ambrein

Also known as (1R,2R,4aS,8aS)-1-[(3E)-6-[(1S)-2,2-dimethyl-6-methylidenecyclohexyl]-4-methylhex-3-en-1-yl]-2,5,5,8a-tetramethyl-hexahydro-1H-naphthalen-2-ol

Ambrein is a triterpene alcohol that is the chief constituent of ambergris, a secretion from the digestive system of the sperm whale. It has been suggested as the possible active component producing the supposed aphrodisiac effects of ambergris. 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.

Chemical data

Formula: C30H52O
Molecular weight: 428.7 g/mol
IUPAC name: (1R,2R,4aS,8aS)-1-[(E)-6-[(1S)-2,2-dimethyl-6-methylidenecyclohexyl]-4-methylhex-3-enyl]-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-2-ol
SMILES: C/C(=C\CC[C@@H]1[C@]2(CCCC([C@@H]2CC[C@@]1(C)O)(C)C)C)/CC[C@@H]3C(=C)CCCC3(C)C
InChIKey: BIADSXOKHZFLSN-RMCJHQKMSA-N
XLogP: 9.6
Polar surface area: 20.2 Å²
H-bond donors: 1
H-bond acceptors: 1
Formal charge: 0

via PubChem

Wikidata facts

Mass: 428.401816284

Show 4 more facts

canonical SMILES: OC1(C)CCC2C(C)(C)CCCC2(C)C1CCC=C(C)CCC3C(=C)CCCC3(C)C
isomeric SMILES: C=C1CCCC(C)(C)[C@@H]1CC/C(C)=C/CC[C@@H]1[C@@]2(C)CCCC(C)(C)[C@@H]2CC[C@@]1(C)O
chemical formula: C₃₀H₅₂O
found in taxon: sperm whale

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Encyclopedic overview

3 sections

Contents

Discovery
Biosynthesis
References

{{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 419851613 | ImageFile = Ambrein.svg | ImageSize = 160 | IUPACName = (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 | OtherNames = Ambrein |Section1= |Section2= |Section3= }} Ambrein is a triterpene alcohol that is the chief constituent of ambergris, a secretion from the digestive system of the sperm whale. It has been suggested as the possible active component producing the supposed aphrodisiac effects of ambergris. 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 and has been proven to increase sexual behavior in rats, providing some support for its traditional aphrodisiac use.

Excerpted from Wikipedia’s “ambrein” article, available under the CC BY-SA 4.0 licence.

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