Androstenone
Encyclopedia
Androstenone is a steroid
Steroid
A steroid is a type of organic compound that contains a characteristic arrangement of four cycloalkane rings that are joined to each other. Examples of steroids include the dietary fat cholesterol, the sex hormones estradiol and testosterone, and the anti-inflammatory drug dexamethasone.The core...

 found in both male and female sweat
SWEAT
SWEAT is an OLN/TSN show hosted by Julie Zwillich that aired in 2003-2004.Each of the 13 half-hour episodes of SWEAT features a different outdoor sport: kayaking, mountain biking, ice hockey, beach volleyball, soccer, windsurfing, rowing, Ultimate, triathlon, wakeboarding, snowboarding, telemark...

 and urine
Urine
Urine is a typically sterile liquid by-product of the body that is secreted by the kidneys through a process called urination and excreted through the urethra. Cellular metabolism generates numerous by-products, many rich in nitrogen, that require elimination from the bloodstream...

. It is also found in boar
Boar
Wild boar, also wild pig, is a species of the pig genus Sus, part of the biological family Suidae. The species includes many subspecies. It is the wild ancestor of the domestic pig, an animal with which it freely hybridises...

's saliva
Saliva
Saliva , referred to in various contexts as spit, spittle, drivel, drool, or slobber, is the watery substance produced in the mouths of humans and most other animals. Saliva is a component of oral fluid. In mammals, saliva is produced in and secreted from the three pairs of major salivary glands,...

, and in celery
Celery
Apium graveolens is a plant species in the family Apiaceae commonly known as celery or celeriac , depending on whether the petioles or roots are eaten: celery refers to the former and celeriac to the latter. Apium graveolens grows to 1 m tall...

 cytoplasm
Cytoplasm
The cytoplasm is a small gel-like substance residing between the cell membrane holding all the cell's internal sub-structures , except for the nucleus. All the contents of the cells of prokaryote organisms are contained within the cytoplasm...

. Androstenone was the first mammal
Mammal
Mammals are members of a class of air-breathing vertebrate animals characterised by the possession of endothermy, hair, three middle ear bones, and mammary glands functional in mothers with young...

ian pheromone
Pheromone
A pheromone is a secreted or excreted chemical factor that triggers a social response in members of the same species. Pheromones are chemicals capable of acting outside the body of the secreting individual to impact the behavior of the receiving individual...

 to be identified. It is found in high concentrations in the saliva of male pigs, and, when sniffed by a female pig that is in heat
In Heat
In Heat is Black 'n Blue's fourth album. It was produced by Kiss bassist Gene Simmons.-Track listing:# "Rock On" # "Sight For Sore Eyes"...

, results in the female assuming the mating stance. Androstenone is the active ingredient in 'Boarmate', a commercial product made by DuPont
DuPont
E. I. du Pont de Nemours and Company , commonly referred to as DuPont, is an American chemical company that was founded in July 1802 as a gunpowder mill by Eleuthère Irénée du Pont. DuPont was the world's third largest chemical company based on market capitalization and ninth based on revenue in 2009...

 sold to pig farmers to test sows for timing of artificial insemination.

Properties

Depending upon the subject, it is reported to be an unpleasant, sweaty, urinous smell, a woody smell, or even a pleasant floral smell.

There are two different genotypes that cause androstenone to smell. The first genotype, which consists of two fully functional copies of the gene, is the RT/RT allele, and the second is the RT/WM allele. The OR7D4 receptor has two non-synonymous single nucleotide polymorphisms, which cause the gene to have two amino acid substitutions, which in turn cause the receptor to act differently. Those in possession of the two proper genes, (RT/RT) for OR7D4 tend to describe the odor for the steroid as the odor of stale urine. Those with only one gene (RT/WM) typically described the odor as weak or were not able to detect it. They can also find the smell 'pleasant', 'sweet' or 'similar to vanilla'.

In small amounts, the odor is hardly detectable by most people. This may be due to a polymorphism
Polymorphism (biology)
Polymorphism in biology occurs when two or more clearly different phenotypes exist in the same population of a species — in other words, the occurrence of more than one form or morph...

 in the receptor gene that codes for the androstenone receptor. However, the ability to detect the odor varies greatly. It has been shown that the odor can be detected by people down to levels of 0.2 parts per billion to 0.2 parts in 100 million. Several groups report, however, that some individuals who initially cannot smell androstenone can learn to smell it by repeated exposures to it.

Detectability as a pheromone

In humans, androstenone also has been suggested to be a pheromone
Pheromone
A pheromone is a secreted or excreted chemical factor that triggers a social response in members of the same species. Pheromones are chemicals capable of acting outside the body of the secreting individual to impact the behavior of the receiving individual...

; however, scientific data to support these claims are scant. The vomeronasal organ
Vomeronasal organ
The vomeronasal organ , or Jacobson's organ, is an auxiliary olfactory sense organ that is found in many animals. It was discovered by Frederik Ruysch and later by Ludwig Jacobson in 1813....

 is an auxiliary olfactory sense organ 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 mammals needed to detect pheromones beyond a smell. Humans also lack the genetic ability to produce these sensory cells actively.

There is also a specific anosmia
Anosmia
Anosmia is a lack of functioning olfaction, or in other words, an inability to perceive odors. Anosmia may be either temporary or permanent. A related term, hyposmia, refers to a decreased ability to smell, while hyperosmia refers to an increased ability to smell. Some people may be anosmic for one...

 to the odor in some humans; they are unable to smell specific odors, but have, otherwise, a normal sense of smell. However, this should, by no means, be regarded as indicative for being labeled as a pheromone, as it is true of over 80 olfactory compounds. There are more promising data for a closely related compound, androstadienone
Androstadienone
Androstadienone, also known as androsta-4,16,-dien-3-one, is a chemical compound that has been described as having strong pheromone-like activities in humans. It is a metabolite of the sex hormone testosterone: however, androstadienone does not exhibit any known androgenic or anabolic effects...

.

To animals, the smell of androstenone can act as a social sign of dominance, or it can be a way of attracting a mate. This smell, to some animals, has a huge impact on behavioral patterns in the specimen.

Commercial use

Some commercially available substances are advertised using claims that the products contain human sexual pheromones and can act as an aphrodisiac
Aphrodisiac
An aphrodisiac is a substance that increases sexual desire. The name comes from Aphrodite, the Greek goddess of sexuality and love. Throughout history, many foods, drinks, and behaviors have had a reputation for making sex more attainable and/or pleasurable...

. These products are the subject of marketing by mass unsolicited e-mail
Spam (electronic)
Spam is the use of electronic messaging systems to send unsolicited bulk messages indiscriminately...

 and typically contain deceitful claims.

See also

  • Androstadienone
    Androstadienone
    Androstadienone, also known as androsta-4,16,-dien-3-one, is a chemical compound that has been described as having strong pheromone-like activities in humans. It is a metabolite of the sex hormone testosterone: however, androstadienone does not exhibit any known androgenic or anabolic effects...

  • Androstenol
    Androstenol
    Androstenol is a sex pheromone in pigs, possessing a musk-like odor.It is found in large quantities in boar saliva, but also in smaller quantities in human sweat glands. It is analogous to sex hormones yet has minimal or no androgenic activity...

  • Androsterone
    Androsterone
    Androsterone is a steroid hormone with weak androgenic activity. It is made in the liver from the metabolism of testosterone. Its beta-isomer is Epiandrosterone.-History:...

  • Dehydroepiandrosterone
    Dehydroepiandrosterone
    5-Dehydroepiandrosterone is a 19-carbon endogenous steroid hormone. It is the major secretory steroidal product of the adrenal glands and is also produced by the gonads and the brain. DHEA is the most abundant circulating steroid in humans....

  • Estratetraenol
    Estratetraenol
    Estratetraenol, also known as estra-1,3,5,16-tetraen-3-ol, is a chemical compound produced by women that has been described as having pheromone-like activities in primates, including humans...

  • McClintock effect
    McClintock effect
    Menstrual synchrony is a phenomenon reported in 1971 wherein the menstrual cycles of women who lived together reportedly became synchronized over time...


External links

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