(2R,14S,15S,17S)-14,17-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

Base Information

• Chemical Name: (2R,14S,15S,17S)-14,17-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
• CAS No.: 1816-85-9
• Molecular Formula: C19H28 O3
• Molecular Weight: 304.43
• Metabolomics Workbench ID: 42047
• Mol file: 1816-85-9.mol

Synonyms:11beta-Hydroxytestosterone;SCHEMBL15920491;(2R,14S,15S,17S)-14,17-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

Chemical Property of (2R,14S,15S,17S)-14,17-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

Chemical Property:

• Vapor Pressure: 4.56E-11mmHg at 25°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: 2.2
• 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:

99% ^*data from raw suppliers

11BETA-HYDROXYTESTOSTERONE 95.00% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn,T
• Statements: 61-40
• Safety Statements: 53-22-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC(=O)C=C1CCC3C2C(CC4(C3CCC4O)C)O
• Isomeric SMILES: C[C@]12CCC(=O)C=C1CCC3C2[C@H](C[C@]4(C3CC[C@@H]4O)C)O

Technology Process of (2R,14S,15S,17S)-14,17-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

There total 14 articles about (2R,14S,15S,17S)-14,17-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one 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: 65.0%

(8S,9S,10R,11S,13S,14S)-11-Hydroxy-10,13-dimethyl-1,6,7,8,9,10,11,12,13,14,15,16-dodecahydro-2H-cyclopenta[a]phenanthrene-3,17-dione (382-44-5) → 11β-hydroxytestosterone (1816-85-9)

Guidance literature:

With sodium tetrahydroborate; In pyridine; methanol;

DOI:10.1016/0039-128X(94)90027-2

Reference yield: 55.0%

→ 11β-hydroxytestosterone (1816-85-9)

Guidance literature:

With sodium periodate; In tetrahydrofuran; methanol; water; at 20 ℃; for 1h;

Reference yield: 9.38%

11β-hydroxyandrostenedione (599-11-1) → 11β-hydroxytestosterone (1816-85-9)

Guidance literature:

With Beauveria bassiana KCH 1065; In acetone; for 96h; Enzymatic reaction;

DOI:10.1016/j.steroids.2014.01.006

upstream raw materials:

(8S,9S,10R,11S,13S,14S)-11-Hydroxy-10,13-dimethyl-1,6,7,8,9,10,11,12,13,14,15,16-dodecahydro-2H-cyclopenta[a]phenanthrene-3,17-dione

adrenosterone

3-pyrrolidino-androsta-3,5-diene-11,17-dione

HYDROCORTISONE

Downstream raw materials:

(3S,10R,11S,13S,14S,17R)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,11,17-triol

17β-benzoyloxy-androsta-4,9(11)-dien-3-one

androst-4,9⁽¹¹⁾-dien-3,17-dione

(5α)-androst-9(11)-ene-3,17-dione

Refernces

• 1、 Bernstein et al.. "-". . p. 1166,1170,1171. Retrieved 1953.
• 2、 -. "Raw synthesis and mitochondrial function postischemic mitochondria diseases related to the lack or for use in new compd. 11β-hydroxysteroid". Paragraph 0248; 0275. . Retrieved 2016/10/08.
• 3、 Ghasemi, Younes,Rasoul-Amini, Sara,Morowvat, Mohammad Hossein,Ghoshoon, Mohammad Bagher,Raee, Mohammad Javad,Khoubani, Soraya,Negintaji, Narges,Nouri, Fatemeh,Parvizi, Rezvan. "C-20 ketone reduction of hydrocortisone by rice field microalga Chlorella vulgaris MCCS 013". experimental part. p. 824 - 828. Retrieved 2010/08/19.