Haven’t seen too much talk on this. Is it being used in any phero products as of yet? Increases sleep quality. Influences respiration and heart rate.
Two studies by Maiworm:
http://wwwpsy.uni-muenster.de/inst2/maiworm/pub3.html
http://wwwpsy.uni-muenster.de/inst2/maiworm/pub4.html
here is a snippet that explains where hexanoic acid fits in to the couplin group
http://everything2.com/index.pl?node_id=1722038
Copulins are short-chain fatty acids that are produced by the human female vagina, as well as the vaginas of other related primates. Copulins are pheromones that have been experimentally proven to somewhat increase the sexual attraction of males to the females that smell of them. The copulins are less effective than the steroid pheromones though. Acetic acid (COOHCH3) is technically not a copulin, but it is often falsely believed to be one by people in the general populace. There are 6 different copulin chemicals, which are:
- propanoic acid aka propionic acid: COOHCH2CH3
- butanoic acid aka butyric acid: COOH(CH)2CH3
- 2-methylpropanoic acid aka isobutyric acid: COOHCH2(CH2)CH3
- pentanoic acid aka valeric acid: COOH(CH2)3CH3
- 3-methylbutanoic acid aka isovaleric acid: COOHCH2CH2(CH3)CH3
- hexanoic acid (http://everything2.com/index.pl?node=hexanoic%20acid) aka caproic acid: COOH(CH2)4CH3
The copulin chemicals smell bad and have been shown to damage mucous membranes when their concentration in the air is high, or when they are applied directly to mucous membranes in a liquid solution. Specificly, the copulins smell rancid, sweaty, dairy, and/or goat-like. In fact, the latin word ‘caper’, from which caproic acid was named, means ‘goat’. Butanoic acid, unlike the other copulins, smells somewhat fruity.
That means that the copulins are clearly not the chemical(s) of the naturally-occurring human female attractant scent.
here is a blog page that says hexanoic acid smells of goat… (hmm, i suppose this has nothing to do with IFM goat smell)
http://archive.tenderbutton.com/?p=108
here is a snippet that explains where hexanoic acid fits in to the couplin group
http://everything2.com/index.pl?node_id=1722038
Copulins are short-chain fatty acids that are produced by the human female vagina, as well as the vaginas of other related primates. Copulins are pheromones that have been experimentally proven to somewhat increase the sexual attraction of males to the females that smell of them. The copulins are less effective than the steroid pheromones though. Acetic acid (COOHCH3) is technically not a copulin, but it is often falsely believed to be one by people in the general populace. There are 6 different copulin chemicals, which are:
- propanoic acid aka propionic acid: COOHCH2CH3
- butanoic acid aka butyric acid: COOH(CH)2CH3
- 2-methylpropanoic acid aka isobutyric acid: COOHCH2(CH2)CH3
- pentanoic acid aka valeric acid: COOH(CH2)3CH3
- 3-methylbutanoic acid aka isovaleric acid: COOHCH2CH2(CH3)CH3
- hexanoic acid (http://everything2.com/index.pl?node=hexanoic%20acid) aka caproic acid: COOH(CH2)4CH3
The copulin chemicals smell bad and have been shown to damage mucous membranes when their concentration in the air is high, or when they are applied directly to mucous membranes in a liquid solution. Specificly, the copulins smell rancid, sweaty, dairy, and/or goat-like. In fact, the latin word ‘caper’, from which caproic acid was named, means ‘goat’. Butanoic acid, unlike the other copulins, smells somewhat fruity.
That means that the copulins are clearly not the chemical(s) of the naturally-occurring human female attractant scent.
here is a blog page that says hexanoic acid smells of goat… (hmm, i suppose this has nothing to do with IFM goat smell)
http://archive.tenderbutton.com/?p=108
interesting comment there sugggests a potential interesting perfume note to play with. tacitus/mharris..?
Scott
April 27th, 2006 | 10:24 am
My favorite odoriferous compound is 3-methyl-2-hexenoic acid. This is the essence of human sweat. One drop makes an entire room smell like the locker room of the Stanford Football team after losing to UC Berkeley in an overtime game on a hot day while wearing already smelly jerseys and soiled jock straps. It is super strong! Interestingly, people suffering from schizophrenia have a much higher concentration of this in their sweat. I have made a cologne consisting of 3-methyl-2-hexenoic acid with androstenedione and have found this to activate bonding and mating behavior in women. It is really amazing stuff!
Yes I would be interested in trying hexenoic acid!!!
Has anyone played with this one?
From my post at: Testosterone + A314
Some random testimonials (probably posted by the same person) I found on the net a while back about another banned ‘prohormone’ that acts as a pheromone when worn externally. This time it is androstenedione. Note that ‘3-methyl-2-hexenoic acid’ is known as the major stinky component of human sweat. I wonder if there is some kind of synergy between this substance (despite the drawback of heavy stink) and pheromones or prohormones that act as pheromones when used externally?
http://www.mazepath.com/uncleal/druguse.htm
“[If alpha geeks out there are experiencing a heterosexual dry spell - like your entire life up until reading this - Uncle Al has two suggestions. First, take a shower (with soap) and shampoo your hair. Second, add a drop of vanilla flavoring, a drop of 3-methyl-2-hexenoic acid, and 50 mg of androstenedione to your cologne (or add a spritz of Boar Mate afterward). That will get distaff rhinencephala smoking.]”
http://blog.tenderbutton.com/?p=108
“My favorite odoriferous compound is 3-methyl-2-hexenoic acid. This is the essence of human sweat. One drop makes an entire room smell like the locker room of the Stanford Football team after losing to UC Berkeley in an overtime game on a hot day while wearing already smelly jerseys and soiled jock straps. It is super strong! Interestingly, people suffering from schizophrenia have a much higher concentration of this in their sweat. I have made a cologne consisting of 3-methyl-2-hexenoic acid with androstenedione and have found this to activate bonding and mating behavior in women. It is really amazing stuff!
Comment by Scott ?€” April 27, 2006 @ 10:24 am”
http://cosmicvariance.com/2006/05/12/eau-de-stilton/
- Uncle Alon May 12th, 2006 at 5:08 pm
“Start with a bottle of cologne. Add one small drop each of vanilla flavoring and 3-methyl-2-hexenoic acid plus 50 mg of androstenedione,alpha-androstenol (5{alpha}-androst-16-en-3{alpha}-ol], or a few drops of Boar Mate. Mix well, apply.
OTOH, it is an amazing babe magnet.
[Remainder of comment edited to comply with family blog values - JoAnne]”
Doesn’t say what size of cologne bottle.
Pheroquirk, I believe the hexanoic acid present in copulin is different from the 3-methyl-2-hexenoic acid.
Also, something about it reminds me of previous NPA posts on the l-s board about giving women sexual dreams about the wearer.
As shown in the study by Maiworm this does have an effect on sleep quality and quite possibly dreams but the study was done on men, now if the same study was done on women we might have a better idea.
Also, there is a place selling androstenedione and androstenediol for use as pheromone. Maybe at that concentration (0.5mg/ml) where the entire bottle wouldn’t be equivalent to one dose of someone who takes those for bodybuilding purposes, it’s not restricted.
Anyone game to try these.
Cologne + Androstenedione + Androstenediol + Hexenoic Acid (small judicious amount until it starts affecting the scent)
Yes - think you’re right.
I’m sure that somebody I know would be, but where might the hexenoic acid be obtained?
[Yes guys I think 3-methyl-2-hexenoic acid and/or 7-octenoic acid may well be ‘psychologically active’. Have a look at the ‘free patent’ online below]
http://www.freepatentsonline.com/5141921.html
A perfume composition containing 3-methyl-2-hexenoic acid and/or 7-octenoic acid is disclosed. The perfume composition has a fresh and natural animal note and excellent diffusibility and tastiness. The perfume composition produces psychological effects on humans, such as an awakening effect and/or a sedative effect.
[From the text below the initial blurb:]
In any case, 3-methyl-2-hexenoic acid has an animal odor and particularly a civet-like or musk-like odor combined with woody, camphor-like, fatty, and fruity elements to give off, as a whole, a sexual odor. The delicate difference in odor between the (E)-isomer and the (Z)-isomer lies in that the latter feels slightly softer than the former.
Synthetic 7-octenoic acid was also confirmed to have a strongly diffusible animal note which agrees with that of the compound isolated from the secretion of human skin. This compound has an animal and fatty odor combined with amber-like, woody and fruity elements to give off, as a whole, a sexual odor.
?€?
The amount of 3-methyl-2-hexenoic acid and/or 7-octenoic acid to be compounded is selected appropriately depending on use. Usually, it is from 0.001 to 2% by weight, and preferably from 0.01 to 1% by weight, based on the whole perfume composition. In concentrations exceeding 2%, these compounds, particularly 3-methyl-2-hexenoic acid would emit an offensive armpit smell (hircismus)-like smell to make the composition rather unpleasant, failing to obtain a desired pleasant animal note. On the other hand, in concentrations less than 0.001%, no effect as a perfume is produced.
?€?
3-Methyl-2-hexenoic acid
Four out of the five males showed values higher than 100%, while four out of the five females showed values lower than 100%, indicating that 3-methyl-2-hexenoic acid gives an awakening effect to males and a sedative effect to females.
7-Octenoic acid
Four out of the five males showed values lower than 100%, while four out of the five females showed values higher than 100%, indicating that 7-octenoic acid gives a sedative effect to males and an awakening effect to females.
It was thus proved that 3-methyl-2-hexenoic acid and 7-octenoic acid give males and females a sedative effect and an awakening effect in an entirely opposite mode according to the sex.
Did anyone get a chance to play with this yet, Pheroquirk, Visionary, tacitus…anyone?
I haven’t tried it but I received the following email reply from Narchem Corporation in reponse to my enquiry:
“Thank you for your message. The product trans-3-Methyl-2-hexenoic acid (E isomer) is our catalog number 27960-21-0 (this is also
the cas number). We are currently offering only the trans isomer.
Pricing is as follows:
1 gram at $200
2 grams at $349.
Purity is min 97%. We currently have stock.
FOB Chicago plant.
Sincerely,
[Narchem staff member]”
I said I was a private buyer and would be interested in a minimal quantity.
Here is their product list: Product List)
They have the following three products in their list that might be of interest:
018951-40-1 C7H12O2 cis-3-Methyl-2-hexenoic acid
C7H12O2 3-Methyl-2-hexenoic acid
027960-21-0 C7H12O2 trans-3-Methyl-2-hexenoic acid
I understand that there are (E)- and (Z)-3-methyl-2-hexenoic acid forms of this molecule and I am assuming that is what the ‘cis’ and ‘trans’ versions in the list refer to.
We need the correct forms though that were used in the studies and the patent in the posts above, and I am not sure the correct form is the trans/(E) isomer.
I think it would be better if Androstics synthesised it and put it in the putatives. And it doesn’t 3-Methy-2-Hexenoic Acid doesn’t have to ridiculously stink either - there is something called cross-adaptation which has been shown to reduce the perceived odour. I will post about ‘cross-adaptation’ soon.
Visionary
I’ve been fascinated by the use of adjunctive fragrants… many of these intermediate weight fatty acids and their chemical relatives are major components of aged cheese… especially the smelly imported traditional cheeses… the local bacteria convert a proportion of the milk fats (technically these are triglycerides, which are three fatty acids linked to a glycerine molecule) into their simpler components… I’ve smelled some cheeses so rank they could clear out a room of Americans who weren’t accustomed to that sort of thing… and I’ve had dinner in top grade european restaurants where the cheese cart is rolled out after the meal and you’d think some unfortunate customer had had colon surgery… eeeeewwwww to the third power… and to think the chef or his deputy personally selected these as the finest example of culinary art ?
hehe cheese cologne sounds like something I want to try… oh wait here it is: New fragrance: Eau de Stilton :: Now Smell This
Okay as I was saying 3-Methyl-2-Hexenoic Acid doesn’t have to stink to high heaven if the correct structurally similar but pleasant smelling odorant is used along with it because of olfactory adaptation (see below). In this way we might enjoy the ‘psychological’ effects of 3M2H without the stink…
Olfactory adaptation refers to the loss of sensitivity to an odor when one is constantly exposed to an odor. Olfactory cross-adaptation occurs when the nose adapts to one odor and then also becomes less sensitive to a second odor that is perceptually or structurally different from the first.
Although it has long been known that perceptual similarity influences cross-adaptation, recent evidence suggests that structural similarity, in the absence of perceptual similarity, can also influence cross-adaptation. Pierce et al., Chem. Senses, 20: 401-411 (1995); Pierce et al., J. Soc. Cosmet. Chem., 47: 363-375 (Dec. 1996). Pierce et al. report the cross-adaptation of sweaty-smelling 3-methyl-2-hexenoic acid (3M2H) by its ethyl esters…
1: Chem Senses. 1995 Aug;20(4):401-11. Links
Cross-adaptation of sweaty-smelling 3-methyl-2-hexenoic acid by a structurally-similar, pleasant-smelling odorant.
Pierce JD Jr,
Zeng XN,
Aronov EV,
Preti G,
Wysocki CJ.
Monell Chemical Senses Center, Philadelphia, PA 19104-3308, USA.
Cross-adaptation has been interpreted as a measure of the degree to which odors share common sensory channels. How structural similarity, in the absence of perceptual similarity, influences cross-adaptation is unknown. The present study assessed cross-adaptation by structurally similar, but perceptually different, odorants. Magnitude estimates for a 10:1 mixture of (E)- and (Z)-3-methyl-2-hexenoic acid (3M2H), a principal component of human underarm odor, decreased following adaptation to a mixture of (E)- and (Z)-ethyl esters of 3M2H (EE3M2H), which possess a pleasant, fruity odor. Cross-adaptation was asymmetric; adaptation to 3M2H did not significantly affect the perceived intensity of EE3M2H. By contrast, there was no significant cross-adaptation between 3M2H and the fruity-smelling ethyl esters of its homologues, 3-methyl-2-octenoic acid (EE3M20) and 3-methyl-2-pentenoic acid (EE3M2P). Similarity ratings revealed no differences among the three ethyl esters in their perceptual similarity to 3M2H (i.e. all were rated equally dissimilar to 3M2H). Molecular modeling studies revealed no difference in the charge distribution of these molecules. Rather, differences in the shape and size of the hydrophobic part of the molecule may determine the extent of cross-adaptation. These results demonstrate that structurally-similar, yet perceptually-distinct, odorants may cross-adapt and suggest that the extent of cross-adaptation may be affected by the degree of structural, as well as perceptual, similarity.
PMID: 8590025 [PubMed - indexed for MEDLINE]
New perfume with Hexenoic Acid: Patent application
Perfume composition - Patent 5141921
A perfume composition containing 3-methyl-2-hexenoic acid and/or 7-octenoic acid is disclosed. The perfume composition has a fresh and natural animal note and excellent diffusibility and tastiness. The perfume composition produces psychological effects on humans, such as an awakening effect and/or a sedative effect.
Yes bull that is what I was referring to in the sixth post of this thread. The only thing is that the patent was filed in the early 1990s and nothing has been heard of this ‘perfume composition’ since. So it might suggest it really isn’t that effective? Also looking at the test results for Androsterone and Androstenol in that patent application, they seem to be quite wrong:
Perfume composition - Patent 5141921
"…ii) Test Results
Androstenol
All the five males showed values lower than 100%, while four out of the five females showed values higher than 100%, indicating thatandrostenol gives a sedative effect to males and an awakening effect to females.
Androsterone
Males showed no specific tendency, while all the five females showed 100% or lower values, indicating that androsterone gives a sedative effect to females.
It can be seen from these results that 3-methyl-2-hexenoic acid and 7-octenoic acid, though having no hormonal activity, give humans psychological effects similar to those produced on smelling male hormones, e.g., androstenol and androsterone. More specifically, 7-octenoic acid is expected to give males and females psychological effects similar to androstenol , while 3-methyl-2-hexenoic acid is expected to give females psychological effects similar to androsterone…"
However the assignee of that patent application, ‘Takasago International Corporation’ (http://www.takasago.com/), may be a good place for purchasing 3-methyl-2-hexenoic acid and 7-octenoic acid, making sure we get the proper ‘psychologically active’ forms of these molecules.
Visionary
My bad! I had forgotten that you already posted it here. You are right this may not have worked as well as expected. It’s not clear if they tried adding it to a cologne along with androstenol and androsterone.