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α-Androstenol

CAT: 0804-HY-W677042-01Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-W677042-01Size:5 mg
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Description
α-Androstenol (5α-Androst-16-en-3α-ol) is a steroid pheromone that has been found in boar testes and human male axillary sweat. α-Androstenol is also a positive modulator of GABAA receptors, which enhances GABA-activated currents in primary mouse cerebellar granule cells (EC50=0.4 μM) . α-Androstenol decreases immobility time in the forced swim test and increases time spent in the open arms of the elevated plus maze in mice. α-Androstenol protects against seizures induced by Pentylenetetrazole or electroshock with anxiolytic-like activity in mice[1][2][3].
CAS Number
1153-51-1
Product Name Alternative
5α-Androst-16-en-3α-ol
UNSPSC
12352211
Hazard Statement
H302, H315, H319, H335
Target
GABA Receptor
Type
Reference compound
Related Pathways
Membrane Transporter/Ion Channel; Neuronal Signaling
Applications
Neuroscience-Neuromodulation
Field of Research
Neurological Disease
Assay Protocol
https://www.medchemexpress.com/α-androstenol.html
Purity
99.9
Solubility
DMSO : 4.17 mg/mL (ultrasonic; warming; heat to 60°C)
Smiles
[H][C@@]12CC=C[C@]1(CC[C@]3([C@]2(CC[C@]4(C[C@@H](CC[C@]34C)O)[H])[H])[H])C
Molecular Formula
C19H30O
Molecular Weight
274.44
Precautions
H302, H315, H319, H335
References & Citations
[1]Brooksbank BW, et al. The detection of 5alpha-androst-16-en-3alpha-ol in human male axillary sweat. Experientia. 1974 Aug 15;30 (8) :864-5.|[2]Kaminski RM, et al. The pheromone androstenol (5 alpha-androst-16-en-3 alpha-ol) is a neurosteroid positive modulator of GABAA receptors. J Pharmacol Exp Ther. 2006 May;317 (2) :694-703. |[3]Starkenmann C, et al. 5α-Androst-16-en-3α-ol β-D-glucuronide, precursor of 5α-androst-16-en-3α-ol in human sweat. Chem Biodivers. 2013 Dec;10 (12) :2197-208.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Natural Products
Clinical Information
No Development Reported

Chemical Information

Androstenol

5alpha-androst-16-en-3alpha-ol is a 3alpha-sterol. It has a role as a pheromone. It derives from a hydride of a 5alpha-androst-16-ene.

CAS Number1153-51-1
PubChem CID101989
IUPAC Name(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
Molecular FormulaC19H30O
Molecular Weight274.4
XLogP5.3
Topological Polar Surface Area20.2
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count1
Rotatable Bond Count0
Heavy Atom Count20
Formal Charge0
Complexity427
SMILES
C[C@]12CC[C@H]3[C@H]([C@@H]1CC=C2)CC[C@@H]4[C@@]3(CC[C@H](C4)O)C
InChI
InChI=1S/C19H30O/c1-18-9-3-4-16(18)15-6-5-13-12-14(20)7-11-19(13,2)17(15)8-10-18/h3,9,13-17,20H,4-8,10-12H2,1-2H3/t13-,14+,15-,16-,17-,18-,19-/m0/s1
InChIKey
KRVXMNNRSSQZJP-PHFHYRSDSA-N
Chemical Structure
2D Structure
2D structure of Androstenol
CAS: 1153-51-1
CID: 101989
Formula: C19H30O
MW: 274.4
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight274.4
XLogP35.3
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count1
Rotatable Bond Count0
Exact Mass274.229665576
Monoisotopic Mass274.229665576
Topological Polar Surface Area20.2 Ų
Heavy Atom Count20
Formal Charge0
Complexity427
Isotope Atom Count0
Defined Atom Stereocenter Count7
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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