7-Oxocholesteryl acetate

Base Information

• Chemical Name: 7-Oxocholesteryl acetate
• CAS No.: 809-51-8
• Molecular Formula: C29H46 O3
• Molecular Weight: 442.682
• European Community (EC) Number: 212-368-1
• NSC Number: 59469
• DSSTox Substance ID: DTXSID701308561
• Nikkaji Number: J193.189J
• Wikidata: Q76009795
• Metabolomics Workbench ID: 34703
• ChEMBL ID: CHEMBL2442166
• Mol file: 809-51-8.mol

Synonyms:7-Oxocholesteryl acetate;809-51-8;7-Oxocholesterol acetate;7-Oxo Cholesterol 3-Acetate;7-Oxocholest-5-en-3-beta-yl acetate;3beta-acetoxy-cholest-5-en-7-one;EINECS 212-368-1;[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-7-oxo-1,2,3,4,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-yl] acetate;Cholest-5-en-7-one, 3.beta.-hydroxy-, acetate;Cholest-5-en-7-one, 3-(acetyloxy)-, (3.beta.)-;Cholest-5-en-7-one, acetate;SCHEMBL4275934;CHEMBL2442166;3beta-Acetoxycholest-5-en-7-one;DTXSID701308561;NSC59469;7-Oxocholest-5-en-3-yl acetate #;LMST01010385;NSC 59469;NSC-59469;Cholest-5-en-7-one, (3.beta.)-;AKOS040734323;5-Cholesten-3.beta.-ol-7-one, acetate;[(3S,8S,9S,10R,13R,14S,17R)-17-[(1R)-1,5-dimethylhexyl]-10,13-dimethyl-7-oxo-1,2,3,4,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-yl] acetate

Chemical Property of 7-Oxocholesteryl acetate

Chemical Property:

• Melting Point: 157-158 °C
• Boiling Point: 526.9±39.0 °C(Predicted)
• Flash Point: 220.9oC
• PSA: 43.37000
• Density: 1.03±0.1 g/cm3(Predicted)
• LogP: 7.13850
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), DMSO (Slightly, Sonicated), Methanol (Slightly, Heated)
• XLogP3: 8.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 442.34469533
• Heavy Atom Count: 32
• Complexity: 766

Purity/Quality:

99%, ^*data from raw suppliers

7-OxoCholesterol3-Acetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CCCC(C)C1CCC2C1(CCC3C2C(=O)C=C4C3(CCC(C4)OC(=O)C)C)C
• Isomeric SMILES: C[C@H](CCCC(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2C(=O)C=C4[C@@]3(CC[C@@H](C4)OC(=O)C)C)C
• Uses: Intermediate in the preparation of various Cholesterol derivatives and metabolites.

Technology Process of 7-Oxocholesteryl acetate

There total 102 articles about 7-Oxocholesteryl acetate 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: 100.0%

cholesterol (57-88-5) + acetic anhydride (108-24-7) → 7-ketocholesteryl acetate (809-51-8)

Guidance literature:

With pyridine; at 37 ℃; Inert atmosphere;

DOI:10.1021/jf506361r

Reference yield: 99.0%

7-Oxocholesterol (566-28-9) + acetic anhydride (108-24-7) → 7-ketocholesteryl acetate (809-51-8)

Guidance literature:

With dmap; triethylamine; In tetrahydrofuran; at 20 ℃; for 20h;

DOI:10.1016/j.bmcl.2013.09.013

Reference yield: 97.0%

Cholesteryl acetate (604-35-3) → 7-ketocholesteryl acetate (809-51-8)

Guidance literature:

With tert.-butylhydroperoxide; [copper(II)(salqu)]; In acetonitrile; at 70 ℃;

DOI:10.1021/jo902637k

upstream raw materials:

cholesteryl acetate

3-β-acetoxycholest-5-one

3β-Acetoxycholest-5-en-7-one oxime

pyridine

Downstream raw materials:

7ξ-phenyl-cholestene-(5)-diol-(3β.7ξ)

cholest-3,5-dien-7-one

(3S,7S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,7-diol

cholest-5-en-3β,7β-diol

Refernces

• 1、 D'yakonov, Vladimir A.,Tuktarova, Regina A.,Dzhemileva, Lilya U.,Ishmukhametova, Svetlana R.,Yunusbaeva, Milyausha M.,Dzhemilev, Usein M.. "Catalytic cyclometallation in steroid chemistry V: Synthesis of hybrid molecules based on steroid oximes and (5Z,9Z)-tetradeca-5,9-dienedioic acid as potential anticancer agents". . p. 14 - 20. Retrieved 2018.
• 2、 Clarke, Ian D.,Hodge, Philip. "Partial separation of enantiomeric 1,2-diols via ketal formation with a polymer-supported chiral ketone". . p. 1395 - 1396. Retrieved 1997.
• 3、 -. "Preparation method of 7-keto-cholesterol acetate". Paragraph 0068-0074. . Retrieved 2021/06/26.
• 4、 Capilato, Joseph N.,Siegler, Maxime A.,Rowshanpour, Rozhin,Dudding, Travis,Lectka, Thomas. "Cooperative Noncovalent Interactions Lead to a Highly Diastereoselective Sulfonyl-Directed Fluorination of Steroidal α,β-Unsaturated Hydrazones". . p. 1300 - 1307. Retrieved 2021/01/09.