ambrein
Identification
| Name | ambrein |
| IUPAC | (2R,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 |
| CAS Number | 473-03-0 |
| EINECS | 207-460-3 |
| FDA UNII | 1N9JB373FJ |
| Molecular Formula | C30 H52 O |
| Molecular Weight | 428.74364000 |
| Beilstein | 3655411 |
Regulatory
Physical Properties
| Appearance | brown solid (est) |
| Assay | 96.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 495.00 to 496.00 °C. @ 760.00 mm Hg |
| Flash Point | 431.00 °F. TCC ( 221.67 °C. ) |
| logP (o/w) | 11.680 |
| Soluble in | alcohol |
| Insoluble in | water |
Cosmetic Information
| CosIng | cosmetic data |
| Cosmetic Uses | perfuming agents |
Organoleptic Properties
| Odor Strength | medium |
| Substantivity | 400 hour(s) at 100.00 % |
| Odor Description | at 100.00 %. |
| Odor sample from | International Flavors & Fragrances Inc. |
Safety Information
| European information | Most important hazard(s): |
| Oral/Parenteral Toxicity | intraperitoneal-mouse LD50 7500 mg/kg |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | cosmetic and fragrance agents |
| RIFM Fragrance Material Safety Assessment | Search |
| Recommendation for ambrein flavor usage levels up to | not for flavor use. |
BOC Sciences
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Potential Uses
Natural Occurrence
Synonyms
(E)-
ambra-13,18(28)-dien-8-ol
trans-
ambra-13,18(28)-dien-8-ol
ambra-13,18(28)-dien-8-ol
(1R,2R,4aS,8aS)- 1-((3E)-6-((1S)-2,2-
dimethyl-6-methylene cyclohexyl)-4-methyl-3-hexenyl)-4-methyl-3-hexenyl)decahydro-2,5,5,8a-tetramethyl-2-naphthalenol
1-(6-(2,2-
dimethyl-6-methylenecyclohexyl)-4-methylhex-3-enyl)decahydro-2,5,5,8a-tetramethyl-2-naphthol
(2R,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
2-
naphthalenol, 1-((3E)-6-((1S)-2,2-dimethyl-6-methylenecyclohexyl)-4-methyl-3-hexenyl)decahydro-2,5,5,8a-tetramethyl-, (1R,2R,4aS,8aS)-
2-
naphthalenol, 1-(6-(2,2-dimethyl-6-methylenecyclohexyl)-4-methyl-3-hexenyl)decahydro-2,5,5,8a-tetramethyl-, (1g-(1a(E(S)),2b,4ab,8aa))-
2-
naphthalenol, decahydro-1-(6-(2,2-dimethyl-6-methylenecyclohexyl)-4-methyl-3-hexenyl)-2,5,5,8a-tetramethyl-, (1R-(1-a(E(S*)),2-b,4a-b,8a-a))-
PubMed:
Cyclization of squalene from both termini: identification of an onoceroid synthase and enzymatic synthesis of ambrein.
PubMed:
Evaluation of ambrein and epicoprostanol for their antioxidant properties: protection against adriamycin-induced free radical toxicity.
PubMed:
Chemical transformation and biological activities of ambrein, a major product of ambergris from Physeter macrocephalus (sperm whale).
PubMed:
Aphrodisiacs past and present: a historical review.
PubMed:
[Chemical constituents in aerial part of Ampelopsis grossedentata(Hand.-Mazz.) W.T. Wang].
PubMed:
Effect of ambrein on smooth muscle responses to various agonists.
PubMed:
Effect of ambrein, a major constituent of ambergris, on masculine sexual behavior in rats.
PubMed:
A study of ambrein treatment for the evaluation of change in plasma biochemical parameters in rats.
PubMed:
Studies on the mode of action of ambrein as a new antinociceptive compound.
PubMed:
Effect of ambrein on blood glucose levels of rats.
PubMed:
Chemical investigation of the internal secretion of the sperm blue whale.
PubMed:
[Not Available].