Sesquiterpenoid & Diterpenoid Related Odorants
by John C. Leffingwell, Ph.D.
Photo by permission of M. Roudintska - Art & Parfum
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Ionones, Irones, Damascones & Structurally Related Odorants |
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Sesquiterpenoid & Diterpenoid Related Odorants |
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(-)-(1R,3R,6S,7S,8S)-patchoulol - a strong, typical patchouli scent with an earthy, slightly camphoraceous, powdery cellar note which was indistinguishable from natural patchoulol; deep woody like patchouli oil |
NA |
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(+)-(1S,3S,6R,7R,8R)-patchoulol - much weaker, less characteristic, nearly indefinable and by no means reminiscent of patchouli. It might have a beta-santalol odour with a green undertone; woody with underlying green notes |
NA |
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(-)-(1S,3R,6S,7S,8S)- patchoulenol - The odour profile of (-)-patchoulenol can be described as patchouli-like camphoraceous whose earthy cellar note is there more pronounced than in (-)-patchouli alcohol. A slight galbanum scent is also recognized. |
NA |
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(+)-(1R,3S,6R,7R,8R)-patchoulenol - is much weaker than its antipode, less earthy and also less patchouli-like; however, it possesses a weak but fine woody, warm amber tone. |
NA |
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NA |
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(2R, 4aR)-(+)-alpha-ambrinol - exhibits a strongly dry earthy, musty tonality, reminiscent of geosmine |
NA |
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(-)-Ambrox® - moist, soft, creamy, persistent, warm, animalic, amber odor with a velvety effect |
0.3 |
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(+)-Ambrox® - accentuated woody note and lacks the strong animalic warmth" of the (-)-isomer |
2.4 |
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(-)-((5S,8R,9R,10S)-8a,13-desoxyambreinolide - Strong; this material was mostly described as woody ambergris-like in the sense of the tonality of the standard odorant Ambrox; the descriptions musky and balsamic followed. Owing to its additional warm animal note this ether resembles ambergris most. |
9 |
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(+)-((5R,8S,9S,10R)-8a,13-desoxyambreinolide - A weaker woody character although its intensity and ambergris tonality differed considerably from that of its enantiomer; 20% of panelists found it to be odorless. The only subject (female ) extremely sensitive to this enantiomer characterized it as camphoraceous, slightly sweaty and urine-like. |
NA |
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(+)-(5S,8S,9R,10S)-8b,13-desoxyambreinolide - Virtually odorless |
NA |
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(-)-(5R,8R,9S,10R)-8b,13-desoxyambreinolide - Strongly odorous, but not ambergris-like. Of the 30 panelists - Minty-camphoraceous (6 females & 8 males), fruity (2 females & 4 males) and balsamic (3 males) were the most frequent replies. Four participants (2 females & 2 males) described this enantiomer as musk-like and woody; However, none of the subjects could identify ambergris-like tonalities in this enantiomer. |
NA |
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(+)-(5S,8R,9R,10S)-20-desmethyl-8a,13-desoxyambreinolide - Moderately strong odor - Mostly described as woody ambergris-like in the sense of the tonality of the standard odorant Ambrox; the descriptions musky and balsamic followed. However, practically 50% of the subjects being extremely odor-sensitive, including all the female participants, indicated tonalities (green, moss and ionone-lke) which cannot or can only with difficulty be associated with ambergris. Less sensitive subjects, however, committed fewer errors. |
NA |
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(-)-(5R,8S,9S,10R)-20-desmethyl-8a,13-desoxyambreinolide - Strong odor; Six out of eight subjects ascribed woody ambergris-like odor qualities to the strong odor of this nor-ether, although its intensity and ambergris tonality differed considerably. The other four highly sensitive participants gave the following description: flowery (female ), cyclohexanone-like (female ) , minty, floor polish (male), and green-peppery (male). |
NA |
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(+)-(5S,8S,9R,10S)-20-desmethyl-8b,13-desoxyambreinolide - Strongly odorous -Mostly described as woody ambergris-likein the sense of the tonality of the standard odorant Ambrox; the descriptions musky and balsamic followed. Of the 30 member panel the strong odor of this enantiomer (diastereoisomer ) was described as fermented herbs by only one person (female), and as menthol-like by another (male). Neither subject could detect ambergris-like scents in any of this series |
NA |
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(-)-(5R,8R,9S,10R)-20-desmethyl-8b,13-desoxyambreinolide - Strong odor, but not ambergris-like; of the 30 member panel, only one (male) recognized this diastereoisomer to be ambergris-like. |
NA |
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(-)-(5S,9R,10S)-9b,13-epoxy-14,15,16,20-tetranorlabdane - Strongly odorous -Mostly described as woody ambergris-likein the sense of the tonality of the standard odorant Ambrox; the descriptions musky and balsamic followed. |
NA |
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(+)-(5R,9S,10R)-9b,13-epoxy-14,15,16,20-tetranorlabdane - Much Weaker odor than its enantiomer and clearly lacking ambergris odor; other descriptors not reported. Imperceptible to 1/3 of panelists |
NA |
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(-)-(5S,9S,10S)-9a,13-epoxy-14,15,16,20-tetranorlabdane - Clearly lacking ambergris odor; other descrptors not reported. |
NA |
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(+)-(5R,9R,10R)-9a,13-epoxy-14,15,16,20-tetranorlabdane - Weaker odor than its enantiomer and clearly lacking ambergris odor; other descrptors not reported. |
NA |
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(5S,8R,9R,10S,13S)-8a,13:13,20-diepoxy-15,16-dinorlabdane - Powerful, woody ambergris-like in the sense of the tonality of the standard odorant Ambrox. |
NA |
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(5R,8S,9S,10R,13R)-8a,13:13,20-diepoxy-15,16-dinorlabdane - Weak somewhat woody odor, imperceptible to 2/3 of panelists - for those who could perceive it, its intensity and ambergris tonality differed considerably from that of its enantiomer. |
NA |
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(5S,8S,9R,10S,13R)-8b,13:13,20-diepoxy-15,16-dinorlabdane - Virtually odorless - imperceptible to all but one of thirty panelists |
NA |
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(5R,8R,9S,10R,13S)-8b,13:13,20-diepoxy-15,16-dinorlabdane - A somewhat woody odor that was imperceptible to 25% of panelists |
NA |
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(4R,4aS,6R)-(+)-nootkatone - strong grapefruit odor, bitter in taste |
800 |
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(4S,4aR,6S)-(-)-nootkatone - weak woody (vetiver noe); no grapefruit character |
600000 |
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(+)-(4R,4aS,6R,8aS)-Tetrahydronootkatone - dusty-woody, fresh, green, sour, spicy, herbal, slightly fruity, animal, erogenic |
5000-20000 |
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(-)-(4S,4aR,6S,8aR)-Tetrahydronootkatone - dusty-woody, spicy, fresh, green, sour, slightly herbal, fruity, animal, erogenic |
30000-70000 |
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600-1000 |
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(4S,4aR)- (-)- alpha-vetivone - completely lacks the fruity character of (+)- alpha-vetivone |
6000-15000 |
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(+)-8-Dehydro-11,12-dihydronootkatone - On an odor rating scale: fresh, green, sour, dusty-woody, herbal-spicy, slightly animal, erogenic, fruity |
5000-10000 |
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(-)-8-Dehydro-11,12-dihydronootkatone - On an odor rating scale: dusty-woody, fresh, green,sour, herbal-spicy, slightly animal, erogenic |
40000-100000 |
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(-)-(1aR,5R,5aS,6aR)-Tricycloketone - On an odor rating scale: dusty-woody, fresh, green, sour, spicy herbal, slightly animal, erogenic |
40000-80000 |
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(+)-(1aS,5S,5aR,6aS)-Tricycloketone - On an odor rating scale: dusty-woody, spicy, slightly fresh, green, sour, herbal, animal, erogenic |
80000-120000 |
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NA |
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S-(-)-(E)-nerolidol - slightly sweet, mild, soft, flowery, different than (S)-(Z)-isomer |
NA |
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NA |
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NA |
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NA |
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(5S,10S)-(+)-beta-vetivone - unpleasant cresolic, medicinal note |
NA |
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(5R,10R)-(-)-6-demethyl-beta-vetivone - a sweet coumarin-like odor with a woody note |
NA |
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(5S,10S)-(+)-6-demethyl-beta-vetivone - a woody smell with a quinoline-like by-note |
NA |
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NA |
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NA |
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NA |
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NA |
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(4R,5R)-(-)-3,5-Dimethyl-4-(4-methyl-pent-3-enyl)-cyclohex-2-enone - nearly odorless |
NA |
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(4S,5S)-(+)-3,5-Dimethyl-4-(4-methyl-pent-3-enyl)-cyclohex-2-enone - nearly odorless |
NA |
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NA |
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NA |
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NA |
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NA |
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(2S,8aR)-3,4-Dihydro-3-oxoedulan - In the mixture of 2S,8aS (see below) and 2S,8aR isomers (2S,8aS : 2S,8aR ratio of 15:85), a camphoraceous note dominated; Using GC sniffing, the 3,4-dihydro-3-oxoedulans exhibited only weak odor intensities |
NA |
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(2R,8aS)-3,4-Dihydro-3-oxoedulan - In the mixture of of 2R,8aR (see below) and 2R,8aS isomers (2R,8aR : 2R,8aS ratio of 15:85), a weak tobacco note was detectable; Using GC sniffing, the 3,4-dihydro-3-oxoedulans exhibited only weak odor intensities |
NA |
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(2S,8aS)-3,4-Dihydro-3-oxoedulan - In the mixture of 2S,8aS and 2S,8aR isomers (2S,8aS : 2S,8aR ratio of 15:85), a camphoraceous note dominated; Using GC sniffing, the 3,4-dihydro-3-oxoedulans exhibited only weak odor intensities |
NA |
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(2R,8aR)-3,4-Dihydro-3-oxoedulan - In the mixture of of 2R,8aR and 2R,8aS isomers (2R,8aR : 2R,8aS ratio of 15:85), a weak tobacco note was detectable; Using GC sniffing, the 3,4-dihydro-3-oxoedulans exhibited only weak odor intensities |
NA |
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(+)-(2R,4aR,8aS)-Polywood® - Odor properties: described as exhibiting a rich, voluminous woody note with a powdery ionone-like undertone. |
NA |
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(-)-(2S,4aS,8aR)-Polywood® - Odor properties: was found less rich than (+)-(2R,4aR,8aS)-Polywood®, still woody, dry, and amber-like. |
NA |
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(-)-(4aS,8aR)-5,5,8a-trimethyloctahydronaphthalen-2(1H)-one - Odor properties: described as strong, woody amber-like, with a distinct note of damp earth, cellar, geosmin. |
NA |
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(+)-(4aR,8aS)-5,5,8a-trimethyloctahydronaphthalen-2(1H)-one - Odor properties: was found woody, patchouli like, and less strong than its enantiomer. |
NA |
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(R,R)-Iso-beta-bisabolol - very strong, flowery, lilley-of-the-valley like and very pleasant odor - stronger than the (1S)-1-[(1S)]-, (1R)-1-[(1S)]-OR (1S)-1-[(1R)]- enantiomers |
NA |
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(S,S)-Iso-beta-bisabolol - while similar, not as strong as (1R)-1-[(1R)]-Iso-beta-bisabolol |
NA |
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(+)-(4aR,5S)-Karanone - a strong bright woody-amber note |
NA |
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(-)-(4aS,5R)-Karanone - weak woody note with a citrus-atmosphere |
NA |
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(+)-(4aR,5S)-Dihydrokaranone - a remarkable and intense woody note |
NA |
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(-)-(4aS,5R)-Dihydrokaranone - has a citrus and mild woody note; it lacks in sharpness and brightness, and is deficient in the charm as compared to its enantiomer, but is pleasant in another aroma direction |
NA |
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(+)-(1S,2S,5R,7R,8R)-Jinkohol II - the woody note characteristic of sesquiterpenes in combination with a somewhat camphorous odor and, when heated or burnt, the characteristic odor of agarwood is strengthened |
NA |
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(-)-(1R,2R,5S,7S,8S)-Jinkohol II - Very similar to (+)-(1S,2S,5R,7R,8R)-Jinkohol II |
NA |
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(+)-(7S)-7,11-epoxymegastigma-5(6)-en-9-one - Weak, somewhat floral-fruity, raspberry, ionone-like |
NA |
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(-)-(7R)-7,11-epoxymegastigma-5(6)-en-9-one - Sweet, food-like, slightly vanillic note |
NA |
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(+)-(7S,9R)-7,11-epoxymegastigma-5(6)-en-9-ol - Weak, citric, acidic, slightly floral |
NA |
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(-)-(7R,9S)-7,11-epoxymegastigma-5(6)-en-9-ol - Weak, floral-fruity, with a woody, cardboard-like nuance and some metallic facets |
NA |
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(+)-(7S,9S)-7,11-epoxymegastigma-5(6)-en-9-ol - Weak, floral smell with technical, acidic component, a bit in the direction of rice wine |
NA |
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(-)-(7R,9R)-7,11-epoxymegastigma-5(6)-en-9-ol - Weak, citric, acidic, with a sweet floral touch |
NA |
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(S)-Tetrahydrozerumbone - hardly any fragrance. |
NA |
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(R)-Tetrahydrozerumbone - a strong balmy fragrance |
NA |
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