EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

ambrein

Sponsors

Name:(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: 473-03-0Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:207-460-3
Beilstein Number:3655411
XlogP3-AA:9.60 (est)
Molecular Weight:428.74364000
Formula:C30 H52 O
NMR Predictor:Predict (works with chrome or firefox)
Category:cosmetic and fragrance agents
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Perfumer and Flavorist:Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
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
 water, 6.895e-007 mg/L @ 25 °C (est)
Insoluble in:
 water
 
Organoleptic Properties:
Odor Type: amber
Odor Strength:medium
Substantivity:400 hour(s) at 100.00 %
ambergris labdanum amber woody
Odor Description:at 100.00 %. ambergris labdanum
Luebke, William tgsc, (1988)
Odor sample from: International Flavors & Fragrances Inc.
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
CosIng:cosmetic data
Cosmetic Uses: perfuming agents
 
Suppliers:
BOC Sciences
For experimental / research use only.
1-(6-(2,2-Dimethyl-6-methylenecyclohexyl)-4-methylhex-3-enyl)decahydro-2,5,5,8a-tetramethyl-2-naphthol
Ernesto Ventós
AMBREINE FIRMENICH 039658
Odor: AMBER NOTE
 
Safety Information:
European information :
Most important hazard(s):
Xi - Irritant
R 36/37/38 - Irritating to eyes, respiratory system, and skin.
S 02 - Keep out of the reach of children.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 36 - Wear suitable protective clothing.
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
intraperitoneal-mouse LD50 7500 mg/kg
BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Japanese Journal of Pharmacology. Vol. 60, Pg. 67, 1992.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category: cosmetic and fragrance agents
 
Recommendation for ambrein flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):473-03-0
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :6433191
National Institute of Allergy and Infectious Diseases:Data
(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
Chemidplus:0000473030
 
References:
 (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
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:473-03-0
Pubchem (cid):6433191
Pubchem (sid):134975669
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2009
(IUPAC):Atomic Weights of the Elements 2009 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
HMDB (The Human Metabolome Database):Search
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
RSC Learn Chemistry:View
 
Potential Blenders and core components note
For Odor
amber
(Z)-
abienol
FL/FR
amber naphthofuran
FL/FR
amber specialty
FR
alpha-
ambrinol
FL/FR
ambroxide
FL/FR
cistus ladaniferus absolute resin
FL/FR
cistus ladaniferus resinoid
FR
labdanum oil
FL/FR
balsamic
abies alba needle oil
FL/FR
hexyl benzoate
FL/FR
linalyl cinnamate
FL/FR
opoponax oil (balsamodendron kafal)
FL/FR
peru balsam oil
FL/FR
tolu balsam
FL/FR
caramellic
immortelle absolute
FL/FR
citrus
lemon oil c.p. california
FL/FR
bitter
orange peel oil brazil
FL/FR
floral
acetophenone
FL/FR
cananga oil
FL/FR
abrialis
lavandin oil
FL/FR
orris rhizome absolute (iris pallida)
FL/FR
fruity
(E)-alpha-
damascone
FL/FR
herbal
acorus calamus root oil
FR
anthemis nobilis flower oil roman
FL/FR
canarium luzonicum oil
FL/FR
clary sage oil france
FL/FR
herbal undecanone
FR
hexyl salicylate
FL/FR
lavender absolute bulgaria
FL/FR
myrtle oil
FL/FR
rosemary oil spain
FL/FR
leathery
castoreum absolute
FL/FR
phenolic
methyl benzoate
FL/FR
spicy
allspice berry oil
FL/FR
elettaria cardamomum seed oil
FL/FR
ginger root oil china
FL/FR
laurus nobilis leaf oil
FL/FR
turmeric root oil china
FL/FR
terpenic
cypress leaf oil
FR
frankincense oil
FL/FR
juniperus communis fruit oil
FL/FR
tonka
deertongue absolute
FR
flouve absolute
FR
melilot absolute
FR
woody
cedarwood oil virginia
FR
cedryl methyl ether
FR
cistus ladaniferus gum
FR
cistus twig/leaf absolute
FR
labdanum concrete
FR
labdanum ethanone
FR
methyl cedryl ketone
FL/FR
patchouli oil
FL/FR
sandalwood oil
FL/FR
sclareolide
FL/FR
For Flavor
No flavor group found for these
ambroxide
FL/FR
laurus nobilis leaf oil
FL/FR
amber
amber
amber naphthofuran
FL/FR
alpha-
ambrinol
FL/FR
cistus ladaniferus absolute resin
FL/FR
labdanum oil
FL/FR
balsamic
opoponax oil (balsamodendron kafal)
FL/FR
peru balsam oil
FL/FR
tolu balsam
FL/FR
citrus
lemon oil c.p. california
FL/FR
floral
cananga oil
FL/FR
fruity
(E)-alpha-
damascone
FL/FR
linalyl cinnamate
FL/FR
bitter
orange peel oil brazil
FL/FR
green
canarium luzonicum oil
FL/FR
hexyl benzoate
FL/FR
immortelle absolute
FL/FR
herbal
anthemis nobilis flower oil roman
FL/FR
clary sage oil france
FL/FR
hexyl salicylate
FL/FR
abrialis
lavandin oil
FL/FR
lavender absolute bulgaria
FL/FR
rosemary oil spain
FL/FR
leathery
castoreum absolute
FL/FR
phenolic
methyl benzoate
FL/FR
powdery
acetophenone
FL/FR
spicy
allspice berry oil
FL/FR
elettaria cardamomum seed oil
FL/FR
ginger root oil china
FL/FR
myrtle oil
FL/FR
turmeric root oil china
FL/FR
sweet
orris rhizome absolute (iris pallida)
FL/FR
terpenic
abies alba needle oil
FL/FR
juniperus communis fruit oil
FL/FR
woody
(Z)-
abienol
FL/FR
frankincense oil
FL/FR
methyl cedryl ketone
FL/FR
patchouli oil
FL/FR
sandalwood oil
FL/FR
sclareolide
FL/FR
 
Potential Uses:
FRabronia
FRacacia
FRaldehydic
FRamber
FRambergris
FRanimal
FRbalsam
FRchypre
FRfern
 fixer
FRjuniper
FRlavender
FRleather
FRnarcissus
FRsandalwood
FRtobacco
FRverbena
FRviolet
FRwoody
 
Occurrence (nature, food, other):note
 ambergris
Search PMC Picture
 
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))-
 

Articles:

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].
 
Notes:
a degraded triterpene; ambrein, cholesterol and benzoic acid are major components of ambergris; from intestinal secretion of sperm blue whale (pyseter carodon).
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