11alpha-Hydroxyandrosta-1,4-diene-3,17-dione

Base Information

• Chemical Name: 11alpha-Hydroxyandrosta-1,4-diene-3,17-dione
• CAS No.: 7801-18-5
• Molecular Formula: C₁₉H₂₄O₃
• Molecular Weight: 300.398
• European Community (EC) Number: 232-256-6
• NSC Number: 49006
• UNII: 3EYK2B885X
• DSSTox Substance ID: DTXSID801277238
• Nikkaji Number: J268.701A
• Wikidata: Q27115841
• Mol file: 7801-18-5.mol

Synonyms:11-HADD;11-hydroxy-1,4-androstadiene-3,17-dione;11-hydroxy-1,4-androstadiene-3,17-dione, (11-beta)-isomer

Chemical Property of 11alpha-Hydroxyandrosta-1,4-diene-3,17-dione

Chemical Property:

• Melting Point: 160 - 162 °C (methanol)
• Boiling Point: 479.0±45.0 °C(Predicted)
• PKA: 14.39±0.60(Predicted)
• Flash Point: 257.6oC
• PSA: 54.37000
• Density: 1.21±0.1 g/cm3(Predicted)
• LogP: 2.83420
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 300.17254462
• Heavy Atom Count: 22
• Complexity: 616

Purity/Quality:

99% ^*data from raw suppliers

11α-Hydroxyandrosta-1,4-dien-3,17-dione ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CC(C3C(C1CCC2=O)CCC4=CC(=O)C=CC34C)O
• Isomeric SMILES: C[C@]12C[C@H]([C@H]3[C@H]([C@@H]1CCC2=O)CCC4=CC(=O)C=C[C@]34C)O
• Uses: 11α-Hydroxyandrosta-1,4-dien-3,17-dione is a metabolite of Testosterone (T155000), a principal hormone in the testes. Also used in the preparation of anti-osteoporosis active compounds.

Technology Process of 11alpha-Hydroxyandrosta-1,4-diene-3,17-dione

There total 6 articles about 11alpha-Hydroxyandrosta-1,4-diene-3,17-dione 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: 42.6%

Androsta-1,4-diene-3,17-dione (897-06-3) → (8S,9S,10R,11S,13S,14S)-11-Hydroxy-10,13-dimethyl-7,8,9,10,11,12,13,14,15,16-decahydro-6H-cyclopenta[a]phenanthrene-3,17-dione (898-84-0) + 7α-hydroxyandrosta-1,4-diene-3,17-dione (21661-22-3) + 11α-hydroxy-androsta-1,4-diene-3,17-dione (898-84-0,96893-16-2,7801-18-5)

Guidance literature:

With phosphate buffer; D-glucose; tieghemella hyalospora; calcium chloride; In methanol; at 28 ℃; for 24h;

DOI:10.1007/BF00758303

Reference yield: 1.5%

Androsta-1,4-diene-3,17-dione (897-06-3) → 11α-hydroxy-androsta-1,4-diene-3,17-dione (898-84-0,96893-16-2,7801-18-5) + 1β,2β-Epoxy-4-androstene-3,17-dione (97455-05-5)

Guidance literature:

for 72h; Rhizopus arrhizus ATCC 11145;

Reference yield:

→ 11β-hydroxy-1,4-androstene-3,17-dione (898-84-0,7801-18-5,96893-16-2)

Guidance literature:

11β,17α,21-Trihydroxy-pregna-1,4-dien-3,20-dion;

upstream raw materials:

Androsta-1,4-diene-3,17-dione

Downstream raw materials:

17β-[Boc-Asp(OBzl)-Ser(Bzl)-amido]-11α-hydroxyandrost-1,4-diene-3-one

17β-[Boc-Asp(OBzl)-Val-amido]-11α-hydroxyandrost-1,4-diene-3-one

C₄₄H₅₅N₃O₈

17β-[Boc-Arg(Tos)-Gly-Asp(OBzl)-Ser(Bzl)-amido]-11α-hydroxyandrost-1,4-diene-3-one

Refernces

• 1、 Holland, Herbert L.,Chenchaiah, P. Chinna. "Microbial hydroxylation of steroids. 11. Hydroxylation of A-nor-, B-homo-Δ1-, and Δ1-testosterone acetates by Rhizopus arrhizus". . p. 1127 - 1131. Retrieved 2007/10/02.