IL25737A - Synthesis of equilin - Google Patents

Synthesis of equilin

Info

Publication number: IL25737A
Authority: IL; Israel
Prior art keywords: atcc; dien; transformation; positions; carried out
Prior art date: 1965-05-13

Application number

IL25737A

Other languages

English (en)

Original Assignee

Ayerst Mckenna & Harrison

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.)

1965-05-13

Filing date

1966-05-10

Publication date

1970-02-19

1966-05-10 Application filed by Ayerst Mckenna & Harrison filed Critical Ayerst Mckenna & Harrison

1970-02-19 Publication of IL25737A publication Critical patent/IL25737A/en

Links

WKRLQDKEXYKHJB-UHFFFAOYSA-N Equilin Natural products OC1=CC=C2C3CCC(C)(C(CC4)=O)C4C3=CCC2=C1 WKRLQDKEXYKHJB-UHFFFAOYSA-N 0.000 title claims description 9
WKRLQDKEXYKHJB-HFTRVMKXSA-N equilin Chemical compound OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4C3=CCC2=C1 WKRLQDKEXYKHJB-HFTRVMKXSA-N 0.000 title claims description 9
230000015572 biosynthetic process Effects 0.000 title description 4
238000003786 synthesis reaction Methods 0.000 title description 4
238000000034 method Methods 0.000 claims description 12
241000894006 Bacteria Species 0.000 claims description 5
241001509401 Gordonia rubripertincta Species 0.000 claims description 4
241000186359 Mycobacterium Species 0.000 claims description 4
SGNBVLSWZMBQTH-FGAXOLDCSA-N Campesterol Natural products O[C@@H]1CC=2[C@@](C)([C@@H]3[C@H]([C@H]4[C@@](C)([C@H]([C@H](CC[C@H](C(C)C)C)C)CC4)CC3)CC=2)CC1 SGNBVLSWZMBQTH-FGAXOLDCSA-N 0.000 claims description 2
BTEISVKTSQLKST-UHFFFAOYSA-N Haliclonasterol Natural products CC(C=CC(C)C(C)(C)C)C1CCC2C3=CC=C4CC(O)CCC4(C)C3CCC12C BTEISVKTSQLKST-UHFFFAOYSA-N 0.000 claims description 2
SGNBVLSWZMBQTH-PODYLUTMSA-N campesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CC[C@@H](C)C(C)C)[C@@]1(C)CC2 SGNBVLSWZMBQTH-PODYLUTMSA-N 0.000 claims description 2
235000000431 campesterol Nutrition 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
230000002906 microbiologic effect Effects 0.000 claims 7
230000009466 transformation Effects 0.000 claims 7
230000015556 catabolic process Effects 0.000 claims 6
238000006731 degradation reaction Methods 0.000 claims 6
244000005700 microbiome Species 0.000 claims 5
150000003431 steroids Chemical class 0.000 claims 3
241001491638 Corallina Species 0.000 claims 2
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims 2
239000007858 starting material Substances 0.000 claims 2
229930194542 Keto Natural products 0.000 claims 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
229940076810 beta sitosterol Drugs 0.000 claims 1
LGJMUZUPVCAVPU-UHFFFAOYSA-N beta-Sitostanol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CC)C(C)C)C1(C)CC2 LGJMUZUPVCAVPU-UHFFFAOYSA-N 0.000 claims 1
NJKOMDUNNDKEAI-UHFFFAOYSA-N beta-sitosterol Natural products CCC(CCC(C)C1CCC2(C)C3CC=C4CC(O)CCC4C3CCC12C)C(C)C NJKOMDUNNDKEAI-UHFFFAOYSA-N 0.000 claims 1
150000001838 cholestanes Chemical class 0.000 claims 1
235000012000 cholesterol Nutrition 0.000 claims 1
230000000593 degrading effect Effects 0.000 claims 1
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
125000000468 ketone group Chemical group 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
229910052760 oxygen Inorganic materials 0.000 claims 1
239000001301 oxygen Substances 0.000 claims 1
KZJWDPNRJALLNS-VJSFXXLFSA-N sitosterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CC[C@@H](CC)C(C)C)[C@@]1(C)CC2 KZJWDPNRJALLNS-VJSFXXLFSA-N 0.000 claims 1
229950005143 sitosterol Drugs 0.000 claims 1
230000001580 bacterial effect Effects 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
238000004587 chromatography analysis Methods 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 4
239000005977 Ethylene Substances 0.000 description 4
239000000203 mixture Substances 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
235000013405 beer Nutrition 0.000 description 3
239000000284 extract Substances 0.000 description 3
239000008103 glucose Substances 0.000 description 3
239000008363 phosphate buffer Substances 0.000 description 3
102000004169 proteins and genes Human genes 0.000 description 3
108090000623 proteins and genes Proteins 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
239000002904 solvent Substances 0.000 description 3
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 2
UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
230000037361 pathway Effects 0.000 description 2
239000000725 suspension Substances 0.000 description 2
GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 1
FBEHFRAORPEGFH-UHFFFAOYSA-N Allyxycarb Chemical compound CNC(=O)OC1=CC(C)=C(N(CC=C)CC=C)C(C)=C1 FBEHFRAORPEGFH-UHFFFAOYSA-N 0.000 description 1
241000186216 Corynebacterium Species 0.000 description 1
241000187654 Nocardia Species 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
241000203720 Pimelobacter simplex Species 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
150000002009 diols Chemical class 0.000 description 1
229940011871 estrogen Drugs 0.000 description 1
239000000262 estrogen Substances 0.000 description 1
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

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
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/822—Microorganisms using bacteria or actinomycetales
- Y10S435/843—Corynebacterium
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/822—Microorganisms using bacteria or actinomycetales
- Y10S435/863—Mycobacterium
- Y10S435/866—Mycobacterium smegmatis
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/822—Microorganisms using bacteria or actinomycetales
- Y10S435/872—Nocardia

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)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Steroid Compounds (AREA)

IL25737A 1965-05-13 1966-05-10 Synthesis of equilin IL25737A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US455578A US3395078A (en)	1965-05-13	1965-05-13	Synthesis of equilin

Publications (1)

Publication Number	Publication Date
IL25737A true IL25737A (en)	1970-02-19

Family

ID=23809406

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL25737A IL25737A (en)	1965-05-13	1966-05-10	Synthesis of equilin

Country Status (5)

Country	Link
US (1)	US3395078A (fr)
CH (1)	CH467765A (fr)
DE (1)	DE1568010A1 (fr)
GB (1)	GB1148671A (fr)
IL (1)	IL25737A (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3507749A (en) *	1967-09-20	1970-04-21	Wisconsin Alumni Res Found	Process for preparing steroids
US3639212A (en) *	1968-08-12	1972-02-01	Sankyo Co	Process for the preparation of estrane compound by fermentation
DE10019861A1 (de) *	2000-04-18	2001-10-31	Schering Ag	Neues Synthesezwischenprodukt, seine mikrobiologische Herstellung und Verwendung zur Synthese von Vitamin D-Derivaten

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2902410A (en) *	1957-09-26	1959-09-01	Upjohn Co	Process for the 1,2-dehydrogenation of a steroid with septomyxa

1965
- 1965-05-13 US US455578A patent/US3395078A/en not_active Expired - Lifetime
1966
- 1966-05-10 IL IL25737A patent/IL25737A/en unknown
- 1966-05-11 GB GB20943/66A patent/GB1148671A/en not_active Expired
- 1966-05-13 DE DE19661568010 patent/DE1568010A1/de active Pending
- 1966-05-13 CH CH700666A patent/CH467765A/fr unknown

Also Published As

Publication number	Publication date
GB1148671A (en)	1969-04-16
DE1568010A1 (de)	1970-02-12
US3395078A (en)	1968-07-30
CH467765A (fr)	1969-01-31

Publication	Publication Date	Title
Eyssen et al.	1973	Biohydrogenation of sterols by Eubacterium ATCC 21,408—nova species
JP2719377B2 (ja)	1998-02-25	９α―ヒドロキシ―１７―ケトステロイドの微生物学的製法
US4397946A (en)	1983-08-09	Process for preparing androstane steroids
Greenspan et al.	1957	Transformation of Steroids by Fungi. Introduction of 1ξ and 2β-HYDROXYL Groups Into Reichstein's Compound S.
US4397947A (en)	1983-08-09	Microbial process for 9α-hydroxylation of steroids
McAleer et al.	1958	Communications-1-Hydroxylation of 9α-Fluorohydrocortisone
US4255344A (en)	1981-03-10	9-α-Hydroxy steroids
Laskin et al.	1964	Microbial hydroxylation of estrone and estradiol in the 6β-, 7α-, and 15α-positions
Ambrus et al.	1995	Microbial transformation of β-sitosterol and stigmasterol into 26-oxygenated derivatives
NL8201874A (nl)	1982-12-01	Werkwijze ter verkrijging van 9-hydroxy-3-oxo-4,17(20)-pregnadieen-20-carbonzuur langs microbiologische weg alsmede daarvoor geschikte micro-organismen.
US3395078A (en)	1968-07-30	Synthesis of equilin
CA1167030A (fr)	1984-05-08	Fermentation de la bille
Dutta et al.	1992	Metabolic blocks in the degradation of β‐sitosterol by a plasmid‐cured strain of Arthrobacter oxydans
US3451892A (en)	1969-06-24	Process for the preparation of steroidal compounds
US4867914A (en)	1989-09-19	Pregnane derivatives and method of producing the same
Ambrus et al.	1995	Novel 26-oxygenated products in microbial degradation of ergosterol
Sax et al.	1964	Microbiological 16-Oxidation of Estr-4-en-3-one
US4273872A (en)	1981-06-16	Method for the microbiological conversion of steroids
US4425429A (en)	1984-01-10	Composition of matter and process
US3476779A (en)	1969-11-04	Novel steroid compounds of the cholestane series
US2992973A (en)	1961-07-18	Dehydrogenation of steroids by azotobacter microorganisms
Bhavnani et al.	1972	In vitro metabolism of 15α-hydroxyprogesterone by rabbit liver
US4405525A (en)	1983-09-20	Composition of matter and process
Miller et al.	1970	Reduction of steroid a ring double bonds by Penicillium decumbens
US3487907A (en)	1970-01-06	Process for the microbiological preparation of steroids having no carbonaceous substituent in the 17-position