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Coenzyme Q

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IdImageCOMMON NAMENAMEDATA No Lipid classINFORMANTSYMBOLFORMULAMOL.WT(average)Download cdx file / Mol format file BIOOGICAL ACTIVITY PHYSICAL AND CHEMICAL PROPERTIES SPECTRAL DATA CHROMATOGRAM DATA SOURCE CHEMICAL SYNTHESIS METABOLISM GENETIC INFORMATION NOTE REFERENCES
MELTING POINTBOILING POINTDENSITYREFRACTIVE INDEXOPTICAL ROTATIONSOLUBILITY UV SPECTRAIR SPECTRANMR SPECTRAMASS SPECTRAOTHER SPECTRA
1Ubiquinone 50, coenzyme Q-199, ubidecarenone, ubiquinone 10, NSC-140865, Adelir, Caomet, Dec afar, Decorenone, Dymion, Heartcin, Inokiton, Iuvacor, Mitocor, Neuquinon, Taidecanone, Ubifact or, Ubiquasar, Ubisan, Ubivis, Ubiten, Udekinon << Ref. 0001>> / Bio-quinone, Neuquinone, Ubiquinone Q10. 2,5-cyclohexadiene-1,4-dione,2-(3,7,11,15,19,23,27,31,35,39-decamethyl- 2,6,10,14,18,22,26, 30,34,38,-tetracontadecaenyl)-5,6-dimethoxy-3-methyl-, (all-E)-(9CI). (CA Index name) / p-Benzoquinone,2-(3,7,11,15,19,23,27,31,35,39-decamethyl-2,6,10,14,18,22,26,30,34,38,-tetra- contadecaenyl)-5,6-dimethoxy-3-methyl- / 2,3-Dimethoxy-5-methyl-farnesylfarnesylgeranyllinaloyl-1,4-benzoquinone. VCQ0001Coenzyme QTetsuya NakamuraCo Q10 C59H90O4 863.344Download ChemDraw structure data The effect of coenzyme Q(Co Q) homologues on the beating of myocardial cells was investigated in cultured cell sheets from mouse fetuses and quail embryos. Myocardial cell sheets grown in Eagle's minimum essential medium with fetal bovine serum showed very weak and irregular beating when this serum was removed from the medium. However, the depressed beating rate and amplitude recovered almost complete within a few minutes by adding CoQ10 to the medium , and the effect of CoQ10 continued over 1 h. CoQ9 showed a cardiostimulatory effect similar to that of CoQ10.<< Ref. 0013>> 49degC<< Ref. 0028>> lmax 270 mm, E1%1cm = 176 in petroleum ether<< Ref. 0037>>
[Spectrum 0001] << Ref. 0037>>
[Spectrum 0002] << Ref. 0037>>
[Table 0001] << Ref. 0037>>
[Spectrum 0003] << Ref. 0037>>
[Table 0002] << Ref. 0037>>
TLC : Rf = 0.47, hexane and ether (3.5 : 1)<< Ref. 0030>> A convenient and reliable liquid chromatographic (LC) method with electrochemical detection (ED) was developed for the determination of reduced (ubiquinol) and total ubiquinones in biological materials. After extraction of samples with n-hexane, ubiquinol was separated on a reversed-phase column and assayed directly by ED. In order to determine the total amount of a ubiquinone in biological samples, the ubiquinone was converted into the corresponding reduced form by treatment with sodium borohydride. No significant interfering peak (plastoquinol-9, ubichromenol-9, etc.) was observed in the elution areas of ubiquinol-7 to -11. This LC-ED method was about 70 times more sensitive than the previous LC-UV method and was able to detect 150 pg of ubiquinol-10. The method was applied satisfactorily to the determination of the contents of ubiquinol homologues in biological materials. The content of ubiquinols is a major component of the total ubiqinones in human plasma and urine and rat plasma and liver, but a minor component in rat heart and kidney. << Ref. 0026>> A comparison of nine different mammalian species, namely mouse, rat, guinea pig, rabbit, pig, goat, sheep, cow, and horse, which vary from 3.5 to 46 years in their maximum longevity indicated that the rate of O2- generation in cardiac submitochondrial particles (SMPs) was directly related to the relative amount of CoQ9 and inversely related to amount of CoQ10, extractable from their cardiac mitochondria. To directly test the relationship between CoQ homologues and the rate of O2- generation, rat heart SMPs, naturally containing mainly CoQ9 and cow heart SMPs, with high natural CoQ10 content , were chosen for depletion/reconstitution experiments. [Table 0003] << Ref. 0011>>
A systematic study for detecting the ubiquinone content in subcellular compartments, cells, and whole-tissue homogenates by a standardized HPLC method performed after an extraction procedure identical for all samples. It was confirmed that the major coenzyme Q homologue in rat tissues is coenzyme Q9; however, it was pointed out that all the rodents samples tested contain more than one coenzyme Q homologue. The coenzyme Q homologue distribution is tissue dependent with relatively high coenzyme Q10 content in brain mitochondria, irrespective of the rat strain used. There is no constant relationship of the coenzyme Q content in mitochondria and microsomes fractions. Most organisms tested (including other mammals, bird and fish specimens) have only coenzyme Q10 , while the protozoan Tetrahymena pyriformis contains only coenzyme Q8.<< Ref. 0027>> [Table 0004] << Ref. 0027>> [Table 0005] << Ref. 0027>> [Table 0006] << Ref. 0027>> [Table 0007] << Ref. 0027>> [Table 0008] << Ref. 0027>>
Three and one-half grams of 2,3-dimethoxy-5-methylhydroquinone , 14 g of farnesyl - farnesylgeranylgeraniol, and 2.5 g of anhydrous zinc chloride are reacted as described under ubiquinone-9 (VCQ0002). The crude quinone (12.3 g) [ultraviolet maximum at 270 nm ( Three and one-half grams of 2,3-dimethoxy-5-methylhydroquinone , 14 g of farnesyl - farnesylgeranylgeraniol, and 2.5 g of anhydrous zinc chloride are reacted as described under ubiquinone-9 (VCQ0002). The crude quinone (12.3 g) [ultraviolet maximum at 270 nm (Ed1%1cm = 52)] is chromatographed on aluminum oxide to give several fractions possessing EEd1%1cm =100-142 (2.8 g). Further purification by recrystallization from alcohol or by rechromatography on polyethylene powder yields pure ubiquinone-10(VCQ0001), m.p. 49deg. Ultraviolet absorption maximum at 270 nm (Ed1%1cm =173) (in petroleum ether, b.p.80- 105deg). Conditions for paper chromatography are the same as described under ubiquinone-9(VCQ0002). << Ref. 0002>> The pharmacokinetics of coenzyme Q10 (Co Q10) in man was studied by utilizing deuterium-labelled coenzyme Q10(d5-Co Q10). The absence of an isotope effect in the disposition of d5-CoQ10 in man was confirmed from the plasma concentration time curves after simultaneous oral dosing of d5-CoQ10 and unlabelled CoQ10. After oral administration of 100 mg of d5-CoQ10 to 16 healthy male subjects, the mean plasma Co Q10 level attained a peak of 1.004pm0.370 mg/ml at 6.5pm1.5 h after administration, and the terminal elimination half-time was 33.19pm5.32 h. In most of the subjects, plasma d5-CoQ10 showed a second peak at 24 h after dosing. << Ref. 0009>> The biosynthesis of ubiquinone was studied in an isolated perfused beating heart preparation from adult male rats to determine rate-limiting steps in the biosynthetic pathway. The isolated hart could incorporate p-hydroxy [U-14C]benzoate into ubiquinones (ubiquinone-9 (VCQ0002) and -10 (VCQ0001)) and two other lipids which were identified as 3-nonaprenyl 4-hydroxybenzoate and 3-decaprenyl 4-hydroxybenzoate. No other their lipids could be detected. Addition of unlabeled mevalonolactone to the perfusate stimulated the rate of incorporation of p-hyudroxy [U-14C]benzoate into 3-nonaprenyl 4-hydroxybenzoate and 3-decaprenyl 4-hydroxybenzoate. The level of radioactivity in these intermediates was much greater than that in ubiquinone-9 and -10. These results show that in the intact heart there is a larger excess capacity of form postmevalonate isoprenoid precursors of ubiquinone and suggest a possible regulatory step at the premevalonate level. Moreover, the accumulation of prenylated derivatives of 4-hydroxybenzoic acid indicates further rate limitation at one or more the subsequent steps in conversion of these intermediates to ubiquinone.<< Ref. 0024>> << Ref.0001 >> AUTHOR: Anonym. (1996) Menadione in The Merck Index , 12th edition (Budavari, S., O'Neil, M. J., Smith, A., Heckelman, P.E., and Kinneary, J., F., eds), pp1679Merck & Co., Inc., Whitehouse Station, N. J. TITLE: NULL JOURNAL: The Merck Index VOLUME: Ubiquinones PAGE: -NULL(NULL)
<< Ref.0002 >> AUTHOR: Mayer,H., and Isler, O. TITLE: Synthesis of ubiquinones JOURNAL: Methods in Enzymology VOLUME: 18 PAGE: 182 -213 (1971)
<< Ref.0009 >> AUTHOR: Tomono, Y., Hasegawa, J., Seki, T., Motegi, K., and Morishita, N. TITLE: Pharmacokinetic study of deuterium-labelled coenzyme Q10 in man PubMed ID:3781673 JOURNAL: Int J Clin Pharmacol Ther Toxicol. VOLUME: 24 PAGE: 536-541(1986)
<< Ref.0011 >> AUTHOR: Lass, A., Agarwal, S., and Sohal, R. S. TITLE: Mitochondrial ubiquinone homologues, superoxide radical generation, and longevity in different mammalian species PubMed ID:9235911 JOURNAL: J Biol Chem. VOLUME: 272 PAGE: 19199-19204(1997)
<< Ref.0013 >> AUTHOR: Kishi, T., Okamoto, T., Takahashi, T., Goshima, K., and Yamagami, T. TITLE: Cardiostimulatory action of coenzyme Q homologues on cultured myocardial cells and their biochemical mechanisms PubMed ID:8241709 JOURNAL: Clin Investig. VOLUME: 71 PAGE: S71-75(1993)
<< Ref.0024 >> AUTHOR: Yamamoto, T., Shimizu, S., Sugawara, H., Momose, K., and Rudney, H. TITLE: Identification of regulatory sites in the biosynthesis of ubiquinone in the perfused rat heart PubMed ID:2916849 JOURNAL: Arch Biochem Biophys. VOLUME: 269 PAGE: 86-92(1989)
<< Ref.0026 >> AUTHOR: Okamoto, T., Fukunaga, Y., Ida, Y., and Kishi, T. TITLE: Determination of reduced and total ubiquinones in biological materials by liquid chromatography with electrochemical detection PubMed ID:3215946 JOURNAL: J Chromatogr. VOLUME: 430 PAGE: 11-19(1988)
<< Ref.0027 >> AUTHOR: Battino, M., Ferri, E., Gorini, A., Federico Villa, R., Rodriguez Huertas, J. F., Fiorella, P., Genova, M. L., Lenaz, G., and Marchetti, M. TITLE: Natural distribution and occurrence of coenzyme Q homologues PubMed ID:2135303 JOURNAL: Membr Biochem. VOLUME: 9 PAGE: 179-190(1990)
<< Ref.0028 >> AUTHOR: Crane, F. L., and Barr, R. (1985) Chemical structure and properties of coenzyme Q related compunds, in Coenzyme Q (Lenaz, G., ed), pp1-37, John Wiley & Sons Ltd. TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0030 >> AUTHOR: He, D. Y., Yu, L., and Yu, C. A. TITLE: Protein ubiquinone interaction. Synthesis and biological properties of 5-alkyl ubiquinone derivatives PubMed ID:7961719 JOURNAL: J Biol Chem. VOLUME: 269 PAGE: 27885-27888(1994)
<< Ref.0037 >> AUTHOR: Sommer,P., and Kofler,M. TITLE: Physicochemical Properties and Methods of Analysis of Phylloquinones, Menaquinones, Ubiquinones, Plastoquinones, Menadione, and Related Compounds. PubMed ID:5340867 JOURNAL: Vitamins and Hormones VOLUME: 24 PAGE: 349 -399 (1966)
2Coenzyme Q9 2,3-Dimethoxy-5-methyl- farnesylfarnesylnerolidyl-1,4-benzoquinone / 2,3-Dimethoxy-5-methyl- solanesyl -1,4-benzoquinone VCQ0002Coenzyme QTetsuya NakamuraCo Q9 C54H82O4 795.226Download ChemDraw structure data The effect of coenzyme Q(Co Q) homologues on the beating of myocardial cells was investigated in cultured cell stheets from mouse fetuses and quail empbrtyos. Myocardial cell sheets grown in Ealge's minimum essential medium with fetal bovine serum showed very weak and irregular beating when this serum was removed from the medium. However, the depressed beating rate and amplitude recovered almost complete within a few minutes by adding CoQ10 to the medium , and the effect of CoQ10 continued over 1 h. CoQ9 showed a cardiostimulatory effect similar to that of CoQ10.<< Ref. 0013>> 44-45degC<< Ref. 0037>> lmax 270 mm, E1%1cm = 187 in petroleum ether<< Ref. 0037>> [Spectrum 0001] << Ref. 0006>> A comparison of nine different mammalian species, namely mouse, rat, guinea pig, rabbit, pig, goat, sheep, cow, and horse, which vary rom 3.5 to 46 years in their maximum longevity indicated that the rate of O2- generation in cardiac submitochondrial particles (SMPs) was directly related to the relative amojunt of CoQ9 and inversely related to amount of CoQ10, extractable from their cardiac mitochorndria. To directly test the relatoinship between CoQ homologues and the rate of O2- generation, rat heart SMPs, naturally containing mainly CoQ9 and cow heart SMPs, with high natural CoQ10 content , were chosen for depletion/reconstitution experiments. << Ref. 0011>> [Table 0001] << Ref. 0011>>
A systematic study for detecting the ubiquinone content in subcellular compartments, cells, and whole-tissue homogenates by a standardized HPLC method performed after an extraction procedure identical for all samples. A comparison of nine different mammalian species, namely mouse, rat, guinea pig, rabbit, pig, goat, sheep, cow, and horse, which vary rom 3.5 to 46 years in their maximum longevity indicated that the rate of O2- generation in cardiac submitochondrial particles (SMPs) was directly related to the relative amojunt of CoQ9 and inversely related to amount of CoQ10, extractable from their cardiac mitochorndria. To directly test the relatoinship between CoQ homologues and the rate of O2- generation, rat heart SMPs, naturally containing mainly CoQ9 and cow heart SMPs, with high natural CoQ10 content , were chosen for depletion/reconstitution experiments. << Ref. 0011>> [Table 0001] << Ref. 0011>> A systematic study for detecting the ubiquinone content in subcellular compartments, cells, and whole-tissue homogenates by a standardized HPLC method performed after an extraction procedure identical for all samples.
A mixture of 3.4 g of 2,3-dimethoxy-5-methylhydroquinone, 13 g of solanesol, 2 g of anhydrous zinc chloride, 0.2 ml of glacial acetic acid, and 150 ml of absolute ether is shaken under nitrogen at room temperature until a clear solution is obtained. The ether is then evaporated in vacuo at 50deg; the residue (17 g) is heated at 50deg for 15 minutes and then dissolved in 350 ml of petroleum ether (b.p. 40deg -45deg) and 100 ml of methanol-water (7.5:2.5). The petroleum ether layer is washed with four 100-ml portions of methanol-water (7.5:2.5), dried over anhydrous sodium sulfate, and evaporated in vacuo. The residue (13.8 g) is dissolved in 150 ml of ether and shaken with 20 g of silver oxide for 1 hour. After filtration and evaporation, 12.4 g of crude product is obtained showing an ultraviolet absorption maximum at 270 nm (E1%1cm =50). Purification is achieved by chromatography on 350 g of aluminum oxide (activity grade I, deactivated with 7% water). With petroleum ether and 2% ether in petroleum ether, fractions are eluted [ultraviolet maximum at 270 nm (E1%1cm =55-114)] , which after evaporation give 3.2 g. This material is further purified by recrystallization from alcohol or preferably by rechromatography on polyethylene powder (Hostalen W). With acetone-water (8:2) pure is obtained, m.p. 45deg. Ultraviolet absorption maximum at 270 nm (E1%1cm =) (in petroleum ether, b.p. 80deg-105deg). << Ref. 0002>> The half-life of ubiquinone-9 in various rat tissues was determined. Rats were injected intraperitoneally with [3H] mevalonate and the decay of radioactivity incorpoated into ubiquinone-9 was followed usjng reverse-phase HPLC. The hakf-life varied between 49 h (testis) and 125 h (kidney).<< Ref. 0036>> [Table 0008] << Ref. 0036>> << Ref.0002 >> AUTHOR: Mayer,H., and Isler, O. TITLE: Synthesis of ubiquinones JOURNAL: Methods in Enzymology VOLUME: 18 PAGE: 182 -213 (1971)
<< Ref.0006 >> AUTHOR: Rüegg,R., Gloor,U., Goel,R.N., Ryser,G., Wiss,O., und Isler,O. TITLE: Synthese von Ubichinon (45) und Ubichinon (59) JOURNAL: Helv Chim Acta VOLUME: 42 PAGE: 2616 -2621 (1959)
<< Ref.0011 >> AUTHOR: Lass, A., Agarwal, S., and Sohal, R. S. TITLE: Mitochondrial ubiquinone homologues, superoxide radical generation, and longevity in different mammalian species PubMed ID:9235911 JOURNAL: J Biol Chem. VOLUME: 272 PAGE: 19199-19204(1997)
<< Ref.0013 >> AUTHOR: Kishi, T., Okamoto, T., Takahashi, T., Goshima, K., and Yamagami, T. TITLE: Cardiostimulatory action of coenzyme Q homologues on cultured myocardial cells and their biochemical mechanisms PubMed ID:8241709 JOURNAL: Clin Investig. VOLUME: 71 PAGE: S71-75(1993)
<< Ref.0036 >> AUTHOR: Thelin, A., Schedin, S., and Dallner, G. TITLE: Half-life of ubiquinone-9 in rat tissues PubMed ID:1426276 JOURNAL: FEBS Lett. VOLUME: 313 PAGE: 118-120(1992)
<< Ref.0037 >> AUTHOR: Sommer,P., and Kofler,M. TITLE: Physicochemical Properties and Methods of Analysis of Phylloquinones, Menaquinones, Ubiquinones, Plastoquinones, Menadione, and Related Compounds. PubMed ID:5340867 JOURNAL: Vitamins and Hormones VOLUME: 24 PAGE: 349 -399 (1966)
3Coenzyme Q8 2,3-Dimethoxy-5-methyl-farnesylfarnesyllinaloyl-1,4-benzoquinone VCQ0003Coenzyme QTetsuya NakamuraCo Q8 C49H76O4 729.125Download ChemDraw structure data The effect of coenzyme Q(Co Q) homologues on the beating of myocardial cells was investigated in cultured cell stheets from mouse fetuses and quail empbrtyos. Myocardial cell sheets grown in Ealge's minimum essential medium with fetal bovine serum showed very weak and irregular beating when this serum was removed from the medium. However, the depressed beating rate and amplitude recovered almost complete within a few minutes by adding CoQ10 to the medium , and the effect of CoQ10 continued over 1 h. CoQ9 showed a cardiostimulatory effect similar to that of CoQ10, but CoQ8, and CoQ7 showed almost no effect.<< Ref. 0013>> 37-38deg<< Ref. 0037>> lmax 270 mm, E1%1cm = 206 in petroleum ether<< Ref. 0037>> A systematic study for detecting the ubiquinone content in subcellular compartments, cells, and whole-tissue homogenates by a standardized HPLC method performed after an extraction procedure identical for all samples. It was confirmed that the major coenzyme Q homologue in rat tissues is coenzyme Q9; however, it was pointed out that all the rodents samples tested contain more than one coenzyme Q homologue. The coenzyme Q homologue distribution is tissue dependent with relatively high coenzyme Q10 content in brain mitochondria, irrespective of the rat strain used. There is no constant relationship of the coenzyme Q content in mitochondria and microsomes fractions. Most organisms tested (including other mammals, bird and fish specimens) have only coenzyme Q10 , while the protozoan Tetrahymena pyriformis contains only coenzyme Q8.<< Ref. 0027>> [Table 0001] [Table 0002] [Table 0003] [Table 0004] Isolation and separation---One kilogram of dry cells of Escherichia coli 08 was extracted by shaking 15 h with 5 litters of ether-ethanol (3:1). The filtrate was evaporated in vacuo, and the residue was dissolved in 300ml of aqueous methanol (95%). After addition of 300 ml of hexane, the mixture was filtered, and the organic phase was separated. The aqueous phase was further shaken with 150 ml of hexane, and the combined extracts were dried over Na2SO4. The solvent was evaporated, and the the residue (14 g) was dissolved in 80 ml of hexane. The orange-brown solution was chromatographed on a column of silica gel (5.2 x 90 cm). The column was developed by elution with 3 liters of hexane followed by increasing one-percent increments of ether in hexane in 3-liter portions, beginning with 1 % ether in hexane. The ubiquinones were eluted with 5% ether in hexane and were collected in two portions. Continued to Note. From 12.5 g of 2,3-dimethoxy-5-methyl-hydroquinone , 7.6 g of all-trans-farnesylfarnesyllinalool and 5 g of anhydrous zinc chloride 8.3g of crude ubiquinone-8 [lmax 270 nm (Ed1%1cm =2113)] can be obtained in analogous manner as ubiquinone-7(VCQ0004). Purification by chromatography on aluminum oxide yields 3.2 g quinone of E1%1cm =188. Recrystallization of this material (three times from petroleum ether at - 20deg gives 1.77 g of orange crystals, m.p.34deg-36deg, which can be further purified by chromatography on 177g of polyethylene powder (Hostalen W). In this way, 604 mg of pure ubiquinone-8 (VCQ0003)is obtained as orange leaflets, m.p. 37deg-38deg Ultraviolet absorption maximum at 270 nm (Ed1%1cm =205).<< Ref. 0002>> The first of these fractions contained practically pure Q8. The residue obtained from the second fraction was dissolved in a small volume of ether and streaked on silica gel G plates (0.5-1 mm). The plates were developed in d chloroform, air dried, and again developed in chloroform. This procedure was repeated three times. The upper and lower halves of the yellow quinone band (1-2 cm wide) were collected separately and eluted with ether. The material obtained from the lower half of the Q-band was subjected to the thin layer chroamtographic procedure described above. Four successive separations were carried out in this manner; each time the upper half of the yellow quinone band was discarded. Finally, a sample was obtained which on chromatography on silicon-coated paper proved to be pure ubiquinone-5. Q8, Q7, Q6, and Q5 were present to different extents in the intervening fractions. << Ref. 0032>> << Ref.0002 >> AUTHOR: Mayer,H., and Isler, O. TITLE: Synthesis of ubiquinones JOURNAL: Methods in Enzymology VOLUME: 18 PAGE: 182 -213 (1971)
<< Ref.0013 >> AUTHOR: Kishi, T., Okamoto, T., Takahashi, T., Goshima, K., and Yamagami, T. TITLE: Cardiostimulatory action of coenzyme Q homologues on cultured myocardial cells and their biochemical mechanisms PubMed ID:8241709 JOURNAL: Clin Investig. VOLUME: 71 PAGE: S71-75(1993)
<< Ref.0027 >> AUTHOR: Battino, M., Ferri, E., Gorini, A., Federico Villa, R., Rodriguez Huertas, J. F., Fiorella, P., Genova, M. L., Lenaz, G., and Marchetti, M. TITLE: Natural distribution and occurrence of coenzyme Q homologues PubMed ID:2135303 JOURNAL: Membr Biochem. VOLUME: 9 PAGE: 179-190(1990)
<< Ref.0032 >> AUTHOR: Friis, P., Daves, G. D., Jr., and Folkers, K. TITLE: Isolation of ubiquinone-5, new member of ubiquinone group PubMed ID:5337718 JOURNAL: Biochem Biophys Res Commun. VOLUME: 24 PAGE: 252-256(1966)
<< Ref.0037 >> AUTHOR: Sommer,P., and Kofler,M. TITLE: Physicochemical Properties and Methods of Analysis of Phylloquinones, Menaquinones, Ubiquinones, Plastoquinones, Menadione, and Related Compounds. PubMed ID:5340867 JOURNAL: Vitamins and Hormones VOLUME: 24 PAGE: 349 -399 (1966)
4Coenzyme Q7 2,3-Dimethoxy-5-methyl- farnesylgeranyllinaloyl -1,4-benzoquinone VCQ0004Coenzyme QTetsuya NakamuraCoQ7 C44H67O4 660.000Download ChemDraw structure data The effect of coenzyme Q(Co Q) homologues on the beating of myocardial cells was investigated in cultured cell stheets from mouse fetuses and quail empbrtyos. Myocardial cell sheets grown in Ealge's minimum essential medium with fetal bovine serum showed very weak and irregular beating when this serum was removed from the medium. However, the depressed beating rate and amplitude recovered almost complete within a few minutes by adding CoQ10 to the medium , and the effect of CoQ10 continued over 1 h. CoQ9 showed a cardiostimulatory effect similar to that of CoQ10. Short homologues (less than CoQ4) inhibited the beating of cell sheets.<< Ref. 0013>> 31-32deg<< Ref. 0037>> lmax 270 mm, E1%1cm = 229 in petroleum ether<< Ref. 0037>> A systematic study for detecting the ubiquinone content in subcellular compartments, cells, and whole-tissue homogenates by a standardized HPLC method performed after an extraction procedure identical for all samples. It was confirmed that the major coenzyme Q homologue in rat tissues is coenzyme Q9; however, it was pointed out that all the rodents samples tested contain more than one coenzyme Q homologue. The coenzyme Q homologue distribution is tissue dependent with relatively high coenzyme Q10 content in brain mitochondria, irrespective of the rat strain used. There is no constant relationship of the coenzyme Q content in mitochondria and microsomes fractions. Most organisms tested (including other mammals, bird and fish specimens) have only coenzyme Q10 , while the protozoan Tetrahymena pyriformis contains only coenzyme Q8. [Table 0001] << Ref. 0027>> Isolation and separation---One kilogram of dry cells of Escherichia coli 08 was extracted by shaking 15 h with 5 litters of ether-ethanol (3:1). The filtrate was evaporated in vacuo, and the residue was dissolved in 300ml of aqueous methanol (95%). After addition of 300 ml of hexane, the mixture was filtered, and the organic phase was separated. The aqueous phase was further shaken with 150 ml of hexane, and the combined extracts were dried over Na2SO4. The solvent was evaporated, and the the residue (14 g) was dissolved in 80 ml of hexane. The orange-brown solution was chromatographed on a column of silica gel (5.2 x 90 cm). The column was developed by elution with 3 liters of hexane followed by increasing one-percent increments of ether in hexane in 3-liter portions, beginning with 1 % ether in hexane. The ubiquinones were eluted with 5% ether in hexane and were collected in two portions. Continued to Note. Five and two-tenths grams of all-trans-farnesylgeranyllinalool and 9.3 g of2,3-dimethoxy-5-methyl-hydroquinone are dissolved in 76 ml of absolute ether; 3.8 g of anhydrous zinc chloride is added, and the solution is evaporated in vacuo at room temperature with the exclusion of water. The residual dark brown mass is heated at 45 After filtration and evaporation, 6.1 g of crude ubiquinone-7(VCQ0004) is obtained as light red oil showing an ultraviolet absorption maximum at 270 nm (E1%1cm = 125) ( in petroleum ether). The crude ubiquinone-7 is purified by chromatography on the 30-fold amount aluminum oxide (activity grade I, deactivated with 7% water). With 2% ether in petroleum ether colorless and yellow impurities are first eluted, and ubiquinone-7 (2.4 g) is obtained with 5% ether in petroleum ether. The material (E1%1cm =208) solidifies on standing in the cold and is recrystallized from a little petroleum ether at -20degto give 1 g of orange crystals, m.p. 29deg-30deg. For further purification, 0.5 g is chromatographed on 50 g of poly-ethylene powder (Hostalen W). Fifteen-milliliter fractions are collected and stored at 5deg. Continued to Genetic Information Several new metabolites of ubiquinone-7 and one of their conjugates were obtained from the excrements and the tissues of rats and rabbits to which ubiquinone-7 had been administered. The three metabolites and one conjugate obtained from the excrements were identified as 2,3-dimethoxy-5-methyl-6-(3'-methyl-4'-oxopentyl)-1,4-benzoquinone (IV), d-2,3-dimethoxy-5-methyl-6-(3'-carboxy-3'-methylpropyl)-1,4-benzoquinone (V) (Q acid-I) (VCQ0014), trans-2,3-dimethoxy-5-methyl-6-(5'-carboxy-3'-methyl-2'-pentenyl)-1,4-benzoquinone (VII) (VCQ0013) (Q acid-II), and the disulfate XIII of the hydroquinone form of V, respectively, by comparison of their spectral data with those of synthetic samples. The earlier assumption that 2,3-dimethoxy-5-methyl-6-(5'-carboxy-3'-hydroxy-3'-methylpentyl)-1,4-benzoquinone lactone (III) (Q Lactone) (VCQ0015) is a metabolic end product was corrected and the lactone was proved to be an artifact formed from the conjugate of VII during the hydrolysis step. [Table 0001] << Ref. 0033>><< Ref. 0034>> The following solvent systems are used: 525 ml of acetone-water (7:3) and 1.2 liters of acetone-water (7.5:2.5). Fractions 1-46 are discarded. Fractions 47-92 furnish 200 mg of ubiquinone-7 as orange leaflets, m.p.31deg-32deg. Ultraviolet absorption maximum at 270 nm (E1%1cm =299) (in petroleum ether). From the filtrates, another 200 mg of quinone can be obtained after evaporation of the acetone in vacuo and extraction with ether.<< Ref. 0002>> The first of these fractions contained practically pure Q8. The residue obtained from the second fraction was dissolved in a small volume of ether and streaked on silica gel G plates (0.5-1 mm). The plates were developed in d chloroform, air dried, and again developed in chloroform. This procedure was repeated three times. The upper and lower halves of the yellow quinone band (1-2 cm wide) were collected separately and eluted with ether. The material obtained from the lower half of the Q-band was subjected to the thin layer chroamtographic procedure described above. Four successive separations were carried out in this manner; each time the upper half of the yellow quinone band was discarded. Finally, a sample was obtained which on chromatography on silicon-coated paper proved to be pure ubiquinone-5. Q8, Q7, Q6, and Q5 were present to different extents in the intervening fractions. << Ref. 0027>> << Ref.0002 >> AUTHOR: Mayer,H., and Isler, O. TITLE: Synthesis of ubiquinones JOURNAL: Methods in Enzymology VOLUME: 18 PAGE: 182 -213 (1971)
<< Ref.0013 >> AUTHOR: Kishi, T., Okamoto, T., Takahashi, T., Goshima, K., and Yamagami, T. TITLE: Cardiostimulatory action of coenzyme Q homologues on cultured myocardial cells and their biochemical mechanisms PubMed ID:8241709 JOURNAL: Clin Investig. VOLUME: 71 PAGE: S71-75(1993)
<< Ref.0027 >> AUTHOR: Battino, M., Ferri, E., Gorini, A., Federico Villa, R., Rodriguez Huertas, J. F., Fiorella, P., Genova, M. L., Lenaz, G., and Marchetti, M. TITLE: Natural distribution and occurrence of coenzyme Q homologues PubMed ID:2135303 JOURNAL: Membr Biochem. VOLUME: 9 PAGE: 179-190(1990)
<< Ref.0033 >> AUTHOR: Imada, I., Watanabe, M., Matsumoto, N., and Morimoto, H. TITLE: Metabolism of ubiquinone-7 PubMed ID:5459540 JOURNAL: Biochemistry. VOLUME: 9 PAGE: 2870-2878(1970)
<< Ref.0034 >> AUTHOR: Watanabe, M., Toyoda, M., Imada, I., and Morimoto, H. TITLE: Ubiquinone and related compounds. XXVI. The urinary metabolites of phylloquinone and a-tocopherol. PubMed ID:4833371 JOURNAL: Chem. Pharm. Bull. VOLUME: 22 PAGE: 176 -182 (1974)
<< Ref.0037 >> AUTHOR: Sommer,P., and Kofler,M. TITLE: Physicochemical Properties and Methods of Analysis of Phylloquinones, Menaquinones, Ubiquinones, Plastoquinones, Menadione, and Related Compounds. PubMed ID:5340867 JOURNAL: Vitamins and Hormones VOLUME: 24 PAGE: 349 -399 (1966)
5Coenzyme Q6 2,3-Dimethoxy-5-methyl- farnesylnerolidyl -1,4-benzoquinone VCQ0005Coenzyme QTetsuya NakamuraCo Q6 C39H58O4 590.875Download ChemDraw structure data A mitochondrial NADH:Q6 oxidoreductase isolated from cells of Saccharomyces cervisiae by a method involving extraction of enzyme from the mitochondrial membrane with TritonX-100, followed by chromatography on DEAE-cellulose and blue Sepharose CL-6B. By this procedure a 2000-fold purification is achieved. The purified NADH dehydrogenase consists of a single subunit with molecular mass 53 kDa as indicated by SDS/polyacrylamide gel electrophoresis. The enzyme contains FAD, non-covalently linked, as the sole prosthetic group with Em,7.6 = -370mV and no iron-sulphur clusters. The enzyme is specific for NADH with apparent Km = 31m M and was found to be inhibited by flavone (I 50 = 95mM), but not by rotenone or piericidin.<< Ref. 0015>> 19-20deg<< Ref. 0037>> lmax 270 mm, E1%1cm = 260 in petroleum ether<< Ref. 0037>> Isolation and separation---One kilogram of dry cells of Escherichia coli 08 was extracted by shaking 15 h with 5 litters of ether-ethanol (3:1). The filtrate was evaporated in vacuo, and the residue was dissolved in 300ml of aqueous methanol (95%). After addition of 300 ml of hexane, the mixture was filtered, and the organic phase was separated. The aqueous phase was further shaken with 150 ml of hexane, and the combined extracts were dried over Na2SO4. The solvent was evaporated, and the the residue (14 g) was dissolved in 80 ml of hexane. The orange-brown solution was chromatographed on a column of silica gel (5.2 x 90 cm). The column was developed by elution with 3 liters of hexane followed by increasing one-percent increments of ether in hexane in 3-liter portions, beginning with 1 % ether in hexane. The ubiquinones were eluted with 5% ether in hexane and were collected in two portions. The first of these fractions contained practically pure Q8. The residue obtained from the second fraction was dissolved in a small volume of ether and streaked on silica gel G plates (0.5-1 mm). The plates were developed in d chloroform, air dried, and again developed in chloroform. This procedure was repeated three times. The upper and lower halves of the yellow quinone band (1-2 cm wide) were collected separately and eluted with ether. The material obtained from the lower half of the Q-band was subjected to the thin layer chroamtographic procedure described above. Four successive separations were carried out in this manner; each time the upper half of the yellow quinone band was discarded. Finally, a sample was obtained which on chromatography on silicon-coated paper proved to be pure ubiquinone-5. Q8, Q7, Q6, and Q5 were present to different extents in the intervening fractions. << Ref. 0032>> Six grams of 2,3-dimethoxy-5-methyl-1,4-benzoquinone dissolved in 50 ml of methanol is hydrogenated at room temoperature and atmospheric pressure in the presence of 0.5 g of Lindlar's catalyst until the hydrogen consumptin is terminated (about 30 minutes). The catalyst is removed by filtration, the solution is evapo- rated in vacuo, and the residue is dried under high vacuum for 1 hour. The crystalline hydroquinone is dissolved in 180 ml of absolute ether ; 0.3ml of glacial acetic acid, 3.3 g of anhydrous zinc chloride, and 20 g of all-trans-frarnesylnerolidol are added. The mixtute is shaken overnight at room temperature under nitrogen and then refluxed for 1.5 hours. The solvent is evaporated in vacuo, and the residue is dissolved in 500 ml of petroleum ether (b.p. 30deg-45deg) and 250 ml of methanol-water (7 : 3) . The petroleum ether layer is extracted with three 250-ml portions of metanol-water (7: 3), and the methanolic solutions are reextracted with 250 ml of petroleum ether in a second separatory funnell. The combined petroleum ether sollutions are washed with water, dried over anhydrous sodium sulfate and evaporated in vacuo. The residual brownish-yellow oil (17.5 g) is dissolved in 50 ml of petroleum ether (b.p. 80deg -110deg) and hydrogenatd in the presence of 1 g of Lindlar's catalyst. The catalyst is removes, the solution is evaporated and the residue is chromatographed on 400 g of aluminum oxide (activity grade I, deactivated with 4% water). Eight grams of by-product are eluted first with 3.5 liters of petroleum ether (b.p. 30deg-45deg) . With ether (1 liter) 8.3 g of condensation product is obtained which is dissolved in 100 ml ether and shaken in the presence of 20 g of silver oxide for 2 hours at room temperature. Continued to Genetic Information The solution is filtered and evaporated to give crude ubiquinone-6 as an orange-yellow oil, exhibiting and ultraviolet absorption maximum at 272 nm. Further purification is achieved by chromatography on 150 g of aluminum oxide (activ ity grade I, deactivated with 7% water). With petroleum ether (b.p. 30deg-45deg), 5.5 g of product is eluted. Of this concentrate [lmax 272 nm ( E1%1cm sim100), in cyclohexane], 116 mg is chromatographed on 10 g of polyethylene powder (Hostalen W) with acetone-water (72 : 28) as mobile phase. One hundred fractions of 5.5 ml each are collected. The yellow fractions are combined (275-380 ml), diluted with water, and excracted with petroleum ether. The petroleum ether extracts are washed with water and evaporated to give 30 mg of deep orange oil showing an ultraviolet absrption maximum at 272 nm (E1%1cm = 260) and a minimum at 237 nm (E1%1cm = 69).The oil is dissolved in a 10-fold amount of absolute alcohol or acetone and crystallized at 115. The precipitatedcystls melt at 19-290. For paper chromatography Whatman No.1 paper impregnated with Dow-Cornng silicone DC 1107 and isopropanol-glacial acetic acid -water (600:25:375) is recommended. Time 15 hours. Rf 0.54. Alternatively, the conditions described under ubiquinone-9 << Ref. 0002>>may be used.<< Ref. 0004>> << Ref.0002 >> AUTHOR: Mayer,H., and Isler, O. TITLE: Synthesis of ubiquinones JOURNAL: Methods in Enzymology VOLUME: 18 PAGE: 182 -213 (1971)
<< Ref.0004 >> AUTHOR: Gloor, U., Isler, O., Morton, R. A., Rüegg., and Wiss, O. TITLE: Die Struktur des Ubichinons aus Hefe JOURNAL: Helv. Chim. Acta VOLUME: 41 PAGE: 2357 -2362 (1958)
<< Ref.0015 >> AUTHOR: de Vries, S., and Grivell, L. A. TITLE: Purification and characterization of a rotenone-insensitive NADH:Q6 oxidoreductase from mitochondria of Saccharomyces cerevisiae PubMed ID:3138118 JOURNAL: Eur J Biochem. VOLUME: 176 PAGE: 377-384(1988)
<< Ref.0032 >> AUTHOR: Friis, P., Daves, G. D., Jr., and Folkers, K. TITLE: Isolation of ubiquinone-5, new member of ubiquinone group PubMed ID:5337718 JOURNAL: Biochem Biophys Res Commun. VOLUME: 24 PAGE: 252-256(1966)
<< Ref.0037 >> AUTHOR: Sommer,P., and Kofler,M. TITLE: Physicochemical Properties and Methods of Analysis of Phylloquinones, Menaquinones, Ubiquinones, Plastoquinones, Menadione, and Related Compounds. PubMed ID:5340867 JOURNAL: Vitamins and Hormones VOLUME: 24 PAGE: 349 -399 (1966)
6p-Benzoquinone, 2,3-dimethoxy-5-methyl-6- (3,7,11,15,19-pentamethyl-2,6,10,14,18- eicosa pent aenyl)- / (all- E)-. p-Benzoquinone, 2,3-dimethoxy-5-methyl-6- (3,7,11,15,19-pentamethyl- 2,6,10, 14,18- eicosapentaenyl)- / Coenzyme Q5/ Ubiquinone 25 / Ubiquinone 5 / Ubiquinone Q5. 2,5-Cyclohexadiene-1,4-dione, 2,3-dimethoxy-5-methyl-6- (3,7,11,15,19-pentamethyl-2,6,10,14, 18- eicosapentaenyl)- VCQ0006Coenzyme QTetsuya NakamuraCo Q5 C34H49O4 521.750Download ChemDraw structure data 20deg<< Ref. 0028>> lmax 270 mm, E1%1cm = 292 in petroleum ether<< Ref. 0037>> Isolation and separation---One kilogram of dry cells of Escherichia coli 08 was extracted by shaking 15 h with 5 litters of ether-ethanol (3:1). The filtrate was evaporated in vacuo, and the residue was dissolved in 300ml of aqueous methanol (95%). After addition of 300 ml of hexane, the mixture was filtered, and the organic phase was separated. The aqueous phase was further shaken with 150 ml of hexane, and the combined extracts were dried over Na2SO4. The solvent was evaporated, and the the residue (14 g) was dissolved in 80 ml of hexane. The orange-brown solution was chromatographed on a column of silica gel (5.2 x 90 cm). The column was developed by elution with 3 liters of hexane followed by increasing one-percent increments of ether in hexane in 3-liter portions, beginning with 1 % ether in hexane. The ubiquinones were eluted with 5% ether in hexane and were collected in two portions. The first of these fractions contained practically pure Q8. The residue obtained from the second fraction was dissolved in a small volume of ether and streaked on silica gel G plates (0.5-1 mm). The plates were developed in d chloroform, air dried, and again developed in chloroform. This procedure was repeated three times. The upper and lower halves of the yellow quinone band (1-2 cm wide) were collected separately and eluted with ether. The material obtained from the lower half of the Q-band was subjected to the thin layer chroamtographic procedure described above. Four successive separations were carried out in this manner; each time the upper half of the yellow quinone band was discarded. Finally, a sample was obtained which on chromatography on silicon-coated paper proved to be pure ubiquinone-5. Q8, Q7, Q6, and Q5 were present to different extents in the intervening fractions. [Table 0001] << Ref. 0032>> << Ref.0028 >> AUTHOR: Crane, F. L., and Barr, R. (1985) Chemical structure and properties of coenzyme Q related compunds, in Coenzyme Q (Lenaz, G., ed), pp1-37, John Wiley & Sons Ltd. TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0032 >> AUTHOR: Friis, P., Daves, G. D., Jr., and Folkers, K. TITLE: Isolation of ubiquinone-5, new member of ubiquinone group PubMed ID:5337718 JOURNAL: Biochem Biophys Res Commun. VOLUME: 24 PAGE: 252-256(1966)
<< Ref.0037 >> AUTHOR: Sommer,P., and Kofler,M. TITLE: Physicochemical Properties and Methods of Analysis of Phylloquinones, Menaquinones, Ubiquinones, Plastoquinones, Menadione, and Related Compounds. PubMed ID:5340867 JOURNAL: Vitamins and Hormones VOLUME: 24 PAGE: 349 -399 (1966)
7Coenzyme Q4 2,3-Dimethoxy-5-methyl-geranyllinaloyl-1,4-benzoquinone VCQ0007Coenzyme QTetsuya NakamuraCo Q4 C29H40O4 452.625Download ChemDraw structure data The effect of coenzyme Q (Co Q) homologues on the beating of myocardial cells was investigated in cultured cell stheets from mouse fetuses and quail empbrtyos. Myocardial cell sheets grown in Ealge's minimum essential medium with fetal bovine serum showed very weak and irregular beating when this serum was removed from the medium. However, the depressed beating rate and amplitude recovered almost complete within a few minutes by adding CoQ10 to the medium , and the effect of CoQ10 continued over 1 h. CoQ9 showed a cardiostimulatory effect similar to that of CoQ10, but CoQ8, and CoQ7 showed almost no effect. Short homologues (less than Co Q4) inhibited the beating of cell sheets.<< Ref. 0013>> lmax 270 mm, E1%1cm = 326 in petroleum ether<< Ref. 0037>> The compound is prepared in analogy to the procedure given for ubiquinone-3 (VCQ0008) starting from 0.83 g of 2,3-dimethoxy-5-methyl-1,4-benzoquinone and 2.64 g of all-trans-geranyllinalool. Yield 26.4%. Ultraviolet absorption maximum at 271 nm (Ed1%1cm =350) (in hexane). << Ref. 0003>> << Ref.0003 >> AUTHOR: Obol'nikova, E. A., Volkova, O. I., and Samokhvalov, G. I. TITLE: Synthetic studies of polyenes XXVIII. Complete synthesis of coenzyme Q2, Q3, Q4, and hexahydro-Q4 JOURNAL: Zhurnal Obshchei Khimii (English translation) VOLUME: 38 PAGE: 459 -462 (1966)
<< Ref.0013 >> AUTHOR: Kishi, T., Okamoto, T., Takahashi, T., Goshima, K., and Yamagami, T. TITLE: Cardiostimulatory action of coenzyme Q homologues on cultured myocardial cells and their biochemical mechanisms PubMed ID:8241709 JOURNAL: Clin Investig. VOLUME: 71 PAGE: S71-75(1993)
<< Ref.0037 >> AUTHOR: Sommer,P., and Kofler,M. TITLE: Physicochemical Properties and Methods of Analysis of Phylloquinones, Menaquinones, Ubiquinones, Plastoquinones, Menadione, and Related Compounds. PubMed ID:5340867 JOURNAL: Vitamins and Hormones VOLUME: 24 PAGE: 349 -399 (1966)
8Coenzyme Q3 2,3-Dimethoxy-5-methyl- nerolidyl -1,4-benzoquinone VCQ0008Coenzyme QTetsuya NakamuraCo Q3 C24H31O4 383.501Download ChemDraw structure data The effect of coenzyme Q(Co Q) homologues on the beating of myocardial cells was investigated in cultured cell sheets from mouse fetuses and quail embryos. Myocardial cell sheets grown in Ealge's minimum essential medium with fetal bovine serum showed very weak and irregular beating when this serum was removed from the medium. However, the depressed beating rate and amplitude recovered almost complete within a few minutes by adding CoQ10 to the medium , and the effect of CoQ10 continued over 1 h. CoQ9 showed a cardiostimulatory effect similar to that of CoQ10, but CoQ8, and CoQ7 showed almost no effect. Short homologues (less than Co Q4) inhibited the beating of cell sheets. Co Q10 stimulated the formation of ATP, not cAMP. CoQ0 and CoQ3 inhibited beating rates by inhibiting ATP formation.<< Ref. 0013>>
The ability of ubiquinone-3 (VCQ0008), a short chain ubiquinone homologue, to prevent Cu2+ induced oxidation of human low density lipoprotein was examined. In the presence of ubiquonone-3 the extent of peroxidation, as determined by the formation of thiobarbituric acid reactive substances, was only one third of that found in its absence; the quinone can also prevent the fragmenation of apolipoprotein B-100 and the increase of the net negative surface charge of the particle.<< Ref. 0018>>
lmax 270 mm, E1%1cm = 390 in petroleum ether<< Ref. 0037>> 2,3-Dimethoxy-5-methylhydroquinone (0.83 g in 33 ml of absolute ether containing 0.9 g of BF3 etherate) and 2.0 g of trans-nerolidol are allowed to stand for 18 hours at room temperature and then boiled under reflex for 1.5 hour. The mixture is cooled, the solvent is distilled of in vacuo, the residue is diluted with 90 ml of petroleum ether (b.p. 40deg-50deg), and worked up with 70% methanol (3 x 45 ml). The methanol solution is treated with 30 ml of petroleum ether (b.p. 40deg-50deg). The petroleum ether solution is washed with water (15 ml) and dried with anhydrous magnesium sulfate. The solvent is removed in vacuo; the product is dissolved in 5 ml of petroleum ether (b.p. 70deg-100deg) and chromatographed on 75 g of alumina (activity grade II). Elution with 650 ml of petroleum ether (b.p. 40deg-50deg) gives 0.15-0.2 g of a by-product of the condensation; then 220 ml of ether elutes the corresponding hydroquinone as a red oil. The hydroquinone thus obtained is dissolved in 20 ml of ether and treated for 2 hours at room temperature with 3.7 g of freshly prepared silver oxide. The mixture is filtered, and the solvent is removed in vacuo. The impure product is dissolved in 3 ml of petroleum ether (b.p. 40deg-50deg) and chromatographed on 10 g of silicic acid. Ubiquinone-3 is eluted with the same petroleum ether. Yield: 20.3%.
Ultraviolet absorption maximum at 275 nm (E1%1cm = 350) (in hexane).
Thin-layer chromatography is carried out on a layer of silica gel impregnated with mineral oil (5% solution of mineral oil in 40deg-60deg petroleum ether). A mixture of dimethylformamide and water is used as a solvent in the ratio 84 : 16. The developer is a 0.25% alcoholic solution of rhodamine Zh-6; the plates are then examined in ultraviolet light. Continued to Genetic Information
Rf value : 0.6.<< Ref. 0003>>
A new regio- and stereocontrolled synthesis of coenzyme Qn (n = 2,3,9,10) is described. Coupling of geranyltrimethyltin with 2,3-dimethoxy-5-methylbenzoquinone was successfully undertaken in the presence of BF3.OEt2. After oxidation of the resulting mixture coenzyme Q2 was obtained in 90% yield with more than 99% 10 Delta2 -trans stereochemistry. Similarly, all-trans coenzyme Q9 and Q10 were obtained in reasonable yields. << Ref. 0029>>
<< Ref.0003 >> AUTHOR: Obol'nikova, E. A., Volkova, O. I., and Samokhvalov, G. I. TITLE: Synthetic studies of polyenes XXVIII. Complete synthesis of coenzyme Q2, Q3, Q4, and hexahydro-Q4 JOURNAL: Zhurnal Obshchei Khimii (English translation) VOLUME: 38 PAGE: 459 -462 (1966)
<< Ref.0013 >> AUTHOR: Kishi, T., Okamoto, T., Takahashi, T., Goshima, K., and Yamagami, T. TITLE: Cardiostimulatory action of coenzyme Q homologues on cultured myocardial cells and their biochemical mechanisms PubMed ID:8241709 JOURNAL: Clin Investig. VOLUME: 71 PAGE: S71-75(1993)
<< Ref.0018 >> AUTHOR: Merati, G., Pasquali, P., Vergani, C., and Landi, L. TITLE: Antioxidant activity of ubiquinone-3 in human low density lipoprotein PubMed ID:1516845 JOURNAL: Free Radic Res Commun. VOLUME: 16 PAGE: 11-17(1992)
<< Ref.0029 >> AUTHOR: Naruta, Y., and Maruyama, K. TITLE: Regio- and stereocontrolled polyprenylation of quinones. A new synthetic method of coenzyme Q2, Q3, Q9, and Q10 JOURNAL: Chem. Letters VOLUME: PAGE: 885 -888 (1979)
<< Ref.0037 >> AUTHOR: Sommer,P., and Kofler,M. TITLE: Physicochemical Properties and Methods of Analysis of Phylloquinones, Menaquinones, Ubiquinones, Plastoquinones, Menadione, and Related Compounds. PubMed ID:5340867 JOURNAL: Vitamins and Hormones VOLUME: 24 PAGE: 349 -399 (1966)
9Coenzyme Q2 2,3-Dimethoxy-5-methyl- linaloyl-1,4-benzoquinone VCQ0009Coenzyme QTetsuya NakamuraCo Q2 C19H22O4 314.376Download ChemDraw structure data lmax 270 mm, E1%1cm = 455 in petroleum ether<< Ref. 0037>> To 1.0 g of 2,3-dimethoxy-5-methyl-hydroquinone in 5 ml of anhydrous dioxane is added at 18deg - 20deg 1 ml of BF3 etherate, and , over the course of 1 hour, 3.35 g of linalool in 10 ml of dioxane. The reaction mixture is stirred for 3 hours and then diluted with ether to a total volume of 150 ml. The ethereal solution is washed (2 x 50 ml) with a 5% solution of sodium bicarbonate and dried over anhydrous magnesium sulfate. The solvent is removed in vacuo, the remaining oil dissolved in 100 ml of anhydrous ether, and treated 18 hours with 5 g of freshly prepared silver oxide and 2 g of anhydrous magnesium sulfate. After filtering and evaporation, the residue is dissolved in 100 ml of petroleum ether (b.p. 40deg - 60deg), washed with water (6 x 100 ml), and dried with anhydrous magnesium sulfate. The solvent is removed in vacuo, and the remaining product is subjected to preparative thin-layer chromatography on a layer of alumina deactivated with % water. Solvent: hexane-ether (3 : 2). The elution of ubiquinone-2 from the alumina is accomplished with ether. Rf value : 0.56; 2,3-dimethoxy- 5-methyl-1,4-benzoquinone shows Rf 0.36. Yield: 16.8%. Ultraviolet absorption maximum at 272 m (E1%1cm = 400) (in hexane).<< Ref. 0003>> A new regio- and stereocontrolled synthesis of coenzyme Qn (n = 2,3,9,10) is described. Coupling of geranyltrimethyltin with 2,3-dimethoxy-5-methylbenzoquinone was successfully undertaken in the presence of BF3.OEt2. After oxidation of the resulting mixture coenzyme Q2 was obtained in 90% yield with more than 99% 10 Delta2 -trans stereochemistry. Similarly, all-trans coenzyme Q9 and Q10 were obtained in reasonable yields.<< Ref. 0029>> Coenzyme Q functions as a lipid-soluble electron carrier in eukaryotes. In Saccharomyces cerevisiae, the enzymes responsible for the assembly of the polyisoprenoid side chain and subsequent transfer to para hydroxybenzoate (PHB) are encoded by the nuclear genes COQ1 and COQ2, respectively. Yeast mutants defective in coenzyme Q biosynthesis are respiratory defective and provide a useful tool to study this non-sterol branch of the isoprenoid biosynthetic pathway. A 5.5-kilobase genomic DNA fragment that was able to functionally complement a coq2 strain was isolated. Additional complementation analyses located the COQ2 gene within a 2.1-kilobase HindIII-BglIII restriction fragment. Sequence analyses revealed the presence of a 1,116-base pair open reading frame coding for a predicted protein of 372 amino acids and a molecular mass of 41,001 daltons. The amino acid sequence exhibits a typical amino-terminal mitochondrial leader sequence and six potential membrane spanning domains. Primer extension and Northern analyses indicate the gene is trascriptionally active. << Ref. 0022>> << Ref.0003 >> AUTHOR: Obol'nikova, E. A., Volkova, O. I., and Samokhvalov, G. I. TITLE: Synthetic studies of polyenes XXVIII. Complete synthesis of coenzyme Q2, Q3, Q4, and hexahydro-Q4 JOURNAL: Zhurnal Obshchei Khimii (English translation) VOLUME: 38 PAGE: 459 -462 (1966)
<< Ref.0022 >> AUTHOR: Ashby, M. N., Kutsunai, S. Y., Ackerman, S., Tzagoloff, A., and Edwards, P. A. TITLE: COQ2 is a candidate for the structural gene encoding para-hydroxybenzoate:polyprenyltransferase PubMed ID:1740455 JOURNAL: J Biol Chem. VOLUME: 267 PAGE: 4128-4136(1992)
<< Ref.0029 >> AUTHOR: Naruta, Y., and Maruyama, K. TITLE: Regio- and stereocontrolled polyprenylation of quinones. A new synthetic method of coenzyme Q2, Q3, Q9, and Q10 JOURNAL: Chem. Letters VOLUME: PAGE: 885 -888 (1979)
<< Ref.0037 >> AUTHOR: Sommer,P., and Kofler,M. TITLE: Physicochemical Properties and Methods of Analysis of Phylloquinones, Menaquinones, Ubiquinones, Plastoquinones, Menadione, and Related Compounds. PubMed ID:5340867 JOURNAL: Vitamins and Hormones VOLUME: 24 PAGE: 349 -399 (1966)
10Coenzyme Q1 2,3-Dimethoxy-5-methyl- methylbutenyl-1,4-benzoquinone VCQ0010Coenzyme QTetsuya NakamuraCo Q1 C14H13O4 245.251Download ChemDraw structure data Interaction of ubiquinol with oxygen radicals was followed by their effects on luminol-activated chemiluminescence. Ubiquinols Q1- Q4 at 0.1 mM completely inhibit the luminol-activated NADPH-dependent chemiluminescent response of microsomes, while homologues Q6-Q10 exert no effect. In contrast to ubiquinol Q10 (ubiquinone Q10) ubiquinone Q1 synergistically enhances NADPH-dependent regeneration of endogenous vitamin E in microsomes thus providing for higher antioxidant protection against lipid peroxidation. The differences in the antioxidant potency of ubiquinols in membranes are suggested to result form differences in partitioning into membranes, intramembrane mobility and non-uniform distribution of ubiquinol resulting in differing efficiency of interaction with oxygen and lipid radicals as well as different efficiency of ubiquinols in regeneration of endogenous vitamin E.<< Ref. 0019>> O2- generation in mitochondrial electron trasport systems, especially the NADPH-coenzyme Q10 oxidorecuctase system, was examined using a model system, NADPH-coenzymeQ 1-dependent cytocrome P-450 reductase. One electron reuction of coenzyme Q1 produces coenzyme Q1- and O2-during enzyme-catalyzed reduction and O2 + coenzyme Q 1- are in equilibrium with O2- + coenzyme Q 1 In the presence of enough O2 , The coenzyme Q1- produced can be completely eliminated by superoxide dismutase, identical to bound coenzyme Q10 radical produced in succinate/ fumarate couple-KCN-submitochondrial system in the presence of O2. Superoxide dismutase promotes electron transfer from reduced enzyme to coenzyme Q1 by the rapid dismutation of O2- generated, thereby preventing the reduction of coenzyme Q1 by O2-. The enzymatic reduction of coenzyme Q1 to coenzyme Q1H2 via coenzyme Q1- is smoothly achieved under anaerobic conditions.<< Ref. 0021>> lmax 270 mm, E1%1cm = 590 in petroleum ether<< Ref. 0037>> (a) ESR spectrum of coenzyme Q1 semiquinone radical. ESR signals dwere taken at 30-140 s after the additionof NADPH at 25degC.[Table 0001] (b) The reacrion mixture contained 1.6 units of NADPH-cytochrome P-450 reductase/1.6 mM coenzyme Q1 /0.8mM NADPH, NADPH-generating system and 0.1 M Tris-HCl buffer (pH 7.5). [Table 0001] << Ref. 0021>> << Ref.0019 >> AUTHOR: Kagan, V. E., Serbinova, E. A., Koynova, G. M., Kitanova, S. A., Tyurin, V. A., Stoytchev, T. S., Quinn, P. J., and Packer, L. TITLE: Antioxidant action of ubiquinol homologues with different isoprenoid chain length in biomembranes PubMed ID:2227528 JOURNAL: Free Radic Biol Med. VOLUME: 9 PAGE: 117-126(1990)
<< Ref.0021 >> AUTHOR: Sugioka, K., Nakano, M., Totsune-Nakano, H., Minakami, H., Tero-Kubota, S., and Ikegami, Y. TITLE: Mechanism of O2- generation in reduction and oxidation cycle of ubiquinones in a model of mitochondrial electron transport systems PubMed ID:2848580 JOURNAL: Biochim Biophys Acta. VOLUME: 936 PAGE: 377-385(1988)
<< Ref.0037 >> AUTHOR: Sommer,P., and Kofler,M. TITLE: Physicochemical Properties and Methods of Analysis of Phylloquinones, Menaquinones, Ubiquinones, Plastoquinones, Menadione, and Related Compounds. PubMed ID:5340867 JOURNAL: Vitamins and Hormones VOLUME: 24 PAGE: 349 -399 (1966)
11Coenzyme Q0 2,3-Dimethoxy-5-methyl-1,4-benzoquinone VCQ0011Coenzyme QTetsuya NakamuraCo Q0 C9H10O4 182.173Download ChemDraw structure data The kinetics of ascorbate (AscH-) and epinephrine (EP) oxidation in the presence of 2,3-dimethoxy-5-methyl-1,4-benzoquinone(VCQ0011) were studied in 0.05M phosphate buffer, pH 7.4, at 37deg by using a Clark electrode and ESR techniques. (VCQ0011) at nanomolar concentrations displayed a pronounced catalytic effect on AscH- oxidation which exceeded that of all reported organic catalysts tested in this system. The capability of (VCQ0011) to catalyze the oxidation of EP exceeded by approximately 25 times that of adrenochrome, a quinoid product of EP oxidation. (VCQ0011) may be considered , in combination with AscH-, as a potential 62degC<< Ref. 0017>> A solution of potassium nitrodisulfonate (6.0 g, 0.022 mole) and sodium phosphate (2.84 g, 0.02 mole) in water (10 is mixed at 25 with a solution of 2,3- dimethoxy-6-methylaniline hydrochloride (2.03 g, 0.01 mole) in water (20 ml) . After 0.5 hour the mixture is acidified with glacial acetic acid (4.0 ml), stirred for an additional 0.5 hour, and extracted with methylene chloride. The dried (MgSO4) extracts are evaporated in vacuo to an orange oily residue which rapidly crystallizes. The yield of coenzyme Q 0 is 1.74 g (95%); m.p. 55deg-57deg. A small sample is sublimed at 45deg/1 mm, giving the quinone with m.p. 59deg. Ultraviolet absorption maximum at 264 nm ( e=13,400) (in methanol). The infrared absorption spectrum shows bands at 1660, 1605, 1450, 1320, 1280, 1220, 1140, 1085, and 885 cm-1 (in CCl4). << Ref. 0002>> << Ref.0002 >> AUTHOR: Mayer,H., and Isler, O. TITLE: Synthesis of ubiquinones JOURNAL: Methods in Enzymology VOLUME: 18 PAGE: 182 -213 (1971)
<< Ref.0010 >> AUTHOR: Roginsky, V. A., Bruchelt, G., and Bartuli, O. TITLE: Ubiquinone-0 (2,3-dimethoxy-5-methyl-1,4-benzoquinone) as effective catalyzer of ascorbate and epinephrine oxidation and damager of neuroblastoma cells PubMed ID:9413934 JOURNAL: Biochem Pharmacol. VOLUME: 55 PAGE: 85-91(1998)
<< Ref.0013 >> AUTHOR: Kishi, T., Okamoto, T., Takahashi, T., Goshima, K., and Yamagami, T. TITLE: Cardiostimulatory action of coenzyme Q homologues on cultured myocardial cells and their biochemical mechanisms PubMed ID:8241709 JOURNAL: Clin Investig. VOLUME: 71 PAGE: S71-75(1993)
<< Ref.0017 >> AUTHOR: Yu, C. A., Nagoaka, S., Yu, L., and King, T. E. TITLE: Evidence of ubisemiquinone radicals in electron transfer at the cytochromes b and c1 region of the cardiac respiratory chain PubMed ID:6252851 JOURNAL: Arch Biochem Biophys. VOLUME: 204 PAGE: 59-70(1980)
12 Coenzyme Q12 / trans-Coenzyme Q12 / Ubiqui none 12 / Ubiquinone Q-12 2,5-Cyclohexadiene-1,4-dione, 2-(3,7,11,15,19,23,27,31,35,39,43,47-dodecamethyl- 2,6,10,14,18, 22,26,30,34,38,42,46-octatetracontadodecaenyl)-5,6-dimethoxy-3-methyl-, (all-E)- / p-Benzoquinone, 2-(3,7,11,15,19,23,27,31,35,39,43,47-dodecamethyl- 2,6,10,14,18, 22,26,30,34,38,42,46-octatetracontadodecaenyl)-5,6-dimethoxy-3-methyl-. 2,3-Dimethoxy- 4-methyl-5- dodecaprenyl -1,4-benzoquinone VCQ0012Coenzyme QTetsuya NakamuraCo Q12 C69H106O6 1031.576Download ChemDraw structure data To a solution of 0.25 g of 2,3-dimethoxy-5-methylbenzohydroquinone and 0.85 g of natural dodecaprenol (possessing eight cis and three trans double bonds counting from the terminal hydroxy-containing isoprenoid unit) in 25 ml of freshly distilled dioxane is added 0.5 ml of freshly distilled BF3 etherate. After stirring this mixture for 4 hours , it is poured into 300 ml of ether and 200 ml of water. The organic phase is separated, washed with water, and then vigorously shaken with excess aqueous methanolic ferric chloride solution. The ether layer is again separated washed with water, and dried. The residue obtained upon evaporation of the solvent subjected to preparative layer chromatography on silica gel G plates (1.0 mm) developed in hexane-ether (9:1) . Ubiquinone-12 appears as an orange band of higher Rf value than the t of a much larger orange band (2,3-dimethoxy- 5-methyl-1,4-benzoquinone ). Further purification is achieved by preparative thin-layer chromatography using hexane-ether (95:5) as developing solvent. The plates are developed five times, the ubiquinone-12 removed, and this chromatographic process is repeated. In this way, 15 mg of ubiquinone-12 is obtained as an orange viscous oil. The ultraviolet adsorption maximum is at 272 nm (in hexane). Nuclear magnetic resonance spectrum (chemical shifts in t; CCl4): multiplet at 4.97 (12 vinylic H), singlet at 6.12 (2OCH3), doublet at 6.92 (J~6.5 Hz) (CH2 next to ring), multiplet at 7.7-8.2 (side chain methylene), signals at 8.30 (cis methyl at C-3 << Ref.0002 >> AUTHOR: Mayer,H., and Isler, O. TITLE: Synthesis of ubiquinones JOURNAL: Methods in Enzymology VOLUME: 18 PAGE: 182 -213 (1971)
<< Ref.0008 >> AUTHOR: Daves, G. D., Jr., Folkers, K., Lenaz, G., Fukawa, H., and Shimizu, T. TITLE: Synthesis and coenzymatic activity of ubiquinone-12 PubMed ID:5726549 JOURNAL: Int Z Vitaminforsch. VOLUME: 38 PAGE: 65-70(1968)
13Q acid I Trans-2,3-dimethoxy-5-methyl-6-(5'-carboxy-3'-methyl-2'-pentenyl)-1,4-benzoquinone VCQ0013Coenzyme QTetsuya Nakamura C16H20O6 308.326Download ChemDraw structure data lEtOHmax oxidized form 275, reduced form 290 mm<< Ref. 0035>> (CCl4)sim2650, 1700, (COOH), 1660, 1650, 1610 cm-1 (quinone)<< Ref. 0035>> (CCl4) trans compound 8.27 (s, 3, C=CCH3), 8.09 (s, 3, ring CH3), 7.72 (b, 4, C=CCH2, CH2COO) , 6.92 (d, 2, ring CH2), 6.12 (s, 6, OCH3). cis compound 8.35 (s, 3, C=CCH3), 7.60 (b, 4, C=CCH2, CH2COO) . << Ref. 0035>> m/e 308 (M), 293 (M - CH3), 247, 235.<< Ref. 0035>> Methanolic KOH (10%) (2 ml) was added to a solution of 2,3-dimethoxy-5-methyl-6-(3'-methyl-5(5'-methoxycarbonyl-2'-pentenyl)-1,4-benzoquinone (20mg) and pyrogallol (200 mg) in methanol (2 ml) and the mixture was heated at 70 deg for 1 hr under N2. Water was added and the reaction mixture was acidified with 10% HCl and extracted with ether. The ether extracts were shaken with a solution of FeCl3 (1 g) in 30% methanol (10 ml) and the ether layer was separated. The residue of the ether layer was purified by thin-layer chromatography using chloroform-ethanol (9:1) to give (VCQ0013) as an orange oil. Yield 10 mg (52.4 %). << Ref. 0035>> Trans-2,3-dimethoxy-5-methyl-6-(5'-carboxy-3'-methyl-2'-pentenyl)-1,4-benzoquinone (Q acid I) (VCQ0013) was obtained in the urine as one of metabolites of ubiquinone-7 administered in rats and rabbits . The disulfate of (VCQ0013) was found also.<< Ref. 0033>> << Ref. 0034>> << Ref.0033 >> AUTHOR: Imada, I., Watanabe, M., Matsumoto, N., and Morimoto, H. TITLE: Metabolism of ubiquinone-7 PubMed ID:5459540 JOURNAL: Biochemistry. VOLUME: 9 PAGE: 2870-2878(1970)
<< Ref.0034 >> AUTHOR: Watanabe, M., Toyoda, M., Imada, I., and Morimoto, H. TITLE: Ubiquinone and related compounds. XXVI. The urinary metabolites of phylloquinone and a-tocopherol. PubMed ID:4833371 JOURNAL: Chem. Pharm. Bull. VOLUME: 22 PAGE: 176 -182 (1974)
<< Ref.0035 >> AUTHOR: Watanabe, M., Imada, I., and Morimoto, H. TITLE: Synthesis of ubiquinone-7 metabolites PubMed ID:5459541 JOURNAL: Biochemistry. VOLUME: 9 PAGE: 2879-2886(1970)
14Q acid II 2,3-dimethoxy-5-methyl-6-(3'-carboxy-3'-methylpropyl)-1,4-benzoquinone VCQ0014Coenzyme QTetsuya Nakamura C14H18O6 282.289Download ChemDraw structure data lEtOHmax (E1%1cm ) oxidized form 278 (505), reduced form 291 mm(112), DE1%1cm at 278 mm 432.<< Ref. 0035>> (CCl4)sim2600, 1700, (COOH), 1660, 1650, 1610 cm-1 (quinone).<< Ref. 0035>> (CCl4) 8.75 (d, 3, side chain CH3), 8.6-8.1(m, 2, CH2), 8.03 (s, 3, ring CH3), 7.54 (t, 2, ring CH2), 7.46 (b, 1, CHCOO), 6.10 (s, 6, OCH3), -1.04 (b, 1, COOH). << Ref. 0035>> m/e 282 (M), 249, 236, 221, 208, 195, 149, 74. << Ref. 0035>> ON(SO3K)2(3 g) in water (60 ml) was added to a solution of X (1.4 g) in 2% NaOH (12 ml) and stirred for 2 hr at room temperature. The reaction mixture was acidified with 10% HCl and extracted with ether. The ether extracts were worked up in the usual manner to give an orange oil (1.3 g) . The oil was purified by column chromatography on silicic acid (50 g) containing 3% of water eluting with chloroform to afford <0014> as a red oil: yield 1.36 g (92.3%).<< Ref. 0035>> 2,3-dimethoxy-5-methyl-6-(3'-carboxy-3'-methylpropyl)-1,4-benzoquinone (Q acid II) (VCQ0014) was obtained in the urine as one of metabolites of ubiquinone-7 administered in rats and rabbits. << Ref. 0033>> << Ref. 0034>> << Ref.0033 >> AUTHOR: Imada, I., Watanabe, M., Matsumoto, N., and Morimoto, H. TITLE: Metabolism of ubiquinone-7 PubMed ID:5459540 JOURNAL: Biochemistry. VOLUME: 9 PAGE: 2870-2878(1970)
<< Ref.0034 >> AUTHOR: Watanabe, M., Toyoda, M., Imada, I., and Morimoto, H. TITLE: Ubiquinone and related compounds. XXVI. The urinary metabolites of phylloquinone and a-tocopherol. PubMed ID:4833371 JOURNAL: Chem. Pharm. Bull. VOLUME: 22 PAGE: 176 -182 (1974)
<< Ref.0035 >> AUTHOR: Watanabe, M., Imada, I., and Morimoto, H. TITLE: Synthesis of ubiquinone-7 metabolites PubMed ID:5459541 JOURNAL: Biochemistry. VOLUME: 9 PAGE: 2879-2886(1970)
15Q lactone 2,3-Dimethoxy-5-methyl--6-(5'-carboxy-3'-hydroxy--3'-methylpentyl)-1,4-benzoquinone lactone VCQ0015Coenzyme QTetsuya Nakamura C16H20O6 308.326Download ChemDraw structure data lmax 276 nm (E1%1cm = 503) (in ethanol).<< Ref. 0002>> 1380(CH3), 1614 and 1652 (quinone), 1767 (lactone), and 2840 mm (OCH3) (in chloroform).<< Ref. 0002>> (a) HCl (10%) (0.5 ml) was added to a solution of Q acid-I (VCQ0013) (1 mg) in tetrahydrofuran (0.5 ml) and the mixture heated at 75deg C for 1.5 h under N2. Water was added and the reaction mixture extracted with ether. The ether extracts were worked up in the usual manner to give an oil. The oil was purified by thin-layer chromatography using ether-chloroform-ethanol (3 : 2: 1) to give Q lactone as an orange oil : yield 0.2 mg (20.0%).<< Ref. 0035>> (b) To a solution of 24.1 g of ceric sulfate in 300 ml of water (acidified with 7.5 ml of concentrated sulfuric acid) is added with stirring within approx 10 minutes a solution of 7.9 g of crude hydroxy acid << Ref. 0002>> in 390 ml of methanol. The reaction mixture is stirred for 15 minutes , then diluted with 850 ml of water and extracted with eight 100-ml portions of ether. The combined ether extracts are washed with three 75-ml portions of saturated sodium chloride solution, dried over magnesium sulfate, and evaporated in vacuo to give 7.1 g (90.5%) of crude quinone . The product is chromatographed on 70 g of aluminum oxide (activity grade II). It is dissolved in 6 ml of chloroform and 20 ml of ether, put on the column , and eluted with ether. In this manner 4.3 g of oily quinone (Q lactone) is obtained which can be distilled at 190deg-195deg/0.05 mm.[Table 0001] << Ref. 0002>> 2,3-Dimethoxy-5-methyl--6-(5'-carboxy-3'-hydroxy--3'-methylpentyl)-1,4-benzoquinone lactone(VCQ0015) was proved to be an artifact formed from the conjugate of Q acid I (VCQ0013) during the hydrolysis step. << Ref. 0033>> << Ref.0002 >> AUTHOR: Mayer,H., and Isler, O. TITLE: Synthesis of ubiquinones JOURNAL: Methods in Enzymology VOLUME: 18 PAGE: 182 -213 (1971)
<< Ref.0033 >> AUTHOR: Imada, I., Watanabe, M., Matsumoto, N., and Morimoto, H. TITLE: Metabolism of ubiquinone-7 PubMed ID:5459540 JOURNAL: Biochemistry. VOLUME: 9 PAGE: 2870-2878(1970)
<< Ref.0035 >> AUTHOR: Watanabe, M., Imada, I., and Morimoto, H. TITLE: Synthesis of ubiquinone-7 metabolites PubMed ID:5459541 JOURNAL: Biochemistry. VOLUME: 9 PAGE: 2879-2886(1970)
16 2,3-Dimethoxy-6-(9'-fluorodecyl)-1,4-benzoquinone VCQ0016Coenzyme QTetsuya Nakamura9FQ C19H29O4F1 340.430Download ChemDraw structure data 9FQ is active (greater than 50% the activity of 2,3-dimethoxy-5-methyl-6-decyl-1,4-benzoquinone) when used as electron acceptors for succinate-ubiquinone reductase. 9FQ is active when used as an electron donor for ubiquinol-cytochrome c reductase or as an electron mediator for succinate-cytochrome c reductase. The lack of significant chemical shift for 9FQ, suggest that the benzoquinone ring is bound near the paramagnetic cytochrome b heme.<< Ref. 0016>> UVEtOH:oxid., 278 nm, red., 290 nm.<< Ref. 0016>> 1H NMR (CDCl3): 0. 95 (q. 3H), 1.31 (m, 12H), 1.59 (m, 2H), 1.59 (m, 2H), 1.98 (s, 3H), 2.45 (t, 2H), 3.97 (s, 6H), 4.63 (m, 1H); 19F NMR (CDCl3): -94.8ppm (m) (Ref. TFA.) << Ref. 0016>> m/e = 340.2046.<< Ref. 0016>>