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A8008

Sigma-Aldrich

5α-Androst-16-en-3-one

Synonym(s):

16-(5α)Androsten-3-one, 3-Keto-5α,16-androstene, Androstenone

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About This Item

Empirical Formula (Hill Notation):
C19H28O
CAS Number:
18339-16-7
Molecular Weight:
272.43
EC Number:
242-220-1
MDL number:
MFCD00010479
UNSPSC Code:
12352200
PubChem Substance ID:
24891306
NACRES:
NA.77

biological source

synthetic (organic)

Quality Level

200

assay

≥98% (TLC)

form

powder

mp

140-145 °C (lit.)

solubility

dichloromethane: 9.80-10.20 mg/mL, clear, colorless to faintly yellow

shipped in

ambient

storage temp.

room temp

SMILES string

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

InChI

1S/C19H28O/c1-18-9-3-4-16(18)15-6-5-13-12-14(20)7-11-19(13,2)17(15)8-10-18/h3,9,13,15-17H,4-8,10-12H2,1-2H3/t13-,15-,16-,17-,18-,19-/m0/s1

InChI key

HFVMLYAGWXSTQI-QYXZOKGRSA-N

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General description

5α-Androst-16-en-3-one (androstenone) is a mammalian pheromone found in boar saliva, human sweat, and human urine.

application

5α-Androst-16-en-3-one has been used:
  • to quantify its concentration in various fat tissues
  • to study its trigeminal percept and implications on the rate of specific anosmia
  • to study the effects of immunocastration on meat quality and sensory properties of pork bellies

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000363599
0000363599
0000352506
13170715
0000279055

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G Zamaratskaia et al.
Reproduction in domestic animals = Zuchthygiene, 39(3), 168-172 (2004-06-09)
This study describes the age-related variation in boar taint compounds, skatole and androstenone, and testosterone, oestradiol-17 beta (E17 beta), oestrone sulphate (ES), dehydroepiandrosterone sulphate (DHEAS), triiodothyronine (T(3)) and insulin-like growth factor-1 (IGF-1) in six boars. Three pairs of littermates of
Gang Chen et al.
Drug metabolism and disposition: the biological fate of chemicals, 36(1), 56-60 (2007-10-03)
CYP2A6 is one of the enzymes involved in the hepatic metabolism of a naturally produced compound, skatole, in the pig. Low CYP2A6 activity has been linked to excessive accumulation of skatole in pig adipose tissue and development of the phenomenon
The scents of androstenone in humans.
Ricardo C Araneda et al.
The Journal of physiology, 554(Pt 1), 1-1 (2003-12-18)
J Peacock et al.
Animal genetics, 39(1), 15-21 (2007-12-29)
The level of cytochrome b5A (CYB5A) in pig testis is correlated with boar taint from androstenone and an AF016388:c.-8G>T polymorphism in CYB5A has been linked with low androstenone levels in the fat of pigs. In this study, we developed a
K Verheyden et al.
Journal of chromatography. A, 1174(1-2), 132-137 (2007-09-25)
Boar taint in entire male pigs remains a problem for fresh pork production. Since castration of pigs will be prohibited in the future on animal welfare reasons, attempts are made to detect boar taint pre and post mortem. Post mortem
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