients are known to those skilled in the art. Many types of fragrances can be used in this invention, and the only limitation is their compatibility with other ingredients used. Suitable fragrances, but are not limited to, include fruits such as almond, apple, cherry, grape, pear, pineapple, orange, strawberry, and raspberry; and floral scents such as musk, lavender-like, rose-like, iris-like, and carnation-like. Other pleasant scents include herbal and woody scents, as well as scents derived from pine, spruce, and other forests. Fragrances can also be derived from various oils such as essential oils or plant materials such as peppermint, spearmint, and similar substances.

[0020] A list of suitable fragrances is provided in U.S. Patent No. 4,534,891, which is incorporated herein by reference as if it were described in its entirety. Other suitable sources of fragrances are listed in Perfumes, Cosmetics and Soaps, Second Edition, edited by WAPoucher, 1959. Among the fragrances listed in this publication are acacia, blackcurrant, chypre, cyclamen, fern, gardenia, hawthorn, heliotrope, honeysuckle, hyacinth, jasmine, lilac, lily, magnolia, mimosa, narcissus, fresh hay, orange blossom, orchid, moss, sweet pea, clover (trefle), tuberose, vanilla, violet, wallflower, and others of the same kind.

[0021] The compounds of the present invention can be used in combination with complementary fragrance compounds. As used herein, the term "complementary fragrance compound" refers to 2-[(4-methylphenyl)methylene]-heptanal (Acalea), isoamyloxyacetate allyl ester (amyl glycolate), (3,3-dimethylcyclohexyl)ethylethylpropane-1,3-geoate (Applelide), (E / Z)-1-ethoxy-1-decene (Arctical), and 2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-butene Bacdanol, 2-methyl-3-[(1,7,7-trimethylbicyclo[2.2.1]hept-2-yl)oxy]exo-1-propanol (Bornafix), 1,2,3,5,6,7-hexahydro-1,1,2,3,3-pentamethyl-4H-inden-4-one (Cashmeran), trimethylcyclopentenylmethyloxabicyclooctane (Cassiffix), 1,1-dimethoxy-3,7-dimethyl-2,6-octadiene (Citral DMA), 3,7-dimethyl-6-octen-1-ol (Citronellol), 3A,4,5,6,7,7A-hexahydro-4,7-methano-1H-indene-5 / 6-ylacetate (Cyclacet), 3A,4,5,6,7,7A-hexahydro-4,7-methano-1H-indene-5 / 6-ylpropionate (Cyclaprop), 3A,4,5,6,7,7A-hexahydro-4,7-methano-1G-indene-5 / 6-ylbutyrate (Cyclobutanate), 1-(2,6,6-trimethyl-3-cyclohexen-1-yl)-2-buten-1-one (Delta Damascone), 3-(4-ethylphenyl)-2,2-dimethylpropanenitrile (Fleuranil), 3-(O / P-ethylphenyl)2,2-dimethylpropionaldehyde (Floralozone), tetrahydro-4-methyl-2-(2-methylpropyl)-2H-pyran-4-ol (Floriffol), 1,3,4,6,7,8-hexahydro-4,6,6,7,8,8-hexamethylcyclopentagamma-2-benzopyran (Galaxolide), 1-(5,5-Dimethyl-1-cyclohexen-1-yl)pento-4-en-1-one (Galbascone), E / Z-3,7-Dimethyl-2,6-octadiene-1-yl acetate (Geranyl Acetate), α-methyl-1,3-benzodioxol-5-propanal (Helional), 1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-1,6-heptadiene-3-one (Hexalon), (Z)-3-hexenyl-2-hydroxybenzoic acid (hexenyl salicylate, CIS-3), 4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one (Ionone) α), 1-(1,2,3,4,5,6,7,8-octahydro-2,3,8,8-tetramethyl-2-naphthalenyl)-ethane-1-one (Iso E Super), methyl 3-oxo-2-pentylcyclopentaneacetate (Kharismal), 2,2,4-trimethyl-4-phenyl-butanenitrile (Khusinil), 3,4,5,6,6-pentamethylhepto-3-en-2-one (Koavone), 3 / 4-(4-hydroxy-4-methylpentyl)cyclohexen-1-carboxyaldehyde (Lyral), 3-methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one (Methyl Ionone) γ), 1-(2,6,6-trimethyl-2-cyclohexen-1-yl)pent-1-en-3-one (Methyl Ionone α Extra), Methyl Ionone N), 3-methyl-4-phenylbutan-2-ol (Muguesia), cyclopentadece-4-en-1-one (Musk Z4), 3,3,4,5,5-pentamethyl-11,13-dioxatricyclo[7.4.0.0<2,6>]tridecet-2(6)-ene (Nebulone), 3,7-dimethyl-2,6-octadiene-1-yl acetate (Neryl Acetate), 3,7-dimethyl-1,3,It is defined as a fragrance compound selected from the group consisting of 6 - octatriene (Ocimene), ortho - tolylethanol (Peomosa), 3 - methyl - 5 - phenylpentanol (Phenoxanol), 1 - methyl - 4-(4 - methyl - 3 - pentenyl) cyclohex - 3 - en - 1 - carboxaldehyde (Precyclemone B), 4 - methyl - 8 - methylene - 2 - adamantanol (Prismantol), 2 - ethyl - 4-(2,2,3 - trimethyl - 3 - cyclopenten - 1 - yl) - 2 - buten - 1 - ol (Sanjinol), 2 - methyl - 4-(2,2,3 - trimethyl - 3 - cyclopenten - 1 - yl) - 2 - buten - 1 - ol (Santaliff), 3 - [cis - 4-(2 - methylpropyl) cyclohexyl] propanal (Starfleur), terpineol, 2,4 - dimethyl - 3 - cyclohexene - 1 - carboxaldehyde (Triplal), decahydro - 2,6,6,7,8,8 - hexamethyl - 2H - indeno[4,5 - B]furan (Trisamber), 2 - tert - butylcyclohexyl acetate (Verdox), (3E) - 4 - methyldec - 3 - en - 5 - one (Veridian), 4 - tert - butylcyclohexyl acetate (Vertenex), acetyl cedrene (Vertofix), 3,6 / 4,6 - dimethylcyclohex - 3 - en - 1 - carboxaldehyde (Vertoliff) and (3Z) - 1 - [(2 - methyl - 2 - propenyl)oxy] - 3 - hexene (Vivaldie).

[0022] As used herein, the terms "a" or "an" are understood to mean one or more. The term "a compound" is understood to mean one or more compounds represented by Formula I or Formula II described herein. The preparation of the compounds of the present invention is described in detail in the examples. Unless otherwise specified, materials were purchased from Aldrich Chemical Company.

[0023] The terms “fragrance formulation,” “fragrance composition,” and “perfume composition” are synonymous and refer to consumer compositions which are mixtures of compounds such as alcohols, aldehydes, ketones, esters, ethers, lactones, nitriles, natural oils, synthetic oils, and mercaptans, in which the combination of scents of individual components is mixed to create a pleasant or desired fragrance. The fragrance formulation of the present invention is a consumer composition comprising the compound of Formula I of the present invention. The fragrance formulation of the present invention is a consumer composition comprising the compounds of Formula I and Formula II of the present invention. The fragrance formulation of the present invention further comprises the compound of the present invention and the complementary fragrance compounds defined above.

[0024] "Fragrance products" and "functional products" are synonymous and refer to consumer products that contain fragrance ingredients that add fragrance or mask unpleasant odors. Fragrance products include, for example, cosmetics such as perfumes, colognes, eau de toilettes, bar soaps, liquid soaps, shower gels, effervescent bath products, creams, lotions, and shaving products; personal care and skincare products; hair care products such as shampoos, rinses, conditioners, bleaches, colorants, dyes, and styling products; deodorants and antiperspirants; feminine care products such as tampons and sanitary napkins; baby care products such as diapers, bibs, and wipes; family care products such as toilet paper, facial tissues, paper handkerchiefs, and paper towels; fabric care products such as fabric softeners and fresheners; air care products such as air fresheners and fragrance delivery systems; cosmetic formulations; cleaning products and disinfectants, such as detergents, dishwashing materials, scrubbing compositions, glass and metal cleaners, such as window cleaners, countertop cleaners, floor and carpet cleaners, toilet cleaners, and bleaches. Examples of additives include washing agents, such as general-purpose washing agents, strong washing agents, hand washing agents or laundry detergents and finishing rinses, fine fabric washing agents, dental and oral hygiene products such as toothpaste, toothpaste gel, dental floss, denture cleaners, denture adhesives, toothpaste, teeth whitening agents, and mouthwashes, healthcare and nutrition products, and food products such as snacks and beverages. The fragrance products of the present invention are consumer products containing the compounds of the present invention. The fragrance products of the present invention further contain the compounds of the present invention and the complementary fragrance compounds defined above.

[0025] In the phrase "improvement, enhancement, or modification of a fragrance formulation," the term "improvement" is understood to mean enhancing the characteristics of the fragrance formulation to make them more desirable. The term "enhancement" is understood to mean increasing the potency of the fragrance formulation or imparting improved characteristics to the fragrance formulation. The term "modification" is understood to mean altering the characteristics of the fragrance formulation.

[0026] The term "olfactory acceptable amount" is understood to mean the amount of a compound in a fragrance formulation that contributes to its individual olfactory properties. However, the olfactory effect of a fragrance formulation is the sum of the effects of each fragrance component. Therefore, the compounds of the present invention can be used to improve or enhance the fragrance characteristics of a fragrance formulation or to modify the olfactory response to which other components in the formulation contribute. The olfactory acceptable amount can vary depending on many factors, including other components, their relative amounts, and the desired olfactory effect.

[0027] The amount of the compound of the present invention used in the fragrance formulation varies between about 0.005 and about 70 weight percent, preferably 0.005 and about 50 weight percent, more preferably about 0.5 and about 25 weight percent, and even more preferably about 1 and about 10 weight percent. Those skilled in the art will be able to adopt any desired amount to impart the desired fragrance effect and strength. In addition to the compound of the present invention, other materials may be used together with the fragrance formulation to encapsulate and / or deliver the fragrance. Well-known materials include, but are not limited to, polymers, oligomers, surfactants, other nonpolymers such as emulsifiers, lipids such as fats, waxes, and phospholipids, organic oils, mineral oils, petrolatum, natural oils, perfume fixatives, fibers, starches, sugars, and artificial marble (solid surface) materials such as zeolites and silica. Preferred polymers include polyacrylates, polyureas, polyurethanes, polyacrylamides, polyesters, polyethers, polyamides, poly(acrylate-co-acrylamide), starch, silica, gelatin and gum arabic, alginates, chitosan, polylactic acid, poly(melamine-formaldehyde), poly(urea-formaldehyde), or combinations thereof.

[0028] When used in fragrance formulations, these components enhance the fragrance by imparting additional notes, making the formulation more desirable and noticeable, and adding perceived value. The olfactory properties of these materials not only beautify and elevate the finished accord, but also help improve the performance of other materials in the fragrance.

[0029] Even more surprisingly, the compounds of the present invention have also been found to exhibit superior performance and unexpected advantages in applications against body sweat, environmental odors such as mold and mildew, and malodors in bathrooms and other similar environments. The compounds of the present invention substantially eliminate the perception of malodors and / or prevent the formation of such malodors, and therefore can be used in a wide range of functional products.

[0030] Examples of functional products are given herein to illustrate various aspects of the present invention. However, these are not intended to limit the scope of the present invention. Examples of functional products include conventional indoor fragrance (or deodorizer) compositions, such as indoor fragrance sprays, aerosols or other sprays, fragrance diffusers, wicks or other liquid systems, or solids, such as wax bases used in candles or scented beads, plastics, powders used in scented sachets, or gels used in dry sprays or solid gel sticks, and clothing deodorizers, fabric refreshers, linen sprays, and closet insect repellents used in washing machines, such as detergents, powders, liquids, bleaches, and fabric softeners. Products such as: closet aerosol sprays to suppress solvent odors remaining on clothing in clothing storage areas or dry cleaning; bathroom supplies, such as paper towels, toilet paper, sanitary napkins, individually packaged wet napkins, disposable towels, disposable diapers and diaper pail deodorizers; cleaning agents such as disinfectants and toilet bowl cleaners; cosmetics, such as antiperspirants and deodorants, body deodorants in powder, aerosol, liquid or solid form; and hair care products, such as hairspray, conditioner, rinse, hair color and dye, and permanent wave agents. Hair care products or shampoos containing ingredients such as depilatory agents, hair straightening agents, pomades, creams, lotions, etc., medicated hair care products or shampoos containing ingredients such as selenium sulfide, coal tar, or salicylate, or foot care products such as foot powders, liquids, colognes, etc., aftershave and body lotions, or soaps and synthetic detergents in solid, liquid, foam, powder form, etc., odor control during manufacturing processes in the textile finishing industry and printing industry (ink and paper), etc., pulping, temporary livestock storage and meat processing, wastewater treatment, garbage bags or food waste disposers, etc., or textile finished goods, rubber finished goodsExamples include odor control products in the goods category, automotive deodorizers, agricultural and pet care products such as wastewater treatment for dog kennels and chicken coops, livestock and pet care products such as deodorizers, shampoos, cleaning agents, and animal waste treatment materials, and large-scale enclosed spaces such as auditoriums, subways, and transportation systems.

[0031] Therefore, it will be found that the formulations of the present invention typically contain an odor inhibitor together with a carrier, and that the odor inhibitor can be introduced into a space where an odor is present or onto a substrate to which an odor is attached, either by or from this carrier. For example, the carrier can be an aerosol propellant such as chlorofluoromethane or a solid such as wax, plastic material, rubber, inert powder, or gel. In the case of a wick-type air deodorizer, the carrier is a substantially odorless, low-volatility liquid. In some applications, the formulations of the present invention contain surfactants or disinfectants, while in other applications, the odor inhibitor is present in a fibrous substrate. Many formulations of the present invention also contain fragrance components that impart fragrance to the formulation. Any of the fragrances mentioned above can be used.

[0032] The effective amount of odor suppression is understood to mean the amount of odor suppressant of the present invention used in a functional product that is sensorily effective in weakening a given odor while reducing the sum of the intensity of the odor levels of a given odor present in the space or attached to a substrate. The exact amount of odor suppressant used may vary depending on the type of odor suppressant, the type of carrier used, and the desired degree of odor suppression. Generally, the amount of odor suppressant present is the usual amount required to obtain the desired result. Such amounts are known to those skilled in the art. In preferred embodiments, when used with odor-emitting solid or liquid functional products, such as soaps and detergents, the compound of the present invention may be present in an amount ranging from about 0.005 to about 50 weight percent, preferably about 0.01 to about 20 weight percent, and more preferably about 0.05 to about 5 weight percent, and when used with odor-emitting gaseous functional products, the compound of the present invention may be present in an amount ranging from about 0.1 to 10 mg per cubic meter of air.

[0033] Specific embodiments of the present invention are shown below. Other modifications of the present invention will be readily apparent to those skilled in the art. Such modifications are understood to be within the scope of the present invention. Unless otherwise specified, all percentages used herein are weight percentages, ppm is understood to mean parts per million, L is understood to mean liters, mL is understood to mean milliliters, g is understood to mean grams, Kg is understood to mean kilograms, mol is understood to mean moles, mmol is understood to mean millimoles, psi is understood to mean pounds per square inch, and mmHg is understood to mean millimeters (mm) of mercury (Hg) columns. IFF used in the examples is understood to mean International Flavors & Fragrances Inc., New York, NY, USA. Another aspect of the present invention may be as follows: [1] Compound 2,2,6,6,7,8,8-heptamethyl-3,3a,4,5,5a,6,7,8-octahydro-2H-indeno[4,5-b]furan. [2] A fragrance preparation containing 2,2,6,6,7,8,8-heptamethyl-3,3a,4,5,5a,6,7,8-octahydro-2H-indeno[4,5-b]furan. [3] The fragrance preparation according to [2], comprising 2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan. [4] 2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan is (3aR,5aR,8aR,8bS)-2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan; (3aS,5aR,8aR,8bS)-2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan; (3aS,5aR,8aS,8bS)-2,2,6,6,7, The fragrance formulation according to [3] above, comprising isomers selected from the group consisting of 8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan; (3aS,5aR,8aR,8bR)-2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan; (3aS,5aR,8aS,8bR)-2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan; and mixtures thereof. [5] The fragrance preparation according to [4], wherein 2,2,6,6,7,8,8-heptamethyl-3,3a,4,5,5a,6,7,8-octahydro-2H-indeno[4,5-b]furan is present in an amount of about 0.1% by weight or more, and 2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan is present in an amount of about 85 to about 99% by weight. [6] 2,2,6,6,7,8,8-heptamethyl-3,3a,4,5,5a,6,7,8-octahydro-2H-indeno[4,5-b]furan is present in an amount of approximately 0.1 to approximately 1% by weight, and 2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan is (3aR,5aR,8aR,8bS)-2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan in an amount of approximately 65-90% by weight; (3aS,5aR,8aR,8bS)-2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan in amounts of approximately 0.1 to approximately 15% by weight; (3aS,5aR,8aS,8bS)-2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan in amounts of approximately 1 to approximately 20% by weight; A fragrance preparation according to [5] above, including the above. [7] The fragrance preparation according to [2], further comprising a polymer. [8] The fragrance formulation according to [7], wherein the polymer is selected from the group consisting of polyacrylate, polyurea, polyurethane, polyacrylamide, polyester, polyether, polyamide, poly(acrylate-co-acrylamide), starch, silica, gelatin and gum arabic, alginate, chitosan, polylactic acid, poly(melamine-formaldehyde), poly(urea-formaldehyde) and combinations thereof. [9] A method for improving, enhancing or modifying a first fragrance formulation, comprising the step of adding a second fragrance formulation to the first fragrance formulation, wherein the second fragrance formulation comprises 2,2,6,6,7,8,8-heptamethyl-3,3a,4,5,5a,6,7,8-octahydro-2H-indeno[4,5-b]furan.

[10] The method according to [9], wherein the second fragrance preparation further comprises 2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan.

[11] 2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan is (3aR,5aR,8aR,8bS)-2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan; (3aS,5aR,8aR,8bS)-2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan; (3aS,5aR,8aS,8bS)-2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno The method according to

[10] , comprising isomers selected from the group consisting of [4,5-b]furan; (3aS,5aR,8aR,8bR)-2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan; (3aS,5aR,8aS,8bR)-2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan; and mixtures thereof.

[12] The method according to

[11] , wherein 2,2,6,6,7,8,8-heptamethyl-3,3a,4,5,5a,6,7,8-octahydro-2H-indeno[4,5-b]furan is present in an amount of about 0.1% by weight or more of the second fragrance preparation, and 2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan is present in an amount of about 85 to about 99% by weight of the second fragrance preparation.

[13] 2,2,6,6,7,8,8-heptamethyl-3,3a,4,5,5a,6,7,8-octahydro-2H-indeno[4,5-b]furan is present in the second fragrance preparation in an amount of about 0.1 to about 1% by weight, and 2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan is (3aR,5aR,8aR,8bS)-2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan in an amount of approximately 65 to approximately 90% by weight of the second fragrance preparation; (3aS,5aR,8aR,8bS)-2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan in an amount of about 0.1 to about 15% by weight of the second fragrance preparation; (3aS,5aR,8aS,8bS)-2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan in an amount of about 1 to about 20% by weight of the second fragrance preparation; The method according to

[12] , including the method described above.

[14] A fragrance product comprising the compound described in [1] above.

[15] The fragrance product according to

[14] , further comprising 2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan.

[16] 2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan is (3aR,5aR,8aR,8bS)-2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan; (3aS,5aR,8aR,8bS)-2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan; (3aS,5aR,8aS,8bS)-2,2,6,6,7,8 The fragrance product according to

[15] , comprising isomers selected from the group consisting of 8-heptamethyldecahydro-2H-indeno[4,5-b]furan; (3aS,5aR,8aR,8bR)-2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan; (3aS,5aR,8aS,8bR)-2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan; and mixtures thereof.

[17] The fragrance product is the fragrance product described in

[14] above, selected from the group consisting of perfumes, colognes, eau de toilettes, bar soaps, liquid soaps, shower gels, effervescent bath products, cosmetics, personal care products, skin care products, hair care products, deodorants, antiperspirants, feminine care products, baby care products, family care products, fabric products, air care products, fragrance delivery systems, cosmetic formulations, cleaning products, disinfectants, cleaning agents, dental and oral hygiene products, healthcare and nutrition products, and food products. [Examples]

[0034] Example I [ka] Preparation of 2,2,6,6,7,8,8-heptamethyl-3,3a,4,5,5a,6,7,8-octahydro-2H-indeno[4,5-b]furan (Formula I): 7-methoxy-1,1,2,3,3-pentamethyl-2,3,3a,4,5,6-hexahydro-1H-indene was prepared according to a known method (e.g., U.S. Patent No. 7,312,187). 7-methoxy-1,1,2,3,3-pentamethyl-2,3,3a,4,5,6-hexahydro-1H-indene (270 g) and citric acid (10 g) were placed in a reaction flask. The reaction mixture was heated to 100°C. The temperature was raised to 169°C to remove light substances while adding metharyl alcohol (98 g) over 1.5 hours. The reaction was stopped with sodium acetate, and by reduced-pressure distillation (rushed over), a crude product (279 g) with a boiling point of 137°C at 3 mmHg was obtained. This was then distilled to obtain 2,2,6,6,7,8,8-heptamethyl-3,3a,4,5,5a,6,7,8-octahydro-2H-indeno[4,5-b]furan (formula I) (175 g). 1 H NMR(500MHz,CDCl3)δ:2.66(m,1H),2.07(m,1H),1.17-2.04(m,2H),1.26-1.88(m,2H),1.17-1.68(m,2H),1.3 2(s,3H),1.29(m,1H),1.26(s,3H),1.08(s,3H),1.06(s,3H),0.89(s,3H),0.77(d,J=7.25Hz,3H),0.59(s,3H)

[0035] 2,2,6,6,7,8,8-heptamethyl-3,3a,4,5,5a,6,7,8-octahydro-2H-indeno[4,5-b]furan (Formula I) was described as having a weak woody, warm fragrance.

[0036] Example II [ka] Preparation of 2,2,6,6,7,8,8-heptamethyl-3,3a,4,5,5a,6,7,8-octahydro-2H-indeno[4,5-b]furan (Formula I): Alternatively, 2,2,6,6,7,8,8-heptamethyl-3,3a,4,5,5a,6,7,8-octahydro-2H-indeno[4,5-b]furan was prepared as follows: 1,1,2,3,3-pentamethyl-7-((2-methylallyl)oxy)-2,3,3a,4,5,6-hexahydro-1H-indene was prepared according to a known method (e.g., U.S. Patent No. 7312187). p-toluenesulfonic acid (p-TsOH) (60 g) and toluene (1500 g) were placed in a reaction flask. The reaction mixture was heated under reflux at approximately 110°C. While continuing to heat under reflux, the temperature was slowly increased from approximately 110°C to approximately 130°C, and 1,1,2,3,3-pentamethyl-7-((2-methylallyl)oxy)-2,3,3a,4,5,6-hexahydro-1H-indene (3000g) was added over 4 hours. The reaction mixture was further treated (aged) under reflux at approximately 130°C for 2 hours to obtain the crude product, which was then purified by fractional distillation to obtain 2,2,6,6,7,8,8-heptamethyl-3,3a,4,5,5a,6,7,8-octahydro-2H-indeno[4,5-b]furan (formula I) (1950g), which has a boiling point of 130°C at 2 mmHg. 1H NMR(500MHz,CDCl3)δ:2.66(m,1H),2.07(m,1H),1.17-2.04(m,2H),1.26-1.88(m,2H),1.17-1.68(m,2H),1.3 2(s,3H),1.29(m,1H),1.26(s,3H),1.08(s,3H),1.06(s,3H),0.89(s,3H),0.77(d,J=7.25Hz,3H),0.59(s,3H)

[0037] Example III Identification of 2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan (Formula II) isomers: The isomers of 2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan (commercially available from IFF) were identified by silica gel chromatography using a Biotage® apparatus.

[0038] (3aR,5aR,8aR,8bS)-2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan (Structure 1) 1 H NMR(400MHz,CDCl3)δ:4.06(m,1H),2.61(m,1H),1.59-1.86(m,2H),1.56-1.83(m,2H),1.14-1.45(m,2H),1.37(m,1H),1.3 6(s,3H),1.22(s,3H),1.12(m,1H),0.99(s,3H),0.95(s,3H),0.86(s,3H),0.83(m,1H),0.76(d,J=7.25Hz,3H),0.64(s,3H)

[0039] (3aR,5aR,8aR,8bS)-2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan (structure 1) was described as having an ambergris-like and woody fragrance.

[0040] (3aS,5aR,8aR,8bS)-2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan (structure 2) 1 H NMR(500MHz,CDCl3)δ:3.15(m,1H),1.01-1.86(m,2H),1.29-1.75(m,2H),1.01-1.62(m,2H),1.45(m,1H),1.37(m,1H),1.2 5(s,3H),1.20(s,3H),1.17(m,1H),0.99(m,1H),0.94(s,3H),0.93(s,3H),0.87(s,3H),0.74(d,J=7.25Hz,3H),0.63(s,3H)

[0041] (3aS,5aR,8aR,8bS)-2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan (structure 2) was described as having an ambergris-like and woody fragrance.

[0042] (3aS,5aR,8aS,8bS)-2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan (structure 3) 1 H NMR(500MHz,CDCl3)δ:3.57(m,1H),2.23(m,1H),1.99(m,1H),1.33-1.86(m,2H),1.75(m,1H),1.24-1.74(m,2H),0.92-1.5 9(m,2H),1.35(m,1H),1.29(s,3H),1.23(s,3H),1.09(s,3H),1.00(s,3H),0.93(s,3H),0.82(s,3H),0.71(d,J=7.25Hz,3H)

[0043] (3aS,5aR,8aS,8bS)-2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan (structure 3) was described as having an ambergris-like, woody, and dusty fragrance.

[0044] (3aS,5aR,8aR,8bR)-2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan (structure 4) 1H NMR(600MHz,CDCl3)δ:4.03(m,1H),1.87(m,1H),1.37-1.79(m,2H),1.54-1.61(m,2H),1.36-1.53(m,2H),1.52(m,1H),1.3 9(m,1H),1.34(s,3H),1.27(m,1H),1.19(s,3H),0.96(s,3H),0.89(s,3H),0.85(s,3H),0.76(d,J=7.25Hz,3H),0.59(s,3H)

[0045] (3aS,5aR,8aR,8bR)-2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan (structure 4) was described as having a weak ambergris-like and woody fragrance.

[0046] (3aS,5aR,8aS,8bR)-2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan (structure 5) 1 H NMR(500MHz,CDCl3)δ:4.06(m,1H),2.29(m,1H),2.06(m,1H),1.77(m,2H),1.27-1.63(m,5H),1.28(m,1 H),1.25(s,3H),1.10(s,3H),0.99(s,3H),0.91(s,3H),0.89(s,3H),0.80(s,3H),0.76(d,J=7.25Hz,3H)

[0047] (3aS,5aR,8aS,8bR)-2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan (structure 5) was described as having a weak ambergris-like and woody fragrance.

[0048] Example IV [ka] Preparation of 2,2,6,6,7,8,8-heptamethyl-3,3a,4,5,6,7,8,8b-octahydro-2H-indeno[4,5-b]furan (Formula III): Compound I (prepared as described above, 40 g), palladium catalyst on carbon (Pd / C, 0.4 g), and acetic acid (2 g) were placed in an autoclave and substituted three times with nitrogen, followed by three substitutions with hydrogen. The reaction mixture was heated to approximately 120°C and pressurized to approximately 300 psi. These reaction conditions were maintained until hydrogen uptake was complete. The resulting crude product was further purified by filtration to obtain 2,2,6,6,7,8,8-heptamethyl-3,3a,4,5,6,7,8,8b-octahydro-2H-indeno[4,5-b]furan (Formula III) (36 g). 1 H NMR(600MHz,CDCl3)δ:4.34(d,J=5.85Hz,1H),2.26(m,1H),1.81-1.96(m,2H),1.50-1.90(m,2H),1.46-1.66(m,2H) ,1.51(m,1H),1.29(s,3H),1.24(s,3H),1.04(s,3H),1.01(s,3H),0.94(s,3H),0.87(s,3H),0.87(d,J=7.35Hz,3H)

[0049] 2,2,6,6,7,8,8-Heptamethyl-3,3a,4,5,6,7,8,8b-Octahydro-2H-Indeno[4,5-b]Fran (Formula III) was described as having a moderately strong ambergris-like, woody, warm fragrance.

[0050] Example V The aromatic properties of fragrance formulations containing the compound of formula II and with the compound of formula I added in different amounts (weight %) were evaluated using (i) odor profile; (ii) odor intensity ("intensity") (on a scale of 0 to 10, where 0 = no odor, 1 = very weak, 5 = moderate, 10 = extremely strong); and (iii) degree of complexity ("complexity") (0 = no complexity, 1 = very weak, 5 = moderate, 10 = extremely strong). The evaluations are as follows:

[0051] [Table 1]

[0052] [Table 2]

[0053] The above evaluation yielded an unexpected finding: samples 4-18 were remarkably superior to samples 1-3. To impart the desired fragrance properties to the fragrance formulation, it was necessary to have at least 0.1% by weight of the compound of formula I. Specifically, the desired fragrance properties were obtained with a fragrance formulation containing at least 0.1% by weight of the compound of formula I and at least 85-99% by weight of the compound of formula II. More specifically, a fragrance formulation containing at least 0.1-1% by weight of the compound of formula I, at least 65-90% by weight of the compound of formula II with structure 1, at least 0.1-15% by weight of the compound of formula II with structure 2, and at least 1-20% by weight of the compound of formula II with structure 3 yielded an unexpectedly excellent and desirable synergistic effect on the fragrance properties.

[0054] In contrast, adding 2,2,6,6,7,8,8-heptamethyl-3,3a,4,5,6,7,8,8b-octahydro-2H-indeno[4,5-b]furan (formula III) (0.1% by weight), an analog of the compound of formula I, to a fragrance preparation containing the compound of formula II did not result in a synergistic fragrance effect.

[0055] Therefore, the present invention has led to the surprising and unexpected discovery that a synergistic effect can be achieved by combining the compounds of Formula I and Formula II in a fragrance formulation at specific mixing levels.

[0056] Example VI The fragrance formulations exemplified below demonstrate that unexpectedly excellent synergistic effects can be obtained in fragrance formulations containing compounds of Formula I and Formula II. The formulation containing Formula I / Formula II contains 0.46% by weight of compound I, 73.57% by weight of compound II of structure 1, 6.04% by weight of compound II of structure 2, and 14.21% by weight of compound II of structure 3. The accord exhibits a warm, ambergris-like and woody scent, with a consistent odor and volume over time, strong persistence, and a pleasant, clean, ambergris-like scent that lingers for a long time.

[0057] [Table 3]

Claims

1. Compound 2,2,6,6,7,8,8-heptamethyl-3,3a,4,5,5a,6,7,8-octahydro-2H-indeno[4,5-b]furan.

2. A fragrance preparation containing 2,2,6,6,7,8,8-heptamethyl-3,3a,4,5,5a,6,7,8-octahydro-2H-indeno[4,5-b]furan.

3. The fragrance formulation according to claim 2, comprising 2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan.

4. 2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan is (3aR,5aR,8aR,8bS)-2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan; (3aS,5aR,8aR,8bS)-2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan; (3aS,5aR,8aS,8bS)-2,2,6,6,7,8 A fragrance formulation according to claim 3, comprising isomers selected from the group consisting of ,8-heptamethyldecahydro-2H-indeno[4,5-b]furan; (3aS,5aR,8aR,8bR)-2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan; (3aS,5aR,8aS,8bR)-2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan; and mixtures thereof.

5. The fragrance formulation according to claim 4, wherein 2,2,6,6,7,8,8-heptamethyl-3,3a,4,5,5a,6,7,8-octahydro-2H-indeno[4,5-b]furan is present in an amount of 0.1% by weight or more, and 2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan is present in an amount of 85 to 99% by weight.

6. 2,2,6,6,7,8,8-heptamethyl-3,3a,4,5,5a,6,7,8-octahydro-2H-indeno[4,5-b]furan is present in an amount of 0.1 to 1% by weight, and 2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan is (3aR,5aR,8aR,8bS)-2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan in an amount of 65-90% by weight; (3aS,5aR,8aR,8bS)-2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan in an amount of 0.1 to 15% by weight; (3aS,5aR,8aS,8bS)-2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan in amounts of 1 to 20% by weight; A fragrance preparation according to claim 5, comprising:

7. The fragrance formulation according to claim 2, further comprising a polymer.

8. The fragrance formulation according to claim 7, wherein the polymer is selected from the group consisting of polyacrylate, polyurea, polyurethane, polyacrylamide, polyester, polyether, polyamide, poly(acrylate-co-acrylamide), starch, silica, gelatin and gum arabic, alginate, chitosan, polylactic acid, poly(melamine-formaldehyde), poly(urea-formaldehyde) and combinations thereof.

9. A method for improving, enhancing, or modifying a first fragrance formulation, comprising the step of adding a second fragrance formulation to the first fragrance formulation, wherein the second fragrance formulation comprises 2,2,6,6,7,8,8-heptamethyl-3,3a,4,5,5a,6,7,8-octahydro-2H-indeno[4,5-b]furan.

10. The method according to claim 9, wherein the second fragrance preparation further comprises 2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan.

11. 2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan is (3aR,5aR,8aR,8bS)-2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan; (3aS,5aR,8aR,8bS)-2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan; (3aS,5aR,8aS,8bS)-2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno The method according to claim 10, comprising isomers selected from the group consisting of [4,5-b]furan; (3aS,5aR,8aR,8bR)-2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan; (3aS,5aR,8aS,8bR)-2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan; and mixtures thereof.

12. The method according to claim 11, wherein 2,2,6,6,7,8,8-heptamethyl-3,3a,4,5,5a,6,7,8-octahydro-2H-indeno[4,5-b]furan is present in an amount of 0.1% by weight or more of the second fragrance formulation, and 2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan is present in an amount of 85 to 99% by weight of the second fragrance formulation.

13. 2,2,6,6,7,8,8-heptamethyl-3,3a,4,5,5a,6,7,8-octahydro-2H-indeno[4,5-b]furan is present in the second fragrance formulation in an amount of 0.1 to 1% by weight, and 2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan is, (3aR,5aR,8aR,8bS)-2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan in an amount of 65 to 90% by weight of the second fragrance preparation; (3aS,5aR,8aR,8bS)-2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan in an amount of 0.1 to 15% by weight of the second fragrance preparation; (3aS,5aR,8aS,8bS)-2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan in an amount of 1 to 20% by weight of the second fragrance preparation; The method according to claim 12, including the method described in claim 12.

14. A fragrance product comprising the compound described in claim 1.

15. The fragrance product according to claim 14, further comprising 2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan.

16. 2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan is (3aR,5aR,8aR,8bS)-2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan; (3aS,5aR,8aR,8bS)-2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan; (3aS,5aR,8aS,8bS)-2,2,6,6,7,8,8 A fragrance product according to claim 15, comprising isomers selected from the group consisting of -heptamethyldecahydro-2H-indeno[4,5-b]furan; (3aS,5aR,8aR,8bR)-2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan; (3aS,5aR,8aS,8bR)-2,2,6,6,7,8,8-heptamethyldecahydro-2H-indeno[4,5-b]furan; and mixtures thereof.

17. The fragrance product according to claim 14, wherein the fragrance product is selected from the group consisting of perfumes, colognes, eau de toilettes, bar soaps, liquid soaps, shower gels, effervescent bath products, cosmetics, personal care products, skin care products, hair care products, deodorants, antiperspirants, feminine care products, baby care products, family care products, fabric products, air care products, fragrance delivery systems, cosmetic formulations, cleaning products, disinfectants, cleaning agents, dental and oral hygiene products, healthcare and nutrition products, and food products.

Images