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Androst-4-ene-3,17-dione ( CASNO:63-05-8 )

Identification and Related Records
Name:
Androst-4-ene-3,17-dione
CAS Registry number:
63-05-8
Synonyms:
17-Ketotestosterone
3,17-Dioxoandrost-4-ene
4-Androstene-3,17-dione
Androstenedione
Fecundin
NSC 9563
SKF 2170
D4-Androstene-3,17-dione
Androstenedione
4-Androstenedione
EINECS(EC#):
200-554-5
Molecular Formula:
C19H26O2
Molecular Weight:
286.41
Inchi:
InChI=1/C19H26O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h11,14-16H,3-10H2,1-2H3/t14-,15-,16-,18-,19-/m0/s1
Canonical SMILES:
CC12CCC(=O)C=C1CCC3C2CCC4(C3CCC4=O)C
Isomers smiles:
C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CCC4=O)C
Chemical and Physical Properties
Appearance:
white to off-white solid
Density:
1.11 g/cm3
Melting Point:
170-173℃
Boiling Point:
431.4 oC at 760 mmHg
Refractive Index:
1.551
Flash Point:
161.1 oC
Solubilities:
Insoluble
Color/Form:
Dimorphous. Needles from acetone; crystals from hexane
Stability:
Stable at normal temperatures and pressures.
HS Code:
29372900
Storage temp:
Keep tightly closed.
Spectral properties:
Specific optical rotation = +191 deg C/D at 30 deg C (alcohol)
UV max = 235 nm
MASS: 62023 (NIST/EPA/MSDC Mass Spectral Data Base, 1990 Version)
IR: 5443 (Coblentz Society Spectral Collection)
UV: 7-847 (Phillip et al., Organic Electronic Spectral Data, John Wiley & Sons, New York)
1H NMR: 9959 (Sadler Research Laboratories Spectral Collection)
13 C NMR: 482 (Johnson and Jankowski, Carbon 13 NMR Spectra, John Wiley & Sons, New York)
Computed Properties:
Molecular Weight:286.40854 [g/mol]
Molecular Formula:C19H26O2
XLogP3:2.7
H-Bond Donor:0
H-Bond Acceptor:2
Rotatable Bond Count:0
Tautomer Count:10
Exact Mass:286.19328
MonoIsotopic Mass:286.19328
Topological Polar Surface Area:34.1
Heavy Atom Count:21
Formal Charge:0
Complexity:546
Isotope Atom Count:0
Defined Atom Stereocenter Count:5
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:2
Feature 3D Ring Count:4
Effective Rotor Count:1.6
Conformer Sampling RMSD:0.6
CID Conformer Count:1
Safety and Handling
Hazard Codes:
Xn
Risk Statements:
R40
Safety Statements:
22-24/25-36
Safety:
An experimental teratogen. Other experimental reproductive effects. Questionable carcinogen with experimental tumorigenic data. When heated to decomposition it emits acrid smoke and irritating fumes.
Specification:

White to Off-White Solid
usageEng:Testosterone precursor and metabolite with androgenic activity. Controlled substance (anabolic sterid)
Safety Statements:22-24/25-36
22:Do not breathe dust
24/25:Avoid contact with skin and eyes
36:Wear suitable protective clothing
Octanol/Water Partition Coefficient:
log Kow = 2.75
Disposal Methods:
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.
Use and Manufacturing
Use and Manufacturing:
Methods of Manufacturing

Preparation: ... Isolation from adrenal cortex.
Usage:
Testosterone precursor and metabolite with androgenic activity. Controlled substance (anabolic sterid)
Biomedical Effects and Toxicity
Therapeutic Uses:
Testosterone precursor and metabolite with androgenic activity. Controlled substance (anabolic sterid)
Biomedical Effects and Toxicity:
It is not known whether anabolic steroids are distributed into breast milk. /Anabolic Steroids/
Environmental Fate and Exposure Potential
Environmental Fate/Exposure Summary:
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 750(SRC), determined from a log Kow of 2.75(2)and a regression-derived equation(3), indicates that androstenedione is expected to have moderate mobility in soil(SRC). Volatilization of androstenedione from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.7X10-8 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Androstenedione is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.8X10-6 mm Hg(SRC), determined from a fragment constant method(5). No biodegradation data were available(SRC, 2005).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 750(SRC), determined from a log Kow of 2.75(2) and a regression-derived equation(3), indicates that androstenedione is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 3.7X10-8 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 26(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). No biodegradation data were available(SRC, 2005).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), androstenedione, which has an estimated vapor pressure of 1.8X10-6 mm Hg at 25 deg C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase androstenedione is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 3.5 hours(SRC), calculated from its rate constant of 1.1X10-10 cu cm/molecule-sec at 25 deg C(SRC) that was derived using a structure estimation method(3). Particulate-phase androstenedione may be removed from the air by wet and dry deposition(SRC). Androstenedione does not absorb light at wavelenghts >290 nm(4) and therefore is not expected to be susceptible to direct photolysis(SRC).
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