Miscellaneous Odorants

by John C. Leffingwell, Ph.D.

Photo by permission of M. Roudintska - Art & Parfum

Cyclic Terpenoid Odorants Bicyclic Terpenoid Odorants Acyclic Terpenoid Odorants

Ionones, Irones, Damascones & Structurally Related Odorants Acyclics (Alcohols, Esters, Acids, Aldehydes) Lactones Sesquiterpenoid Related Odorants

Steroid Urine Type Odorants Sandalwood Type Odorants Musk Odorants Miscellaneous

Enantiomer & Odor Description Odour Threshold (PPB) Miscellaneous (-)-(6S,7S)-5,6,7,8-tetrahydro-3,5,5,6,7,8,8-heptamethyl-2-naphthalenecarbonitrile - earthy and musky odor, the bottom note of which is provided with a humus-like and earthy character, possesses a stronger and woodier note than its (+)-(6R,7R) enantiomer NA (+)-(6R,7R) -5,6,7,8-tetrahydro-3,5,5,6,7,8,8-heptamethyl-2-naphthalenecarbonitrile - earthy and musky odor, the bottom note of which is provided with a humus-like and earthy character, weaker & less and woody note than its (-)-(6S,7S)- enantiomer NA (-)-( 6S ,7S )-5,6,7,8-tetrahydro-3,5,5,6,7,8,8-heptamethyl-2-naphthalenecarbaldehyde - possesses the best developed odor properties. Its musky, markedly earthy, slightly amber character is particularly powerful. It possesses a note which distinguishes itself from that of the (+)-(6R,7R) isomer NA (+)-(6R,7R)-5,6,7,8-tetrahydro-3,5,5,6,7,8,8-heptamethyl-2-naphthalenecarbaldehyde - develops a fragrance of a less earthy character, with a woody side and the strength of which is clearly inferior to the (-)-( 6S ,7S )-isomer NA (-)-(2R)-2-ethyl-4,4-dimethyl-1-cyclohexanone - develops the more strongly herbaceous and thujonic odor of the two, with a pronounced fruity subnote having almost a spicy-berry-like character.  NA (+)-(2S)-2-Ethyl-4,4-dimethyl-1-cyclohexanone - also possesses a herbaceous odor note, which however is less thujonic and drier than that of its enantiomer. Additionally, an earthy, rooty cellar aspect is also present. NA (2R,4S)-(-)-cis-2-methyl-4-propyl.-1,3-oxathiane - sulfurous, herbaceous-green, roasty, linseed oil-like, onion; described by Ohloff as fresh, floral, less sulfury than the 2S,4R-isomer 4 (2S,4R)-(+)-cis-2-methyl-4-propyl.-1,3-oxathiane - sulfurous, fatty, fruity-green, tropical fruits, grapefruits 2 (2R,4R)-(–)-trans-2-methyl-4-propyl.-1,3-oxathiane - green grass, root, earthy, red radish note NA (2S,4S)-(+)-trans-2-methyl-4-propyl.-1,3-oxathiane - sulfurous, slight bloomy-sweet NA (2R,3S,4S)-(-)-cis-2-methyl-4-propyl.-1,3-oxathiane-S-oxide - Grassy, green long lasting, unpleasnnt sulfur note NA (2S,3R,4R)-(+)-cis-2-methyl-4-propyl.-1,3-oxathiane-S-oxide - Intensive, green sulfur note (reminiscent of rhubarb) NA (2R,3R,4S)-(+)-cis-2-methyl-4-propyl.-1,3-oxathiane-S-oxide - Intensive, pungent green foul sulfur note (H2S) NA (2S,3S,4R)-(-)-cis-2-methyl-4-propyl.-1,3-oxathiane-S-oxide - Intensive, exotic fruit note, very volatile NA (1R,2R)-(-)-Z-Methyl jasmonate - weak odor >70 ppb (1S,2S)-(+)-Z-Methyl jasmonate - odorless NA (1R,2S)-(+)-Z-Methyl epijasmonate - Strong odor; floral, true jasmin-like 3 ppb (1S,2R)-(-)-Z-Methyl epijasmonate - odorless NA (1R,2R)-(-)-Methyl dihydrojasmonate - Floral, sweet, jasminelike 240 (recognition) (1R,2R)-(-)-Methyl dihydrojasmonate - Floral, sweet, jasminelike 15360 (recognition) (1R,2S)-(+)-Methyl epidihydrojasmonate - Intensely floral, jasminelike, bright, cis-jasmone, slightly fatty, woody, ß-ionone like, extremely long lasting 15 (recognition) (1S,2R)-(-)-Methyl epidihydrojasmonate - Herbal, fatty, tea-like, tobacco, ß-damascone, cis-jasmone 12500 (recognition) (3S,7R)-(-)-Z-Methyl 4,5-didehydrojasmonate - the natural (3S,7R)-enantiomer has a fresh natural, sweet floral fruity odor, reminiscent of Jasmin and Ylang Ylang flower, more intensive and tenacious that was superior to that of the unnatural (3R,7S)-enantiomer. (3R,7S)-(-)-Z-Methyl 4,5-didehydrojasmonate - a floral green odor with slight metallic green aspect, less intensive than the natural form. (S)-(+)-Lilial® - lily of the valley odor but slightly less strong than the (R)-(-)-isomer NA (R)-(-)-Lilial®- lily of the valley odor but slightly stronger odor than the (S)-(+)-isomer NA (+)-(3S)-1-Methoxyhexane-3-thiol - In addition to the herbaceous and (clary) sage odor tonalities it has strong connotations of burnt sulfur and alliaceous notes and evokes associations with human olfactory axillary perspiration. NA (-)-(3R)-1-Methoxyhexane-3-thiol - sulfury, herbaceous and onion-like and definitely lacks the unique clary-sage signal. NA (-)-(S)-1-methoxyheptane-3-thiol - a nice natural black-currant note accompanied by green and tropical fruit notes. NA (+)-(R)-1-methoxyheptane-3-thiol - 1-methoxyheptane-3-thiol (racemic) imparts a floral, green gardenia note recalling the floral-fruity odor of styrallyl acetate, whereas 1-ethoxyhexane-3-thiol is able to impart a berry, blackberry type and vegetable note. NA (-)-(1R,2S,2'S,4R)-1,2',7,7-tetramethyl-spiro[bicyclo[2.2.1]heptane-2,4'-[1,3]dioxane] - Woody, ambery, camphor, animal, earthy/mossy, musky NA (+)-(1S,2R,2'R,4S)-1,2',7,7-tetramethyl-spiro[bicyclo[2.2.1]heptane-2,4'-[1,3]dioxane] - Woody, animal, camphor, ambery, earthy/mossy, fruity NA (1R,2S,2'S,4R,6'S)-1,2',6',7,7-pentamethylspiro[bicyclo[2.2.1]heptane-2,4'-[1,3]dioxane] - Woody, ambery, animal, earthy/mossy, metallic, musky (see note on assumed configurations at the 2' & 6' positions) NA (1S,2R,2'R,4S,6'R)-1,2',6',7,7-pentamethylspiro[bicyclo[2.2.1]heptane-2,4'-[1,3]dioxane] - odor description of camphor, ambery, woody, agrestic, earthy/mossy, leather is for the racemate (see note on assumed configurations at the 2' & 6' positions) NA (1R,2S,2'S,4R)-2'-ethyl-1,7,7-trimethylspiro[bicyclo[2.2.1]heptane-2,4'-[1,3]dioxane] - Woody, ambery (see note on assumed configuration at the 2' position) NA (1S,2R,2'R,4S)-2'-ethyl-1,7,7-trimethylspiro[bicyclo[2.2.1]heptane-2,4'-[1,3]dioxane] - odor description of woody, ambery, fruity, agrestic, earthy/mossy, camphor, green is for the racemate (see note on assumed configuration at the 2' position) NA (-)-(1R,2S,2'S,4R)-2'-isopropyl-1,7,7-trimethylspiro[bicyclo[2.2.1]heptane-2,4'-[1,3]dioxane] - Amber, woody, cedarwood, animal, strong 0.2 ng/liter (in air) (+)-(1S,2R,2'R,4S)-2'-isopropyl-1,7,7-trimethylspiro[bicyclo[2.2.1]heptane-2,4'-[1,3]dioxane] - Woody, camphoraceous, amber, spicy, weak 88 ng/liter (in air) (+)-(1R,2S,2'R,4R)-2'-isopropyl-1,7,7-trimethylspiro[bicyclo[2.2.1]heptane-2,4'-[1,3]dioxane] - Woody, cedarwood, rosy, spicy, weak 40 ng/liter (in air) (-)-(1S,2R,2'S,4S)-2'-isopropyl-1,7,7-trimethylspiro[bicyclo[2.2.1]heptane-2,4'-[1,3]dioxane] - Woody, piney, slightly amber, weak 40 ng/liter (in air) (1R,2S,4R)-1,7,7-trimethyl-dispiro[bicyclo[2.2.1]heptane-2,4'-(1,3 -dioxane)-2',1"-cyclopentane] - Woody, ambery, fatty, earthy/mossy, tobacco, camphor NA (1S,2R,4S)-1,7,7-trimethyl-dispiro[bicyclo[2.2.1]heptane-2,4'-(1,3 -dioxane)-2',1"-cyclopentane] - odor description of woody, ambery, fruity, agrestic, earthy/mossy, camphor is for the racemate NA (1'S)-(-)-2-Methyl-4-(2,2,3)-trimethylcyclopent-3-en-1-yl)- but-2- enal - Woody, fruity, spicy, fennel-like, sweet, and smooth NA 1'R)-(+)-2-Methyl-4-(2,2,3- trimethylcyclopent-3- en-1- yl)-but-2-enal - Similar to the (-)-antipode, but substantially weaker NA (1'S)-(-)-campholenic aldehyde = (1'S)-(-)-2-(2,2,3- Trimethylcyclopent-3-en-1-yl)-ethanal - Odor Not perceptible NA (1'R)-(+)-campholenic aldehyde = (1'R)-(+ )-2-(2,2,3-Trimethylcyclopent-3-en-1-yl)-ethanal - Intensive green grass like, reminiscent of leaf-aldehyde, spicy NA (R)-(-)-2-Cyclododecylpropanol - strongly ambergris-like/woody with dominating ambergris character and linear scent development NA (S)-(+)-2-Cyclododecylpropanol - very weak, virtually odorless NA (R)-Benzylisobutylcarbinol - a green rose fragrance note NA (S)-Benzylisobutylcarbinol - a particularly interesting floral-green, mimosa, powdery fragrance note, with a very natural effect NA (2R,4S)-cis-2-Methyl-4-phenyl-[1,3]dioxolane - Strong, clear, indole, rose-jasmine, the strongest- and best-smelling enantiomer 125 µg/liter of air (2S,4R)-cis-2-Methyl-4-phenyl-[1,3]dioxolane - Styrene, indole, skatole, hyacinths 384 µg/liter of air (2S,4S)-trans-2-Methyl-4-phenyl-[1,3]dioxolane - Floral, woody, diphenyl ether, rose, animal, chocolate note 384 µg/liter of air (2R,4R)-trans-2-Methyl-4-phenyl-[1,3]dioxolane - Floral, lilac, woody, orange liquid, chocolate note 589 µg/liter of air (+)-(S)-Florhydral® - In comparison with the racemate, the (+)-enantiomer has a more green, less watery, and more powerful fragrance 0.035 ng/l air (-)-R)-Florhydral® - The (-)- enantiomer has a typical racemic Florhydral® smell - floral, fresh, green, muguet-like, but more marine, and more plastic 0.88 ng/l air (+)-2,5-dimethyl-2-indanmethanol has a floral, lily of the valley note evoking the bottom note of Lilial®. NA (-)-2,5-dimethyl-2-indanmethanol is closer to hydroxycitronellal in fragrance than the (+)-isomer. NA (-)-(4S,4aS,8aR)-Geosmin - earthy-musty. The (-) enantiomer is much more odoriferous than the (+) form. The (-)-enantiomer is the one found in nature. 0.0082-0.018 ppb (+)-(4R,4aR,8aS)-Geosmin - earthy-musty. The (+) enantiomer is much weaker in odor than the (-) form 0.066-0.090 ppb (R)-3-methylthiobutanal - exhibits the odour typical of cooked potatoes. NA (S)-3-methylthiobutanal - odourless NA (2S)-(+)-2-hexylcyclopentanone - Powerful diffusive warm jasmine-like floral odor with coconut-like fruity and slightly herbaceous note 70 (2R)-(-)-2-hexylcyclopentanone - Powerful diffusive warm jasmine-like floral odor with somewhat mandarin-like citrus side note and more tenacious than the (S)-isomer 70 (2S)-(+)-2-heptylcyclopentanone - Heavy, coconut-like oily fruity and jasmine-like floral odor with somewhat herbaceous side note 10 (2R)-(-)-2-heptylcyclopentanone - Powerful diffusive warm jasmine-like floral odor with somewhat mandarin-like citrus side note and more tenacious than the (S)-isomer 10 (3R,3aR,7aS)-Dill ether - faintly herbal, unspecific NA (3S,3aS,7aR)-Dill ether - Dill; The naturally occurring dill ether - showed the typical odour of dill oil. NA (3S,3aR,7aS)-Dill ether - herbal, sweet NA (3R,3aS,7aR)-Dill ether - fruity-sweet NA (1R)-(+)-menthofuran - Mint-like, leafy, herbal, camphor-like 0.000001-0.000002 (1S)-(-)-menthofuran - Herbal, fatty, thyme-like, turpentine NA (-)-(R)-2-methoxy-3-[1-methylpropyl]pyrazine - a burdocklike, green and earthy odor; Qualitatively, there is no significant difference between the organoleptic properties of the (S)-(+)-, (R)-(-) enantiomers or the racemate but the (-)-(R)-2-methoxy-3-[1-methylpropyl]pyrazine appears to have a somewhat more burdock like aroma than its antipode. 0.01 (+)-(S)-2-methoxy-3-[1-methylpropyl]pyrazine - a burdock like, green and earthy odor 0.1 (2R,4S)-cis-Doremox® (ee=92%) - rose oxide, diphenyl oxide, metallic, slightly plastic NA (2S,4R)-cis-Doremox® (ee=80%) - rose oxide, powerful, nice. The (2S,4R)-cis-enantiomer is, thus, the nicest and the most powerful isomer of the series. This stereoisomer, incidentally, has the same absolute configuration of the most appreciated of rose oxide isomers, i.e. (2S,4R)-cis-rose oxide NA (2R,4R)-trans-Doremox® (ee=50%) - rosy, rose oxide, metallic, off note NA (2S,4S)-trans-Doremox® (ee=72%) - weak, rosy, plastic, citronellol, a rose oxide note is also present. NA (-)-(2S,4R,6S)-Floropal® - described as typically Vertacetal, with a characteristic rhubarb note. This is the preferred enantiomer. NA (-)-(2R,4S,6R)-Floropal® - less interesting than the (-)-(2S,4R,6S)-enantiomer (Brenna et. al.); the racemate is described as strong, herbal-fresh, green, and typical grapefruit (Pickenhagen, et. al.) NA (2R,4R,6R)-Floropal® - less interesting than the (-)-(2S,4R,6S)-enantiomer (Brenna et. al.); the racemate is described as very weak, chemical solvent-like, and to have a detracting influence upon the odour properties of the mixture (Pickenhagen, et. al.). NA (2S,4S,6S)-Floropal® - less interesting than the (-)-(2S,4R,6S)-enantiomer (Brenna et. al.); the racemate is described as very weak, chemical solvent-like, and to have a detracting influence upon the odour properties of the mixture (Pickenhagen, et. al.). NA (-)-(1S,3S,4aR,9aS)-Magnolan "B" - was highly appreciated and found rosy, floral (geranium, magnolia), citronellyl acetate, citric-fruity, with a slight green nuance. (-)-(1S,3S,4aR,9aS)-Magnolan is the most interesting enantiomer of the diastereoisomers. It should be noted that relative configuration for this enantiomer is the same as observed for the preferred enantiomer of Floropal NA (+)-(1R,3R,4aS,9aR)-Magnolan "B" - was described as weak, acidic, floral, rosy, sweet, warm NA (+)-(1R,3R,4aR,9aS)-Magnolan "A" - while the odor of the individual enantiomers was not given, the odor of the racemic Magnolan "A" was described as being richer than commercial Magnolan, less plastic and more floral, but the racemic Magnolan "B" was described to be more powerful, much fresher and with an additional pleasant marine tonality, also more substantive on blotter NA (-)-(1S,3S,4aS,9aR)-Magnolan "A" - while the odor of the individual enantiomers was not given, the odor of the racemic Magnolan "A" was described as being richer than commercial Magnolan, less plastic and more floral, but the racemic Magnolan "B" was described to be more powerful, much fresher and with an additional pleasant marine tonality, also more substantive on blotter NA (2R)-2-phenylpropanol - Faint flowery, no specific odor 1000 (in air) (2S)-2-phenylpropanol - No fragrance impression at >2.5 ppm in air >2500 (in air) (2R)-2-phenylpropanal - No fragrance impression at >2.5 ppm in air >2500 (in air) (2S)-2-phenylpropanal - Intensive flowery, green, reminiscent of hyacinth odor, pleasant up to a high concentration without negative impression 20 (in air) (R)-2-phenylpropanal dimethyl acetal - Strong, a little bit duffy or musty, mushroom like odour 250 (in air) (2S)-2-phenylpropanal dimethyl acetal - No fragrance impression at >2.5 ppm in air >2500 (in air) (1S)-(-)-styrallyl alcohol - a mild hyacinth, gardenia aroma with strawberry nuances (enantiomeric excess of about 87.5) NA (1R)-(+)-styrallyl alcohol - floral, earthy-green, honeysuckle odor; green-fruity taste (description for racemate) NA (1S)-(-)-styrallyl acetate - a fresh strawberry, green, dried fruit aroma with a green, avocado taste profile and strawberry jam nuances. From a fragrance standpoint, this substance is described as having a strawberry, green, dried fruit aroma with strawberry topnotes (enantiomeric excess of about 78.3) NA (1R)-(+)-styrallyl acetate - a fruity, floral, jasmine, mimosa, gardenia aroma with apricot, apple and strawberry jam flavor nuances (enantiomeric excess of about 81.1) NA (+)-methyl (1R)-1,4-dimethylcyclohex-3-ene-1-carboxylate - very fresh, fruity-mint-anisic with a light pear note 5.85 ppb (-)-methyl (1S)-1,4-dimethylcyclohex-3-ene-1-carboxylate - herbaceous, humus, woody and slight spicy in the direction of resinous-fenugreek, also a little chemical and moldy 20.1 ppb (+)-(2R)-5-methyl-2-[(1R)-1-methylprop-2-enyl]hex-4-en-1-ol - a floral, rose fragrance with an edge of Rosacene, with a more pronounced rose scent than the (-)-(S,S,)-enantiomer. Rosacene (a floral composition), is a registered trademark of Firmenich SA NA (-)-(2S)-5-methyl-2-[(1S)-1-methylprop-2-enyl]hex-4-en-1-ol - a floral, rose, natural, very delicate fragrance with a slight trace of cork, slightly rosinol and green, with an overall scent reminiscent of rose and geranium. A fragrance more like citronellol than the (+)-(R,R)-enantiomer NA (S)-para-Cassiffix® - floral, narciss, woody, cassis NA (R)-para-Cassiffix® - weak, dusty, woody, fruity, cassis NA 1-[(2R)-2-methylbutyl]pyrrolidine - Strong roasted element. Metallic, oily, sharp ammonia-like odour. Image of roasted shell of shrimp, burned skin of fish. NA 1-[(2S)-2-methylbutyl]pyrrolidine - Strong seafood-like element. Mild aldehyde-like odour. Image of body of shrimp, crab, shellfish, squid, fish guts pickled in salt. NA (2S,2'S)-1-[(2'-methylbutyl]-2-methylpyrrolidine - Weak, mould-like and less stimulating odour; with slightly fruity element and sweet like chocolate. NA (2R,2'R)-1-[(2'-methylbutyl]-2-methylpyrrolidine - Metallic, stimulating roast odour; aromatic image of burned seafood. NA (2S,2'R)-1-[(2'-methylbutyl]-2-methylpyrrolidine - Earthy and mould-like odour, slightly ammonia-like; after several hours, sweet nuances like chocolate are also detectable in the scent. NA (2R,2'S)-1-[(2'-methylbutyl]-2-methylpyrrolidine - Weak odour, roasted element of seafood. Image of dish made from walleye pollack roe ured in salt and red pepper. NA (2S)-2-methyl-N-((2'R)-2'-methylbutylidene)butan-1-amine - Metallic, slightly heavy, cocoa-like odor with esteric, fruity element. Sweeter odor than the (2S,2'S)-stereoisomer. Image of burned fish, shrimp. NA (2R)-2-methyl-N-((2'S)-2'-methylbutylidene)butan-1-amine - Seafood, including fish odor wuth phenolic, esteric, fruity element. NA (2S)-2-methyl-N-((2'S)-2'-methylbutylidene)butan-1-amine - Light, metallic, oily character.Seafood (internal organs of shrimp) with sweet butter-like and esteric scent. NA (2R)-2-methyl-N-((2'R)-2'-methylbutylidene)butan-1-amine - Mild, sweet, fruity, slightly phenolic element, including the peel of mango, apple, citrus. NA 3-methyl-N-((2'S)-2'-methylbutylidene)butan-1-amine - Light and strong seafood element with fruity element including apple, pineapple, chinese quince, pear. NA 3-methyl-N-((2'R)-2'-methylbutylidene)butan-1-amine - Heavy and strong seafood element. Image of seaweed (wakame), layer with sweet butter-like odor. NA (2S)-2-methyl-N-(3'-methylbutylidene)butan-1-amine - Amine, internal organs of shrimp, cocoa-like element with sweet butter-like odor NA (2R)-2-methyl-N-(3'-methylbutylidene)butan-1-amine - Heavier esteric odor than the (S)-enantiomer. Fruity Cereal-like with slightly fishy scent. NA (+)-(2R,4S)-Clarycet® - Fruity, rosy, rose ketone, good, touch earthy, dry, sweet, woody, sage, dry down floral-sage. NA (-)-(2S,4R)-Clarycet® - Floral, agrestic, fruity, touch acetic-green-tobacco, dry down slightly fruity, but very weak. NA (-)-(2S,4S)-Clarycet® - Green, fresh, earthy, fruity (sage), dry down odorless NA (+)-(2R,4R)-Clarycet® - Pine, pine oil, terpenic, woody, dry down dusty dirty. NA (-)-(2R,4S)-Florol® - The second weakest in the series of Florol stereoisomers. Relatively weak, mainly fruity, grape-like, but also reminiscent of linalyl acetate and clary sage oil, with some nuances of dry herbs 520 ng/l air (+)-(2S,4R)-Florol® - Odorless on GC olfactometry. The weakest of all Florol ¾ stereoisomers. Very weak in odor, mainly linalool and coumarine like, with some citric and hesperidic nuances. >600 ng/l air (+)-(2S,4S)-Florol® - Second most intense Florol stereoisomer, but already much weaker. Similar fresh-floral note as the enantiomer, but less sweet and also more linalool-type, more herbaceous, and more earthy in tonality. 26 ng/l air (-)-(2R,4R)-Florol® - Most pronounced and most intense Florol stereoisomer. Fresh, soft, sweet, and natural floral odor reminiscent of muguet with some rose oxide side note and earthy nuances. 1.21 ng/l air (-)-(2R,4S)-Rhubafuran® - The most pleasant one, floral, linalool-like, rhubarb and citrus, green, slightly eucalyptus. (2R,4S)-, followed by its enantiomer, are the closest to the commercial Rhubafuran. NA (+)-(2S,4R)-Rhubafuran® - Citric, rhubarb, slightly green, slightly animalic. NA (-)-(2S,4S)-Rhubafuran® - Grapefruit-like, bitter, cassis, slightly oxane-like and reminiscent of dimethyloctenone. Dry down (24 h) bitter, grapefruit, oxane. NA (+)-(2R,4R)-Rhubafuran® - Nuts, acidic, animalic, slightly rhubarb. NA (+)-(2R)-Tropional® - floral (Lily of the valley and cyclamen), aldehydic, sweet fruity (lemon) 3.43 ng/l in air (-)-(2S)-Tropional® - green floral, marine, ozone-like and salty aspect, fruity sweet, cumin-like undertone 0.64 ng/l in air (-)-(2R)-Cyclamen aldehyde - cyclamen-like odor NA (+)-(2S)-Cyclamen aldehyde - lily bell-like odor NA (-)-(1R)-1-methyl-2-phenylethylamine - musty NA (+)-(1S)-1-methyl-2-phenylethylamine - fecal NA (2R,4R,5R,6R)-2,4,5,6-tetramethyl-4-phenyl-1,3-dioxane - (ee = 99%): animalic, green, evernyl (methyl 2,4-dihydroxy-3,6-dimethylbenzoate), floral, benzyl salicylate, marine, camphoraceous, orcinyl (3-hydroxy-5-methoxytoluene), on dry-down very weak to odourless. NA (2S,4S,5S,6S)-2,4,5,6-Tetramethyl-4-phenyl-[1,3]-dioxane - (ee = 99%): earthy, floral, acidic, with an acidic–citric touch, on dry-down weak, touch of fruity. NA (+)-(2R,4S,6R)-2,4,6-trimethyl-4-[(E)-2-phenylvinyl]-1,3-dioxane - (ee = 92%): animalic, woody, green, cumin oil, not clean, after 24 hours dry-down, unpleasant, cuminic–dirty–animalic. NA (-)-(2S,4R,6S)-2,4,6-trimethyl-4-[(E)-2-phenylvinyl]-1,3-dioxane - (ee = 79%): green, vegetable note, not clean, after 24 hours unpleasant cuminic. NA (-)-(3R,5R)-3,5-Dimethylcyclohexanone - minty, resembling iospulegone in character NA (+)-(3S,5S)-3,5-dimethylcyclohexanone - fruity, ester like odor NA (-)-(1R,2S)-Georgywood® = "Georgyone" - Woody-ambery; Bottom note: Fresh, minty, green, sweet (Frater, et. al.); Hong & Corey describe the odor as "an intense clean woody odor". 20 pg/L (+)-(1S,2R)-Georgywood® = ent-Georgyone - Weakly woody; Bottom note: musty (Frater, et. al.); Hong & Corey found this enantiomer to possess a relatively weak odor which is best described as distinctly unpleasant-acrid-musty. 3.5 ng/L (2R,4S)-Pamplefleur® - natural, fruity odor in the direction of grapefruit and rhubarb, close to Gardenol ("methyl phenyl carbinyl acetate") and 2,5-dimethyloct-2-en-6-one, slightly metallic NA (2S,4R)-Pamplefleur®- fruity-citric odor, with some harsh,animalic, and slightly woody nuances, also abit rubbery NA (2R,4R)-Pamplefleur® - floral-fruity odor in the direction of rhubarb with a touch of grapefruit, also reminiscent of Gardenol NA (2S,4S)-Pamplefleur® - floral-fruity odor in the direction of grapefruit and linalool, with earthy, woody and bitter nuances, also reminiscent of 2,5-dimethyloct-2-en-6-one and of some aspects of veitiver oil NA (+)-(1R,2R)-2-tert-butylcyclohexyl acetate - reminiscent of a peach and a plum - it had a distinctly characteristic sweet fruity aroma. 80 mg/L in air (-)-(1S,2S)-2-tert-butylcyclohexyl acetate - strong woody camphor aroma with no characteristic fruity note 160 mg/L in air (-)-(1R,2R)-2-tert-butylcyclohexanol - strong fresh green aroma with Woody camphor notes 40 mg/L in air (+)-(1S,2S)-2-tert-butylcyclohexanol - camphoraceous with weak green aroma 80 mg/L in air (-)-(6R)-dictyopterene D - seaweed, green notes - moss like scent (accompanied by the feeling of Green with diffusibility in floral perfume compositions) NA (+)-(6S)-dictyopterene D - a little spicy impression - with a strong seaweed like scent NA (+)-(1S,4R,5R,9S)-1-hydroxy-1,4,7,7,9-pentamethylspiro[4.5]decan-2-one - Powerful patchouli-like odor 0.067 ng/L air for racemate (-)-(1R,4S,5S,9R)-1-hydroxy-1,4,7,7,9-pentamethylspiro[4.5]decan-2-one - Odorless (-)-[(1R,3S)-3-isopropyl-1-methylcyclopentyl]methanol - floral, green, jasmine, lily-of-the-valley, fresh, clean. NA (+)-[(1S,3R)-3-isopropyl-1-methylcyclopentyl]methanol - floral, fruity, green, rosy, hesperidic (grapefruit). NA (-)-1-[(1R,1'RS,3S)-3-isopropyl-1-methylcyclopentyl]ethanol - floral, earthy/mossy, slightly terpineol, earthy NA (+)-1-[(1S,1'RS,3R)-3-isopropyl-1-methylcyclopentyl]ethanol - hesperidic/citrus, fruity, green, fresh (grapefruit, rhubarb) NA (-)-1-[(1R,1'RS,3S)-3-isopropyl-1-methylcyclopentyl]propan-1'-ol - anisic, floral, green, marine NA (+)-1-[(1S,1'RS.3R)-3-isopropyl-1-methylcyclopentyl]propan-1'-ol - fruity, green, leathery, floral. NA (-)-1-[(1R,2'RS,3S)-3-isopropyl-1-methylcyclopentyl]propan-2'-ol - earthy/mossy, woody, camphoraceous, ambery, sweet. NA (+)-1-[(1S,2'RS,3R)-3-isopropyl-1-methylcyclopentyl]propan-2'-ol - Odour description: hesperidic/citrus, fruity, fresh (grapefruit). NA (-)-1-[(1R,2'RS,3S)-3-isopropyl-1-methylcyclopentyl]butan-2'-ol - camphoraceous, earthy/mossy, woody, slightly patchouli. NA (+)-1-[(1S,2'RS,3R)-3-isopropyl-1-methylcyclopentyl]butan-2'-ol - fruity, floral, green (pineapple). NA (-)-1-[(1R,3S)-3-isopropyl-1-methylcyclopentyl]ethanone - earthy/mossy, green, woody. NA (+)-1-[(1S,3R)-3-isopropyl-1-methylcyclopentyl]ethanone - floral, agrestic, fruity, green. NA (-)-1-[(1R,3S)-3-isopropyl-1-methylcyclopentyl]propan-1-one - green, earthy/mossy, fruity, floral. NA (+)-1-[(1S,3R)-3-isopropyl-1-methylcyclopentyl]propan-1-one - earthy/mossy, fruity, green. NA (+)-(2S,3R)-Magnolione® - floral, jasmine, fruity, fresh most intense 0.29 ng/L (-)-(2R,3S)-Magnolione® - citrus, fruity, floral, fresh, green, jasmine very weak 7.10 ng/L (2S,3S)-Magnolione® - mushrooms, food like, metallic, floral, jasmine weak 0.60 ng/L (2R,3R)-Magnolione® - floral, jasmine, animalic touch, metallic weak 0.74 ng/L (-)-(2R,3S)-Muguesia (ee = 99%) - top note: floral, rosy, buttery, rich, slightly green; dry down: floral, sweet, lily of the valley and linalool-like. NA (+)-(2S,3R)-Muguesia (ee = 99%) - top note: weak, floral-hesperidic, tea-like; dry down: empty. NA (-)-(2S,3S)-Muguesia (ee = 99%) - top note: floral, balsamic, sweet, floral, slightly fruity; dry down: floral, cinnamic, balsamic, sweet. NA (+)-(2R,3R)-Muguesia (ee = 99%) - top note: very weak, slightly acidic and agrestic, dry down: empty NA (+)-(1R,2R,8aS)-Arborone - possesses an intense woody odor that was clean and very pleasant. <5 x 10-12 g/L (-)-(1S,2S,8aR)-Arborone = ent-Arborone - a very faint odor. NA (-)-(1R,2R,8R,8aR)-desMethyl Arborone - possesses an intense warm woody-amber odor in common with Georgyone and Arborone. Its odor also has a slight fresh minty note. NA (+)-(1S,2S,8S,8aS)-desMethyl Arborone = ent-desMethyl Arborone - possesses a relatively weak odor. NA (+)-((S)-2,3-dihydro-2,5-dimethyl-1H-inden-2-yl)methanol - Muguet, floral, Lilial, hydroxycitronellal, stronger and more powerful, less hydroxycitronellal than enantiomer, base mor Lilial NA (-)-((R)-2,3-dihydro-2,5-dimethyl-1H-inden-2-yl)methanol - Floral, muguet, hydroxycitronellal, slightly plastic, similar to enantiomer, more plastic, base more hydroxycitronellal NA (2R,6R)-cis-exoPelargene - (99% pure, ee 98%); Weak, green, agrestic, and herbaceous odor, with a slightly fruity side. Dry down very weak green, fruity. NA (2S,6S)-cis-exoPelargene - (97% pure, ee 90%); Weak, fruity-floral, mushroom-like odor. Dry down very weak, fruity-floral, somewhat technical. NA (2S,6R)-trans-exoPelargene - (39.5% pure, ee 98%); Green, Rose Oxide like, fruity, orange-type, and somewhat dusty odor. Dry down weak, green, fruity. NA (2R,6S)-trans-exoPelargene - (33% pure, ee 90%); Harsh, green, technical, pyrazine-type, vegetal odor, with acetic, Rose Oxide type, floral-rosy facets. Dry down green, fruity, and rosy. NA (2R,6R)-cis-Pelargene "A" - (94% pure, ee 98%); Green, metallic, Rose Oxide like odor, with fruity, slightly earthy, and potato-like aspects. Dry down weak, green, fruity. This compound is weaker and less-substantive than (2R,6S)-trans-Pelargene "B". NA (2S,6S)-cis-Pelargene "A" - (93% pure, ee 90%); Rather weak, sharp, green, Rose Oxide like, stem odor, with a slightly fruity and acetic tonality. Dry down very weak, slightly green. NA (2S,6R)-trans-Pelargene "A" - (98% pure, ee 98%); Green, petit-grain and orange flower-type pleasant odor, with aspects of neroli oil. Dry down linear, but more herbal, buccoxime-like. NA (2R,6S)-trans-Pelargene "A" - (92% pure, ee 90%); Green, floral odor, with slightly wine- and food-like nuances, and somewhat oily, technical aspects. Dry down linear, weak, green, vegetal. NA (2R,6R)-cis-Pelargene "B" - (97% pure, ee 98%); Fruity, green, metallic odor. Dry down green fruity. NA (2S,6S)-cis-Pelargene "B" - (94% pure, ee 90%); Strong, floral-green Rose Oxide odor, with a metallic inflection and atypical rose tonality. Dry down linear, Rose Oxide like, floral, rosy. NA (2R,6S)-trans-Pelargene "B" - (99% pure, ee 98%); Green, metallic, Rose Oxide note, stronger than (2S,6R)-trans-Pelargene "A" and (2R,6R)-cis-Pelargene "A". Dry down green, fruity, buccoxime-like. NA (2S,6R)-trans-Pelargene "B" - (94% pure, ee 90%); Strong, green-fruity, fresh, but also somewhat harsh-technical odor. Dry down fruity, Rose Oxide like, with a sweet rosy touch. NA (-)-(3S,4R)-Jasmal - Fruity, floral, and slightly technical. NA (+)-(3R,4S)-Jasmal - Weak, floral, acidic. NA (+)-(3S,4S)-Jasmal - Acidic, metallic, fruity. NA (-)-(3R,4R)-Jasmal - Strong, floral, jasminic, spicy, and slightly acidic. NA (+)-(3S,4R,5S)-Jessemal - Weak, powder-waxy, slightly floral odor, in the direction of jasmine but not pronounced. NA (-)-(3R,4S,5R)-Jessemal - The most powerful of this series, floral-fruity, agrestic odor in the direction of jasmine with herbaceous facets. NA (-)-(3R,4R,5R)-Jessemal - Strong, floral-jasminic, slightly aromatic. NA (+)-(3S,4S,5S)-Jessemal - Very weak, slightly agrestic, fruity-floral. NA (+)-(4S,4aS,8aS)-dehydrogeosmin - strong, camphoraceous, earthy-musty tonality which is reminiscent of freshly ploughed soil - the natural (+) stereoisomer exhibiting a fresher and stronger camphoraceous tonality than the (-) isomer. 140 pg/liter in air (-)-(4R,4aR,8aR)-dehydrogeosmin - similarr odor to (+)-dehydrogeosmin, but not as fresh or camphoraceous 10 pg/liter in air (2S)-(+)-Gardamide - Strong grapefruit aroma associated with a tropical fruit NA (2R)-(-)-Gardamide - Woody, weak grapefruit aroma having a camphor-element NA (2S)-(+)-N,2-dimethyl-N-meta-toluamide - Grapefruit aroma with a woody-element NA (2S)-(-)-N,2-dimethyl-N-meta-toluamide - Pericarp-aroma of fresh grapefruit having an aroma like a sulfur-containing compound NA (+)-2-{[(1S)-1-methylpropyl]oxy}pyrazine - Green, dusty. Qualitatively, there appears to be no significant difference between the organoleptic properties of the enantiomers or racemate. 100 (-)-2-{[(1R)-1-methylpropyl]oxy}pyrazine - Green, dusty 100 (+)-2-{[(1S)-1-methylbutyl]oxy}pyrazine - Fatty, metallic, green. Qualitatively, there appears to be no significant difference between the organoleptic properties of the enantiomers or racemate. 100 (-)-2-{[(1R)-1-methylbutyl]oxy}pyrazine - Fatty, metallic, green. 100 (+)-2-{[(1S)-1-methylhexyl]oxy}pyrazine - Green, metallic, fatty, burdock. Qualitatively, there appears to be no significant difference between the organoleptic properties of the enantiomers or racemate. 70 (-)-2-{[(1R)-1-methylhexyl]oxy}pyrazine - Green, metallic, fatty, burdock. 200 (+)-2-{[(1S)-1-methylheptyl]oxy}pyrazine - Green, fishy, amine-like, fatty. Qualitatively, there appears to be no significant difference between the organoleptic properties of the enantiomers or racemate. 30 (-)-2-{[(1R)-1-methylheptyl]oxy}pyrazine - Green, fishy, amine-like, fatty. 90 (+)-2-(1S,2R,5S)-menthyloxypyrazine - Fruity, sweet. Qualitatively, there appears to be no significant difference between the organoleptic properties of the enantiomers or racemate. 10 (-)-2-(1R,2S,5R)-menthyloxypyrazine - Fruity, sweet. 2

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