5.ALPHA.-ANDROST-16-EN-3-ONE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C19H28O
Molecular Weight	272.425
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of 5.ALPHA.-ANDROST-16-EN-3-ONE

Structure Search

SMILES

[H][C@@]12CC=C[C@@]1(C)CC[C@@]3([H])[C@@]2([H])CC[C@@]4([H])CC(=O)CC[C@]34C

InChI

InChIKey=HFVMLYAGWXSTQI-QYXZOKGRSA-N

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

HIDE SMILES / InChI

Molecular Formula	C19H28O
Molecular Weight	272.425
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	6 / 6
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.wikidoc.org/index.php/Androstenone
Curator's Comment: description was created based on several sources, including: http://images.raiffeisen.com/Raicom/sdb/354/2290_22139_boarmate.pdf

The compound believed to be principally responsible for the unpleasant odor sometimes produced during cooking of pork or bacon from boars has been isolated and identified as 5a-androst-16-en-3-one. It is the first mammalian pheromone to be identified. Androstenone is the active ingredient in a commercial products which were developed for farmers and breeders who need help determining the best fertilization time for sows and gilts. In humans, androstenone also has been suggested to be a pheromone. Excessive exposures may affect human health, as follows: Upper respiratory tract: Irritation, Dizziness, Drowsiness, Headache, Nausea; Skin: Redness.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
olfactory receptor family 7 subfamily D member 4 1 Target ID: 125958.0 Gene Symbol: OR7D4 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17873857	Activator 1430		30.0 µM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Artificial insemination 1 Sources: http://www.kerbl.com/ftp/prod_documents/2290=22139=22156=PI_Boarmate_0312_EN_screen.pdf	Palliative		Approved 8429	Boarmate Approved Use Androstenone is the active ingredient in Boarmate, a commercial product sold to pig farmers to test sows for timing of artificial insemination.

PubMed

Title	Date	PubMed
The biosynthesis of 5 alpha-androst-16-en-3-one from progesterone by boar testis homogenate.	1968 Sep 2	5692903
Human olfactory responses to 5-alpha-androst-16-en-3-one--principal component of boar taint.	1970 Jan	5418189

Patents

Sample Use Guides

In Vivo Use Guide

Spray product at the gilt or sows snout for two seconds from a distance of approximately 60 centimetres, then apply pressure to the back of the sow (the „back pressure“ test).

Route of Administration: Irrigation

In Vitro Use Guide

Analysis of receptor binding of 5alpha-androst-16-en-3-one gave a value for the affinity constant (Ka) of approx. 8.3-10(8) M-1 and the value for the molar concentration of binding sites (n[M]) was approx. 3.3 pmol/mg protein.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:51:06 UTC 2023` Edited by `admin` on `Fri Dec 15 18:51:06 UTC 2023`
Record UNII	BWD3D5941J
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

5.ALPHA.-ANDROST-16-EN-3-ONE

Systematic Name

English

ANDROSTENONE [MI]

Common Name

English

5.ALPHA.-ANDROSTENONE

Common Name

English

5A-ANDROSTA-16-ENE-3-ONE

Common Name

English

ANDROSTENONE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C2298