4-Androstene-3,17-dione (CAS 117598-81-9) — formula C19H26O2, molecular weight 286.4.
| CAS Number | 117598-81-9 |
|---|---|
| Molecular Formula | C19H26O2 |
| Molecular Weight | 286.4 |
| Melting Point | 158 |
| LogP | 2.75 |
| Applications | Uses: Anabolic steroids, including 4-androstenedione (DEA Code Number: 4000) are Schedule III controlled substances., Schedule III Controlled Substance: (A) The drug or other substance has a potential for abuse less than the drugs or other substances in schedules I and II. (B) The drug or other substance has a currently accepted medical use in treatment in the United States. (C) Abuse of the drug or other substance may lead to moderate or low physical dependence or high psychological dependence., MEDICATION, Use Classification: Pharmaceuticals, Methods of Manufacturing: Androstanes, ie, pregnanes without the C-17 side chain, are important intermediates in the synthesis of progestins. One approach to the synthesis of androstanes is simply side-chain degradation of pregnanes. 16-Dehydropregnenolone acetate, an intermediate in the diosgenin to progesterone scheme, may be converted to androstenedione. 16-Dehydropregnenolone acetate is converted to its oxime. Treatment of the oxime with a Lewis acid induces a Beckmann rearrangement providing an enamide, hydrolysis and Oppenauer oxidation of the resulting alcohol forms androstenedione., Many microorganisms have been found that partially or completely degrade cholesterol. Enzyme inhibitors or modified microbial agents have been used to control these degradations in order to form commercially useful steroidal intermediates. When mixed with metal ions (Ni, Co, Pb, or Se), chelating agents, or 8-hydroxyquinoline, various mycobacteria have been demonstrated to produce significant quantities of androsta-1, 4-diene-3, 17-dione from cholesterol. In a commercialized process for the microbial conversion of cholesterol to androsta-1, 17-dione, the 9a-hydroxylation step was inhibited by a, a-dipyridyl. In another commercial process, uv-generated mutations of Mycobacterium sp. have been used to produce androsta-4-ene-3, 17-dione and androsta-1, 17-dione from beta-sitosterol., Biotransformation of phytosterol (PS) by a newly isolated mutant Mycobacterium neoaurum ZJUVN-08 to produce androstenedione has been investigated in this paper. The parameters of the biotransformation process were optimized using fractional factorial design and response surface methodology. Androstenedione was the sole product in the fermentation broth catalyzed by the mutant M. neoaurum ZJUVN-08 strain. Results showed that molar ratio of hydroxypropyl-beta-cyclodextrin (HP-beta-CD) to PS and substrate concentrations were the two most significant factors affecting androstenedione production. By analyzing the statistical model of three-dimensional surface plot, the optimal process conditions were observed at 0.1 g, L inducer, pH 7.0, molar ratio of HP-beta-CD to PS 1.92:1, 8.98 g, L PS, and at 120 hr of incubation time. Under these conditions, the maximum androstenedione yield was 5.96 g, L and nearly the same with the non-optimized (5.99 g, L), while the maximum PS conversion rate was 94.69% which increased by 10.66% compared with the non-optimized (84.03%). The predicted optimum conditions from the mathematical model were in agreement with the verification experimental results. It is considered that response surface methodology was a powerful and efficient method to optimize the parameters of PS biotransformation process., General Manufacturing Information: Androstenedione (Anabolic steroids (DEA Code Number 4000)) is a Schedule III controlled substance, Synthetic analogs of androgens have been used by professional, as well as amateur, athletes for possible performance enhancement., Anabolic Steroid Control Act of 2004. Public Law 108-358 (October 22, 2004)... includes, androstenedione, as an anabolic steroid |
Documented applications: Uses: Anabolic steroids, including 4-androstenedione (DEA Code Number: 4000) are Schedule III controlled substances., Schedule III Controlled Substance: (A) The drug or other substance has a potential for abuse less than the drugs or other substances in schedules I and II. (B) The drug or other substance has a currently accepted medical use in treatment in the United States. (C) Abuse of the drug or other substance may lead to moderate or low physical dependence or high psychological dependence., MEDICATION, Use Classification: Pharmaceuticals, Methods of Manufacturing: Androstanes, ie, pregnanes without the C-17 side chain, are important intermediates in the synthesis of progestins. One approach to the synthesis of androstanes is simply side-chain degradation of pregnanes. 16-Dehydropregnenolone acetate, an intermediate in the diosgenin to progesterone scheme, may be converted to androstenedione. 16-Dehydropregnenolone acetate is converted to its oxime. Treatment of the oxime with a Lewis acid induces a Beckmann rearrangement providing an enamide, hydrolysis and Oppenauer oxidation of the resulting alcohol forms androstenedione., Many microorganisms have been found that partially or completely degrade cholesterol. Enzyme inhibitors or modified microbial agents have been used to control these degradations in order to form commercially useful steroidal intermediates. When mixed with metal ions (Ni, Co, Pb, or Se), chelating agents, or 8-hydroxyquinoline, various mycobacteria have been demonstrated to produce significant quantities of androsta-1, 4-diene-3, 17-dione from cholesterol. In a commercialized process for the microbial conversion of cholesterol to androsta-1, 17-dione, the 9a-hydroxylation step was inhibited by a, a-dipyridyl. In another commercial process, uv-generated mutations of Mycobacterium sp. have been used to produce androsta-4-ene-3, 17-dione and androsta-1, 17-dione from beta-sitosterol., Biotransformation of phytosterol (PS) by a newly isolated mutant Mycobacterium neoaurum ZJUVN-08 to produce androstenedione has been investigated in this paper. The parameters of the biotransformation process were optimized using fractional factorial design and response surface methodology. Androstenedione was the sole product in the fermentation broth catalyzed by the mutant M. neoaurum ZJUVN-08 strain. Results showed that molar ratio of hydroxypropyl-beta-cyclodextrin (HP-beta-CD) to PS and substrate concentrations were the two most significant factors affecting androstenedione production. By analyzing the statistical model of three-dimensional surface plot, the optimal process conditions were observed at 0.1 g, L inducer, pH 7.0, molar ratio of HP-beta-CD to PS 1.92:1, 8.98 g, L PS, and at 120 hr of incubation time. Under these conditions, the maximum androstenedione yield was 5.96 g, L and nearly the same with the non-optimized (5.99 g, L), while the maximum PS conversion rate was 94.69% which increased by 10.66% compared with the non-optimized (84.03%). The predicted optimum conditions from the mathematical model were in agreement with the verification experimental results. It is considered that response surface methodology was a powerful and efficient method to optimize the parameters of PS biotransformation process., General Manufacturing Information: Androstenedione (Anabolic steroids (DEA Code Number 4000)) is a Schedule III controlled substance, Synthetic analogs of androgens have been used by professional, as well as amateur, athletes for possible performance enhancement., Anabolic Steroid Control Act of 2004. Public Law 108-358 (October 22, 2004)... includes, androstenedione, as an anabolic steroid.
4-Androstene-3,17-dione is a chemical compound with CAS registry number 117598-81-9 and molecular formula C19H26O2 (molecular weight 286.4).
CAS number: 117598-81-9
Its molecular formula C19H26O2 comprises 19 C, 26 H, 2 O atoms.
Also known as: 4-Androstene-3,17-dione · 4-雄烯-3,17-二酮
The CAS registry number of 4-Androstene-3,17-dione is 117598-81-9.
Molecular formula C19H26O2, molecular weight 286.4.
It is also registered under: 4-Androstene-3,17-dione, 4-雄烯-3,17-二酮.
Recorded applications: Uses: Anabolic steroids, including 4-androstenedione (DEA Code Number: 4000) are Schedule III controlled substances., Schedule III Controlled Substance: (A) The drug or other substance has a potential for abuse less than the drugs or other substances in schedules I and II. (B) The drug or other substance has a currently accepted medical use in treatment in the United States. (C) Abuse of the drug or other substance may lead to moderate or low physical dependence or high psychological dependence., MEDICATION, Use Classification: Pharmaceuticals, Methods of Manufacturing: Androstanes, ie, pregnanes without the C-17 side chain, are important intermediates in the synthesis of progestins. One approach to the synthesis of androstanes is simply side-chain degradation of pregnanes. 16-Dehydropregnenolone acetate, an intermediate in the diosgenin to progesterone scheme, may be converted to androstenedione. 16-Dehydropregnenolone acetate is converted to its oxime. Treatment of the oxime with a Lewis acid induces a Beckmann rearrangement providing an enamide, hydrolysis and Oppenauer oxidation of the resulting alcohol forms androstenedione., Many microorganisms have been found that partially or completely degrade cholesterol. Enzyme inhibitors or modified microbial agents have been used to control these degradations in order to form commercially useful steroidal intermediates. When mixed with metal ions (Ni, Co, Pb, or Se), chelating agents, or 8-hydroxyquinoline, various mycobacteria have been demonstrated to produce significant quantities of androsta-1, 4-diene-3, 17-dione from cholesterol. In a commercialized process for the microbial conversion of cholesterol to androsta-1, 17-dione, the 9a-hydroxylation step was inhibited by a, a-dipyridyl. In another commercial process, uv-generated mutations of Mycobacterium sp. have been used to produce androsta-4-ene-3, 17-dione and androsta-1, 17-dione from beta-sitosterol., Biotransformation of phytosterol (PS) by a newly isolated mutant Mycobacterium neoaurum ZJUVN-08 to produce androstenedione has been investigated in this paper. The parameters of the biotransformation process were optimized using fractional factorial design and response surface methodology. Androstenedione was the sole product in the fermentation broth catalyzed by the mutant M. neoaurum ZJUVN-08 strain. Results showed that molar ratio of hydroxypropyl-beta-cyclodextrin (HP-beta-CD) to PS and substrate concentrations were the two most significant factors affecting androstenedione production. By analyzing the statistical model of three-dimensional surface plot, the optimal process conditions were observed at 0.1 g, L inducer, pH 7.0, molar ratio of HP-beta-CD to PS 1.92:1, 8.98 g, L PS, and at 120 hr of incubation time. Under these conditions, the maximum androstenedione yield was 5.96 g, L and nearly the same with the non-optimized (5.99 g, L), while the maximum PS conversion rate was 94.69% which increased by 10.66% compared with the non-optimized (84.03%). The predicted optimum conditions from the mathematical model were in agreement with the verification experimental results. It is considered that response surface methodology was a powerful and efficient method to optimize the parameters of PS biotransformation process., General Manufacturing Information: Androstenedione (Anabolic steroids (DEA Code Number 4000)) is a Schedule III controlled substance, Synthetic analogs of androgens have been used by professional, as well as amateur, athletes for possible performance enhancement., Anabolic Steroid Control Act of 2004. Public Law 108-358 (October 22, 2004)... includes, androstenedione, as an anabolic steroid.
Independent reference data for 4-Androstene-3,17-dione (CAS 117598-81-9), compiled from public chemistry databases.
| CAS Registry Number | 117598-81-9 |
|---|---|
| PubChem CID | 6128 |
| Molecular formula | C19H26O2 |
| IUPAC name | (8R,9S,10R,13S,14S)-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17-dione |
| UNII (FDA) | 409J2J96VR |
| Molecular Weight | 286.4 |
|---|---|
| XLogP3 | 2.7 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 0 |
| Exact Mass | 286.193280068 |
| Monoisotopic Mass | 286.193280068 |
| Topological Polar Surface Area | 34.1 |
| Heavy Atom Count | 21 |
| Melting Point | 158 |
|---|---|
| Melting Point | 170 - 173 °C |
| Solubility | 57.8 |
| Solubility | 0.0578 mg/mL |
| LogP | 2.75 |
| LogP | log Kow = 2.75 |
| Collision Cross Section | 182.8 Ų [M+H]+ |
| Collision Cross Section | 203.4 Ų [M+Na]+ |
| Collision Cross Section | 172.5 Ų [M+H]+ |
androstenedione; Androst-4-ene-3,17-dione; 4-Androstene-3,17-dione; 63-05-8; 4-Androstenedione; Androtex; delta-4-Androstenedione; 3,17-Dioxoandrost-4-ene; SKF 2170; delta-4-Androsten-3,17-dione; DTXSID8024523; NSC 9563; delta(sup 4)-Androstene-3,17-dione; NSC-9563; (8R,9S,10R,13S,14S)-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17-dione; CHEBI:16422
| Reported hazard statements | H302 (97.9%), H351 (95.8%), H360 (93.8%), H362 (95.8%) |
|---|
H302 (97.9%): Harmful if swallowed [Warning Acute toxicity, oral]
H351 (95.8%): Suspected of causing cancer [Warning Carcinogenicity]
4-Androstene-3,17-dione · CAS 117598-81-9 · C19H26O2. UNII 409J2J96VR. Melting Point: 158; Melting Point: 170 - 173 °C; Solubility: 57.8.
Source: PubChem / Wikidata; the batch COA governs where values differ.
Supplier: Jinan Shenghe Chemical Co., Ltd.
中文页面: 4-雄烯-3,17-二酮