CH401028A - Verfahren zur Gewinnung von Coenzym Q - Google Patents

Verfahren zur Gewinnung von Coenzym Q

Info

Publication number: CH401028A
Authority: CH; Switzerland
Prior art keywords: coenzyme; isooctane; quinone; ethanol; solution
Prior art date: 1958-07-07

Application number

CH7542359A

Other languages

German (de)

English (en)

Inventor

Loring Crane Frederick

Leonard Lester Robert

Ezra Green David

Original Assignee

Wisconsin Alumni Res Found

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.)

1958-07-07

Filing date

1959-07-07

Publication date

1965-10-31

1958-09-03 Priority claimed from US758838A external-priority patent/US3162654A/en

1959-07-07 Application filed by Wisconsin Alumni Res Found filed Critical Wisconsin Alumni Res Found

1965-10-31 Publication of CH401028A publication Critical patent/CH401028A/de

Links

ACTIUHUUMQJHFO-UPTCCGCDSA-N coenzyme Q10 Chemical compound COC1=C(OC)C(=O)C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)=C(C)C1=O ACTIUHUUMQJHFO-UPTCCGCDSA-N 0.000 title claims description 88
235000017471 coenzyme Q10 Nutrition 0.000 title claims description 65
238000000034 method Methods 0.000 title claims description 18
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 92
NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 claims description 39
JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 claims description 39
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 31
241000283690 Bos taurus Species 0.000 claims description 15
239000000284 extract Substances 0.000 claims description 13
WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 claims description 13
238000000605 extraction Methods 0.000 claims description 11
239000000463 material Substances 0.000 claims description 11
210000004536 heart mitochondria Anatomy 0.000 claims description 10
240000004808 Saccharomyces cerevisiae Species 0.000 claims description 7
235000014680 Saccharomyces cerevisiae Nutrition 0.000 claims description 7
241000006364 Torula Species 0.000 claims description 7
238000007127 saponification reaction Methods 0.000 claims description 7
229940079877 pyrogallol Drugs 0.000 claims description 6
239000003960 organic solvent Substances 0.000 claims description 5
210000005003 heart tissue Anatomy 0.000 claims description 4
YCOZIPAWZNQLMR-UHFFFAOYSA-N heptane - octane Natural products CCCCCCCCCCCCCCC YCOZIPAWZNQLMR-UHFFFAOYSA-N 0.000 claims description 3
230000001419 dependent effect Effects 0.000 claims 3
239000011541 reaction mixture Substances 0.000 claims 2
229910001854 alkali hydroxide Inorganic materials 0.000 claims 1
150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 58
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
235000019441 ethanol Nutrition 0.000 description 31
238000002844 melting Methods 0.000 description 22
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
230000008018 melting Effects 0.000 description 21
239000000243 solution Substances 0.000 description 20
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
239000002244 precipitate Substances 0.000 description 15
239000002904 solvent Substances 0.000 description 15
JYIMWRSJCRRYNK-UHFFFAOYSA-N dialuminum;disodium;oxygen(2-);silicon(4+);hydrate Chemical compound O.[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[Na+].[Na+].[Al+3].[Al+3].[Si+4] JYIMWRSJCRRYNK-UHFFFAOYSA-N 0.000 description 14
238000004587 chromatography analysis Methods 0.000 description 13
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 description 12
239000013078 crystal Substances 0.000 description 12
239000000047 product Substances 0.000 description 12
239000000203 mixture Substances 0.000 description 10
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
150000001875 compounds Chemical class 0.000 description 9
238000002360 preparation method Methods 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 8
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 8
150000004053 quinones Chemical class 0.000 description 8
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 8
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical group CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 7
210000003470 mitochondria Anatomy 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
229960000583 acetic acid Drugs 0.000 description 6
235000012000 cholesterol Nutrition 0.000 description 6
239000005515 coenzyme Substances 0.000 description 6
239000003921 oil Substances 0.000 description 6
235000019198 oils Nutrition 0.000 description 6
238000001228 spectrum Methods 0.000 description 6
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 5
125000002252 acyl group Chemical group 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
238000005119 centrifugation Methods 0.000 description 5
230000000694 effects Effects 0.000 description 5
238000001914 filtration Methods 0.000 description 5
238000005984 hydrogenation reaction Methods 0.000 description 5
125000000687 hydroquinonyl group Chemical group C1(O)=C(C=C(O)C=C1)* 0.000 description 5
239000007788 liquid Substances 0.000 description 5
239000010413 mother solution Substances 0.000 description 5
239000011591 potassium Substances 0.000 description 5
229910052700 potassium Inorganic materials 0.000 description 5
238000001953 recrystallisation Methods 0.000 description 5
NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 5
239000000126 substance Substances 0.000 description 5
239000006228 supernatant Substances 0.000 description 5
JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
229910000503 Na-aluminosilicate Inorganic materials 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
235000015278 beef Nutrition 0.000 description 4
238000002425 crystallisation Methods 0.000 description 4
230000008025 crystallization Effects 0.000 description 4
150000002430 hydrocarbons Chemical class 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
125000004151 quinonyl group Chemical group 0.000 description 4
239000000377 silicon dioxide Substances 0.000 description 4
239000000429 sodium aluminium silicate Substances 0.000 description 4
235000012217 sodium aluminium silicate Nutrition 0.000 description 4
239000001384 succinic acid Substances 0.000 description 4
241000589151 Azotobacter Species 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
241000235646 Cyberlindnera jadinii Species 0.000 description 3
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
102000004895 Lipoproteins Human genes 0.000 description 3
108090001030 Lipoproteins Proteins 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
-1 alkyl hydroxide Chemical compound 0.000 description 3
ZYBWTEQKHIADDQ-UHFFFAOYSA-N ethanol;methanol Chemical compound OC.CCO ZYBWTEQKHIADDQ-UHFFFAOYSA-N 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
238000000746 purification Methods 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
239000007787 solid Substances 0.000 description 3
150000003505 terpenes Chemical group 0.000 description 3
229930195735 unsaturated hydrocarbon Chemical group 0.000 description 3
GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
238000000862 absorption spectrum Methods 0.000 description 2
230000001476 alcoholic effect Effects 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
230000008033 biological extinction Effects 0.000 description 2
238000009835 boiling Methods 0.000 description 2
150000001746 carotenes Chemical class 0.000 description 2
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239000004927 clay Substances 0.000 description 2
239000012230 colorless oil Substances 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
239000012535 impurity Substances 0.000 description 2
238000002329 infrared spectrum Methods 0.000 description 2
229940040102 levulinic acid Drugs 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
238000004816 paper chromatography Methods 0.000 description 2
150000003904 phospholipids Chemical class 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
229920001296 polysiloxane Polymers 0.000 description 2
IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
108090000623 proteins and genes Proteins 0.000 description 2
102000004169 proteins and genes Human genes 0.000 description 2
238000010992 reflux Methods 0.000 description 2
238000000926 separation method Methods 0.000 description 2
229910001923 silver oxide Inorganic materials 0.000 description 2
108010011792 succinate oxidase Proteins 0.000 description 2
239000000725 suspension Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
238000004448 titration Methods 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
VCZXRQFWGHPRQB-UHFFFAOYSA-N CC(C)CC(C)(C)C.CC(C)CC(C)(C)C Chemical compound CC(C)CC(C)(C)C.CC(C)CC(C)(C)C VCZXRQFWGHPRQB-UHFFFAOYSA-N 0.000 description 1
XYGKGASSKJWLTN-UHFFFAOYSA-N CCCCCCC.CCCCCCC Chemical compound CCCCCCC.CCCCCCC XYGKGASSKJWLTN-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
241000272201 Columbiformes Species 0.000 description 1
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
UPYKUZBSLRQECL-UKMVMLAPSA-N Lycopene Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1C(=C)CCCC1(C)C)C=CC=C(/C)C=CC2C(=C)CCCC2(C)C UPYKUZBSLRQECL-UKMVMLAPSA-N 0.000 description 1
102000006404 Mitochondrial Proteins Human genes 0.000 description 1
108010058682 Mitochondrial Proteins Proteins 0.000 description 1
241000221961 Neurospora crassa Species 0.000 description 1
235000019502 Orange oil Nutrition 0.000 description 1
102100027378 Prothrombin Human genes 0.000 description 1
108010094028 Prothrombin Proteins 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
241000700159 Rattus Species 0.000 description 1
102000019259 Succinate Dehydrogenase Human genes 0.000 description 1
108010012901 Succinate Dehydrogenase Proteins 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
229930003427 Vitamin E Natural products 0.000 description 1
229930003448 Vitamin K Natural products 0.000 description 1
239000002253 acid Substances 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
DNEHKUCSURWDGO-UHFFFAOYSA-N aluminum sodium Chemical compound [Na].[Al] DNEHKUCSURWDGO-UHFFFAOYSA-N 0.000 description 1
239000003146 anticoagulant agent Substances 0.000 description 1
229940127219 anticoagulant drug Drugs 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
230000003078 antioxidant effect Effects 0.000 description 1
235000006708 antioxidants Nutrition 0.000 description 1
239000003698 antivitamin K Substances 0.000 description 1
238000013459 approach Methods 0.000 description 1
239000006286 aqueous extract Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
230000001174 ascending effect Effects 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
235000021336 beef liver Nutrition 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
210000000481 breast Anatomy 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
235000021466 carotenoid Nutrition 0.000 description 1
150000001747 carotenoids Chemical class 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
210000002808 connective tissue Anatomy 0.000 description 1
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238000010908 decantation Methods 0.000 description 1
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238000001035 drying Methods 0.000 description 1
238000010828 elution Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
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239000012259 ether extract Substances 0.000 description 1
OBUNLFQVPAABFB-UHFFFAOYSA-N ethoxyethane;heptane Chemical compound CCOCC.CCCCCCC OBUNLFQVPAABFB-UHFFFAOYSA-N 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 1
239000011491 glass wool Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
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239000002198 insoluble material Substances 0.000 description 1
JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
150000002632 lipids Chemical class 0.000 description 1
210000002311 liver mitochondria Anatomy 0.000 description 1
HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 1
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235000019792 magnesium silicate Nutrition 0.000 description 1
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235000015097 nutrients Nutrition 0.000 description 1
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MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
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NCYCYZXNIZJOKI-UHFFFAOYSA-N vitamin A aldehyde Natural products O=CC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C NCYCYZXNIZJOKI-UHFFFAOYSA-N 0.000 description 1
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PJVWKTKQMONHTI-UHFFFAOYSA-N warfarin Chemical compound OC=1C2=CC=CC=C2OC(=O)C=1C(CC(=O)C)C1=CC=CC=C1 PJVWKTKQMONHTI-UHFFFAOYSA-N 0.000 description 1
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Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/12—Ketones
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C50/00—Quinones
- C07C50/26—Quinones containing groups having oxygen atoms singly bound to carbon atoms
- C07C50/28—Quinones containing groups having oxygen atoms singly bound to carbon atoms with monocyclic quinoid structure
- 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
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/66—Preparation of oxygen-containing organic compounds containing the quinoid structure

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
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CH7542359A 1958-07-07 1959-07-07 Verfahren zur Gewinnung von Coenzym Q CH401028A (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US74678758A	1958-07-07	1958-07-07
US758838A US3162654A (en)	1958-09-03	1958-09-03	Tetra-substituted benzoquinones and derivatives of the same

Publications (1)

Publication Number	Publication Date
CH401028A true CH401028A (de)	1965-10-31

Family

ID=27114647

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH7542359A CH401028A (de)	1958-07-07	1959-07-07	Verfahren zur Gewinnung von Coenzym Q

Country Status (4)

Country	Link
BE (1)	BE580391A (fr)
CH (1)	CH401028A (fr)
ES (1)	ES250767A1 (fr)
GB (1)	GB925581A (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3426125A (en) *	1965-04-07	1969-02-04	Yukio Shigeta	Method of treating diabetes mellitus
US4525350A (en) *	1975-02-20	1985-06-25	The New England Institute, Inc.	Methods of stimulating host defense system with coenzymes Q4 to Q.sub.1
IT1284873B1 (it) *	1996-07-26	1998-05-22	Idi Farmaceutici Spa	Derivati stabili di ubichinolo procedimenti per la loro produzione e loro impiego farmaceutico

1959
- 1959-07-01 GB GB2262759A patent/GB925581A/en not_active Expired
- 1959-07-04 ES ES0250767A patent/ES250767A1/es not_active Expired
- 1959-07-06 BE BE580391A patent/BE580391A/fr unknown
- 1959-07-07 CH CH7542359A patent/CH401028A/de unknown

Also Published As

Publication number	Publication date
BE580391A (fr)	1960-01-06
GB925581A (en)	1963-05-08
ES250767A1 (es)	1960-03-01

Publication	Publication Date	Title
Crane et al.	1959	Studies on the electron transport system: XVIII. Isolation of coenzyme Q (Q275) from beef heart and beef heart mitochondria
DD202581A5 (de)	1983-09-21	Verfahren zur isolierung von sterolen oder sterolmischungen
CH401028A (de)	1965-10-31	Verfahren zur Gewinnung von Coenzym Q
DE2236930A1 (de)	1973-02-15	Verfahren zur herstellung von desmosterol
AT232191B (de)	1964-03-10	Verfahren zur Gewinnung des Coenzyms Q
DE1103868B (de)	1961-04-06	Verfahren zur Gewinnung des Coenzyms Q
DE1217390B (de)	1966-05-26	Verfahren zur Desmethylierung von CoIchicein- und Thiocolchicein-alkyläthern
DE1642646A1 (de)	1971-04-08	Verfahren zur Herstellung der Coenzyme Q9,Q10,Q11 und Q12
DE1793478A1 (de)	1972-02-24	Alisol-Verbindungen
DE2019835C3 (de)	1974-08-15	Verfahren zur Gewinnung von Solanesol
US3162654A (en)	1964-12-22	Tetra-substituted benzoquinones and derivatives of the same
DE1028118B (de)	1958-04-17	Verfahren zur Herstellung von Vitamin A-aldehyd, -alkohol bzw. dessen Estern
Subramanian et al.	1963	Flavonoids of the flowers of Guazuma tomentosa and Delonix elata
DE705312C (de)	1941-04-26	Verfahren zur Herstellung des Wirkstoffes aus hydriertem Tachysterin
DE677866C (de)	1939-07-04	Verfahren zur Herstellung entbitterter Praeparate aus Getreidekeimen
DE1301814B (de)	1969-08-28	Verfahren zur Herstellung von kristallisiertem Vitamin D3
DE634034C (de)	1936-08-17	Verfahren zur Darstellung kristallisierter Digitalisglucoside
DE940850C (de)	1956-03-29	Verfahren zur Herstellung von Produkten mit Vitamin-B-Aktivitaet
Lin et al.	1957	Triterpenoids. II Isolation of triterpenoid sapogenins from the fruits of Barringtonia racemosa Blume
DE954331C (de)	1956-12-13	Verfahren zur Abtrennung von Aldosteron aus Nebennierenextrakten
DE955058C (de)	1956-12-27	Verfahren zur Herstellung von 14ª‡-Oxyprogesteron
AT139605B (de)	1934-11-26	Verfahren zum partiellen Abbau von Digitalisglucosiden.
DE870407C (de)	1953-03-12	Verfahren zur Herstellung von Oxydationsprodukten von Cholesten und seinen Derivaten
DE1668665C (de)	1972-12-07	Verfahren zur Herstellung von 13-Alky 1-gona-1,3,5( 10)-trienen. Ausscheidung aus: 1443123
Clark	1934	Toxicarol. V. 7-Hydroxytoxicarol and Related Compounds