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androst-16-en-3-one, (5a)-

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CAS Number: 18339-16-7Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:242-220-1
XlogP3-AA:4.90 (est)
Molecular Weight:272.43136000
Formula:C19 H28 O
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:fragrance agents
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
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Pubchem Patents:Search
Physical Properties:
Appearance:white solid (est)
Assay: 97.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 140.00 to 145.00 °C. @ 760.00 mm Hg
Boiling Point: 371.00 to 372.00 °C. @ 760.00 mm Hg
Flash Point: 316.00 °F. TCC ( 157.78 °C. )
logP (o/w): 5.568 (est)
Soluble in:
 water, 3.159 mg/L @ 25 °C (est)
Insoluble in:
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
Cosmetic Information:
None found
BOC Sciences
For experimental / research use only.
5a-Androst-16-en-3-one 95%
For experimental / research use only.
Santa Cruz Biotechnology
For experimental / research use only.
Sigma-Aldrich: Sigma
For experimental / research use only.
Safety Information:
Preferred SDS: View
European information :
Most important hazard(s):
None - None found.
S 02 - Keep out of the reach of children.
S 23 - Do not breath vapour.
S 24/25 - Avoid contact with skin and eyes.
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
Safety in Use Information:
fragrance agents
RIFM Fragrance Material Safety Assessment: Search
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice
Recommendation for 5alpha-androst-16-en-3-one flavor usage levels up to:
 not for flavor use.
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :86705
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:18339-16-7
Pubchem (cid):86705
Pubchem (sid):135044287
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
HMDB (The Human Metabolome Database):HMDB34406
Export Tariff Code:2937.99.8050
VCF-Online:VCF Volatile Compounds in Food
Potential Blenders and core components note
None Found
Potential Uses:
None Found
Occurrence (nature, food, other):note
 celery shoot
Search Trop Picture
 parsnip root
Search Trop Picture
 androst-16-en-3-one, (5a)-


PubMed:Responsiveness of human neonates to the odor of 5α-androst-16-en-3-one: a behavioral paradox?
PubMed:Development of an analytical approach for identification and quantification of 5-α-androst-16-en-3-one in human milk.
PubMed:Measurement of boar taint in porcine fat using a high-throughput gas chromatography-mass spectrometry protocol.
PubMed:RNA deep sequencing reveals novel candidate genes and polymorphisms in boar testis and liver tissues with divergent androstenone levels.
PubMed:Use of gas chromatographic-mass spectrometric techniques in studies of androst-16-ene and androgen biosynthesis in human testis; cytosolic specific binding of 5alpha-androst-16-en-3-one.
PubMed:Estimation of the odorous steroid, 5 alpha-androst-16-en-3-one, in human saliva.
PubMed:A note on the metabolism of 5 alpha-androst-16-en-3-one in the young boar in vivo.
PubMed:Axillary 5 alpha-androst-16-en-3-one, cholesterol and squalene in men; preliminary evidence for 5 alpha-androst-16-en-3-one being a product of bacterial action.
PubMed:Aerosolized 5 alpha-androst-16-en-3-one reduced agonistic behavior and temporarily improved performance of growing pigs.
PubMed:Axillary 5 alpha-androst-16-en-3-one in men and women: relationships with olfactory acuity to odorous 16-androstenes.
PubMed:On the existence of receptors to the pheromonal steroid, 5 alpha-androst-16-en-3-one, in porcine nasal epithelium.
PubMed:Human (Homo sapiens) responses to the pig (Sus scrofa) sex pheromone 5 alpha-androst-16-en-3-one.
PubMed:Studies on the receptors to 5alpha-androst-16-en-3-one and 5alpha-androst-16-en-3alpha-ol in sow nasal mucosa.
PubMed:Studies on 5alpha-androst-16-en-3-one binding to porcine serum, plasma and testicular cytosolic fraction and to human serum.
PubMed:Binding of 5 alpha-androst-16-en-3-one to glycoproteins of porcine olfactory tissue.
PubMed:The 'boar taint' steroid 5 alpha-androst-16-en-3-one: an immunisation trial.
PubMed:The validation and use of a radioimmunoassay for 5 alpha-androst-16-en-3-one in human axillary collections.
PubMed:Binding of the pheromonal steroid, 5alpha-androst-16-en-3-one, to membrane-enriched fractions of boar and rat olfactory epithelium; preliminary evidence for binding protein being a glycoprotein.
PubMed:Binding of 5 alpha-androst-16-en-3-one to pig olfactory tissue.
PubMed:[Synthesis of mammalian pheromone 5 alpha-androst-16-en-3-one and 5 alpha-Androst-16-en-3 alpha-ol].
PubMed:Effect of season upon 5 alpha-androst-16-en-3-one (boar taint) concentrations in the subcutaneous fat of commercial weight boars.
PubMed:Effects of live weight and processing on the sensory traits, androstenedione concentration and 5-alpha-androst-16-en-3-one (androstenone) concentration in boar meat.
PubMed:An improved microtitre enzyme immunoassay to measure the boar taint steroid 5α-androst-16-en-3-one in blood plasma of pigs.
PubMed:Male subjects who could not perceive the pheromone 5a-androst-16-en-3-one, produced similar orbitofrontal changes on PET compared with perceptible phenylethyl alcohol (rose).
PubMed:Effect of 5alpha-androst-16-en-3-one on oxytocin release in oestrous sows.
PubMed:A radioimmunoassay for 5alpha-androst-16-en-3-one in porcine adipose tissue.
PubMed:Studies on the metabolism of 5alpha-androst-16-en-3-one in boar tests in vivo.
PubMed:Development and validation of a UHPLC-HR-Orbitrap-MS method for the simultaneous determination of androstenone, skatole and indole in porcine meat and meat products.
PubMed:The suppressive effect of apricot kernel extract on 5alpha-Androst-16-en-3-one generated by microbial metabolism.
PubMed:Diurnal rhythm of 5 alpha-androst-16-en-3-one and testosterone in peripheral plasma of boars.
PubMed:Development of a candidate reference method for the simultaneous quantitation of the boar taint compounds androstenone, 3α-androstenol, 3β-androstenol, skatole, and indole in pig fat by means of stable isotope dilution analysis-headspace solid-phase microextraction-gas chromatography/mass spectrometry.
PubMed:The search for human pheromones: the lost decades and the necessity of returning to first principles.
PubMed:Fatty acid composition of subcutaneous adipose tissue from entire male pigs with extremely divergent levels of boar taint compounds--an exploratory study.
PubMed:Pre-slaughter conditions influence skatole and androstenone in adipose tissue of boars.
PubMed:Asian low-androstenone haplotype on pig chromosome 6 does not unfavorably affect production and reproduction traits.
PubMed:How olfactory acuity affects the sensory assessment of boar fat: a proposal for quantification.
PubMed:Analysis of the genetics of boar taint reveals both single SNPs and regional effects.
PubMed:Quantitative determination of the boar taint substance 5alpha-androst-16-en-3-one in fat.
PubMed:Proceedings: Studies on the receptors to the odoriferous steroid, 5alpha-androst-16-en-3-one, in sow nasal epithelium.
PubMed:Determination of 5 -androst-16-en-3-one, a boar taint steroid in pigs, with reference to relationships to testosterone.
PubMed:Isolation and identification of 3 -hydroxy-5 -androst-16-ene and 5 -androst-16-en-3-one from procine adipose tissue.
PubMed:Human olfactory responses to 5-alpha-androst-16-en-3-one--principal component of boar taint.
PubMed:The biosynthesis of 5 alpha-androst-16-en-3-one from progesterone by boar testis homogenate.
PubMed:[Relationships between concentrations of testosterone and the boar taint steroid 5alpha-androst-16-en-3-one in blood and adipose tissue; histometric finding in the testes of swine].
PubMed:Development of a radioimmunoassay for 5 alpha-androst-16-en-3-one in pig peripheral plasma.
PubMed:[Radioimmunoassay of 5-alpha-androst-16-en-3-one, steroid responsible for boar odor, in the adipose tissue of swine].
PubMed:Proceedings: Studies on the metabolism of the odoriferous ketones, 5alpha-androst-16-en-3-one and androsta-4,16-dien-3-one, by the nasal epithelium of the mature and immature sow.
PubMed:On the relationship between an Asian haplotype on chromosome 6 that reduces androstenone levels in boars and the differential expression of SULT2A1 in the testis.
PubMed:The effect of short-term exposure to the volatile steroid androstenone on the behavior and hormonal status in male mice.
PubMed:Genetic relationship between boar taint compounds, human nose scores, and reproduction traits in pigs.
PubMed:Learning to smell: repeated exposure increases sensitivity to androstenone, a major component of boar taint.
PubMed:Genetic parameters for androstenone and skatole as indicators of boar taint and their relationship to production and litter size traits in Danish Landrace.
PubMed:Consumer perception of boar meat as affected by labelling information, malodorous compounds and sensitivity to androstenone.
PubMed:In vivo effect confirmation of anti-androgenic compounds in sediment contact tests with Potamopyrgus antipodarum.
PubMed:Steroid hormones, boar taint compounds, and reproductive organs in pigs according to the delay between immunocastration and slaughter.
PubMed:A single nucleotide polymorphism in the CYP2E1 gene promoter affects skatole content in backfat of boars of two commercial Duroc-sired crossbred populations.
PubMed:Consumer studies on sensory acceptability of boar taint: a review.
PubMed:Predicting the likelihood of developing boar taint: early physical indicators in entire male pigs.
PubMed:Pleasantness of the odor of androstenone as a function of sexual intercourse experience in women and men.
PubMed:Molecular characterization of the porcine TEAD3 (TEF-5) gene: examination of a promoter mutation as the causal mutation of a quantitative trait loci affecting the androstenone level in boar fat.
PubMed:Heck reactions of steroidal alkenyl iodides.
PubMed:16-unsaturated C 19 3-oxo steroids as metabolic intermediates in boar testis.
PubMed:Capillary gas chromatography with chemical ionization negative ion mass spectrometry in the identification of odorous steroids formed in metabolic studies of the sulphates of androsterone, DHA and 5alpha-androst-16-en-3beta-ol with human axillary bacterial isolates.
PubMed:Large scale genome-wide association and LDLA mapping study identifies QTLs for boar taint and related sex steroids.
PubMed:The sensitivity of Flemish citizens to androstenone: influence of gender, age, location and smoking habits.
PubMed:Boar taint detection using parasitoid biosensors.
PubMed:Purification, cloning and characterisation of odorant- and pheromone-binding proteins from pig nasal epithelium.
PubMed:GC-MS studies of 16-androstenes and other C19 steroids in human semen.
PubMed:Changes in sensitivity to the odor of androstenone during adolescence.
PubMed:Reduction of pig agonistic behavior by androstenone.
PubMed:Factors affecting the pheromone composition of voided boar saliva.
PubMed:Quantitative determination of androstenone in pig adipose tissue.
PubMed:Seasonal changes of steroid concentrations in seminal plasma of a European wild boar.
PubMed:Immunization of pigs against the boar taint steroid androstenone.
PubMed:Absence of HLA association or linkage for variations in sensitivity to the odor of androstenone.
PubMed:Development and validation of a method for simultaneous analysis of the boar taint compounds indole, skatole and androstenone in pig fat using liquid chromatography-multiple mass spectrometry.
PubMed:Differential responses to odorant analogs after recovery from nerve transection.
PubMed:Positive relationship between menstrual synchrony and ability to smell 5alpha-androst-16-en-3alpha-ol.
PubMed:Enhanced sensitivity to androstenone following regular exposure to pemenone.
PubMed:Individual differences in the perceived intensity and quality of specific odors following self- and cross-adaptation.
PubMed:Ability to perceive androstenone can be acquired by ostensibly anosmic people.
PubMed:Evidence for aggression-modulating pheromones in prepuberal pigs.
PubMed:Comparative rates of formation, in vivo, of 16-androstenes, testosterone and androstenedione in boar testis.
PubMed:Ability to smell androstenone is genetically determined.
PubMed:Simultaneous quantification of five odorous steroids (16-androstenes) in the axillary hair of men.
PubMed:Steroidal alkenylphosphonates via palladium-catalyzed coupling reactions.
PubMed:The isolation, purification and some properties of pheromaxein, the pheromonal steroid-binding protein, in porcine submaxillary glands and saliva.
PubMed:Examination of testicular gene expression patterns in Yorkshire pigs with high and low levels of boar taint.
PubMed:The role of porcine cytochrome b5A and cytochrome b5B in the regulation of cytochrome P45017A1 activities.
PubMed:The effect of a c.-8G>T polymorphism on the expression of cytochrome b5A and boar taint in pigs.
PubMed:Regulation of CYP2A6 protein expression by skatole, indole, and testicular steroids in primary cultured pig hepatocytes.
PubMed:Genetic variation in a human odorant receptor alters odour perception.
PubMed:Olfactory sensitivity through the course of psychosis: Relationships to olfactory identification, symptomatology and the schizophrenia odour.
PubMed:Olfactory responsiveness to two odorous steroids in three species of nonhuman primates.
PubMed:Testicular sulfoconjugation of the 16-androstene steroids by hydroxysteroid sulfotransferase: its effect on the concentrations of 5alpha-androstenone in plasma and fat of the mature domestic boar.
PubMed:Concordant preferences for opposite-sex signals? Human pheromones and facial characteristics.
PubMed:Synthesis of steroidal diacyl hydrazines and their 1,3,4-oxadiazole derivatives.
PubMed:Relationship between metabolism of androstenone and skatole in intact male pigs.
PubMed:Effects of treating young boars with a GnRH depot formulation on endocrine functions, testis size, boar taint, carcass composition and muscular structure.
PubMed:Pemenone and androstenone do not cross-adapt reciprocally.
PubMed:Semantic-free scaling of odor quality.
PubMed:Rapid high-performance liquid chromatographic method for simultaneous determination of androstenone, skatole and indole in back fat from pigs.
PubMed:Pregnenolone metabolism in testicular homogenates of macaques (Macaca fascicularis): some effects of relaxin and freezing.
PubMed:The effects of immunization against luteinizing hormone-releasing hormone on performance, sexual development, and levels of boar taint-related compounds in intact male pigs.
PubMed:Immunological approaches to fertility regulation in domestic livestock.
PubMed:Induction of olfactory receptor sensitivity in mice.
PubMed:Life span changes in the verbal categorization of odors.
PubMed:Evidence for genetic determination in human twins of olfactory thresholds for a standard odorant.
PubMed:Metabolism of androstenedione and 11-ketotestosterone in the kidney of the three-spined stickleback, Gasterosteus aculeatus.
PubMed:Applications of gas chromatography-mass spectrometry in the study of androgen and odorous 16-androstene metabolism by human axillary bacteria.
PubMed:Smelling better. Smell-blindness "cure" may point to olfactory mechanism.
PubMed:Sex differences in response to the odor of alpha androstenone.
PubMed:Conversion of 5 alpha-pregnane-3,20-dione, 3 alpha-hydroxy-5 alpha-pregnan-20-one and 3 beta-hydroxy-5 alpha-pregnan-20-one to delta 16-C19 steroids by the reconstituted delta 16-C19-steroid synthetase system.
PubMed:Odor thresholds of the C(19)-Δ(16)-steroids responsible for boar odor in pork.
PubMed:Evaluation of the contribution of skatole, indole, androstenone and androstenols to boar-taint in back fat of pigs by HPLC and capillary gas chromatography (CGC).
PubMed:Effects of age and live weight on fat 5 alpha-androstenone levels in young boars fed two planes of nutrition.
PubMed:Transformation of steroids by axillary coryneform bacteria.
PubMed:Murine aggression induced by a boar chemosignal: a stimulus presentation dependency.
PubMed:[Active immunization of male pigs against gonadoliberin: effect on the secretion of gonadotropic hormones and on 5 alpha-androst-16-ene-one levels in adipose tissue].
PubMed:Biosynthesis of androgens and pheromonal steroids in neonatal porcine testicular preparations.
PubMed:Relationships between fat and plasma androstenone and plasma testosterone in fatty and lean young boars following castration.
PubMed:Volatile components of the occipital gland secretion of the bactrian camel (Camelus bactrianus).
PubMed:[Radioimmunoassay for the determination of boar pheromone delta 16-androsterone plasma levels in boars, sows and hogs as well as studies of the correlation between boar pheromone concentrations in plasma and adipose tissue].
PubMed:[Trials to eliminate the sex odor of growing boars through active immunization with an androstenone-protein conjugate].
PubMed:The boar-pheromone steroid identified in vegetables.
PubMed:Androgen metabolism by rat epididymis. Metabolic conversion of 3H 5alpha-androstane-3alpha,17beta-diol, in vitro.
PubMed:Ligand specificity and evolution of liver X receptors.
PubMed:Gene expression profiles in testis of pigs with extreme high and low levels of androstenone.
PubMed:The influence of boar pheromones on the vasoreactivity of the facial superficial veins in ovariectomized and estradiol-treated pubertal gilts.
PubMed:Interpersonal defensiveness and diminished perceptual acuity for the odor of a putative pheromone: androstenone.
PubMed:The influence of boar pheromones on the contractile reactivity of the isolated superficial veins of the nose and face in ovariectomized prepubertal gilts and in gilts during sexual maturation.
PubMed:The influence of male pheromones on the contractile reactivity of the isolated superficial veins of the nose and face during the estrous cycle in gilts.
PubMed:Age-related variation of plasma concentrations of skatole, androstenone, testosterone, oestradiol-17 beta, oestrone sulphate, dehydroepiandrosterone sulphate, triiodothyronine and IGF-1 in six entire male pigs.
PubMed:Characterisation of androstenone metabolism in pig liver microsomes.
PubMed:Monitoring androstenone levels in boars by direct immunochemical analysis of serum samples.
PubMed:Gender-specific induction of enhanced sensitivity to odors.
PubMed:Synthetic musks in environmental samples: indicator compounds with relevant properties for environmental monitoring.
PubMed:Social effects and boar taint: significance for production of slaughter boars (Sus scrofa).
PubMed:Sensitivity to androstenone in female subjects is associated with an altered brain response to male body odor.
PubMed:Lipocalins of boar salivary glands binding odours and pheromones.
PubMed:[Interspecies effect of the boar sex pheromone: effect on the status of the female cattle sex cycle].
PubMed:Steroid metabolism by rabbit olfactory-specific P450 2G1.
PubMed:Efficient immunocastration of male piglets by immunoneutralization of GnRH using a new GnRH-like peptide.
PubMed:Comparison of 16-androstene steroid concentrations in sterile apocrine sweat and axillary secretions: interconversions of 16-androstenes by the axillary microflora--a mechanism for axillary odour production in man?
PubMed:Biosynthesis of 16-androstene steroids and testosterone by porcine testis tissue in vitro: effect of age and relationships with fat 5 alpha-androstenone levels in vivo.
PubMed:16-Ene-steroids in the human testis.
PubMed:Olfactory sensitivity to androstenone in schizophrenic patients.
PubMed:[Receptors of boar sex pheromones in the sow nasal cavity].
PubMed:[The boar taint substance, 16-androstenone: radioimmunoassay of adipose tissue following semi-micro saponification].
PubMed:Testosterone metabolism by isolated human axillary Corynebacterium spp.: a gas-chromatographic mass-spectrometric study.
PubMed:Photoperiodic influences on reproduction of domestic boars. I. Light influences on testicular steroids in peripheral blood plasma and seminal plasma.
PubMed:Olfactory acuity to a pheromonal substance and psychotic illness.
PubMed:Sexual dimorphism involving steroidal pheromones and their binding protein in the submaxillary salivary gland of the Göttingen miniature pig.
PubMed:Transformations of C21 and C19 steroids in porcine ovarian preparations and the chromatographic separation of the metabolites.
PubMed:Seasonal effect on steroids in blood plasma and seminal plasma of boars.
PubMed:Relationships between fat and plasma androstenone and plasma testosterone in fatty and lean young boars during growth and after hCG stimulation.
PubMed:[Electrophysiological study of sex pheromone reception in the boar, Sus scrofa].
PubMed:Relationship between androstenone content in fat, intensity of boar taint and size of accessory sex glands in boars.
PubMed:5alpha-Androstenone concentrations in sow plasma during the estrous cycle.
PubMed:Diurnal variations in peripheral plasma levels of testosterone, androstenone and cortisol in boars.
PubMed:Androgen metabolism by rat epididymis. 5. Metabolic conversion and nuclear binding after injection of 5alpha-androstane-3alpha, 17beta-diol, in vivo.
PubMed:Studies on the biosynthesis in vivo and excretion of 16-unsaturated C 19 steroids in the boar.
PubMed:Uptake and metabolism of androgens by bovine spermatozoa.
boar taint steroid. Androgen metabolite which causes ``boar taint'' in pigmeat products
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