GB813317A - New steroid compounds and method for the transformation of epoxy-ketones by the action of fermenting yeast - Google Patents
New steroid compounds and method for the transformation of epoxy-ketones by the action of fermenting yeastInfo
- Publication number
- GB813317A GB813317A GB2456/56A GB245656A GB813317A GB 813317 A GB813317 A GB 813317A GB 2456/56 A GB2456/56 A GB 2456/56A GB 245656 A GB245656 A GB 245656A GB 813317 A GB813317 A GB 813317A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- epoxy
- pregnadiene
- diol
- triol
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P33/00—Preparation of steroids
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/02—Oxygen as only ring hetero atoms
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
The invention comprises pregnan-3,4,5-triol-20 - one, 17b - methyl - 18 - nor - D 4,13 - 17a -pregnadiene-16a , 20-diol-3-one, its diacetate, 17b - methyl - 18 - nor - D 5,13 - 17a - pregnadiene - 3b ,16a ,20 - triol, its triacetate, 17b -methyl - 18 - nor - D 13 - 17a - pregnene - 16a , 20-diol-3-one and 17b -methyl-18-nor- D 5,13-17a -pregnadiene - 3b ,16a ,20,21 - tetrol 21 - acetate, together with processes for converting an a ,b -epoxyketone to a polyhydric compound having hydroxyl groups attached to the a - and b -carbon atoms and in which the carbonyl group is reduced to a secondary hydroxyl group, and for converting an a -b -epoxy-ketone of partial formula: <FORM:0813317/IV (b)/1> (where R is alkyl containing not more than four carbon atoms or an acylated hydroxyalkyl group) especially a 16 : 17 - oxido - 20 - keto steroid, into the corresponding molecularly rearranged unsaturated diol of partial formula: <FORM:0813317/IV (b)/2> by the action of fermenting yeast in each case. In examples: (1) benzalacetophenone epoxide in ethanol is added to fermenting yeast and the mixture left for 10 days at 32 DEG C., adding more yeast at 48 hour intervals; 1,3-diphenylglycerol is then isolated by extraction with ethyl acetate; (2) 4,5-epoxy-pregnan-3,20-dione is treated with yeast as in (1), giving pregnane-3,4,5-triol-20-one; similarly (3) 16,17- epoxy - progesterone gives 17b - methyl - 18 - nor - D 4,13 - 17a - pregnadiene - 16a ,20 - diol-3-one, characterized as its diacetate; (4) 16,17-epoxy - D 5 - pregnen - 3b - ol - 20 - one yields 17b - methyl - 18 - nor - D 5,13 - 17a - pregnadiene-3b ,16a ,20-triol and then the triacetate; (5) 16,17 - epoxy - pregnane - 3,20 - dione gives 17b - methyl - 18 - nor - D 13 - 17a - pregnene-16a ,20 - diol - 3 - one; and (6) 16,17 - epoxy-D 5 - pregnene - 3b ,21 - diol - 20 - one - 21 - acetate yields 17b -methyl-18-nor- D 5,13-17a -pregnadiene-3b ,16a ,20, 21-tetrol 21-acetate.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IT813317X | 1955-02-03 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB813317A true GB813317A (en) | 1959-05-13 |
Family
ID=11317177
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2456/56A Expired GB813317A (en) | 1955-02-03 | 1956-01-25 | New steroid compounds and method for the transformation of epoxy-ketones by the action of fermenting yeast |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB813317A (en) |
-
1956
- 1956-01-25 GB GB2456/56A patent/GB813317A/en not_active Expired
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