Androstenone

From Wikipedia, the free encyclopedia

Androstenone

IUPAC name	(5S,8R,9S,10S,13R,14S)-10, 13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15- dodecahydrocyclopenta[a]phenanthren-3-one
Other names	5α-Androst-16-en-4-one
Identifiers
CAS number	[18339-16-7]
PubChem	6852393
SMILES	CC12CCC3C(C1CC=C2)CCC4C3(CCC(=O)C4)C
Properties
Molecular formula	C₁₉H₂₈O
Molar mass	272.42502
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Androstenone (5α-androst-16-en-4-one) is a steroid found in both male and female sweat and urine. It is also found in boar's saliva. Androstenone was the first mammalian pheromone to be identified. It is found in high concentrations in the saliva of male pigs and, when sniffed by a female pig who is in heat, results in the female assuming the mating stance. Androstenone is the active ingredient in BoarTaint, a commercial product sold to pig farmers to test sows for timing of artificial insemination.

1 Properties
- 1.1 Detectability As a Pheromone
- 1.2 Commercial Use
2 See Also
3 External links
4 References

[edit] Properties

Depending upon who is doing the smelling, it is reported to be an unpleasant, sweaty, urinous smell, a woody smell, or even a pleasant floral smell.^[1]^[2]^[3] The differences in perceived odor can be accounted for by the genetic differences in the OR7D4 receptor which detects the chemical. People who possess 2 proper genes for OR7D4 tend to describe the odor for the steroid as likable to urine. Those with only 1 gene typically described the odor as weak or were not able to detect it. Those with mutated copies of the gene described the odor as pleasant or sweet. ^[4]

In small amounts, the odor is hardly detectable by most people. This may be due to a polymorphism in the receptor gene that codes for the androstenone receptor.^[5] However, the range of abilities to detect the odor vary greatly. It has been proven that the odor can be detected by people in levels in a range of 0.2 parts per billion and 0.2 parts in 100 million.^[6] Several groups report, however, that some individuals who initially cannot smell androstenone can learn to smell it by repeated exposures to it.^[7]

[edit] Detectability As a Pheromone

In humans androstenone also has been suggested to be a pheromone, however, scientific data to support these claims are scant. The vomeronasal organ is an auxiliary olfactory sense organ that is responsible for the detection of pheromones as more than just an odor. Most adult humans possess something resembling this organ, but there is no active function. Humans lack the sensory cells that exist in other mammalians needed to detect pheromones beyond a smell. Humans also lack the genetic ability to produce these sensory cells actively. ^[8]

There is also a specific anosmia to the odor in some humans; they are unable to smell specific odors but have besides that a normal sense of smell. However, this should by no means be seen as indicative for being labeled as a pheromone, as it is true of over 80 olfactory compounds. ^[9] There is more promising data for a closely related compound, androstadienone.

[edit] Commercial Use

Some commercially-available substances are advertised using claims that the products contain human sexual pheromones and can act as an aphrodisiac. However these often lack credibility due to an excessive marketing of pheromones by unsolicited e-mail.