GB792803A - Oxidation products from compounds of the steroid series and process of making same - Google Patents
Oxidation products from compounds of the steroid series and process of making sameInfo
- Publication number
- GB792803A GB792803A GB24354/54A GB2435454A GB792803A GB 792803 A GB792803 A GB 792803A GB 24354/54 A GB24354/54 A GB 24354/54A GB 2435454 A GB2435454 A GB 2435454A GB 792803 A GB792803 A GB 792803A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dione
- days
- androstene
- progesterone
- fusarium
- 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
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)
- Steroid Compounds (AREA)
Abstract
The invention comprises a process for the manufacture of oxidation products from compounds of the steroid series, wherein saturated and unsaturated compounds of the pregnane or androstane series which contain in the 3,20- or 3,17-positions respectively a free or protected hydroxyl or oxo group, are brought into contact with enzymes produced by a culture of fungi of the species Fusarium solani, Fusarium caucasicum and Rhizopus suinus, and the saturated or unsaturated androstanes which contain in the 3- and 17-positions free or protected hydroxyl or oxo groups or saturated or unsaturated testolactones formed are isolated. The invention also comprises the compound 1:2-dihydrotestolactone <FORM:0792803/IV (b)/1> melting at 219 DEG to 220 DEG C. and having the specific rotation <FORM:0792803/IV (b)/2> (c=1.025 in chloroform); ultra-violet absorption maximum at 242 mm (log e =4.23). As starting materials there may be used, for example, progesterone, or 11-dehydro-, 11-keto- or 11-, 12-, or 14-hydroxyprogesterones, D 5- or D 4-pregnene-3-ol-20-ones, D 5-pregnene-3:20-diols, 11-desoxycorticosterone, corticosterone, 11-dehydro-corticosterone, D 4- or D 5-androstene-3:17-dione, testosterone, D 5-androstene-3-ol-17-one, adrenosterone, pregnane-3:20-dione, pregnane-3-ol-20-one, androstane - 3:17 - dione, allopregnane - 3:20 - dione, 3b - acetoxy - allopregnane - 20 - one and corresponding compounds with protected hydroxyl or oxo groups. There may also be present double bonds in the 4-, 5-, 6-, 7-, 8-, 9:11-, 11- or 14-position or additional substituents such as free or protected hydroxyl, oxo or carboxyl groups, or epoxy groups or halogen atoms, for example in the 4-, 5-, 6-, 7-, 8-, 9-, 11-, 12-, 14- or 21-position. In examples: (1) progesterone is added to a nutrient medium which has been previously inoculated with a culture of Fusarium solani and allowed to grow. After 48 hours further standing at 25 DEG C. and filtration there is recovered and purified by chromatography the compound D 1:4-androstadiene3:17-dione. Fusarium caucasicum may replace the Fusarium solani in a similar process. 11 - Desoxy - corticosterone or D 4- androstene-3:17-dione may be used in place of progesterone; (2) D 5-androstene-3b -ol-17-one is prepared by a similar process from D 5-pregnene-3b -ol-20-one; (3) D 1:4-androstadiene-3:17-dione is obtained, using a similar culture of Fusarium solani, from a neutral portion containing chiefly D 4-androstene-3:17-dione and progesterone obtained by the chromic acid oxidation of cholesteryl-acetate dibromide followed by debromination, hydrolysis and dehydrogenation by the method of Oppenauer; (4) D 1:4-androstadiene-3:17-dione is added to a previously prepared culture of Fusarium caucasicum and after 7 days incubation there is recovered from the filtrate 1:2-dehydro-testolactone. This compound can also be obtained from progesterone, D 5-pregnene-3:20-dione, D 4 - pregnene - 3b - ol - 20 - one, 11 - desoxy - corticosterone or D 4-androstene-3:17-dione, using conditions similar to those of Example (1) but extending the incubation period to 6 to 10 days; (5) to three separate cultures of Fusarium solani in nutrient medium there is added allopregnane-3:20-dione, the cultures then being incubated for 1, 2 and 7 days respectively. Extracts of the first two yield androstane-3:17-dione and that of the third yields D 1:4-androstadiene-3:17-dione. Treatment of 3b -acetoxy - allopregnene - 20 - one yields similar products. Similar treatment of androstane-3:17-dione yields unchanged starting material after 1 and 2 days and D 1:4-androstadiene-3:17-dione after 7 days; (6) 11-desoxy-corticosterone is added to a culture of Rhizopus suinus in nutrient medium and from the mixture after 6 days' incubation there is recovered testolactone; (7) progesterone is added to portions of the mycelia recovered from the growth of Fusarium solani in nutrient medium. After 36 hours incubation at 26 DEG C. 1:4-androstadiene-3:17-dione is recovered. After 7 days incubation the product is 1:2-dehydrotestolactone. Specification 724,094 is referred to.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH792803X | 1953-08-21 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB792803A true GB792803A (en) | 1958-04-02 |
Family
ID=4537090
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB24354/54A Expired GB792803A (en) | 1953-08-21 | 1954-08-20 | Oxidation products from compounds of the steroid series and process of making same |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB792803A (en) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3083210A (en) * | 1961-05-11 | 1963-03-26 | Olin Mathieson | Testololactone derivatives |
US3083212A (en) * | 1961-11-10 | 1963-03-26 | Olin Mathieson | Testololactone derivatives |
US3098079A (en) * | 1962-04-30 | 1963-07-16 | Olin Mathieson | Alpha-nortestololactones |
US3129229A (en) * | 1963-01-29 | 1964-04-14 | Olin Mathieson | Testololactones |
US3174982A (en) * | 1962-01-11 | 1965-03-23 | Olin Mathieson | delta12-13, 17-seco-androstene compounds and lactone intermediates therefor |
US3278556A (en) * | 1964-02-03 | 1966-10-11 | Squibb & Sons Inc | Synthesis of steroids |
-
1954
- 1954-08-20 GB GB24354/54A patent/GB792803A/en not_active Expired
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3083210A (en) * | 1961-05-11 | 1963-03-26 | Olin Mathieson | Testololactone derivatives |
US3083212A (en) * | 1961-11-10 | 1963-03-26 | Olin Mathieson | Testololactone derivatives |
US3174982A (en) * | 1962-01-11 | 1965-03-23 | Olin Mathieson | delta12-13, 17-seco-androstene compounds and lactone intermediates therefor |
US3098079A (en) * | 1962-04-30 | 1963-07-16 | Olin Mathieson | Alpha-nortestololactones |
US3129229A (en) * | 1963-01-29 | 1964-04-14 | Olin Mathieson | Testololactones |
US3278556A (en) * | 1964-02-03 | 1966-10-11 | Squibb & Sons Inc | Synthesis of steroids |
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