(3alpha,5alpha)-androst-16-en-3-ol
3a-hydroxyandrost-16-ene
 
Notes:
Aroma substance from the Perigord truffle tuber Androstenol is a steroidal compound belonging to the group of odorous 16-androstenes, first isolated from boar testes and also found in humans. Androstenol has pheromone-like properties in both animals and humans, but the molecular targets of its pheromonal activity are unknown. Androstenol as a pheromone is well suited because of high volatility and lipophilicity. (PMID: 1419890, 8142319, 16415088); ; 3a-Hydroxyandrost-16-ene is a steroidal compound belonging to the group of odorous 16-androstenes, first isolated from boar testes and also found in humans. 3a-Hydroxyandrost-16-ene has pheromone-like properties in both animals and humans, but the molecular targets of its pheromonal activity are unknown. 3a-Hydroxyandrost-16-ene is structurally similar to endogenous A-ring reduced neurosteroids that act as positive modulators of GABAA receptors. 3a-Hydroxyandrost-16-ene has neurosteroid-like activity as a GABAA receptor modulator. The various actions of 3a-Hydroxyandrost-16-ene in the whole-animal models are consistent with its activity as a GABAA receptor modulator. GABAA receptors could represent a target for 3a-Hydroxyandrost-16-ene as a pheromone, for which it is well suited because of high volatility and lipophilicity, or as a conventional hormonal neurosteroid. (PMID: 1419890, 8142319, 16415088); Androstenol is an sex pheromone in pigs, possessing a musk-like odor.; The Pheromone Androstenol (5{alpha}-Androst-16-en-3{alpha}-ol) Is a Neurosteroid Positive Modulator of GABAA Receptors -- Kaminski RM, Marini H, Ortinski PI, Vicini S, Rogawski MA 317 (2): 694 -- Journal of Pharmacology and Experimental Therapeutics; The pheromone androstenol (5?-androst-16-en-3?-ol) is a neurosteroid positive modulator of GABAA receptors
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(3R,5S,8R,9S,10S,13R,14S)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol (Click)
CAS Number: 1153-51-1Picture of molecule
ECHA EINECS - REACH Pre-Reg: 214-573-1
FDA UNII: 48K9VAM062
Nikkaji Web: J109.628A
MDL: MFCD00051224
XlogP3-AA: 5.30 (est)
Molecular Weight: 274.44730000
Formula: C19 H30 O
BioActivity Summary: listing
NMR Predictor: Predict (works with chrome or firefox)
Category: fragrance agents
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar: Search
Google Books: Search
Google Scholar: with word "volatile"Search
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Google Scholar: with word "odor"Search
Perfumer and Flavorist: Search
Google Patents: Search
US Patents: Search
EU Patents: Search
IBM Patents: Obtain
Pubchem Patents: Search
PubMed: Search
NCBI: Search
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Physical Properties:
Appearance: white powder (est)
Assay: 98.00 to 100.00 % 
Food Chemicals Codex Listed: No
Melting Point: 141.00 to  143.00 °C. @ 760.00 mm Hg
Boiling Point: 374.07 °C. @ 760.00 mm Hg (est)
Flash Point: > 212.00 °F. TCC ( > 100.00 °C. )
logP (o/w): 6.030 (est)
Soluble in:
 alcohol
 water, 3.642 mg/L @ 25 °C (est)
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Organoleptic Properties:
Odor Type: musk
Odor Strength: medium
 animal  musk  natural  
Odor Description:
at 100.00 %. 
animal musk natural
  
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Cosmetic Information:
None found
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Suppliers:
Carbosynth
For experimental / research use only.
5a-Androst-16-en-3a-ol
Sigma-Aldrich: Sigma
For experimental / research use only.
5a-Androst-16-en-3a-ol
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Safety Information:
Preferred SDS: View
 
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:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: fragrance agents
Recommendation for (3alpha,5alpha)-androst-16-en-3-ol usage levels up to:
  1.0000 % in the fragrance concentrate.
 
Recommendation for (3alpha,5alpha)-androst-16-en-3-ol flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
EPA Substance Registry Services (TSCA): 1153-51-1
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 101989
National Institute of Allergy and Infectious Diseases: Data
WGK Germany: 3
 (3R,5S,8R,9S,10S,13R,14S)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
Chemidplus: 0001153511
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References:
 (3R,5S,8R,9S,10S,13R,14S)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
NIST Chemistry WebBook: Search Inchi
Canada Domestic Sub. List: 1153-51-1
Pubchem (cid): 101989
Pubchem (sid): 135143040
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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
CHEBI: View
CHEMBL: View
HMDB (The Human Metabolome Database): HMDB05935
FooDB: FDB012828
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
RSC Learn Chemistry: View
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Potential Blenders and core components note
 
For Odor
No odor group found for these
(Z)-oleyl alcoholFR
amber
 amber furanFR
 ambergris naphtholFR
 ambrinolFR
alpha-ambrinolFL/FR
animal
 animal carbolactoneFR
isobutyl quinolineFR
isobutyl quinolineFR
 civet absoluteFL/FR
 costus valerolactoneFR
para-cresyl caprylateFL/FR
para-cresyl isobutyrateFL/FR
para-cresyl phenyl acetateFL/FR
 indolallFR
 indoleFL/FR
 indoletalFR
para-methyl tetrahydroquinolineFL/FR
 piperidineFL/FR
 skatoleFL/FR
1-oxaspiro-4,7-dodecaneFR
balsamic
 amyl phenyl acetateFL/FR
 guaiyl butyrateFR
 opoponax oil (balsamodendron kafal)FL/FR
 opoponax resinoid (balsamodendron kafal)FR
chocolate
isoamyl phenyl acetateFL/FR
earthy
 muscogeneFR
ethereal
 propyl valerateFL/FR
fatty
delta-juniper lactoneFL/FR
floral
para-cresyl acetateFL/FR
(E)-2,5,9-trimethyl-4,9-decadien-1-alFR
fruity
 linalyl hexanoateFL/FR
green
 valerian rhizome oil CO2 extract chinaFL/FR
herbal
 petitgrain heptaneFR
 valerian rhizome oilFL/FR
 valerian rhizome oil chinaFL/FR
leathery
 castoreum absoluteFL/FR
marine
 marine pyridineFR
musk
(Z)-civet decenoneFL/FR
 ethylene dodecanoateFR
 exaltone (Firmenich)FR
 juniper lactoneFL/FR
delta-muscenoneFR
dextro,laevo-musconeFL/FR
 musk dimethyl indaneFL/FR
 musk lactoneFR
 musk nonaneFR
(Z)-musk pentaneFR
omega-pentadecalactoneFL/FR
spicy
(E,E)-piperineFL/FR
tobacco
para-cresyl isovalerateFL/FR
woody
 spikenard oilFL/FR
 
For Flavor
 
No flavor group found for these
alpha-ambrinolFL/FR
 amyl phenyl acetateFL/FR
(Z)-civet decenoneFL/FR
para-cresyl caprylateFL/FR
para-cresyl isovalerateFL/FR
2,6-dimethoxy-4-vinyl phenolFL
 ethyl 3-(furfuryl thio) propionateFL
 linalyl hexanoateFL/FR
4-methyl cyclohexanoneFL
para-methyl tetrahydroquinolineFL/FR
 musk dimethyl indaneFL/FR
omega-pentadecalactoneFL/FR
 piperidineFL/FR
(E,E)-piperineFL/FR
 propyl valerateFL/FR
 skatoleFL/FR
 spikenard oilFL/FR
ammoniacal
 pyrrolidineFL
animal
 civet absoluteFL/FR
 indoleFL/FR
aromatic
para-cresyl acetateFL/FR
para-cresyl isobutyrateFL/FR
para-cresyl phenyl acetateFL/FR
balsamic
 opoponax oil (balsamodendron kafal)FL/FR
fatty
delta-juniper lactoneFL/FR
floral
isoamyl phenyl acetateFL/FR
 valerian rhizome oilFL/FR
 valerian rhizome oil chinaFL/FR
 valerian rhizome oil CO2 extract chinaFL/FR
leathery
 castoreum absoluteFL/FR
musk
 juniper lactoneFL/FR
dextro,laevo-musconeFL/FR
sour
3-methyl valeric acidFL
 
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Potential Uses:
 amberFR
 animalFR
 muskFR
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Occurrence (nature, food, other): note
 swine testes
Search  Picture
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Synonyms:
5-a-androst-16-en-3-a-ol
 androst-16-en-3-ol
(3a,5a)-androst-16-en-3-ol
 androst-16-en-3-ol, (3a,5a)-
5alpha-androst-16-en-3,alpha-ol
 androst-16-en-3a-ol
5a-androst-16-en-3a-ol
5alpha-androst-16-en-3alpha-ol
alpha-delta-16-androsten-3-ol
16,17-androstene-3-ol
3-a-androstenol
(3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15-dodecahydro-1H-cyclopenta(a)phenanthren-3-ol
(3R,5S,8R,9S,10S,13R,14S)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
3a-hydroxyandrost-16-ene
3alpha-hydroxyandrost-16-ene
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