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A7883

Sigma-Aldrich

5α-Androst-16-en-3α-ol

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Synonym(s):
Androstenol, 16-(5α)Androsten-3α-ol, 3α-Hydroxy-5α-androst-16-ene
Empirical Formula (Hill Notation):
C19H30O
CAS Number:
1153-51-1
Molecular Weight:
274.44
EC Number:
214-573-1
MDL number:
MFCD00051224
UNSPSC Code:
12352200
PubChem Substance ID:
24891288
NACRES:
NA.77

biological source

synthetic (organic)

Quality Level

200

Assay

≥98% (TLC)

form

powder

drug control

regulated under CDSA - not available from Sigma-Aldrich Canada

technique(s)

GC/MS: suitable

mp

140-141 °C (lit.)

solubility

ethanol: 19.60-20.40 mg/mL, clear, colorless

shipped in

ambient

storage temp.

room temp

SMILES string

C[C@]12CC[C@H]3[C@@H](CC[C@H]4C[C@H](O)CC[C@]34C)[C@@H]1CC=C2

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

InChI key

KRVXMNNRSSQZJP-PHFHYRSDSA-N

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Application

5-α-androst-16-en-3-α-ol (androstenol) is an androgen believed to act as a pheromone. Androstenol has been used in a study to develop a combined gas chromatography/thermal conversion/isotope ratio mass spectrometry (GC/TC/IRMS) method for D/H ratio determination of endogenous urinary steroids.

Biochem/physiol Actions

5alpha-androst-16-en-3alpha-ol (androstenol), is an androgen believed to act as a pheromone.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Jeremy Vincent et al.
Acta crystallographica. Section F, Structural biology and crystallization communications, 61(Pt 1), 156-159 (2006-03-02)
The constitutive androstane receptor (CAR) is a member of the nuclear receptor superfamily. In contrast to classical nuclear receptors, which possess small-molecule ligand-inducible activity, CAR exhibits constitutive transcriptional activity in the apparent absence of ligand. CAR is among the most
Guan Wang et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 870(2), 209-215 (2008-07-01)
A novel method using solid-phase extraction coupled with gas chromatography and flame ionization detector (FID)/electron impact mass spectrometry (EIMS) was developed for the determination of 5alpha-androst-16-en-3alpha-ol (androstenol), a steroidal compound belonging to the group of musk odorous 16-androstenes, in truffle
Thomas Piper et al.
Rapid communications in mass spectrometry : RCM, 23(13), 1917-1926 (2009-05-23)
The development and application of a combined gas chromatography/thermal conversion/isotope ratio mass spectrometry (GC/TC/IRMS) method for D/H ratio determination of endogenous urinary steroids are presented. The key element in sample preparation was the consecutive cleanup with high-performance liquid chromatography of
D Benton et al.
Biological psychology, 22(2), 141-147 (1986-04-01)
The hypothesis that 5-alpha-androst-16-en-3 alpha-ol increases the sexual arousal of the human female was examined. This substance is produced by the male and has been suggested to be a possible human pheromone. Groups of female subjects were asked to read
W D Booth
The Journal of endocrinology, 100(2), 195-202 (1984-02-01)
Submaxillary glands of mature Göttingen miniature pigs were examined for the presence of a sexual dimorphism. Gland weights, serous cell hypertrophy and total protein in the glands were much greater in male than female pigs. High concentrations of the pheromonal
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