Ambrein is a

triterpene Triterpenes are a class of chemical compounds composed of three terpene units with the molecular formula C30H48; they may also be thought of as consisting of six isoprene units. Animals, plants and fungi all produce triterpenes, including squa ...

alcohol that is the chief constituent of

ambergris Ambergris ( or , la, ambra grisea, fro, ambre gris), ''ambergrease'', or grey amber is a solid, waxy, flammable substance of a dull grey or blackish colour produced in the digestive system of sperm whales. Freshly produced ambergris has a mari ...

, a secretion from the digestive system of the sperm whale, and has been suggested as the possible active component producing the supposed

aphrodisiac An aphrodisiac is a substance that increases sexual desire, sexual attraction, sexual pleasure, or sexual behavior. Substances range from a variety of plants, spices, foods, and synthetic chemicals. Natural aphrodisiacs like cannabis or cocai ...

effects of ambergris. Although ambrein itself is odorless, it serves as the biological precursor for a number of aromatic derivatives such as ambroxan and is thought to possess fixative properties for other odorants. It has been shown to act as an analgesic and it has been proven to increase sexual behavior in rats, providing some support for its traditional aphrodisiac use. Apart from its supposed aphrodisiac effects, ambrein has been shown to decrease spontaneous contractions of smooth muscles in rats, guinea pigs, and rabbits. It is able to reduce these contractions by serving as an antagonist and interfering with the Ca²⁺ ions from outside of the cell.

Discovery

In 1946, Ruzicka and Lardon "established that the fragrance of

is based on the

(named) ambrein".

Biosynthesis

Ambrein is synthesized from common triterpenoid precursor

squalene Squalene is an organic compound. It is a triterpenoid with the formula C30H50. It is a colourless oil, although impure samples appear yellow. It was originally obtained from shark liver oil (hence its name, as ''Squalus'' is a genus of sharks). A ...

. The

Squalene-hopene cyclase Squalene-hopene cyclase (SHC) () or ''hopan-22-ol hydro-lyase'' is an enzyme in the terpene cyclase/mutase family. It catalyzes the interconversion of squalene into a pentacyclic triterpenes, hopene and hopanol. This enzyme catalyses the following ...

(SHC) catalyzes cyclization of

into the monocyclic 3-deoxyachilleol A. Tetraprenyl-beta-curcumene synthase(BmeTC) converts 3-deoxyachilleol A into the tricyclic ambrein.

References

{{reflist Perfume ingredients Whale products Animal glandular products Triterpenes Decalins Tertiary alcohols