Synthesis of ergosterol peroxide

Preparation of ergosterol peroxide

Preparation of ergosterol peroxide

Preparation of ergosterol peroxide

A solution of ergosterol (4g) in 95 % alcohol (1200 ml) is warmed to 60°, treated with a little eosin (6 mg), and irradiated in a large beaker as follows: Into the vessel containing this solution dips a narrower beaker inside which burns a 200-W lamp under water; this inner beaker is fitted for inflow and outflow of water. A slow stream of oxygen is passed through the ergosterol solution, until, after about 3 hours, addition of alcoholic digitonin to a portion no longer causes a precipitate, i.e., until all the ergosterol has been consumed. Most of the alcohol is then evaporated in a vacuum; the crystals separating from the residue are isolated and recrystallized from alcohol or acetone to constant m.p. 178°. The yield is 70%.

Ann. Chem., 460, 225 (1928).

InChI

InChI=1S/C28H44O3/c1-18(2)19(3)7-8-20(4)22-9-10-23-25(22,5)13-12-24-26(6)14-11-21(29)17-27(26)15-16-28(23,24)31-30-27/h7-8,15-16,18-24,29H,9-14,17H2,1-6H3/b8-7+/t19-,20+,21-,22+,23+,24+,25+,26+,27+,28-/m0/s1

InChI Key

VXOZCESVZIRHCJ-KGHQQZOUSA-N

Canonical SMILES

CC(C)C(C)C=CC(C)C1CCC2C1(CCC3C24C=CC5(C3(CCC(C5)O)C)OO4)C

Isomeric SMILES

C[C@H](/C=C/[C@H](C)C(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@]24C=C[C@@]5([C@@]3(CC[C@@H](C5)O)C)OO4)C

MeSH Synonyms

3-hydroxy-5,7-epidioxyergosta-6,22-diene, 5,8-epidioxyergosta-6,22-dien-3-ol, ergosterol endoperoxide, ergosterol peroxide, ergosterol-5,8-peroxide

Depositor-Supplied Synonyms

Ergosterol peroxide, Ergosterol endoperoxide, Peroxyergosterol, Ergosterol-5,8-peroxide, Ergosterol 5alpha,8alpha-epidioxide, UNII-UG9TN81TGH, UG9TN81TGH, CHEMBL434750, CHEBI:65858, NSC31324, 5alpha,8alpha-epidioxyergosta-6,22-dien-3beta-ol, 2061-64-5, 5alpha,8alpha-epidioxy-22E-ergosta-6,22-dien-3beta-ol, (22E,24R)-5alpha,8alpha-epidioxyergosta-6,22-dien-3beta-ol, (3beta,5alpha,8alpha,22E)-5,8-epidioxyergosta-6,22-dien-3-ol, (24R)-5alpha,8alpha-epidioxy-24-methylcholesta-6,22-dien-3beta-ol, (3S,5S,8S,9R,10R,13R,14R,17R)-17-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-10,13-dimethyl-1,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-2H-5,8-epidioxycyclopenta[a]phenanthren-3-ol, NSC 31324, Ergosterol 5-alpha,8-alpha-epidioxide, BRN 0096852, Ergosterol 5.alpha.,8.alpha.-epidioxide, 5,8-Epidioxy-5-alpha,8-alpha-ergosta-6,22-dien-3-beta-ol, 5-alpha,8-alpha-ERGOSTA-6,22-DIEN-3-beta-OL, 5,8-EPIDIOXY-, SCHEMBL3281353, BDBM50334064, NSC-31324, PL008688, 5.alpha.,22-dien-3.beta.-ol, 5,8-epidioxy-, 5-19-03-00043 (Beilstein Handbook Reference), 5alpha,8alpha-Epidioxyergosta-6,22-diene-3beta-ol, 5alpha,8alpha-Ergosta-6,22-dien-3beta-ol, 5,8-epidioxy- (8CI), Ergosta-6, 5,8-epidioxy-, (3.beta.,5.alpha.,8.alpha.,22E)-, Ergosta-6,22-dien-3-ol, 5,8-epidioxy-, (3-beta,5-alpha,8-alpha,22E)- (9CI), Ergosta-6,22-dien-3-ol, 5,8-epidioxy-, (3beta,5alpha,8alpha,22E)- (9CI), (1S,2R,5R,6R,9R,10R,13S,15S)-5-[(2R,3E,5R)-5,6-DIMETHYLHEPT-3-EN-2-YL]-6,10-DIMETHYL-16,17-DIOXAPENTACYCLO[13.2.2.0(1),?.0(2),?.0(1)?,(1)?]NONADEC-18-EN-13-OL, (1S,2R,5R,6R,9R,10R,13S,15S)-5-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-6,10-dimethyl-16,17-dioxapentacyclo[13.2.2.0^{1,9}.0^{2,6}.0^{10,15}]nonadec-18-en-13-ol, (3S,5S,8S,9R,10R,13R,14R,17R)-17-((2R,5R,E)-5,6-dimethylhept-3-en-2-yl)-10,13-dimethyl-1,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-2H-5,8-epidioxycyclopenta[a]phenanthren-3-ol

Removed Synonyms

o-(Trifluoromethyl)cinnamic acid, 5,8-epidioxyergosta-6,22-dien-3-ol, CID5351516, 3-hydroxy-5,7-epidioxyergosta-6,22-diene, C036071

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