5α-androst-2-ene-17-one

5α-androst-2-ene-17-one is a steroid and pheromone found in humans and other animals. It is also known as androstenone and is produced in the adrenal glands and testes of males.

Chemistry

5α-androst-2-ene-17-one is a 19-carbon steroid hormone. It is a ketone and an alkene, and is derived from dehydroepiandrosterone (DHEA). The structure of 5α-androst-2-ene-17-one includes a double bond between the second and third carbon atoms and a ketone group at the 17th carbon atom.

Biosynthesis

The biosynthesis of 5α-androst-2-ene-17-one involves several steps. First, cholesterol is converted into pregnenolone by the enzyme cholesterol side-chain cleavage enzyme. Pregnenolone is then converted into progesterone by the enzyme 3β-hydroxysteroid dehydrogenase. Progesterone is converted into androstenedione by the enzymes 17α-hydroxylase and 17,20-lyase. Androstenedione is then converted into 5α-androst-2-ene-17-one by the enzyme 5α-reductase.

Function

5α-androst-2-ene-17-one is a pheromone that is found in the sweat and urine of males. It is thought to play a role in human attraction and mate selection. Some studies have suggested that women may be more attracted to men with higher levels of 5α-androst-2-ene-17-one, although this is still a topic of ongoing research.

See also

• Androstenol
• Androstadienone
• Androsterone