16alpha-Hydroxyprogesterone

Base Information

• Chemical Name: 16alpha-Hydroxyprogesterone
• CAS No.: 438-07-3
• Molecular Formula: C21H30 O3
• Molecular Weight: 330.467
• NSC Number: 523249,53910
• UNII: Y7JT9A46EO
• DSSTox Substance ID: DTXSID001017030
• Nikkaji Number: J145.723C
• Wikipedia: 16%CE%B1-Hydroxyprogesterone
• Wikidata: Q27098246
• Metabolomics Workbench ID: 35461
• ChEMBL ID: CHEMBL1908005
• Mol file: 438-07-3.mol

Synonyms:16alpha-Hydroxyprogesterone;438-07-3;16alpha-Hydroxy Progesterone;16.alpha.-Hydroxyprogesterone;16-ALPHA-HYDROXYPROGESTERONE;NSC 53910;UNII-Y7JT9A46EO;NSC 523249;16alpha-hydroxyprogesterone1;Y7JT9A46EO;16alpha-Hydroxypregn-4-ene-3,20-dione;CHEBI:15826;NSC-53910;NSC-523249;(8S,9S,10R,13S,14S,16R,17R)-17-acetyl-16-hydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one;Pregn-4-ene-3,20-dione, 16.alpha.-hydroxy-;Pregn-4-ene-3,20-dione, 16-hydroxy-, (16.alpha.)-;16a-hydroxyprogesterone;Pregn-4-ene-3, 16.alpha.-hydroxy-;Pregn-4-ene-3, 16-hydroxy-, (16.alpha.)-;16|A-Hydroxy Progesterone;SCHEMBL638332;CHEMBL1908005;DTXSID001017030;NSC53910;LMST02030182;NSC523249;16a-hydroxy-4-pregnene-3,20-dione;16.ALPHA.-HYDROXY-4-PREGNENE-3,20-DIONE;16-Hydroxypregn-4-ene-3,20-dione-, (16.alpha.)-;Q27098246;16.ALPHA.-HYDROXY-.DELTA.4-PREGNENE-3,20-DIONE

Chemical Property of 16alpha-Hydroxyprogesterone

Chemical Property:

• Vapor Pressure: 1.51E-11mmHg at 25°C
• Melting Point: 225-226 °C
• Boiling Point: 487.4°Cat760mmHg
• PKA: 14.56±0.70(Predicted)
• Flash Point: 262.7°C
• PSA: 54.37000
• Density: 1.15g/cm³
• LogP: 3.69430
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly, Heated, Sonicated)
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 330.21949481
• Heavy Atom Count: 24
• Complexity: 621

Purity/Quality:

98%min ^*data from raw suppliers

16α-HydroxyProgesterone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=O)C1C(CC2C1(CCC3C2CCC4=CC(=O)CCC34C)C)O
• Isomeric SMILES: CC(=O)[C@H]1[C@@H](C[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C)O
• Uses: 16α-Hydroxyprrogesterone is a hydroxylated metabolite of Progesterone (P755900). 16α-Hydroxyprogesterone binds to human progesterone receptors hPR-A and hPR-B and act as an agonist for both receptors.

Technology Process of 16alpha-Hydroxyprogesterone

There total 7 articles about 16alpha-Hydroxyprogesterone 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: 5.6%

Progesterone (57-83-0) → 21-Hydroxyprogesterone (64-85-7) + 16α-hydroxyprogesterone (438-07-3) + 6β-hydroxypregn-4-en-3,20-dione (604-19-3) + 2beta-Hydroxyprogesterone (604-29-5,604-28-4,123287-83-2)

Guidance literature:

With Chlorella pyrenoidose T₃₄₃; 4,4'-butylidenebis(6-tert-butyl-m-cresol); at 20 ℃; for 360h; Further byproducts given; illumination;

DOI:10.1016/0031-9422(95)00996-5

Reference yield:

Progesterone (57-83-0) → 14-hydroxy-4-pregnene-3,20-dione (16031-66-6) + 21-Hydroxyprogesterone (64-85-7) + 16α-hydroxyprogesterone (438-07-3) + 9α-hydroxypregn-4-ene-3,20-dione (15981-54-1) + 6β-hydroxypregn-4-en-3,20-dione (604-19-3) + 2beta-Hydroxyprogesterone (604-29-5,604-28-4,123287-83-2)

Guidance literature:

In 1,4-dioxane; for 720h; Product distribution; Ambient temperature; axenic culture of Chlorella emersonii C₂₁₁-8H in BBM during the exponential phase of growth of the strain; also with 3percent NaCl; also at pH 3.5;

DOI:10.1016/0031-9422(95)00786-5

Reference yield:

Progesterone (57-83-0) → 21-Hydroxyprogesterone (64-85-7) + Cortexolone (152-58-9) + 16β-hydroxyprogesterone (17779-71-4,438-07-3,2781-78-4,14264-44-9) + 2beta-Hydroxyprogesterone (604-29-5,604-28-4,123287-83-2)

Guidance literature:

With Bacillus megaterium cytochrome P₄₅₀ BM₃ monooxygenase (R₄₇Y/T₄₉F/V₇₈T/A₈₂F/F₇₈A)-expressing cells; at 25 ℃; for 24h; diastereoselective reaction;

DOI:10.1038/nchem.1113

upstream raw materials:

Progesterone

acetic acid

methylammonium carbonate

16α,17α-epoxyprogesterone

Downstream raw materials:

11α,16α-dihydroxyprogesterone

16-dehydroprogesterone

Refernces

• 1、 Geier, Martina,Braun, Andreas,Fladischer, Patrik,Stepniak, Piotr,Rudroff, Florian,Hametner, Christian,Mihovilovic, Marko D.,Glieder, Anton. "Double site saturation mutagenesis of the human cytochrome P450 2D6 results in regioselective steroid hydroxylation". . p. 3094 - 3108. Retrieved 2013/07/26.
• 2、 Pollio, Antonino,Pinto, Gabriele,Della Greca, Marina,Fiorentino, Antonio,Previtera, Lucio. "Biotransformations of progesterone by Chlorella spp.". . p. 685 - 688. Retrieved 2007/10/03.