| Name: | 10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15-dodecahydrocyclopenta[a]phenanthren-3-one |
| CAS Number: | 18339-16-7 |  3D/inchi
|
| ECHA EINECS - REACH Pre-Reg: | 242-220-1 |
| FDA UNII: | BWD3D5941J |
| MDL: | MFCD00010479 |
| 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:
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
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| Boiling Point: | 371.00 to 372.00 °C. @ 760.00 mm Hg
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| Flash Point: | 316.00 °F. TCC ( 157.78 °C. )
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| logP (o/w): | 5.568 (est) |
| Soluble in: |
| | alcohol | | | water, 3.159 mg/L @ 25 °C (est) |
| Insoluble in: |
| | water |
Organoleptic Properties:
| Odor and/or flavor descriptions from others (if found). |
Cosmetic Information:
Suppliers:
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.
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| |
| 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 |
| |
| Pictogram | |
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| Hazard statement(s) |
| None found. |
| Precautionary statement(s) |
| None found. |
| Oral/Parenteral Toxicity: |
|
Not determined
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| Dermal Toxicity: |
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Not determined
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| Inhalation Toxicity: |
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Not determined
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Safety in Use Information:
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 |
| 10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15-dodecahydrocyclopenta[a]phenanthren-3-one |
| Chemidplus:0018339167 |
References:
| | 10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15-dodecahydrocyclopenta[a]phenanthren-3-one |
| NIST Chemistry WebBook: | Search Inchi |
| Canada Domestic Sub. List: | 18339-16-7 |
| Pubchem (cid): | 86705 |
| Pubchem (sid): | 135044287 |
Other Information:
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
Synonyms:
| | androst-16-en-3-one | | 5a- | androst-16-en-3-one | | | androst-16-en-3-one, (5a)- | | 10,13- | dimethyl-1,2,4,5,6,7,8,9,11,12,14,15-dodecahydrocyclopenta[a]phenanthren-3-one |
Articles:
| 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. |
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