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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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
P A Sinclair et al.
Journal of animal science, 83(2), 358-365 (2005-01-13)
This study examined the relationship between sulfoconjugation and the degree to which 5alpha-androstenone can accumulate in fat. Analysis of the unconjugated and sulfoconjugated fractions of peripheral plasma from 25 mature Yorkshire boars and testicular vein plasma from an additional 20
Jochen Fischer et al.
Analytical chemistry, 83(17), 6785-6791 (2011-08-02)
The steroidal pig pheromones androstenone (5α-androst-16-en-3-one), 3α-androstenol (5α-androst-16-en-3α-ol), and 3β-androstenol (5α-androst-16-en-3β-ol) as well as the heterocyclic aromatic amines skatole and indole, originating from microbial degradation of tryptophan in the intestine of pigs, are frequently recognized as the major compounds responsible
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
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