ANDROSTADIENONE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C19H26O
Molecular Weight	270.4091
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@]34C)[C@@H]1CC=C2

InChI

InChIKey=HNDHDMOSWUAEAW-VMXHOPILSA-N

InChI=1S/C19H26O/c1-18-9-3-4-16(18)15-6-5-13-12-14(20)7-11-19(13,2)17(15)8-10-18/h3,9,12,15-17H,4-8,10-11H2,1-2H3/t15-,16-,17-,18-,19-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C19H26O
Molecular Weight	270.4091
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

Approval Year

PubMed

Title	Date	PubMed
Genetic variation in the odorant receptors family 13 and the mhc loci influence mate selection in a multiple sclerosis dataset.	2010-11-10	21067613
Human olfaction: a constant state of change-blindness.	2010-08	20603708
Androstenol--a steroid derived odor activates the hypothalamus in women.	2010-02-17	20174662
Pheromone signal transduction in humans: what can be learned from olfactory loss.	2009-09	19235878
Chemosensory cues to conspecific emotional stress activate amygdala in humans.	2009-07-29	19641623
High fetal testosterone and sexually dimorphic cerebral networks in females.	2009-05	18854582
Putative human pheromone androstadienone attunes the mind specifically to emotional information.	2009-04	19470369
Behavioral changes of patients after orthognathic surgery develop on the basis of the loss of vomeronasal organ: a hypothesis.	2009-01-22	19161592
Detection and classification of human body odor using an electronic nose.	2009	22399995
Towards a neuroscience of love: olfaction, attention and a model of neurohypophysial hormone action.	2009	19597547
Evidence that androstadienone, a putative human chemosignal, modulates women's attributions of men's attractiveness.	2008-11	18601928
Male-to-female transsexuals show sex-atypical hypothalamus activation when smelling odorous steroids.	2008-08	18056697
Pattern of the divergence of olfactory receptor genes during tetrapod evolution.	2008-06-11	18568087
Thresholds and chemosensory event-related potentials to malodors before, during, and after puberty: differences related to sex and age.	2008-04-15	18302986
Genetic variation in a human odorant receptor alters odour perception.	2007-09-27	17873857
Repetitive olfactory exposure to the biologically significant steroid androstadienone causes a hedonic shift and gender dimorphic changes in olfactory-evoked potentials.	2007-08	17251914
Smelling a single component of male sweat alters levels of cortisol in women.	2007-02-07	17287500
The effects of the steroid androstadienone and pleasant odorants on the mood and pain perception of men and women.	2007-02	16546426
Nose thyself: individuality in the human olfactory genome.	2007	18086317
A putative social chemosignal elicits faster cortical responses than perceptually similar odorants.	2006-05-01	16413793
Sex-specific differences in olfactory sensitivity for putative human pheromones in nonhuman primates.	2006-05	16719588
Effects of reproductive state on olfactory sensitivity suggest odor specificity.	2006-03	16084006
Changes in the odor quality of androstadienone during exposure-induced sensitization.	2006-01	16280418
Subthreshold amounts of social odorant affect mood, but not behavior, in heterosexual women when tested by a male, but not a female, experimenter.	2005-12	16242537
Synthesis of free and sulphoconjugated 16-androstene steroids by the Leydig cells of the mature domestic boar.	2005-07	15955694
Screening of anabolic steroids in horse urine by liquid chromatography-tandem mass spectrometry.	2005-04-29	15862683
Androstadienone odor thresholds in adolescents.	2005-03	15708759
Sniffing a human sex-steroid derived compound affects mood and autonomic arousal in a dose-dependent manner.	2004-11	15288708
Sniffing human sex-steroid derived compounds modulates mood, memory and autonomic nervous system function in specific behavioral contexts.	2004-06-04	15135965
The putative pheromone androstadienone activates cortical fields in the human brain related to social cognition.	2004-06	15016474
Concordant preferences for opposite-sex signals? Human pheromones and facial characteristics.	2004-03-22	15156922
Production of malodorous steroids from androsta-5,16-dienes and androsta-4,16-dienes by Corynebacteria and other human axillary bacteria.	2003-12	14698214
Sex-steroid derived compounds induce sex-specific effects on autonomic nervous system function in humans.	2003-12	14674833
Psychological effects of subthreshold exposure to the putative human pheromone 4,16-androstadien-3-one.	2003-12	14644633
Microbial pathways leading to steroidal malodour in the axilla.	2003-10	14630096
Individual differences in sensitivity to the odor of 4,16-androstadien-3-one.	2003-09	14578126
Psychological effects of musky compounds: comparison of androstadienone with androstenol and muscone.	2002-11	12460587
Context-dependent effects of steroid chemosignals on human physiology and mood.	2001-09-21	11564447
Sustained human chemosignal unconsciously alters brain function.	2001-08-08	11496116

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:54:15 GMT 2025` Edited by `admin` on `Mon Mar 31 19:54:15 GMT 2025`
Record UNII	ZUZ4FHD36E
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ANDROSTADIENONE

Official Name

English

NSC-93234

Preferred Name

English

(+)-ANDROSTADIENONE

Systematic Name

English

.DELTA.4,16-ANDROSTADIEN-3-ONE

Common Name

English

4,16-ANDROSTADIEN-3-ONE

Systematic Name

English

ANDROSTA-4,16-DIEN-3-ONE

Systematic Name

English

Code System Code Type Description

CAS

4075-07-4