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Bicyclic Terpenoid
Odorants
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(1R,5R)-(+)-alpha-pinene
- harsh, terpene-like, minty
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NA
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(1S,5S)-(-)-alpha-pinene
- harsh, terpene-like, coniferous
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NA
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(S)-(+)-isoborneol
- camphoraceous, celluloid-like (Boelens
et al.); Camphoraceous, India ink-like
(Nishimura)
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NA
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(R)-(-)-isoborneol
- camphoraceous, sweet & musty
(Boelens et al.); Camphoraceous, India ink-like
(Nishimura)
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NA
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(S)-(+)-2-methylisoborneol
- camphoraceous,
rubbery
(Tyler)
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NA
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(R)-(-)-2-methylisoborneol
- camphoraceous, rubbery (Tyler); also
described as musty, mold-like, earthy by Blank
& Grosch
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0.006-0.012 ng/liter (air)
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(R)-(+)-2-methylborneol
- camphoraceous, rubbery
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NA
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(S)-(-)-2-methylborneol
- camphoraceous, rubbery
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NA
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(1R,2R,4S)-2-methylfenchol
(94:6 endo/exo) - main odor character - earthy,
secondary odor character - woody
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NA
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(1S,2S,4R)
-2-methylfenchol (95:5 endo/exo) - main odor
character - earthy, secondary odor character -
musk
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NA
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(1R,2R,4S)-2-ethylfenchol
(93:7 endo/exo) - main odor character - earthy,
secondary odor character - camphor
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NA
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(1S,2S,4R)-2-ethylfenchol
(93:7 endo/exo) - main odor character - earthy,
secondary odor character - moldy
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NA
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(1R,2R,4S)-2-butylfenchol
(99:1 endo/exo) - main odor character - earthy,
secondary odor character - camphor
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NA
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(1S,2S,4R)-2-butylfenchol
(99:1 endo/exo) - main odor character - earthy,
secondary odor character - camphor
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NA
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(1R,4S)-(+)-fenchone
- camphoraceous, strong, diffusive, sweet
odor
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240-510
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(1S,4R)-(-)-fenchone
- camphoraceous, strong, diffusive, sweet
odor
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350-440
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(1R,4R)-(+)-camphor
- camphoraceous
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1000-1290
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(1S,4S)-(-)-camphor
- camphoraceous
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520
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(1S,2S,4R)-(+)-2-Acetoxy-1,8-cineole
- woody (weak) - Kubota et al.; Sharp,
fruity, sweet odor - Miyazawa and Hashimoto
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NA
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(1R,2R,4S)-(-)-2-Acetoxy-1,8-cineole
- woody, Alpinia galanga like and
stronger than the (1S,2S,4R)- isomer - Kubota et
al; Camphorous, dry odor - Miyazawa and
Hashimoto
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NA
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(1S,2R,4R)-2-Acetoxy-1,8-cineole
- weak
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NA
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(1R,2S,2S)-2-Acetoxy-1,8-cineole
- fruity, sweet
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NA
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(1S,3R,4R)-3-acetoxy-1,8-cineole
- sweet floral, weak
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NA
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(1R,3S,4S)-3-Acetoxy-1,8-cineole
- sweet floral, weak
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NA
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(1S,3S,4R)-3-Acetoxy-1,8-cineole
- camphoraceous (Kubota, et al.); camphor-like,
smooth (Loandos et al.)
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NA
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(1R,3R,4S)-3-Acetoxy-1,8-cineole
- mild woody (Kubota, et al.); woody (Loandos
et al.)
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NA
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(1S,2S,4R)-(-)-2-Hydroxy-1,8-cineole
- Cineole-like, sweet odor (Miyazawa and
Hashimoto); Also described as Citrus (2), sweet
(1), grape juice (1), eucalyptus (1) as evaluated
by 6 panelists by GC-O (Kirsch and Buettner)
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NA
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(1R,2R,4S)-(+)-2-Hydroxy-1,8-cineole
- Camphorous odor (Miyazawa and Hashimoto); Also
described as Eucalyptus (5), pine needle (4),
fresh/pungent (3), citrus (2), cleanser (2), soapy
(1), flowery (1), sweet (1) as evaluated by 6
panelists by GC-O (Kirsch and Buettner)
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NA
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(1S,2R,4R)-(-)-2-Hydroxy-1,8-cineole
- Eucalyptus (4), pine needle (3), faecal (2),
earthy (1), plastic (1) as evaluated by 5 panelists
by GC-O (Kirsch and Buettner)
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NA
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(1R,2S,4S)-(+)-2-Hydroxy-1,8-cineole
- Eucalyptus (6), fresh/pungent (1), earthy (1),
musty (1), soapy (1), sweet (1) as evaluated by 6
panelists by GC-O (Kirsch and Buettner)
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NA
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(8S)-(+)-9-Hydroxy-1,8-cineole
- Eucalyptus (5), pine needle (1), fatty (1) as
evaluated by 5-6 panelists by GC-O (Kirsch and
Buettner)
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NA
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(8R)-(-)-9-Hydroxy-1,8-cineole
- Eucalyptus (4), plastic (4), musty (2), rotten
(1), sweet (1), dusty (1) as evaluated by 5-6
panelists by GC-O (Kirsch and Buettner)
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NA
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(1S,3S,4R)-(+)-3-Hydroxy-1,8-cineole
- spicy (weak)
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NA
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(1R,3R,4S)-(-)-3-Hydroxy-1,8-cineole
- camphoraceous, sweet
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NA
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(1S,4S)-(-)-3-Oxo-cineole
- spicy
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NA
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(1R,4R)-(+)-3-Oxo-cineole
- sweet, cineole-like (weak)
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NA
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(1S,2R,4S)-(-)-borneol
- camphoraceous, India ink like ( odor
evaluation by GC-olfactometry) (Nishimura);
(-)-Borneol has a camphoraceous and evident woody
odor (Tabanca et. al & Jogdeo)
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80 ppb
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(1R,2S,4R)-(+)-borneol
- camphoraceous, India ink like, slight
fatty-putrid ( odor evaluation by GC-olfactometry)
(Nishimura); The (+) form has a camphoraceous odor
and a slightly sharp, earthy-peppery note different
from that of the (-) form (Tabanca et. al).
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180 ppb
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(1S,2S,5R)-(-)-Isopinocamphone
- Sweet camphoraceous, cheap spruce needle oil,
also musty-woody
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NA
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(1R,2R,5S)-(+)-Isopinocamphone
- Camphoraceaous, borneol-like, spruce needle note,
later also terpineol-like
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NA
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(1S,2S,4E,5S)-(-)-4-propylidene-isopinocamphone
- Woody, musty, terpineol-like, stale
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NA
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(1R,2R,4E,5R)-(+)-4-propylidene-isopinocamphone
- Damascone-like, fine rose odour,
ethylrosat®-like, camphoraceous and herbaceous
side note
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NA
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(1S,2S,4E,5S)-(-)-4-heptylidene-isopinocamphone
- Mushroom flavour, champignon-like
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NA
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(1R,2R,4E,5R)-(+)-4-heptylidene-isopinocamphone
- Anethol-like, menthol note with a cooling effect,
camphoraceous
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NA
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(1S,2S,4E,5S)-(-)-4-dodecylidene-isopinocamphone
- Difficult to describe, eventually a bit spicy,
methylnonene-acetaldehyde-like
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NA
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(1R,2R,4E,5R)-(+)-4-dodecylidene-isopinocamphone
- Weak, sweet, cocoa note
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NA
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(1S,2S,4E,5S)-(-)-4-benzylidene-isopinocamphone
- Weak odour reminiscent of cresol, sweet,
biscuit-like
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NA
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(1R,2R,4E,5R)-(+)-4-benzylidene-isopinocamphone
- Difficult to describe, eventually vanilla
note
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NA
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(1S,2S,4E,5S)-(-)-4-cinnamylidene-isopinocamphone
- Strong cinnamic flavour, styrax note,
balsamic
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NA
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(1R,2R,4E,5R)-(+)-4-cinnamylidene-isopinocamphone
- Very weak, indefinable
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NA
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(1S,2S,4E,5S)-(-)-4-[2-pyridinylmethylene]-isopinocamphone
- Weak, sweet, aniseed note
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NA
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(1R,2R,4E,5R)-(+)-4-[2-pyridinylmethylene]-isopinocamphone
- Fatty, green, toluyl-acetaldehyde-like, later
woody, sweetish
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NA
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(1S,2S,4E,5S)-(-)-4-furfurylidene-isopinocamphone
- Phenolic, benzaldehyde, chemical, reminiscent of
Peruvian balm
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NA
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(1R,2R,4E,5R)-(+)-furfurylidene-isopinocamphone
- Phenolic, later benzaldehyde, marzipan note
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NA
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(1S,2S,4E,5S)-(-)-4-(4'-methoxybenzylidene)-isopinocamphone
- Very weak woody, soft, eventually sweetish
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NA
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(1R,2R,4E,5R)-(+)-4-(4'-methoxybenzylidene)-isopinocamphone
- Very weak woody
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NA
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(1S,2S,4E,5S)-(-)-4-(3'-methoxybenzylidene)-isopinocamphone
- Very weak, aromatic, sweetish
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NA
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(1R,2R,4E,5R)-(+)-4-(3'-methoxybenzylidene)-isopinocamphone
- Very weak, aromatic, ionone-like
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NA
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(1S,2S,4E,5S)-(-)-4-cyclohexylmethylene-isopinocamphone
- Fatty, oily, marzipan-like, peanut note
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NA
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(1R,2R,4E,5R)-(+)-4-cyclohexylmethylene-isopinocamphone
- Woody, cedarwood, later note of camomile tea
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NA
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(3R,3aR,7aS)-Dill
ether - faintly herbal, unspecific
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NA
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(3S,3aS,7aR)-Dill
ether - Dill; The naturally occurring dill
ether - showed the typical odour of dill oil.
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25 ppb in water
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(3S,3aR,7aS)-Dill
ether - herbal, sweet
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NA
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(3R,3aS,7aR)-Dill
ether - fruity-sweet
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NA
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(1R)-(+)-menthofuran
- Mint-like, leafy, herbal, camphor-like
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0.1-0.2 ppb in air
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(1S)-(-)-menthofuran
- Herbal, fatty, thyme-like, turpentine
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NA
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(1S,5R)-(+)-Myrtenal
- Probability levels of significant differentiation
between the enantiomer pairs - >99.0% with 96
untrained panelists; >99.0% with 28 expert
panelists; overall >99.9% (all 124 panelists).
Theimer's personal comments indicates that he had
no problem in differentiating the enantiomers - the
d- and l-myrtenals suggested cuminic aldehyde and
cyclohexyl acetaldehyde respectively.
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NA
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(1R,5S)-(-)-Myrtenal
- Probability levels of significant differentiation
between the enantiomer pairs - >99.0% with 96
untrained panelists; >99.0% with 28 expert
panelists; overall >99.9% (all 124 panelists).
Theimer's personal comments indicates that he had
no problem in differentiating the enantiomers - the
d- and l-myrtenals suggested cuminic aldehyde and
cyclohexyl acetaldehyde respectively.
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NA
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(1S,5R)-(+)-Myrtenal
diethyl acetal - Probability levels of
significant differentiation between the enantiomer
pairs - >25.0% with 37 untrained panelists;
>90.0% with 29 expert panelists; overall
>98.0% (all 66 panelists). No comments on the
odor of the enantiomers was provided in Theimer's
paper.
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NA
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(1R,5S)-(-)-Myrtenal
diethyl acetal - Probability levels of
significant differentiation between the enantiomer
pairs - >25.0% with 37 untrained panelists;
>90.0% with 29 expert panelists; overall
>98.0% (all 66 panelists). No comments on the
odor of the enantiomers was provided in Theimer's
paper.
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NA
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(1S,5R)-(+)-Pinoacetaldehyde
- Probability levels of significant differentiation
between the enantiomer pairs - >95.0% with 42
untrained panelists; >95.0% with 20 expert
panelists; overall >98.0% (all 62 panelists).
Theimer's personal comments indicates that he had
no problem in differentiating the enantiomers of
the pinoacetaldehydes since the laevo had a
"hydroxycitronellal" character and the dextro
reminded of cyclohexyl acetaldehyde.
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NA
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(1R,5S)-(-)-Pinoacetaldehyde
- Probability levels of significant differentiation
between the enantiomer pairs - >95.0% with 42
untrained panelists; >95.0% with 20 expert
panelists; overall >98.0% (all 62 panelists).
Theimer's personal comments indicates that he had
no problem in differentiating the enantiomers of
the pinoacetaldehydes since the laevo had a
"hydroxycitronellal" character and the dextro
reminded of cyclohexyl acetaldehyde.
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NA
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(1S,3R,5S)-(+)-trans-Pinocarvyl
propionate - Probability levels of significant
differentiation between the enantiomer pairs -
>99.9% with 32 untrained panelists; >99.9%
with 19 expert panelists; overall >99.9% (all 51
panelists). No comments on the odor of the
enantiomers was provided in Theimer's paper.
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NA
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(1R,3S,5R)-(-)-trans-Pinocarvyl
propionate - Probability levels of significant
differentiation between the enantiomer pairs -
>99.9% with 32 untrained panelists; >99.9%
with 19 expert panelists; overall >99.9% (all 51
panelists). No comments on the odor of the
enantiomers was provided in Theimer's paper.
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NA
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(1S,3R,5S)-(+)-trans-Pinocarveol
- Probability levels of significant differentiation
between the enantiomer pairs - >90.0% with 99
untrained panelists; >99.9% with 29 expert
panelists; overall >99.9% (all 128 panelists).
Theimer's personal comments indicates that he had
no problem in differentiating the enantiomers - the
(-)- and (+)-pinocarveols "were easily separated by
reminding of geraniol palmarosa and camphor
respectively".
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NA
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(1R,3S,5R)-(-)-trans-Pinocarveol
- Probability levels of significant differentiation
between the enantiomer pairs - >90.0% with 99
untrained panelists; >99.9% with 29 expert
panelists; overall >99.9% (all 128 panelists).
Theimer's personal comments indicates that he had
no problem in differentiating the enantiomers - the
(-)- and (+)-pinocarveols "were easily separated by
reminding of geraniol palmarosa and camphor
respectively".
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NA
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(+)-(1S,4R)-Fenchone
oxime - roasted onion fragrance
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NA
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(-)-(1R,4S)-Fenchone
oxime - weak, turnip fragrance
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NA
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(+)-(1S,4R)-Fenchone
oxime O-methyl ether - borneol–turpentine
fragrance
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NA
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(-)-(1R,4S)-Fenchone
oxime O-methyl ether - turpentine fragrance
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NA
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