Ambrein
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IUPAC name
(1R,2R,4aS,8aS)-1-{(3E)-6-[(1S)-2,2-dimethyl-6-methylidenecyclohexyl]-4-methylhex-3-en-1-yl}-2,5,5,8a-tetramethyldecahydronaphthalen-2-ol
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Other names
Ambrein
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Identifiers | |
3D model (
JSmol ) |
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ChEBI | |
ChemSpider | |
ECHA InfoCard
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100.006.784 |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C30H52O | |
Molar mass | 428.745 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Ambrein is a
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. It reduces these contractions by serving as an antagonist and interfering with Ca2+ ions from outside the cell.[4]
Discovery
In 1946, Ruzicka and Lardon "established that the fragrance of ambergris is based on the triterpene (named) ambrein".[5][6][7]
Biosynthesis
Ambrein is synthesized from the common triterpenoid precursor squalene. 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.[8]