Algestone

Base Information

• Chemical Name: Algestone
• CAS No.: 595-77-7
• Molecular Formula: C21H30O4
• Molecular Weight: 346.467
• European Community (EC) Number: 209-869-2
• UNII: 3JEB53B3WT
• DSSTox Substance ID: DTXSID40208200
• Nikkaji Number: J13.587I
• Wikipedia: Algestone
• Wikidata: Q4724191
• NCI Thesaurus Code: C166678
• Pharos Ligand ID: HH1JUYV15BZ2
• Metabolomics Workbench ID: 35450
• ChEMBL ID: CHEMBL2311120
• Mol file: 595-77-7.mol

Synonyms:16 alpha,17-Dihydroxypregn-4-ene-3,20-dione;Algestone;Alphasone;Dihydroxyprogesterone;Pregn-4-ene-3,20-dione, 16,17-dihydroxy-, (16alpha)-

Chemical Property of Algestone

Chemical Property:

• Appearance/Colour: white or white crystalline powder
• Vapor Pressure: 3.03E-12mmHg at 25°C
• Melting Point: 210-225°C
• Refractive Index: 1.576
• Boiling Point: 503.4 °C at 760 mmHg
• PKA: 12.50±0.70(Predicted)
• Flash Point: 272.4 °C
• PSA: 74.60000
• Density: 1.21 g/cm³
• LogP: 2.80920
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly, Heated)
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 346.21440943
• Heavy Atom Count: 25
• Complexity: 667

Purity/Quality:

99%, ^*data from raw suppliers

Algestone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1(C(CC2C1(CCC3C2CCC4=CC(=O)CCC34C)C)O)O
• Isomeric SMILES: CC(=O)[C@]1([C@@H](C[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C)O)O
• Uses: Algestone is a pregnane steroid, its acetonide is used as anti-inflammatory drug (topical) and combination with enanthate as injectable contraceptive.

Technology Process of Algestone

There total 20 articles about Algestone 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: 88.0%

16-dehydroprogesterone (1096-38-4) → R-16α,17-dihydroxy-pregn-4-ene-3,20-dione (595-77-7)

Guidance literature:

With pyridine; osmium(VIII) oxide; for 2h;

DOI:10.1021/jm00061a001

Reference yield:

3,3-ethane-1,2-diyldioxy-pregna-5,16-dien-20-one (65635-59-8) → R-16α,17-dihydroxy-pregn-4-ene-3,20-dione (595-77-7)

Guidance literature:

3,3-ethane-1,2-diyldioxy-pregna-5,16-dien-20-one; With potassium permanganate; sodium hydrogen sulfate; at -10 ℃; for 1h;

With hydrogenchloride; In water; at -10 ℃; for 10h; Temperature; Reagent/catalyst;

Reference yield:

17-hydroxyprogesterone (68-96-2) → Androstenedione (63-05-8) + Cortexolone (152-58-9) + R-16α,17-dihydroxy-pregn-4-ene-3,20-dione (595-77-7) + C21H30O5

Guidance literature:

With zebrafish P₄₅₀ 17A₁ enzyme; 1,2-dilauroyl-sn-glicero-3-phosphatidylcholine; In aq. phosphate buffer; at 37 ℃; pH=7.4; Reagent/catalyst; Enzymatic reaction;

DOI:10.1074/jbc.RA117.000504

upstream raw materials:

16-dehydroprogesterone

3,3-ethane-1,2-diyldioxy-pregna-5,16-dien-20-one

17-hydroxyprogesterone

17α-hydroperoxyprogesterone

Downstream raw materials:

algestone acetophenide

[3H]-16-alpha-Hydroxyandrostenedione

16α-hydroxytestosterone

16-dehydroprogesterone

Refernces

• 1、 Gonzalez, Eric,Johnson, Kevin M.,Pallan, Pradeep S.,Phan, Thanh T.N.,Zhang, Wei,Lei, Li,Wawrzak, Zdzislaw,Yoshimoto, Francis K.,Egli, Martin,Peter Guengerich. "Inherent steroid 17α,20-lyase activity in defunct cytochrome P450 17A enzymes". . p. 541 - 556. Retrieved 2018/02/14.
• 2、 -. "Method for reducing or preventing transplant rejection in the eye and intraocular implants for use therefor". . . Retrieved 2008/06/13.