15-Hydroxytestosterone

Base Information

• Chemical Name: 15-Hydroxytestosterone
• CAS No.: 2226-70-2
• Molecular Formula: C19H28 O3
• Molecular Weight: 304.42382
• European Community (EC) Number: 636-577-6
• NSC Number: 60794
• UNII: T193O3374B
• DSSTox Substance ID: DTXSID40176798
• Nikkaji Number: J239.115E
• Wikidata: Q27104281
• Mol file: 2226-70-2.mol

Synonyms:15 alpha-hydroxytestosterone;15-hydroxytestosterone;15-hydroxytestosterone, (15beta,17beta)-isomer;15-hydroxytestosterone, (17 beta)-isomer

Chemical Property of 15-Hydroxytestosterone

Chemical Property:

• Vapor Pressure: 4.56E-11mmHg at 25°C
• Melting Point: 195-197°C
• Boiling Point: 476.2°Cat760mmHg
• Flash Point: 255.9°C
• PSA: 57.53000
• Density: 1.19g/cm³
• LogP: 2.85000
• Storage Temp.: 2-8°C
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 304.20384475
• Heavy Atom Count: 22
• Complexity: 539

Purity/Quality:

98% ^*data from raw suppliers

15ALPHA-HYDROXY TESTOSTERONE 95.00% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 20/21/22-40-63
• Safety Statements: 22-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC(=O)C=C1CCC3C2CCC4(C3C(CC4O)O)C
• Isomeric SMILES: C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3[C@H](C[C@@H]4O)O)C

Technology Process of 15-Hydroxytestosterone

There total 32 articles about 15-Hydroxytestosterone 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: 96.0%

17β-(dimethylthexylsiloxy)-15β-hydroxyandrost-4-en-3-one (174815-61-3) → 15beta-Hydroxytestosterone (2226-70-2,39605-73-7,87936-17-2,117407-11-1)

Guidance literature:

With hydrogenchloride; In methanol; benzene; for 7h;

DOI:10.1016/0039-128X(95)00196-W

Reference yield: 60.0%

testosterone (58-22-0) → 15alpha-Hydroxytestosterone (2226-70-2)

Guidance literature:

With Colletotrichum lini ST-1; at 30 ℃; pH=7; stereoselective reaction; Microbiological reaction; Enzymatic reaction;

DOI:10.1016/j.molcatb.2015.07.003

Reference yield: 55.0%

testosterone (58-22-0) → 15beta-Hydroxytestosterone (2226-70-2,39605-73-7,87936-17-2,117407-11-1) + 2β-hydroxytestosterone (4075-14-3,10390-14-4,39605-71-5)

Guidance literature:

With glucose dehydrogenase; D-glucose; cytochrome P_450BM3 R₄₇L/Y₅₁F/F₈₇A/H₁₇₁L/Q₃₀₇H/N₃₁₉Y mutant; β-nicotinamide adenine dinucleotide phosphate sodium salt; In methanol; aq. phosphate buffer; at 25 ℃; for 2h; pH=7.5; Enzymatic reaction;

DOI:10.1002/chem.201502020

upstream raw materials:

androst-4-ene-3,17-dione

testosterone

15α,17β-Dihydroxy-4-androsten-3-on-bis-(tert.-butyldimethylsilyl)-ether

5-Androsten-3β,15α,17β-triol-15,17-bis-(tert.-butyldimethylsilyl)-ether

Refernces

• 1、 Wu, Yan,Li, Hui,Zhang, Xiao-Mei,Gong, Jin-Song,Rao, Zhi-Ming,Shi, Jin-Song,Zhang, Xiao-Juan,Xu, Zheng-Hong. "Efficient hydroxylation of functionalized steroids by Colletotrichum lini ST-1". . p. 111 - 118. Retrieved 2015.
• 2、 Luirink, Rosa A.,Verkade-Vreeker, Marlies C. A.,Commandeur, Jan N. M.,Geerke, Daan P.. "A Modified Arrhenius Approach to Thermodynamically Study Regioselectivity in Cytochrome P450-Catalyzed Substrate Conversion". . p. 1461 - 1472. Retrieved 2020/03/03.
• 3、 Yildirim, Kudret,Kuru, Ali,Y?lmaz, ?engül. "Biotransformation of testosterone by Cladosporium sphaerospermum". . p. 409 - 413. Retrieved 2019/04/10.