GB506515A - Manufacture of oxidation products from sterols or bile acids - Google Patents

Manufacture of oxidation products from sterols or bile acids

Info

Publication number
GB506515A
GB506515A GB32908/37A GB3290837A GB506515A GB 506515 A GB506515 A GB 506515A GB 32908/37 A GB32908/37 A GB 32908/37A GB 3290837 A GB3290837 A GB 3290837A GB 506515 A GB506515 A GB 506515A
Authority
GB
United Kingdom
Prior art keywords
acid
acids
keto
cholestenone
dione
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
GB32908/37A
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.)
BASF Schweiz AG
Original Assignee
Gesellschaft fuer Chemische Industrie in Basel CIBA
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 Gesellschaft fuer Chemische Industrie in Basel CIBA filed Critical Gesellschaft fuer Chemische Industrie in Basel CIBA
Publication of GB506515A publication Critical patent/GB506515A/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
    • C07J3/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by one carbon atom
    • 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

506,515. Sex hormones. SOC. OF CHEMICAL INDUSTRY IN BASLE. Nov. 29, 1937, Nos. 32908, 32909, and 32910. Convention dates, April 28, 1937, June 25, 1937, and Oct. 22, 1937. [Class 2 (iii)] Sterols or bile acids which contain a nuclear carbonyl group are oxidized to give products wholly or partially degraded in the side chain. Nuclear double bands when present may be protected by the addition of halogen or halogen hydride: Oxidizing agents mentioned include chromic acid, permanganate, peroxide, lead tetracetate or by the use of electrolysis. , Suitable starting materials mentioned are cholestenone, sitostenone, cinchone, stigmastadienone, cholestanone, coprostanone, dibromo- or dichloro-cholestenone, chloro- or bromo-cholestanone, 3-keto bile acids such as 3-ketocholenic, cholanic or allo - cholanic acids. Derivatives of the bile acids such as esters or amides or compounds in which the carboxyl group has been exchanged for a carbonyl group. The neutral polycarbonyl compounds may be withdrawn by means of ketone reagents or by the action of concentrated solutions of acid agents such as hydrochloric, hydrobromic, perchloric, sulphuric, phosphoric, and formic acids. The car-boxylic acids are separated in the form of their salts by means of alkalies. The acids may be purified by recrystallization or by conversion into esters or amides. In examples: (1) cholestenone is oxidized in glacial acetic acid solution with chromium trioxide to give #<4>-3-keto-cholenic acid and #<4>-3-keto-etio-cholenic acid as the acidic fraction, and #<4>-androstene-dione and #<4>- pregnene-dione-3 : 20 as the neutral, fraction. The acid fraction is isolated by treatment with caustic soda, and the neutral fraction is separated therefrom by ether extraction, and separated into its constituents by fractional crystallization from hexane ; (2) cholestenone-3 is oxidized and worked up as described in example 1 to give 3-keto-allo-cholanic acid, 3-keto-all-etio-cholanic acid, androstane-dione and allo-pregnane-dione-3 : 20.
GB32908/37A 1937-04-28 1937-11-29 Manufacture of oxidation products from sterols or bile acids Expired GB506515A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH506515X 1937-04-28

Publications (1)

Publication Number Publication Date
GB506515A true GB506515A (en) 1939-05-30

Family

ID=4517186

Family Applications (1)

Application Number Title Priority Date Filing Date
GB32908/37A Expired GB506515A (en) 1937-04-28 1937-11-29 Manufacture of oxidation products from sterols or bile acids

Country Status (1)

Country Link
GB (1) GB506515A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2769822A (en) * 1954-05-26 1956-11-06 Monsanto Chemicals Preparing delta-3-keto-etienic acids

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2769822A (en) * 1954-05-26 1956-11-06 Monsanto Chemicals Preparing delta-3-keto-etienic acids

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