| Name: | (8S,9S,10R,13R,14S)-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15-decahydrocyclopenta[a]phenanthren-3-one |
| CAS Number: | 4075-07-4 |  3D/inchi
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| FDA UNII: | ZUZ4FHD36E |
| Nikkaji Web: | J80.741I |
| XlogP3-AA: | 4.50 (est) |
| Molecular Weight: | 270.41542000 |
| Formula: | C19 H26 O |
| NMR Predictor: | Predict (works with chrome, Edge or firefox) |
Category:fragrance agents
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Physical Properties:
| Assay: | 95.00 to 100.00
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| Food Chemicals Codex Listed: | No |
| Boiling Point: | 389.00 to 391.00 °C. @ 760.00 mm Hg (est)
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| Flash Point: | 355.00 °F. TCC ( 179.20 °C. ) (est)
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| logP (o/w): | 4.815 (est) |
| Soluble in: |
| | water, 2.175 mg/L @ 25 °C (est) |
Organoleptic Properties:
| Odor and/or flavor descriptions from others (if found). |
Cosmetic Information:
Suppliers:
Safety Information:
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| Hazards identification |
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| Classification of the substance or mixture |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) |
| None found. |
| GHS Label elements, including precautionary statements |
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| Pictogram | |
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| Hazard statement(s) |
| None found. |
| Precautionary statement(s) |
| None found. |
| Oral/Parenteral Toxicity: |
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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 :92979 |
| National Institute of Allergy and Infectious Diseases:Data |
| (8S,9S,10R,13R,14S)-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15-decahydrocyclopenta[a]phenanthren-3-one |
| Chemidplus:0004075074 |
References:
| | (8S,9S,10R,13R,14S)-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15-decahydrocyclopenta[a]phenanthren-3-one |
| NIST Chemistry WebBook: | Search Inchi |
| Pubchem (cid): | 92979 |
| Pubchem (sid): | 135050724 |
Other Information:
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
Synonyms:
| | androsta-4,16-dien-3-one | | 4,16- | androstadien-3 | | delta4,16- | androstadien-3-one | | (8S,9S,10R,13R,14S)-10,13- | dimethyl-1,2,6,7,8,9,11,12,14,15-decahydrocyclopenta[a]phenanthren-3-one |
Articles:
| PubMed:Gender effects and sexual-orientation impact on androstadienone-evoked behavior and neural processing. |
| PubMed:Hypothalamic response to the chemo-signal androstadienone in gender dysphoric children and adolescents. |
| PubMed:Heterosexual men and women both show a hypothalamic response to the chemo-signal androstadienone. |
| PubMed:A putative human pheromone, androstadienone, increases cooperation between men. |
| PubMed:Androstadienone in motor reactions of men and women toward angry faces. |
| PubMed:Is androstadienone a putative human pheromone? |
| PubMed:Putative human pheromone androstadienone attunes the mind specifically to emotional information. |
| PubMed:Subliminally perceived odours modulate female intrasexual competition: an eye movement study. |
| PubMed:The search for human pheromones: the lost decades and the necessity of returning to first principles. |
| PubMed:Pathways and genes involved in steroid hormone metabolism in male pigs: a review and update. |
| PubMed:Formation of Δ(1) and Δ(6) testosterone metabolites by human hepatocytes. |
| PubMed:Individual differences in sensitivity to the odor of 4,16-androstadien-3-one. |
| PubMed:Psychological effects of subthreshold exposure to the putative human pheromone 4,16-androstadien-3-one. |
| PubMed:Evidence that androstadienone, a putative human chemosignal, modulates women's attributions of men's attractiveness. |
| PubMed:Psychological effects of musky compounds: comparison of androstadienone with androstenol and muscone. |
| PubMed:Synthesis of 2-carboxy-11 beta, 17 beta-dihydroxy-17-methyl-1, 4-androstadien-3-one and related compounds. |
| PubMed:Pheromones and their effect on women's mood and sexuality. |
| PubMed:The effects of the steroid androstadienone and pleasant odorants on the mood and pain perception of men and women. |
| PubMed:Androstadienone odor thresholds in adolescents. |
| PubMed:The effects of progesterone, 4,16-androstadien-3-one and MK-434 on the kinetics of pig testis microsomal testosterone-4-ene-5alpha-reductase activity. |
| PubMed:Studies on anabolic steroids. The mass spectra of 17 alpha-methyl-17 beta-hydroxy-1,4-androstadien-3-one (Dianabol) and its metabolites. |
| PubMed:The identification of 17 -hydroxy-17-methyl-1,4-androstadien-3-one as a metabolite of the anabolic steroid drug 17 -hydroxy-17-methyl-1,4-androstadien-3-one in man. |
| PubMed:Repetitive olfactory exposure to the biologically significant steroid androstadienone causes a hedonic shift and gender dimorphic changes in olfactory-evoked potentials. |
| PubMed:Behavioral and electrophysiological effects of androstadienone, a human pheromone. |
| PubMed:Simultaneous determination of testosterone and androstadienone (sex attractant) in human plasma by gas chromatography-mass spectrometry with high-resolution selected-ion monitoring. |
| PubMed:Olfactory function in Wave 2 of the National Social Life, Health, and Aging Project. |
| PubMed:Changes in the odor quality of androstadienone during exposure-induced sensitization. |
| PubMed:The putative pheromone androstadienone activates cortical fields in the human brain related to social cognition. |
| PubMed:Global Survey of Variation in a Human Olfactory Receptor Gene Reveals Signatures of Non-Neutral Evolution. |
| PubMed:[Identification of a photolabelled site of the plasma binding protein for testosterone and estradiol (SBP) using tritiated 17 beta-hydroxy- 4,6-androstadien-3-one]. |
| PubMed:Contractile responses of rat lateral gastrocnemius and soleus to dianabol (17 beta-hydroxy-17-methyl-1,4-androstadien-3-one) and exercise. |
| PubMed:Metabolism of 1,4-androstadiene-3,17-dione by human placental microsomes. Enzyme properties and kinetic parameters in the formation of estrogens and 17 beta-hydroxy-1,4-androstadien-3-one. |
| PubMed:Binding of the photoaffinity ligand 17 beta-hydroxy-4,6-androstadien-3-one to rat androgen-binding protein: comparison with the binding of 17 beta-hydroxy-5alpha-androstan-3-one. |
| PubMed:[Metabolism of steroid pharmaceuticals. 9. 5alpha-and 5beta-hydrated metabolites of 4-chloro-17-alpha-methyl-17beta-hydroxy-1,4-androstadien-3-one in vitro by the rat and in vivo by the baboon]. |
| PubMed:The metabolism in vivo 4,16-androstadien-3-one in man. Occurrence of 16-dehydro C 19 steroids, androstane-3,16,17-triols and other metabolites in urine. |
| PubMed:[Metabolism of steroid drugs. II. Isolation and identification of metabolites of 4-chlor-17 alpha-methyl-17 beta-hydroxy-1,4-androstadien-3-one]. |
| PubMed:-side catalytic hydrogenation and the molecular structure of 17 -hydroxy-1,4-androstadien-3-one:p-bromophenol (1:1). |
| PubMed:An ultraviolet spectrophotometric method for the determination of delta 3,5 androstadienone-17 in the urine. |
| PubMed:[Pathway of biosynthesis of androstadienone (delta 16-C19-steroid) from pregnenolone catalyzed by pig testicular microsomes]. |
| PubMed:Psychological state and mood effects of steroidal chemosignals in women and men. |
| PubMed:Chemosensory communication of gender through two human steroids in a sexually dimorphic manner. |
| PubMed:Sustained human chemosignal unconsciously alters brain function. |
| PubMed:Subthreshold amounts of social odorant affect mood, but not behavior, in heterosexual women when tested by a male, but not a female, experimenter. |
| 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:Gas chromatographic-mass spectrometric study of metabolites of C21 and C19 steroids in neonatal porcine testicular microsomes. |
| PubMed:Smelling a single component of male sweat alters levels of cortisol in women. |
| PubMed:Methandrostenolone metabolism in humans: potential problems associated with isolation and identification of metabolites. |
| PubMed:Methandrostenolone: metabolism in the rabbit. |
| PubMed:Accelerated sample treatment for screening of banned doping substances by GC-MS: ultrasonication versus microwave energy. |
| PubMed:Applications of gas chromatography-mass spectrometry in the study of androgen and odorous 16-androstene metabolism by human axillary bacteria. |
| PubMed:Context-dependent effects of steroid chemosignals on human physiology and mood. |
| PubMed:Concordant preferences for opposite-sex signals? Human pheromones and facial characteristics. |
| PubMed:Microbial pathways leading to steroidal malodour in the axilla. |
| 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:Simultaneous quantification of five odorous steroids (16-androstenes) in the axillary hair of men. |
| PubMed:Biosynthesis of 16 alpha, 17 alpha-epoxy-4-androsten-3-one in rat liver microsomes. |
| PubMed:Photoaffinity labeling of rat androgen binding protein. |
| PubMed:Hydroxylation of testosterone at carbons 1, 2, 6, 7, 15 and 16 by the hepatic microsomal fraction from adult female C57BL/6J mice. |
| PubMed:Androstenol--a steroid derived odor activates the hypothalamus in women. |
| PubMed:Time-dependent density functional theory for calculating origin-independent optical rotation and rotatory strength tensors. |
| PubMed:Pheromone signal transduction in humans: what can be learned from olfactory loss. |
| PubMed:Thresholds and chemosensory event-related potentials to malodors before, during, and after puberty: differences related to sex and age. |
| PubMed:A putative social chemosignal elicits faster cortical responses than perceptually similar odorants. |
| PubMed:The vomeronasal organ is not involved in the perception of endogenous odors. |
| PubMed:Cytochrome b5 promotes the synthesis of delta 16-C19 steroids by homogeneous cytochrome P-450 C21 side-chain cleavage from pig testis. |
| PubMed:Male-to-female transsexuals show sex-atypical hypothalamus activation when smelling odorous steroids. |
| PubMed:Metabolic studies of turinabol in horses. |
| PubMed:Brain response to putative pheromones in lesbian women. |
| PubMed:Brain response to putative pheromones in homosexual men. |
| PubMed:Sniffing a human sex-steroid derived compound affects mood and autonomic arousal in a dose-dependent manner. |
| PubMed:Sniffing human sex-steroid derived compounds modulates mood, memory and autonomic nervous system function in specific behavioral contexts. |
| PubMed:Sex-steroid derived compounds induce sex-specific effects on autonomic nervous system function in humans. |
| PubMed:Differential effects of trilostane and cyanoketone on the 3 beta-hydroxysteroid dehydrogenase-isomerase reactions in androgen and 16-androstene biosynthetic pathways in the pig testis. |
| PubMed:Novel oxidative cleavage of C17-C20 bond in pregnane by a Pseudomonas sp. |
| PubMed:GC-MS studies of 16-androstenes and other C19 steroids in human semen. |
| PubMed:Kinetic evidence for separate 3 beta-hydroxysteroid dehydrogenase-isomerases in androgen and 16-androstene biosynthetic pathways in the pig testis. |
| PubMed:Phospholipases modulate immature pig testicular androgen and 16-androstene biosynthetic pathways in vitro. |
| PubMed:Analysis of the steroid binding domain of rat androgen-binding protein. |
| PubMed:Steroidogenesis in interstitial cells and microsomal fraction of immature pig testes. |
| PubMed:Differential metabolism of pregnenolone by testicular homogenates of humans and two species of macaques. Lack of synthesis of the human sex pheromone precursor 5,16-androstadien-3 beta-ol in nonhuman primates. |
| PubMed:The microheterogeneity of rabbit testosterone-binding globulin is due to differential glycosylation of its single protomer. |
| PubMed:The mechanism of the synthesis of 16-androstenes in human testicular homogenates. |
| PubMed:Odor thresholds of the C(19)-Δ(16)-steroids responsible for boar odor in pork. |
| PubMed:The apparent molecular weight of androgen-binding protein (ABP) in the blood of immature rats differs from that of ABP in the epididymis. |
| PubMed:The ontogeny of biologically active androgen-binding protein in rat plasma, testis, and epididymis. |
| PubMed:Biosynthesis of androgens and pheromonal steroids in neonatal porcine testicular preparations. |
| PubMed:Comparative rates of formation, in vivo, of 16-androstenes, testosterone and androstenedione in boar testis. |
| PubMed:Synthesis of some 6 beta-acetylthio hydroxysteroids. |
| PubMed:Relative binding affinity of anabolic-androgenic steroids: comparison of the binding to the androgen receptors in skeletal muscle and in prostate, as well as to sex hormone-binding globulin. |
| PubMed:Transformations of C21 and C19 steroids in porcine ovarian preparations and the chromatographic separation of the metabolites. |
| PubMed:Demonstration of heavy and light protomers of human testosterone-estradiol-binding globulin. |
| PubMed:GC and capillary column GC/MS determination of synthetic anabolic steroids. II. 4-chloro-methandienone (oral turinabol) and its metabolites. |
| PubMed:Photoaffinity modification of delta 5-3-ketosteroid isomerase by light-activatable steroid ketones covalently coupled to agarose beads. |
| PubMed:Some physicochemical characteristics of photoaffinity-labeled rabbit testosterone-binding globulin. |
| PubMed:Some physicochemical characteristics of photoaffinity-labeled rabbit androgen-binding protein. |
| PubMed:The use of 17-epimethyltestosterone radioimmunoassay in following excretion of methandienone metabolites in urine. |
| PubMed:Effects of cholesterol side chain cleavage inhibitors on 11 beta-hydroxylation: linkage of mitochondrial oxygenase systems. |
| PubMed:Investigations into the possible effects of naturally occurring steroids on biosynthesis of 16-androstenes and androgens in microsomes of boar testis. |
| PubMed:Effect of an anabolic steroid (metandienone) on central and peripheral blood flow in well-trained male athletes. |
| PubMed:Production of male pseudohermaphroditism in rats by two new inhibitors of steroid 17alpha-hydroxylase and C 17-20 lyase. |
| PubMed:Effect of an anabolic steroid (metandienon) on plasma LH-FSH, and testosterone and on the response to intravenous administration of LRH. |
| PubMed:Electron transport systems of lung microsomes and their physiological functions. Enzymic hydroxylation of aniline and steroids. |
| PubMed:Dynamic functional evolution of an odorant receptor for sex-steroid-derived odors in primates. |
| PubMed:Genetic variation in a human odorant receptor alters odour perception. |
| 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:Induction of rat liver microsomal epoxide hydrolase by its endogenous substrate 16 alpha, 17 alpha-epoxyestra-1,3,5-trien-3-ol. |
| 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:High fetal testosterone and sexually dimorphic cerebral networks in females. |
| PubMed:Synthesis of free and sulphoconjugated 16-androstene steroids by the Leydig cells of the mature domestic boar. |
| PubMed:Evidence for involvement of cytochrome P-450-linked oxygenase system in the conversion of C21-steroids to delta 16-C19-steroids catalyzed by pig testicular microsomes. |
| PubMed:Effects of reproductive state on olfactory sensitivity suggest odor specificity. |
| PubMed:Screening of anabolic steroids in horse urine by liquid chromatography-tandem mass spectrometry. |
| PubMed:Identification of phospholipids capable of modulating the activities of some enzymes involved in androgen and 16-androstene biosynthesis in the immature pig testis. |
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