Chirality & Odour Perception

Musk 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 & Furanones

Sesquiterpenoid Related Odorants

Steroid Urine Type Odorants

Sandalwood Type Odorants

Musk Odorants

Miscellaneous

Enantiomer & Odor Description
 Odour Threshold (PPB)

Musk Odorants

.

(4S,7R)-(-)-galaxolide - powerful musk odor

0.00063 (in air)

(4R,7S)-(+)-galaxolide - weak to almost odorless

0.13 (in air)

(4R,7R)-(+)-galaxolide - weak to almost odorless

0.44 (in air)

(4S,7S)-(-)-galaxolide - powerful musk odor

0.001 (in air)

(R)-(-)-muscone - rich, powerful, musky; very nice musky note, rich and powerful,”

61

(S)-(+)-muscone - poor, weakly musky

233

 (12R,9Z)- Nirvanolide® - intense musky, fruity, powdery odor with lactonic nuances

 0.05

(12S,9Z)- Nirvanolide® - odorless

odorless

(+)-(11R)-11-methyl-12-dodecanolide - a faint musk note with very fresh nuances of clary sage and bergamot is accompanied by cedar-wood accents. Only a slightly earthy-musty undertone has to be accounted.

NA

(-)-(11S)-11-methyl-12-dodecanolide - The smell of the (S)-enantiomer does not differ much in its sensory qualities, however it is of weaker intensity.

NA

(12S)-(-)-12-methyl-13-tridecanolide - animalic, musky, camphoraceous

NA

(12R)-(+)-12-methyl-13-tridecanolide - sandalwood-like musk note

NA

(12S,13R)-(-)-12-methyl-13-tetradecanolide - animalic cedar wood profile with camphoraceous aspects; devoid of musk notes

NA

(12R,13S)-(+)-12-methyl-13-tetradecanolide - strong woody odor with a pronounced musk character

NA

(12R)-(-)-12-methyl-9-oxa-14-tetradecanolide - intense musky-floral, powdery odor reminiscent of the nitro musk musk ambrette, with additional woody, myrrh-type factors

0.09

(12S)-(+)-12-methyl-9-oxa-14-tetradecanolide - odorless

odorless

(-)-(S)-Muscolide - weak intensity, but possesses a very pleasant musk note with a more distinctive erogenous-animalic character.

NA

(+)-(R)-muscolide - slightly erogenous, animalic, resembling that of natural musk tincture.

NA

(-)-(S)-Oxo-muscolide - possesses a weak musk note, without animalic character, and is dominated by an odour reminiscent of ironed linen.

NA

(+)-(R)-Oxo-muscolide - slightly musky and sweet, but not erogenous-animalic.

NA

(+)-(1'R,4S)-Helvetolide - Odor properties: musky, ambrette, pear. The fragrance effect imparted by the above-cited preferred compound of the invention is even more powerful and muskier when said compound is used in the form of one of its optically active isomers, i.e., (+)-Helvetolide

1.1 ng/liter in air

(-)-(1'S,4R)-Helvetolide - Odor properties: nicely musky and ambrette, pear, floral.

NA

(1S,1'R)-Romandolide® or (1S,1'R)-1-[(3',3'-dimethyl-1'-cyclohexyl)-ethoxycarbonyl]methyl propanoate - The odor properties are best represented in the enantiomer of the configuration (1S, 1'R), which renders this compound a choice ingredient of the invention. This compound possesses a classical musky type odor, reminiscent of that of Galaxolide® (7,8-dihydro-4,6,6,7,8,8-hexamethyl-6H-cyclopenta[9]-2-benzopyrane; and confers an olfactive impression which is that of a sweet and natural musky odor, with a velvety connotation, and which provides much volume. There is also found a light ambrette nuance which is accompanied by an undernote reminiscent of the odor of green fruits.

0.7 ng/liter in air

(1R,1'S)-Romandolide® or (1R,1'S)-1-[(3',3'-dimethyl-1'-cyclohexyl)-ethoxycarbonyl]methyl propanoate - This compound is less preferred than the (1S, 1'R) enantiomer.

NA

(+)-(1S,1'R)-Rosamusk - powerful rose/ionone character with fruity and musk-like undertones

NA

(-)-(1R,1'S)-Rosamusk - This compound is less preferred than the (1S, 1'R) enantiomer.

NA

(3S)-(-)-3-Methyl-1,4-dioxacyclopentadecan-2-one - musk, sweet-flowery, ambergris, erogenous, animalic, reminiscent of ambrette musk and nitromusk, weaker than the enantiomer mixture.

NA

(3R)-(+)-3-Methyl-1,4-dioxacyclopentadecan-2-one - musk, sweet-flowery, ambergris, erogenous, animalic, reminiscent of ambrette musk and nitromusk, stronger than the (S)-(-)-enantiomer.

NA

(3S)-(-)-3-Methyl-1,4-dioxacyclohexadecan-2-one - musk, sweet-woody, ambergris, erogenous, animalic, reminiscent of ambrette musk and nitromusk, weaker than the enantiomer mixture.

NA

(3R)-(+)-3-Methyl-1,4-dioxacyclohexadecan-2-one - musk, sweet-woody, ambergris, erogenous, animalic, reminiscent of ambrette musk and nitromusk, stronger than the (S)-(-)-enantiomer.

NA

(+)-(3R)-3,7-dimethyloct-6-enyl ethyl oxalate - Floral musk

200 ppb

(-)-(3S)-3,7-dimethyloct-6-enyl ethyl oxalate - Rose-like floral

500 ppb

(4R)-(-)-4-methyloxacyclopentadec-9-en-2-one - Diffusive powdery musk odor

NA

(4S)-(+)-4-methyloxacyclopentadec-9-en-2-one - Weak poor musk odor

NA

(3R)-(+)-3-Methyl-1,4-dioxa-(E/Z)-6-cyclopentadecen-2-one - Odor: musk, sweet-flowery, ambergris, erogenous, reminiscent of ambrette musk, more musk-like and erogenous than the (S)-(-)-enantiomer.

NA

(3S)-(-)-3-Methyl-1,4-dioxa-(E/Z)-6-cyclopentadecen-2-one - Odor: weakly musk, sweet-flowery, erogenous, weaker than the enantiomer mixture.

NA

(3R)-(+)-3-Methyl-1,4-dioxa-(E/Z)-6-cyclohexadecen-2-one - Odor: musk, sweet-woody, ambergris, erogenous, animalic, reminiscent of ambrette musk, stronger than the enantiomer mixture.

NA

(3S)-(-)-3-Methyl-1,4-dioxa-(E/Z)-6-cyclohexadecen-2-one - Odor: weakly musk, sweet-woody, erogenous.

NA

(+)-(1R,3R)-Muscol - strong musk scent and softness, excellent in diffusibility, and had a graceful aroma for musks

NA

(-)-(1S,3S)-Muscol - aromatic, weak animal woody with slight hay-rucksack smells, some fruity sweetness

NA

(-)-(1R,3S)-Muscol - aromatic, weak animal woody with slight hay-rucksack smells

NA

(+)-(1S,3R)-Muscol - very weak musk scent,chemical-like

NA

(3S)-(-)-Fixolide - strong musk

NA

(3R)-(+)-Fixolide - light, sweet, aromatic

NA

(S,S)-(-)-Vulcanolide - this enantiomer possesses the best developed odor properties. Its musky, markedly earthy, slightly amber character is particularly powerful.

NA

(R,R)-(+)-Vulcanolide - this enantiomer develops a fragrance of a less earthy character, with a woody side and the strength of which is clearly inferior to the (S,S)-enantiomer.

NA

(S,S)-(-)-Vulcanonitrile - stronger earthy, musky and woodier note than its (+)-(6R,7R) enantiomer.

NA

(R,R)-(+)-Vulcanonitrile - similar, but less musky and woody than the (-)-(6S,7S) enantiomer

NA

(-)-(3R,5Z)-3-methylcyclopentadec-5-en-1-one - Strong and pure smell of musk with some sweaty notes -

NA

(+)-(3S,5E)-3-methylcyclopentadec-5-en-1-one - Weak musk with a little woody feeling

NA

(-)-(3R,5E)-3-methylcyclopentadec-5-en-1-one - Strong and pure smell of musk

NA

(+)-(3S,5E)-3-methylcyclopentadec-5-en-1-one - Weak musk with a little woody feeling

NA

(+)-(S)-13-Tetradecanolide - Complex, woody-cedar, balsamic odor; very similar to is enantiomer

NA

(-)-(R)-13-Tetradecanolide - Complex, woody-cedar, balsamic odor; very similar to is enantiomer

NA

Ethyl (1S)-1-[(1'R)-3,3-dimethylcyclohexyl]ethyl malonate - Powerful Musky, Fruity, Woody, Ambery

Rel. Odor Int. = 7.5

Ethyl (1RS)-1-[(1'RS)-3,3-dimethylcyclohexyl]ethyl malonate - Fruity, Apple, Musky

Rel. Odor Int. = 5.0

Ethyl (1S)-1-[(1'RS)-3,3-dimethylcyclohexyl]ethyl malonate - Musky, Fruity, Honey, Woody, Ambery

Rel. Odor Int. = 6.0

Ethyl (1R)-1-[(1'RS)-3,3-dimethylcyclohexyl]ethyl malonate - Masky, Dirty Honey, Fruity, Woody

Rel. Odor Int. = 4.0

(R)-(+)-Tonalide - light and sweet aromatic odor

NA

(S)-(-)-Tonalide - strongly musky odor with a good fixation property

NA

(14S)-14-ethyloxacyclotetradecan-2-one - distinct woody, fresh and fruity, clearly musk

NA

(14R)-14-ethyloxacyclotetradecan-2-one - weak musk odour with a smell of burning, musty, not fresh

NA

(17S)-17-ethyloxacycloheptadecan-2-one - weak, a touch of musk, slightly woody and fruity

NA

(17R)-17-ethyloxacycloheptadecan-2-one - distinct musk odour: pleasant powdery and slightly fresh

NA

(14S)-14-Ethyl-11-methylideneoxacyclotetradecan-2-one - weak musk odour with a musty-woody tonality

NA

(14R)-14-Ethyl-11-methylideneoxacyclotetradecan-2-one - strong musk note, fresh and clearly woody with cedarwood-like aspects

NA

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