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A8008

Sigma-Aldrich

5α-Androst-16-en-3-one

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Synonym(s):
16-(5α)Androsten-3-one, 3-Keto-5α,16-androstene, Androstenone
Empirical Formula (Hill Notation):
C19H28O
CAS Number:
Molecular Weight:
272.43
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

biological source

synthetic (organic)

Quality Level

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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1 of 4

This Item
A3009A7883E3375
5α-Androst-16-en-3-one

A8008

5α-Androst-16-en-3-one

4-Androsten-11β-ol-3,17-dione

A3009

4-Androsten-11β-ol-3,17-dione

5α-Androst-16-en-3α-ol

A7883

5α-Androst-16-en-3α-ol

trans-Androsterone

E3375

trans-Androsterone

form

powder

form

powder

form

powder

form

powder

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

storage temp.

room temp

storage temp.

room temp

storage temp.

room temp

storage temp.

room temp

solubility

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

solubility

chloroform: 49-51 mg/mL, clear, colorless to faintly yellow

solubility

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

solubility

chloroform: 50 mg/mL, clear to slightly hazy, colorless to faintly yellow

shipped in

ambient

shipped in

ambient

shipped in

ambient

shipped in

ambient

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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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
Maren Moe et al.
BMC genomics, 8, 405-405 (2007-11-09)
Boar taint is a major obstacle when using uncastrated male pigs for swine production. One of the main compounds causing this taint is androstenone, a pheromone produced in porcine testis. Here we use microarrays to study the expression of thousands
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
S Ampuero Kragten et al.
Animal : an international journal of animal bioscience, 5(10), 1634-1642 (2012-03-24)
Today, different analytical methods are used by different laboratories to quantify androstenone in fat tissue. This study shows the comparison of methods used routinely in different laboratories for androstenone quantification: Time-resolved fluoroimmunoassay in Norwegian School of Veterinary Science (NSVS; Norway)
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

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