10,13-dimethyl-17-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate

Base Information

• Chemical Name: 10,13-dimethyl-17-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate
• CAS No.: 53-43-0
• Molecular Formula: C19H28O2
• Molecular Weight: 288.43
• Hs Code.: 29372900
• NSC Number: 755876
• ChEMBL ID: CHEMBL3039094
• Mol file: 53-43-0.mol

Synonyms:Spectrum_001089;Spectrum2_001130;Spectrum3_001280;Spectrum4_000244;Spectrum5_000703;BSPBio_002880;KBioGR_000648;KBioSS_001569;SPECTRUM270029;SCHEMBL370342;SPBio_000999;CHEMBL3039094;KBio2_001569;KBio2_004137;KBio2_006705;KBio3_002380;Dehydro Epiandrosterone 3-Acetate;HMS1922F18;Pharmakon1600-00270029;CCG-40086;NSC755876;NSC-755876;NCGC00178411-01;SBI-0207089.P001;AB01563185_01;AA-504/07224052;10,13-dimethyl-17-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate

Chemical Property of 10,13-dimethyl-17-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate

Chemical Property:

• Appearance/Colour: white fine crystalline powder
• Vapor Pressure: 4.54E-09mmHg at 25°C
• Melting Point: 149-151 °C(lit.)
• Refractive Index: 1.56
• Boiling Point: 426.7 °C at 760 mmHg
• PKA: 15.02±0.60(Predicted)
• Flash Point: 182.1 °C
• PSA: 37.30000
• Density: 1.12 g/cm³
• LogP: 3.87920
• Storage Temp.: Hormones
• Solubility.: insoluble in H2O; ≥13.7 mg/mL in DMSO; ≥58.6 mg/mL in ETOH
• Water Solubility.: 21.8mg/L(23.5 oC)
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 330.21949481
• Heavy Atom Count: 24
• Complexity: 606

Purity/Quality:

99% ^*data from raw suppliers

DHEA ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,T,F
• Statements: 36/37/38-39/23/24/25-23/24/25-11
• Safety Statements: 26-36-24/25-45-36/37-16-7

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)OC1CCC2(C3CCC4(C(C3CC=C2C1)CCC4=O)C)C
• Isomeric SMILES: CC(=O)O[C@H]1CC[C@@]2(C3CC[C@]4(C(C3CC=C2C1)CCC4=O)C)C
• Bone Loss Prevention: Subsequent trials have examined prasterone as a treatment to limit bone loss in women with SLE.; Studies have shown that prasterone can increase bone mineral density in patients who have been taking glucocorticoids for six months or longer, compared to placebo.
• Investigation for Systemic Lupus Erythematosus (SLE): Prasterone, a synthetic dehydroepiandrosterone product, has been investigated for use in women with SLE who are taking glucocorticoids. Initial trials focused on improving disease activity and symptoms in women with mild to moderate SLE, but the FDA did not approve prasterone's labeling for these indications.
• Potential Drug Interactions: Prasterone may interact with 5-alpha reductase inhibitors and exhibit additive or antagonistic effects with androgens, estrogens, oral contraceptives, and progestins.
• Dosage: In clinical trials, oral prasterone dosages of 100鈥?200 mg/day were administered, resulting in supraphysiological hormone levels.
• Intravaginal Use: Intravaginal prasterone, marketed as Intrarosa庐, is approved for the treatment of vulvar and vaginal atrophy (VVA) in postmenopausal women with moderate to severe symptoms.; Clinical trials have demonstrated that intravaginal prasterone significantly improves signs and symptoms of VVA, including dyspareunia, compared to placebo.; Prasterone is generally well-tolerated, with the most common adverse event being application site discharge.; Serum concentrations of estrogenic and androgenic metabolites of DHEA increased during treatment with intravaginal prasterone but remained within normal postmenopausal ranges.

Technology Process of 10,13-dimethyl-17-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate

There total 141 articles about 10,13-dimethyl-17-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.54%

prasterone acetate (853-23-6) → dehydroepiandrosterone (53-43-0)

Guidance literature:

With sodium hydroxide; In methanol;

DOI:10.3109/14756366.2015.1070843

Reference yield: 96.0%

(1aR,3aR,3bS,5aS,8aS,8bR,10aR)-10-Hydroxy-3a,5a-dimethyl-tetradecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-one (1028084-93-6) → dehydroepiandrosterone (53-43-0)

Guidance literature:

With Me₃SiN=CMe⁽¹⁺⁾*BF₄^(1-); water; In acetonitrile;

DOI:10.1016/S0040-4039(00)99942-8

Reference yield: 96.0%

Acetic acid (1aR,3aR,3bS,5aS,8aS,8bR,10aR)-3a,5a-dimethyl-6-oxo-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-10-yl ester (24357-31-1,58691-91-1) → dehydroepiandrosterone (53-43-0)

Guidance literature:

With Me₃SiN=CMe⁽¹⁺⁾*BF₄^(1-); water; In acetonitrile;

DOI:10.1016/S0040-4039(00)99942-8

upstream raw materials:

cholesterol

β-sitosterol

dehydroepiandrosterone sulfate

5-androstenedione

Downstream raw materials:

5-androstenediol

androst-5-ene-3β,17α-diol

17βH-pregn-5-ene-3β,17-diol

prasterone acetate

Refernces

• 1、 Miescher,Fischer. "". . p. 158,160. Retrieved 1938.
• 2、 DINGEMANSE,HUIS IN T VELD,HARTOGH-KATZ. "Isolation of new androstenol-3()-on-17 from the urine of a patient with". . p. 848 - 848. Retrieved 1948.
• 3、 Belostotskii, Anatoly M.,Hassner, Alfred. "Etherification of Hydroxystereoids via Triflates". . p. 5075 - 5076. Retrieved 1994.
• 4、 Han, Bing,He, Yi-Heng,Pan, Jia-Hao,Wang, Yuan-Rui,Yu, Wei,Zhang, Jian-Wu. "Deconstructive Oxygenation of Unstrained Cycloalkanamines". supporting information. p. 3900 - 3904. Retrieved 2020/02/11.
• 5、 -. "Method for preparing 4-androstenedione from dehydroepiandrosterone acetate". Paragraph 0026; 0027; 0028; 0032-0034; 0038-0040. . Retrieved 2019/07/04.