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androstadienone

fragrance agents
2D:
3D:
CAS Number: 4075-07-4
FDA UNII: ZUZ4FHD36E
Category: fragrance agents
IUPAC Name: androstadienone
InChI : InChI=1/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
Std.InChI: 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
InChIKey : HNDHDMOSWUAEAW-VMXHOPILBA
Std.InChIKey: HNDHDMOSWUAEAW-VMXHOPILSA-N
SMILES : C[C@]12CC[C@H]3[C@H]([C@@H]1CC=C2)CCC4=CC(=O)CC[C@]34C
Molar Refractivity : 81.51 ± 0.4 cm3 (est)
Parachor : 636.2 ± 6.0 cm3 (est)
Index of Refraction : 1.559 ± 0.03 (est)
Surface Tension : 40.4 ± 5.0 dyne/cm (est)
Density : 1.07 ± 0.1 g/cm3 (est)
Polarizability : 32.31 ± 0.5 10-24cm3 (est)

US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:

Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Perfumer and Flavorist:Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search

Physical Properties:

Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 389.00 to 391.00 °C. @ 760.00 mm Hg (est)
Flash Point: 355.00 °F. TCC ( 179.20 °C. ) (est)
logP (o/w): 4.815 (est)
Soluble in:
water, 2.175 mg/L @ 25 °C (est)

Cosmetic Information:

CosIng:cosmetic data
Cosmetic Uses: fragrance

Suppliers:

BOC Sciences
For experimental / research use only.
4,16-Androstadien-3-one

Safety Information:

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
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:

Category:
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 androstadienone 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 :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:

(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):Search
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View

Potential Blenders and core components :

None Found

Potential Uses:

None Found

Occurrence (nature, food, other):

male tissues

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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