NaughtieGirl
04-27-2005, 02:46 PM
would
love to read this article but the html page is no longer active. did anyone by any chance download it or copy it?
thanks
Hey Metro!
When I clicked on it, I came up with this (see below) That makes me suspect your
browser is at fault. Which one are you using?
Intriguing link btw, that I will delve into tomorrow.
Thanks!our Perception
http://www.leffingwell.com/chirality/image.gif
Steroid Urine Type Odorants &
Sandalwood Type Odorants
by John C. Leffingwell,
Ph.D.
Photo by permission of M. Roudintska -
Art &
Parfum (http://www.art-et-parfum.com/)
Cyclic
Terpenoid Odorants (http://www.leffingwell.com/chirality/cyclic_terpenoid.htm)
Bicyclic Terpenoid
Odorants (http://www.leffingwell.com/chirality/bicyclic_terpenoid.htm)
Acyclic
Terpenoid
Odorants (http://www.leffingwell.com/chirality/acyclic_terpenoid.htm)
Ionones,
Irones, Damascones & Structurally Related
Odorants (http://www.leffingwell.com/chirality/ionone_irone.htm)
Acyclics
(Alcohols, Esters, Acids,
Aldehydes) (http://www.leffingwell.com/chirality/acyclics.htm)
Lactones
(http://www.leffingwell.com/chirality/lactones.htm)
Sesquiterpenoi
d Related
Odorants (http://www.leffingwell.com/chirality/sesquiterpenoid_%26_diterpen.htm)
Steroi
d Urine Type Odorants (http://www.leffingwell.com/chirality/steroid_&_sandalwood.htm)
Sandalwood Type
Odorants (http://www.leffingwell.com/chirality/steroid_&_sandalwood.htm)
Musk
Odorants (http://www.leffingwell.com/chirality/musk.htm)
Miscellaneous
(http://www.leffingwell.com/chirality/miscellaneous.htm)
Enantiomer & Odor Description Odour Threshold
(PPB)
Steroid Type
Odorants
.
(+)-androstenone
- strong urine
odor (http://www.leffingwell.com/chirality/androstenone.htm)
0.18
(-)-andros
tenone -
odorless (http://www.leffingwell.com/chirality/androstenone.htm)
Odorless
(-)-androsta-4,16-dien-3-one -
odorless (http://www.leffingwell.com/chirality/androstadienone.htm)
Odorless
(+)-androsta-4,16-dien-3-one - very persistent odor of urine &
sweat (http://www.leffingwell.com/chirality/androstadienone.htm)
0.98
(+)-5-alph
a-androst-16-en-3-alpha-ol (http://www.leffingwell.com/chirality/androstenol.htm) - Animalic, musk-like odor with a strong (fine) sandalwood
tonality
0.02
ent-(-)-5-alpha-andro
st-16-en-3-alpha-ol (http://www.leffingwell.com/chirality/androstenol.htm) - Weaker with a detection threshold level about six orders of magnitude higher
than 5-alpha-androst-16-en-3-alpha-ol
NA
Nature Identical Sandalwood
Odorants
(-)-(1'S,2'R,4'R)-
(Z)-beta-santalol (http://www.leffingwell.com/chirality/santalol.htm)- Typical sandalwood scent, identical to the natural
product.
NA
(+)-(1'R,2'S,4'S)-(Z)-b
eta-santalol (http://www.leffingwell.com/chirality/santalol.htm) - No scent
(odorless).
Odorless
(-)-(1'S,2'R,4R)- (E)-beta-santalol (http://www.leffingwell.com/chirality/santalol.htm) - Scent similar to (-)-(1'S,2'R,4'R)-(Z)-beta-santalol but less
intense.
NA
(+)-(1'R,2'S,4'S)-
(E)-beta-santalol (http://www.leffingwell.com/chirality/santalol.htm) - No scent (odorless).
Odorless
Sandalwood Type Odorants from
Campholenic aldehyde
(-)-(1'R)-4-(2',2',3'-trimethyl-
3'-cyclopenten-1'-yl)-4-penten-1-al - fragrance further possessing an aldehydic note,
reminiscent of citronellal, citrusy, spicy, recalling the odor of the citronella leaves. As to its bottom note, it
has a character which is reminiscent of the odor of 3-(4-tert-butyl-1-phenyl)-2-methylpropanal, but with an even
greener connotation and a slightly orangy
aspect (http://www.leffingwell.com/chirality/sandalwood_5.htm)
NA
(+)-(1'S)
-4-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl)-4-penten-1-al - a more metallic and
aldehydic odor, recalling that of trans-4-decenal, and the bottom note of which is more floral and even stronger in
the aqueous character. The use of this latter compound to enhance the latter odor character in perfumed compositions
and articles is in fact preferred to that of its
(-)-(1'R)-enantiomer (http://www.leffingwell.com/chirality/sandalwood_5.htm)
NA
(-)-(1'R)-2-methyl-4-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl)-4-pentenenitrile -
a woody-citrus, fruity and slightly fatty odor prefered to the
(+)-(1'S)-isomer (http://www.leffingwell.com/chirality/sandalwood_7.htm)
NA
(+)-(1'S)-2-methyl-4-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl)-4-pentenenitrile - not
as prefered an odor as the
(-)-(1'R)-isomer (http://www.leffingwell.com/chirality/sandalwood_7.htm)
NA
(-)-(1'R,2R)-2-methyl-4-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl) -4-pentenenitrile -
citrus, fruity and fresh character accompanied by a sandalwood bottom
character (http://www.leffingwell.com/chirality/sandalwood_7.htm)
NA
(+)-(1S,2s)-2-methyl-4-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl) -4-pentenenitrile - odor not
described other than to say the (1'R)-isomers are
preferred (http://www.leffingwell.com/chirality/sandalwood_7.htm)
(-)-(1'R,2S)
-2-methyl-4-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl) -4-pentenenitrile - a sandalwood
odor wherein the desired fruity-citrus character of the (-)-(1'R,2R)-isomer is no longer
present (http://www.leffingwell.com/chirality/sandalwood_7.htm)
NA
(+)-(1'S
,2R)-2-methyl-4-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl) -4-pentenenitrile - odor not
described other than to say the (1'R)-isomers are
preferred (http://www.leffingwell.com/chirality/sandalwood_7.htm)
(-)-(1'R,2R)
-2-methyl-4-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl) -4-penten-1-ol - elegant and powerful sandalwood note
(prefered of the four
isomers) (http://www.leffingwell.com/chirality/sandalwood_6.htm)
NA
(+)-(1'
S,2S)-2-methyl-4-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl) -4-penten-1-ol - odor is less
rich in the precious "lait de santal" type odor character present in the (-)-(1'R,2R)- and (-)-(1'R,2S)-
isomers (http://www.leffingwell.com/chirality/sandalwood_6.htm)
NA
(-)-(1'R
,2S)-2-methyl-4-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl) -4-penten-1-ol - sandalwood
note is not as powerful as the (-)-(1'R,2R)-isomer but is accompanied of a more marked woody-cedar
character (http://www.leffingwell.com/chirality/sandalwood_6.htm)
NA
(+)-(1S,2R)-2-methyl-4-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl) -4-penten-1-ol - odor is
less rich in the precious "lait de santal" type odor character present in the (-)-(1'R,2R)- and (-)-(1'R,2S)-
isomers (http://www.leffingwell.com/chirality/sandalwood_6.htm)
NA
(-)-(1'R
,E)-3,3-dimethyl-5-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl)-4-penten-2-ol - develops a
sandalwood note, the character of which is strongly reminiscent of the typical milky odor of
sandalwood (http://www.leffingwell.com/chirality/sandalwood_1.htm)
NA
(+)-(1
'S,E)-3,3-dimethyl-5-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl)-4-penten-2-ol - drier,
more woody-cedar and less milky than that of its (-)-(1'R,E)-
isomer (http://www.leffingwell.com/chirality/sandalwood_1.htm)
NA
(+)-(1'S,
2S,E)-3,3-dimethyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol - develops a
sandalwood note of remarkable strength, wherein the typical milky character is represented at its best and
accompanied by a slightly animal note; prefered of four possible
isomers (http://www.leffingwell.com/chirality/sandalwood_1.htm)
NA
(-)-(1'R
,2R,E)-3,3-dimethyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol - weakest and less
characteristic sandalwood note than any of the other
isomers (http://www.leffingwell.com/chirality/sandalwood_1.htm)
NA
(+)-(1'S
,2R,E)-3,3-dimethyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol - ranked in 3d place
of 4 isomers for its sandalwood
odor (http://www.leffingwell.com/chirality/sandalwood_1.htm)
NA
(-)-(1'R,2S
,E)-3,3-dimethyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol - weaker and less
characteristic sandalwood note than the (+)-(1'S,2S,E)-isomer but superior to the (+)-(1'S,2R,E)- or
(-)-(1'R,2R,E)-
isomers (http://www.leffingwell.com/chirality/sandalwood_1.htm)
NA
(1'R,E)-
(+)-2-Methyl-4-(2',2',3'-trimethyl-cyclopent-3-enyl)-but-2-en-1-ol - fresh and strong
sandalwood oil odor associated with green
trees (http://www.leffingwell.com/chirality/sandalwood_3.htm)
51
(1'S,E)-(-
)-2-Methyl-4-(2',2',3'-trimethyl-cyclopent-3-enyl)-but-2-en-1-ol - dry and weak sandalwood
oil odor with a milky and floral
note (http://www.leffingwell.com/chirality/sandalwood_3.htm)
424
(1'R,E)-(-
)-2-Ethyl-4-(2',2',3'-trimethyl-cyclopent-3-enyl)-but-2-en-1-ol - clean, bright and strong
sandalwood oil odor with richness and a woody
note (http://www.leffingwell.com/chirality/sandalwood_2.htm)
0.85
(1'S,E)-(
-)-2-Ethyl-4-(2,2,3-trimethyl-cyclopent-3-enyl)-but-2-en-1-ol - milky sandalwood oil odor
with a cedar
character (http://www.leffingwell.com/chirality/sandalwood_2.htm)
44
(-)-(1R)-2-methyl-4-(2',2',3'- trimethyl-3'-cyclopenten-1'-yl) -4-penten-1-al - possesses an
unexpected odor in view of the prior knowledge regarding the odor properties of campholenic aldehyde derivatives. It
develops a woody-sandalwood type odor note, slightly aldehydic, which is more reminiscent of the cedar-pine odor
connotation than of the sandalwood type one, which note is combined with a distinct marine, ozone character. The
latter is reinforced in the bottom note, which is strongly ozone-marine-like, recalling the odor of seaweeds. In
addition, the odor of this compound has a good strength and
tenacity. (http://www.leffingwell.com/chirality/sandalwood_4.htm)
NA
(+)-(1S)-2-methyl-4-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl) -4-penten-1-al - woody,
sandalwood, aldehydic, faintly
aqueous (http://www.leffingwell.com/chirality/sandalwood_4.htm)
NA
(1'S,1''S,2'S,3''R,5''R)-Javanol - sandalwood, creamy, warm,
strong (http://www.leffingwell.com/chirality/javanol.htm)
NA
(1'R,1''R,2R,3''S,5''S)-Javanol - lactonic, lily of the
valley (http://www.leffingwell.com/chirality/javanol.htm)
NA
(1'R,1''S,2R,3''R,5''R)-Javanol - lactonic, with a sandalwood
aspect (http://www.leffingwell.com/chirality/javanol.htm)
NA
(1'S,1''R,2S,3''S,5''S)-Javanol - floral, rosy, milky,
sandalwood (http://www.leffingwell.com/chirality/javanol.htm)
NA
(-)-(1
S,E)-5-(2',2-dimethyl-3'-methylene-1'-cyclohexyl)-3,3-dimethyl-4-penten-2-ol (http://www.leffingwell.com/chirality/sandalwood_8.htm) - Woody, sandal, sweet
note, reminiscent of the odor of the bark and milk of the sandalwood
tree.
NA
(+)-(1'R,E)-5-(2',2-dim
ethyl-3'-methylene-1'-cyclohexyl)-3,3-dimethyl-4-penten-2-ol (http://www.leffingwell.com/chirality/sandalwood_8.htm)- Sandalwood odor, but distinctly
different than the (-)-(1S,E)-isomers
NA
Other Sandalwood
Odorants
(1R,3R
,1'S,2'R,4'S,6'S)-(+)-threo-trans-3-isocamphylcyclohexanol (http://www.leffingwell.com/chirality/isocamphylcyclohexanols.htm) - Strong, diffusive, and
sandalwood-like odor; natural sandalwood odor, but very strong and
keen
0.2
(1S,3S,1'R,2S,4'R,6'R)-(-)-threo-trans-3-isocamphylcyclohexanol (http://www.leffingwell.com/chirality/isocamphylcyclohexanols.htm) - weak, moldy and woody
odor
200
(1S,3S,1'S,2R,4'S,6'S) (+)-erythro-trans-3-isocamphylcyclohexanol (http://www.leffingwell.com/chirality/isocamphylcyclohexanols.htm) - sandalwood like odor without moldy feeling,
and it is sufficiently
diffusive
7
(1R,3R,1'R
,2'S,4'R,6'R)-(-)-erythro-trans-3-isocamphylcyclohexanol (http://www.leffingwell.com/chirality/isocamphylcyclohexanols.htm) - strong, warm sandalwood
odor
3
(+)-(1S,3R,6
R,8R)-8-tertbutylbicyclo[4.4.0]decan-3-ol (http://www.leffingwell.com/chirality/tertbutylbicyclodecan-3-ols.htm) - strong, sandalwood like, warm, sweet and fatty, long
persisting,
NA
(-)-
(1R,3S,6S,8S)-8-tertbutylbicyclo[4.4.0]decan-3-ol (http://www.leffingwell.com/chirality/tertbutylbicyclodecan-3-ols.htm) - very weak, fatty, hardly perceptible, remote
reminiscent to animal
notes.
NA
(2S,3R,4E)-3-m
ethyl-4-[(1R,2R,6R,7R)-tricyclo[5.2.1.02,6]dec-4-en-8-ylidene]butan-2-ol (http://www.leffingwell.com/chirality/tricyclodecenylbutanol.htm)- very strong, sandal(wood),
animalic
5
(2R,3S,4E)-3-
methyl-4-[(1S,2S,6S,7S)-tricyclo[5.2.1.02,6]dec-4-en-8-ylidene]butan-2-ol (http://www.leffingwell.com/chirality/tricyclodecenylbutanol.htm)- weak,
woody
168
(2R,3S,4E)-3-m
ethyl-4-[(1R,2R,6R,7R)-tricyclo[5.2.1.02,6]dec-4-en-8-ylidene]butan-2-ol (http://www.leffingwell.com/chirality/tricyclodecenylbutanol.htm) - sandal(wood),
animalic
70
(2S,3R,4E)-3
-methyl-4-[(1S,2S,6S,7S)-tricyclo[5.2.1.02,6]dec-4-en-8-ylidene]butan-2-ol (http://www.leffingwell.com/chirality/tricyclodecenylbutanol.htm) -
woody
72
(2R,3R,4E)-3-me
thyl-4-[(1R,2R,6R,7R)-tricyclo[5.2.1.02,6]dec-4-en-8-ylidene]butan-2-ol (http://www.leffingwell.com/chirality/tricyclodecenylbutanol.htm) - sandal(wood),
floral
137
(2S,3S,4E)-3-
methyl-4-[(1S,2S,6S,7S)-tricyclo[5.2.1.02,6]dec-4-en-8-ylidene]butan-2-ol (http://www.leffingwell.com/chirality/tricyclodecenylbutanol.htm)- very weak
floral
159
(2S,3S,4E)-3-
methyl-4-[(1R,2R,6R,7R)-tricyclo[5.2.1.02,6]dec-4-en-8-ylidene]butan-2-ol (http://www.leffingwell.com/chirality/tricyclodecenylbutanol.htm)- strong sandal(wood),
floral
46
(2R,3R,4E)-3-m
ethyl-4-[(1S,2S,6S,7S)-tricyclo[5.2.1.02,6]dec-4-en-8-ylidene]butan-2-ol (http://www.leffingwell.com/chirality/tricyclodecenylbutanol.htm) - weak
floral
204
(1R,2'R,3'S)-Ebanol
(http://www.leffingwell.com/chirality/ebanol.htm) - weak, no sandalwood odor relevance
>100 (relative in
series)
(1S,2'S,3'R)-Ebanol (http://www.leffingwell.com/chirality/ebanol.htm)
- Powerful sandalwood, more than 100X more powerful than its enantiomer (based on relative GC sniff threshold) and
more than 3X stronger than (1R,2'S,3'R)-Ebanol
1 (relative in
series)
(1R,2'S,3'S)-Ebanol (http://www.leffingwell.com/chirality/ebanol.htm)
- Slight sandalwood relevance, both enantiomers weak
>100 (relative in
series)
(1S,2'R,3'R)-Ebanol (http://www.leffingwell.com/chirality/ebanol.htm)
- No sandalwood relevance, both enantiomers weak
>100 (relative in
series)
(1R,2'S,3'R)-Ebanol (http://www.leffingwell.com/chirality/ebanol.htm)
- Powerful sandalwood, more than 33X more powerful than its enantiomer and more than 3X weaker than
(1S,2'S,3'R)-Ebanol
3 (relative in
series)
(1S,2'R,3'S)-Ebanol (http://www.leffingwell.com/chirality/ebanol.htm)
- no sandalwood relevance
>100 (relative in
series)
(1R,2'R,3'R)-Ebanol (http://www.leffingwell.com/chirality/ebanol.htm)
- no sandalwood relevance
>100 (relative in
series)
(1S,2'S,3'S)-Ebanol (http://www.leffingwell.com/chirality/ebanol.htm)
- no sandalwood relevance
>100 (relative in
series)
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