Ambrein

Ambrein is a triterpene alcohol that is the chief constituent of ambergris, a secretion from the digestive system of the sperm whale.[1] Although ambrein itself is odorless, it serves as the biological precursor for aromatic derivatives such as ambroxide and is thought to possess fixative properties for other odorants.It has been shown to act as an analgesic[2] and has been proven to increase sexual behavior in rats,[3] 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.The squalene-hopene cyclase (SHC) catalyzes the cyclization of squalene into the monocyclic 3-deoxyachilleol A. Tetraprenyl-beta-curcumene synthase (BmeTC) converts 3-deoxyachilleol A into the tricyclic ambrein.
Biosynthetic pathway of Ambrein
IUPAC nameCAS NumberChemSpiderECHA InfoCardPubChemCompTox DashboardSMILESChemical formulaMolar massstandard statetriterpeneambergrissperm whaleaphrodisiacambroxideanalgesicRuzickasqualenesqualene-hopene cyclaseTetraprenyl-beta-curcumene synthasePrelog, VladimirBiogr. Mem. Fellows R. Soc.