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Merck
CN

A8008

Sigma-Aldrich

5α-Androst-16-en-3-one

synthetic (organic), ≥98% (TLC), pheromone, powder

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

Key Documents

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Product Name

5α-Androst-16-en-3-one,

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

涉药品监管产品
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Certificates of Analysis (COA)

Lot/Batch Number
0000462384
0000462385
0000445516
0000445516
0000462385

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Eli Grindflek et al.
BMC genomics, 12, 362-362 (2011-07-15)
Boar taint is observed in a high proportion of uncastrated male pigs and is characterized by an unpleasant odor/flavor in cooked meat, primarily caused by elevated levels of androstenone and skatole. Androstenone is a steroid produced in the testis in
The effects of immunocastration on meat quality and sensory properties of pork bellies
Jeon JY, et al.
Food science of animal resources (2011)
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 M Bekaert et al.
Meat science, 88(3), 548-552 (2011-03-15)
Skatole and androstenone are the main boar taint compounds. Whereas nearly everybody is sensitive to skatole, the sensitivity to androstenone is genetically determined and differs between countries. In this study the methodology for testing androstenone sensitivity was refined and applied
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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