http://www.leffingwell.com/chirality...sandalwood.htm
There's a odorless -none (-).
Printable View
http://www.leffingwell.com/chirality...sandalwood.htm
There's a odorless -none (-).
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article but the html page is no longer active.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!Quote:
Originally Posted by metropolitan
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
Cyclic
Terpenoid Odorants
Bicyclic Terpenoid
Odorants
Acyclic
Terpenoid
Odorants
Ionones,
Irones, Damascones & Structurally Related
Odorants
Acyclics
(Alcohols, Esters, Acids,
Aldehydes)
Lactones
Sesquiterpenoi
d Related
Odorants
Steroi
d Urine Type Odorants
Sandalwood Type
Odorants
Musk
Odorants
Miscellaneous
Enantiomer & Odor Description Odour Threshold
(PPB)
Steroid Type
Odorants
.
(+)-androstenone
- strong urine
odor
0.18
(-)-andros
tenone -
odorless
Odorless
[color=#0000ff
](-)-androsta-4,16-dien-3-one[/color] -
odorless
Odorless
[color=#0000ff
](+)-androsta-4,16-dien-3-one[/color] - very persistent odor of urine &
sweat
0.98
(+)-5-alph
a-androst-16-en-3-alpha-ol - Animalic, musk-like odor with a strong (fine) sandalwood
tonality
0.02
ent-(-)-5-alpha-andro
st-16-en-3-alpha-ol - 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 - Typical sandalwood scent, identical to the natural
product.
NA
(+)-(1'R,2'S,4'S)-(Z)-b
eta-santalol - No scent
(odorless).
Odorless
(-)-(1'S,2'R,4R)- (E)-beta-santalol - 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 - 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
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
NA
[color=#00
00ff](-)-(1'R)-2-methyl-4-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl)-4-pentenenitrile[/color] -
a woody-citrus, fruity and slightly fatty odor prefered to the
(+)-(1'S)-isomer
NA
[color=#0000ff
](+)-(1'S)-2-methyl-4-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl)-4-pentenenitrile[/color] - not
as prefered an odor as the
(-)-(1'R)-isomer
NA
[color=#0000ff
](-)-(1'R,2R)-2-methyl-4-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl) -4-pentenenitrile[/color] -
citrus, fruity and fresh character accompanied by a sandalwood bottom
character
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
(-)-(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
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
(-)-(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)
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
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
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
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
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
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
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
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
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
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
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
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
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
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.
NA
(+)-(1S)-2-methyl-4-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl) -4-penten-1-al - woody,
sandalwood, aldehydic, faintly
aqueous
NA
(1'S,1''S,2'S,3''R,5''R)-Javanol - sandalwood, creamy, warm,
strong
NA
(1'R,1''R,2R,3''S,5''S)-Javanol - lactonic, lily of the
valley
NA
(1'R,1''S,2R,3''R,5''R)-Javanol - lactonic, with a sandalwood
aspect
NA
(1'S,1''R,2S,3''S,5''S)-Javanol - floral, rosy, milky,
sandalwood
NA
(-)-(1
S,E)-5-(2',2-dimethyl-3'-methylene-1'-cyclohexyl)-3,3-dimethyl-4-penten-2-ol - 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 - 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 - 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 - weak, moldy and woody
odor
200
(1S,3S,1'S,2R,4'S,6'S) (+)-erythro-trans-3-isocamphylcyclohexanol - 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 - strong, warm sandalwood
odor
3
(+)-(1S,3R,6
R,8R)-8-tertbutylbicyclo[4.4.0]decan-3-ol - strong, sandalwood like, warm, sweet and fatty, long
persisting,
NA
(-)-
(1R,3S,6S,8S)-8-tertbutylbicyclo[4.4.0]decan-3-ol - 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 - 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 - 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 - 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 -
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 - 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 - 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 - 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 - weak
floral
204
(1R,2'R,3'S)-Ebanol
- weak, no sandalwood odor relevance
>100 (relative in
series)
(1S,2'S,3'R)-Ebanol
- 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
- Slight sandalwood relevance, both enantiomers weak
>100 (relative in
series)
(1S,2'R,3'R)-Ebanol
- No sandalwood relevance, both enantiomers weak
>100 (relative in
series)
(1R,2'S,3'R)-Ebanol
- 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
- no sandalwood relevance
>100 (relative in
series)
(1R,2'R,3'R)-Ebanol
- no sandalwood relevance
>100 (relative in
series)
(1S,2'S,3'S)-Ebanol
- no sandalwood relevance
>100 (relative in
series)
HOME
[color=#
ffffff]Copyright 2002 - Leffingwell & Associates[/color]
when i try the link now it
works, so maybe the site was down.
thanks for posting the info. been playing with essential oils and fragrance
oils and sandalwood is a great one.
i recommend checking out the body shop perfume oils.
Quote:
Originally Posted by metropolitan
I agree, essential oils and aromatherapy seem to be the perfect complement to pheromones. Some of the nicer EO's
are quite pricey though. Sandalwood is one of the nice ones I did splurge on. There is tons of good info on this
forum about EO's as well. You can access it with the search function.
Quote:
Originally Posted by metropolitan
Browsers and the internet itself can get finicky. Often when I get an "unable to find" or other failure, if I come
back a while later all is fine. Although sometimes things *do* seem to screw up the browser software and I find it
best to shut it down and start anew (sometimes just the browser, othertimes I turn off the whole system and reboot.
Only way to totally clear out any junk in the RAM memory.)
These are what are known asQuote:
Originally Posted by bjf
opto-isomers. Identical except one is a mirror image of the other. There are many such compounds in nature. The ones
with the "wrong" mirror image don't fit into the proper receptor sites in the body and are therefore usually not
biologically active.
In other words, there is an odorless none, but it is not a pheromone.
Bass
Quote:
Originally Posted by metropolitan
Me too! If you're new at it I can recommend Mindy Green's "Natural Perfumes" I just bought it from Amazon.com.
It even has a paragraph or two about pheromones in the introduction.
Contents go a bit like this:
- basics of
aromatherapy
- blending fundamentals,
- a review of 40 oils
- 2 beginning blending lessons
- 30 fragrance
recipes
- elemental blends
- resource directory
What I like about it is that she suggests blends and then
tells you which particular oil to vary in quantity to make it suit your own taste. Proportions for fragrance
products. EO note type and odor intensity.
But I'm really new at it. You might already know all that stuff.
BassMan: Thanks for the info. Learned something new today! I was somewhat mystified by that link.
You mean there's a good chance it's not, don't you? Can we be certain?Quote:
Originally Posted by BassMan
yeah, i also have the mindy
green book!
another good book is
Per
fumes, Splashes & Colognes : Discovering and Crafting Your Personal Fragrances
by
Nancy M. Booth
a lot of informatioin on perfumery, essential oils, categories of scents and a lot more.
worth buying if you're into personal perfumery.
i also recently got
Sce
nts & Scentuality: Essential Oils & Aromatherapy for Romance, Love, and Sex (Paperback)
by
Valerie Ann Worwood
and this is an excellent aromatherapy for love, sex and romance. a tons of formulas and
recipes and what the intended results are for. it uses different angle. less concerned with perfumery and more with
the emotional, psychological, and sensual reactions we have to certain essential oils. very very good.
HeyQuote:
Originally Posted by metropolitan
thanks! :thumbsup: I already bought Nancy Booth's book along with Mindy Green's but I haven't read it yet. I
spent the evening last night highlighting in Mindy Green's book. V.A. Worwood's book is definitely next on my
list. I just love the "learning curve" of new endeavors!
Hi Madini.com is also a
good site if you want EO's or essences. This is were I get my honeysuckle, violet and rose oils from. Their prices
are reasonable too.
The Countess
i checked them out, sounds interesting, so i just orderedQuote:
Hi Madini.com is
also a good site if you want EO's or essences.
some of their samples.
It would probably be better to state itQuote:
Originally Posted by DrSmellThis
as:
If the odorless molecule _is_ a pheromone, it's probably a quite different one from the odorous one.
For example, the drug thalidomide - it was prescribed for morning sickness, later found to cause profound birth
defects. One isomer controlled the morning sickness, the other the birth defects.
Another example - vitamin E.
The D form is active in the body, the L form inactive. Which is why synthetic E (which is a mixture of the D and L
forms) is only half as potent as natural E (which is almost all D).
So, yeah, I probably overstated it, but
optical rotation usually makes a very large difference in biological activity.
-Bass
Thanks for the clarification.
:)
Yeah, D and L phenylalanine have
totally different functions, both generally positive, but very different.
So do R and S ALA. I don't
remember which, but one is negative, one is beneficial. Together, they sort of even out into a zero sum
game.
With something like androstadienone, there's a definite receptor, and we know what it is (the
vno).
With something like androstenol, we see a physiological change in subjects, but have no idea why it's
occuring. It's not through the vno.
That doesn't mean that a chiral switch of pheromones can't be tested,
however. Everyone of us here is testing mones all the time, but there's a catch with chiral forms, and that's that
there's barely ever enough to test...
Chiral switches are hard to get, and most known synthesis routes are
way too costly to be ready for even a smidge of prime time. You suffer from the fact that you don't have the
research dollars in this industry that you do in pharmaceuticals. Even those multibillion dollar companies avoided
chiral switches for years, due to the costs of development.
This article says that it took 15 years
(supposedly) to get Nexium out of Prilosec. Guh! Nexium is one half the man that Prilosec is. Lots of good info
here:
http://pubs.acs.org/cen/coverstory/8...18chiral2.html