GB537030A - Sterol compounds and process for their preparation - Google Patents

Sterol compounds and process for their preparation

Info

Publication number
GB537030A
GB537030A GB24999/39A GB2499939A GB537030A GB 537030 A GB537030 A GB 537030A GB 24999/39 A GB24999/39 A GB 24999/39A GB 2499939 A GB2499939 A GB 2499939A GB 537030 A GB537030 A GB 537030A
Authority
GB
United Kingdom
Prior art keywords
acid
hydroxy
ester
compound
chromic
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB24999/39A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Publication of GB537030A publication Critical patent/GB537030A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J75/00—Processes for the preparation of steroids in general

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Steroid Compounds (AREA)

Abstract

537,030. Sterol derivatives: DU PONT DE NEMOURS & CO., E. I. Aug. 31, 1939, No. 24999. Convention date, Sept. 2, 1938. [Class 2 (iii)] 7-Dehydro compounds of sterols are prepared by oxidizing an aromatic ester of a sterol having a hydroxy group in the 3-position and a double bond in the 5:6-position, reducing the 7-oxo-ester so produced to the corresponding 7-hydroxy-3-mono-ester, and esterifying this compound to a di-ester. The compounds are stated to be of great value as provitamines. The preferred acid to be used for the esterification is benzoic acid, but substituted benzoic acids may also be used. Substituents mentioned include halogens, alkoxy, normal and branched-chain alkyl group and aryl group. Naphthalenic acid may also be used. Oxidizing agents include chromic acid and chromic anhydride, and selenium dioxide, either alone or in the presence of iodine. Reducing agents include aluminium alcoholates such as methylate ethylate, propylate isobutylate and isoamylate. The corresponding alcoholates of other earth metals such as zirconium and magnesium may also be used either alone or in admixture with solvents such as hydrocarbons and alcohols. The esterification of the 7-hydroxy group may be carried out by the usual agents such as acid chlorides or anhydrides preferably in the presence of a base such as pyridine, piperidine piperazine aniline, morphaline and aliphatic amines. In examples (1) cholesterol benzoate is oxidized with chromic acid in glacial acetic acid solution and the 7-oxocompound so produced is reduced with aluminium isopropylate to the corresponding 7- hydroxy compound and this converted into the dibenzoate of 3:7-dihydroxy cholestene ; (2) Cholesterol benzoate is oxidized with chromic anhydride in glacial acetic acid solution and the 7-oxo-compound reduced to the corresponding 7-hydroxy compound by means of aluminium isopropylate in isopropyl alcohol solution. The 7-hydroxy-cholesterol-3-monobenzoate is then esterified with acetic anhydride in the presence of pyridine. Specification 454,260 is referred to.
GB24999/39A 1938-09-02 1939-08-31 Sterol compounds and process for their preparation Expired GB537030A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US537030XA 1938-09-02 1938-09-02

Publications (1)

Publication Number Publication Date
GB537030A true GB537030A (en) 1941-06-05

Family

ID=21985975

Family Applications (1)

Application Number Title Priority Date Filing Date
GB24999/39A Expired GB537030A (en) 1938-09-02 1939-08-31 Sterol compounds and process for their preparation

Country Status (1)

Country Link
GB (1) GB537030A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102030794A (en) * 2010-12-01 2011-04-27 安徽丰原发酵技术工程研究有限公司 Method for preparing 7-dehydrocholesterol

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102030794A (en) * 2010-12-01 2011-04-27 安徽丰原发酵技术工程研究有限公司 Method for preparing 7-dehydrocholesterol

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