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Safety Information

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

监管及禁止进口产品

Certificates of Analysis (COA)

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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
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
Julie A Boyle et al.
Journal of neurobiology, 66(13), 1501-1510 (2006-10-03)
Specific anosmia is a term that describes an inability to perceive a particular odorant in the context of an otherwise normal olfactory acuity. The most common example, for the odor of androstenone, has been ascribed a prevalence ranging from 2
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)
The effects of immunocastration on meat quality and sensory properties of pork bellies
Jeon JY, et al.
Food science of animal resources (2011)
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