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Vitamin K

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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
1vitamin K1 / 3-phytylmenadione / phytomenadione / phylloquinone 2-Methyl-3-(3,7,11,15-tetramethyl-2-hexadecenyl)-1,4-naphthalenedione / 2-methyl-3-phytyl-1,4-naphthoquinone VVK0001Vitamin KTetsuya NakamuraVK1 C31H46O2 450.696Download ChemDraw structure data Involvement of vitamin K-dependent clotting factors in coagulation. The vitamin K-dependent proteins ( ellipses) circulate as inactive forms of serine proteases until converted to their active (subscript a) forms. These conversions occur in stages where an active protease, a substrate, and a protein cofactor (triangles) from a Ca2+-mediated association with a phospholipid surface. The protein cofactors V and VII are activated by thrombin (IIa) to achieve their full activity. The clotting system is traditionally divided into two pathways: the extrinsic pathway which involves a tissue factor (TO) in addition to blood components, and an intrinsic pathway, which involves components present in the blood. Protein C is activated by Ida in the presence of an endothelial cell protein called thrombomodulin (TM). Protein C is not a procoagulant but rather functions in a complex with protein S to inactivate Va and VIIIa [Table 0007] << Ref. 0006>>. Yellow viscous oil << Ref. 0001>> n20D=1.5263<< Ref. 0010>> [a]25D=-28deg<< Ref. 0001>>Optical rotation [Table 0001] << Ref. 0010>> Insol in water. Sparingly sol in methanol; sol in ethanol, acetone, benzene, petr ether, hexane, dioxane, chloroform, ether, other fat solvents and in vegetable oils<< Ref. 0001>> Uv max (petr ether) 242, 248, 260, 269, 325 nm (E1%1cm396, 419, 383, 387, 68) << Ref. 0001>>. Uv max (ethanol) 243, 248, 262, 270, 330 nm << Ref. 0002>>. [Spectrum 0001] << Ref. 0010>>Em at 248 nm (EtOH) =18,900 << Ref. 0002/0006>>. (liquid) : 6.05m (CO), 6.21, 6.28m (aromatic nucleus) << Ref. 0008>> [Spectrum 0002] << Ref. 0010>> [Table 0002] << Ref. 0010>> at 60 MHz in CDCl3, i nternal standard Si(CH3)4: multiplet at 453-486 Hz (4 aromatic H), triplet at 302 Hz (J=7 Hz) (olefinic H at C2. , doublet at 201 Hz ) (J=7 Hz) (CH2.-1), singlet at 130 Hz (CH3-2), signal at 107 Hz (trans-methyl group at C3. .<< Ref. 0008>> [Spectrum 0003] << Ref. 0010>> Proton magnetic resonance data [Table 0003] <<0010> [Spectrum 0004] << Ref. 0005>> The content of vitamin K1 (phylloquinone) was determined in 27 species of green vegetables by HPLC and correlation between Vitamin K1 content and chlorophyll content was investigated. The ratio of vitamin K1 to chlorophyll was about 9 mmol/mol. VK1 content (mg/100g fresh wt.): Parsley (0.73), Perilla (Leaves) (0.65), Ashitaba (Leaves) (0.59), Watercress (0.39), Toumyao (Chinese vegetable) (0.38), Mitsuba (Leaf stalk and leaves) (0.37) [Table 0004] << Ref. 0007>>
Vitamin K contents in human liver [Table 0005] << Ref. 0022>>
To a dichloromethane solution (20ml) of 2-methyl-1,4-naphthoquinone (172mg, 1.0mmol) BF3.Et2O (3.0mmol) was added under N2 at -78 degC. After that phytyltrimethyltin was (532mg, 1.2mmol) was added, and the temperature of the resulting solution was gradually elevated within 1h. Then, ether and aqueous saturated NaCl solution were added to the reaction mixture. The organic layer and the combined ether extract were dried over anhydrous magnesium sulfate. Subsequent oxidation with excess silver oxide gave crude vitamin K1 after solvent was evaporated in vacuo. The resulting crude product was purified by preparative TLC on silica gel; affording vitamin K1(176mg) << Ref. 0009>> [Table 0006] << Ref. 0008>>. The synthesis of prothrombin in Chinese hamster ovary cells stably transfected with the prothrombin c DNA by immunofluorescent staining. Uncarboxylated proprothrombin undergoes complete g- carboxylation in the endoplasmic reticulum and that g- carboxylation precedes propeptide cleavage during prothrombin biosynthesis << Ref. 0011>>. << Ref.0001 >> AUTHOR: Anonym. (1989) Vitamin K1 in The Merck Index , 11th edition (Budavari, S., O'Neil, M. J., Smith, A., and Heckelman, P.E., eds), pp1580, Merck & Co., Inc., Rahway, N. J. TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0002 >> AUTHOR: Dunphy,P.J., and Brodie,A.F. TITLE: The structure and function of quinones in respiratory metabolism. JOURNAL: Methods in Enzymology VOLUME: 18 PAGE: 407 -461 (1971)
<< Ref.0005 >> AUTHOR: Di Mari, S. J., Supple, J. H., and Rapoport, H. TITLE: Mass spectra of naphthoquinones. Vitamin K1(20) PubMed ID:5910960 JOURNAL: J Am Chem Soc. VOLUME: 88 PAGE: 1226-1232(1966)
<< Ref.0006 >> AUTHOR: Suttie,W.J. (1991) Vitamin K, in Handbook of Vitamins (2nd ed., Machlin,L.J., ed) , pp145-194, Marcel Dekker, Inc., New York TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0007 >> AUTHOR: Kodaka,K., Ujiie,T.,Ueno,T., and Saito,M. TITLE: Contents of Vitamin K1 and Chlorophyll in Green Vegetables. JOURNAL: J Jpn Soc Nutr Food Sci VOLUME: 39 PAGE: 124 -126 (1986)
<< Ref.0008 >> AUTHOR: Mayer,H., and Isler,O . TITLE: Synthesis of Vitamin K. JOURNAL: Methods in Enzymology VOLUME: 18 PAGE: 491 -547 (1971)
<< Ref.0009 >> AUTHOR: Naruta,Y., and Maruyama,K. TITLE: Regio- and sterocontrolled polyprenylation of quinones. A new synthetic method of vitamin K series. JOURNAL: Chemistry Lett VOLUME: PAGE: 881 -884 (1979)
<< Ref.0010 >> AUTHOR: Sommer,P., and Kofler,M. TITLE: Physicochemical Properties and Methods of Analysis of Phylloquinones, Menaquinones, Ubiquinones, and Related Compounds. PubMed ID:5340867 JOURNAL: Vitamins and Hormones VOLUME: 24 PAGE: 349 -399 (1966)
<< Ref.0011 >> AUTHOR: Bristol, J. A., Ratcliffe, J. V., Roth, D. A., Jacobs, M. A., Furie, B. C., and Furie, B. TITLE: Biosynthesis of prothrombin: intracellular localization of the vitamin K-dependent carboxylase and the sites of gamma-carboxylation PubMed ID:8839851 JOURNAL: Blood. VOLUME: 88 PAGE: 2585-2593(1996)
<< Ref.0022 >> AUTHOR: Usui, Y., Nishimura, N., Kobayashi, N., Okanoue, T., Kimoto, M., and Ozawa, K. TITLE: Measurement of vitamin K in human liver by gradient elution high-performance liquid chromatography using platinum-black catalyst reduction and fluorimetric detection PubMed ID:2753953 JOURNAL: J Chromatogr. VOLUME: 489 PAGE: 291-301(1989)
2Menaquinone 1. 1,4-Naphthalenedione, 2-methyl-3-(3-methyl-2-butenyl)- / 1,4-Naphthoquinone, 2-methyl-3-(3-methyl-2-butenyl)- VVK0002Vitamin KTetsuya NakamuraMK-1 C16H16O2 240.297Download ChemDraw structure data n20D=1.5840<< Ref. 0010>> lmax, 248.5 mm, 1%1cm =756<< Ref. 0010>> Condensation of 2-methyl-1,4-naphthohydroquinone (I) with methylbutenol (II). I (27.5g) is dissolved in 65 ml of dry dioxane, 1.5 g of zinc chloride, and 3.5 ml of borontrifluoride etherate are added with stirring, and the mixture is heated to 50deg. A solution of 0.87 mole of II per mole of I in 25 ml of dry dioxane is added, and the reaction mixture is stirred for 20 min longer. After cooling water and ether are added, the layers were separated and the etheral layer is washed. The ether solution is evaporated. The residue is dissolved in 200 ml of petroleum ether, the solution cooled to -50deg. The precipitate centrifuged. The precipitate dissolved in 100 ml of ether, 20 g of dry silver oxide is added and the mixture shaken for 30 min. After filtration the etheral solution is evaporated in vacuo, the residue dissolved in petroleum ether and chramatogphed. << Ref. 0017>> << Ref.0010 >> AUTHOR: Sommer,P., and Kofler,M. TITLE: Physicochemical Properties and Methods of Analysis of Phylloquinones, Menaquinones, Ubiquinones, and Related Compounds. PubMed ID:5340867 JOURNAL: Vitamins and Hormones VOLUME: 24 PAGE: 349 -399 (1966)
<< Ref.0017 >> AUTHOR: Mayer,H., and Isler,O. TITLE: Synthesis of vitamin K. JOURNAL: Methods in Enzymology VOLUME: 18 PAGE: 491 -547 (1971)
3Menaquinone 2 / Vitamin K2(10) 1,4-Naphthalenedione, 2-(3,7-dimethyl-2,6-octadienyl)-3-methyl- / 1,4-Naphthoquinone, 2-(3,7-dimethyl-2,6-octadienyl)-3-methyl- VVK0003Vitamin KTetsuya NakamuraMK-2 C21H24O2 308.414Download ChemDraw structure data 53deg<< Ref. 0010>> E1%1cm (248mm) =613-617, in ethanol ; petroleum ether<< Ref. 0010>> Condensation of 2-methyl-1,4-naphthohydroquinone (I) with linalool (II). I (27.5g) is dissolved in 65 ml of dry dioxane, 1.5 g of zinc chloride, and 3.5 ml of borontrifluoride etherate are added with stirring, and the mixture is heated to 50deg. A solution of 0.87 mole of II per mole of I in 25 ml of dry dioxane is added, and the reaction mixture is stirred for 20 min longer. After cooling water and ether are added, the layers were separated and the etheral layer is washed. The ether solution is evaporated. The residue is dissolved in 200 ml of petroleum ether, the solution cooled to -50deg. The precipitate centrifuged. The precipitate dissolved in 100 ml of ether, 20 g of dry silver oxide is added and the mixture shaken for 30 min. After filtration the etheral solution is evaporated in vacuo, the residue dissolved in petroleum ether and chramatogphed. << Ref. 0017>> << Ref.0010 >> AUTHOR: Sommer,P., and Kofler,M. TITLE: Physicochemical Properties and Methods of Analysis of Phylloquinones, Menaquinones, Ubiquinones, and Related Compounds. PubMed ID:5340867 JOURNAL: Vitamins and Hormones VOLUME: 24 PAGE: 349 -399 (1966)
<< Ref.0017 >> AUTHOR: Mayer,H., and Isler,O. TITLE: Synthesis of vitamin K. JOURNAL: Methods in Enzymology VOLUME: 18 PAGE: 491 -547 (1971)
4Menaquinone 3 / Vitamin K2(15)/ Vitamin MK3 1,4-Naphthalenedione, 2-methyl-3-(3,7,11-trimethyl-2,6,10-dodecatrienyl)- / 1,4-Naphthoquinone, 2-methyl-3-(3,7,11-trimethyl-2,6,10-dodecatrienyl)- VVK0004Vitamin KTetsuya NakamuraMK-3 C26H32O2 376.531Download ChemDraw structure data 35degC<< Ref. 0010>> n20D=1.5588<< Ref. 0010>> E1%1cm (248mm) =496, in petroleum ether<< Ref. 0010>> Condensation of 2-methyl-1,4-naphthohydroquinone (I) with nerolidol (II). I (27.5g) is dissolved in 65 ml of dry dioxane, 1.5 g of zinc chloride, and 3.5 ml of borontrifluoride etherate are added with stirring, and the mixture is heated to 50deg. A solution of 0.87 mole of II per mole of I in 25 ml of dry dioxane is added, and the reaction mixture is stirred for 20 min longer. After cooling water and ether are added, the layers were separated and the etheral layer is washed. The ether solution is evaporated. The residue is dissolved in 200 ml of petroleum ether, the solution cooled to -50deg. The precipitate centrifuged. The precipitate dissolved in 100 ml of ether, 20 g of dry silver oxide is added and the mixture shaken for 30 min. After filtration the etheral solution is evaporated in vacuo, the residue dissolved in petroleum ether and chramatogphed. << Ref. 0017>> << Ref.0010 >> AUTHOR: Sommer,P., and Kofler,M. TITLE: Physicochemical Properties and Methods of Analysis of Phylloquinones, Menaquinones, Ubiquinones, and Related Compounds. PubMed ID:5340867 JOURNAL: Vitamins and Hormones VOLUME: 24 PAGE: 349 -399 (1966)
<< Ref.0017 >> AUTHOR: Mayer,H., and Isler,O. TITLE: Synthesis of vitamin K. JOURNAL: Methods in Enzymology VOLUME: 18 PAGE: 491 -547 (1971)
5Menaquinone 4 / Vitamin K2(20) / Vitamin MK4 / Menaquinone MK4 / Kaytwo / Menatetrenone. 1,4-Naphthalenedione, 2-methyl-3-(3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenyl)- / 1,4-Naphthoquinone, 2-methyl-3-(3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenyl)- VVK0005Vitamin KTetsuya NakamuraMK-4 C31H40O2 444.648Download ChemDraw structure data Menatetrenone at greater than 3 x 10 -6 M significantly inhibited the calcium release from mouse calvaria induced by 2 x 10 -10M of 1,25 (OH)2D3 or 10 -7M of prostaglandin E2, and also inhibited osteoclast-like multinuleated cell formation induced by 10 -8M of 1,25(OH)2D3 in co-culture of spleen ells and stromal cells at the same concentrations. The inhibitory effect f menaterenone on the calcium release from calvaria was not affected by the addition of 3 x 10-5M of warfarin an inhibtor of vitamin K cycle. << Ref. 0018>> 35degC<< Ref. 0001>> E1%1cm (248mm) =438-440, in petroleum ether<< Ref. 0001>> Rats were made vitamin K-deficiency by feeding them diet devoid of vitamin K. after one week, circulating prothrombin concentrations were between 5 and 10% of initial values and various amounts of phylloquinone, menaquinone-4, and menaquinone-9 were given in a single dose either subcutaneously, orally, or colorectally. The relative 'vitamin K acitivties' of these compounds were assessed by comparing their activity to support prothrombin synthesis after subcutaneous injection. The stimulation of prothormbin synthesis by menaquinone-9 lasted much longer than that by the two other K-vitamers, resulting in a substantially higher 'vitamin K activity' of menaquinone-9.<< Ref. 0032>> [Table 0001] << Ref. 0032>> Condensation of 2-methyl-1,4-naphthohydroquinone (I) with geranyllinalool (II). I (27.5g) is dissolved in 65 ml of dry dioxane, 1.5 g of zinc chloride, and 3.5 ml of borontrifluoride etherate are added with stirring, and the mixture is heated to 50deg. A solution of 0.87 mole of II per mole of I in 25 ml of dry dioxane is added, and the reaction mixture is stirred for 20 min longer. After cooling water and ether are added, the layers were separated and the etheral layer is washed. The ether solution is evaporated. The residue is dissolved in 200 ml of petroleum ether, the solution cooled to -50deg. The precipitate centrifuged. The precipitate dissolved in 100 ml of ether, 20 g of dry silver oxide is added and the mixture shaken for 30 min. After filtration the etheral solution is evaporated in vacuo, the residue dissolved in petroleum ether and chramatogphed. << Ref. 0017>> Four metabolites of menaquinone-4 (MQ-4) were isolated from rat urine, bile and liver, and identified. On the basis of their structures, the metabolic pathways of MQ-4 are proposed as shown in [Table 0002]. This pathway begins with w-methyl oxidation of the side chain followed by b-oxidation of the resultant MQ-4-COOH to K acid 1 and K acid 2. In the presence of warfarin, 2,3-epoxy-phylloquinone. This suggests that 2,3-epoxy-MQ-4 is converted to MQ-4 in the normal rat and that the reaction is inhibited by warfarin.<< Ref. 0003>> << Ref.0001 >> AUTHOR: Anonym. (1989) Vitamin K1 in The Merck Index , 11th edition (Budavari, S., O'Neil, M. J., Smith, A., and Heckelman, P.E., eds), pp1580, Merck & Co., Inc., Rahway, N. J. TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0003 >> AUTHOR: Tadano, K., Yuzuriha, T., Sato, T., Fujita, T., Shimada, K., Hashimoto, K., and Satoh, T. TITLE: Identification of menaquinone-4 metabolites in the rat PubMed ID:2630633 JOURNAL: J Pharmacobiodyn. VOLUME: 12 PAGE: 640-645(1989)
<< Ref.0017 >> AUTHOR: Mayer,H., and Isler,O. TITLE: Synthesis of vitamin K. JOURNAL: Methods in Enzymology VOLUME: 18 PAGE: 491 -547 (1971)
<< Ref.0018 >> AUTHOR: Hara, K., Akiyama, Y., Nakamura, T., Murota, S., and Morita, I. TITLE: The inhibitory effect of vitamin K2 (menatetrenone) on bone resorption may be related to its side chain PubMed ID:7756045 JOURNAL: Bone. VOLUME: 16 PAGE: 179-184(1995)
<< Ref.0032 >> AUTHOR: Groenen-van Dooren, M. M., Ronden, J. E., Soute, B. A., and Vermeer, C. TITLE: Bioavailability of phylloquinone and menaquinones after oral and colorectal administration in vitamin K-deficient rats PubMed ID:7575640 JOURNAL: Biochem Pharmacol. VOLUME: 50 PAGE: 797-801(1995)
6Menaquinone 5 / Vitamin K2(25) / Vitamin MK5 / Menaquinone 5. 1,4-Naphthalenedione, 2-methyl-3-(3,7,11,15,19-pentamethyl-2,6,10,14,18-eicosapentaenyl)- / 1,4-Naphthoquinone, 2-methyl-3-(3,7,11,15,19-pentamethyl-2,6,10,14,18-eicosapentaenyl)- VVK0006Vitamin KTetsuya NakamuraMK-5 C36H48O2 512.765Download ChemDraw structure data 39degC << Ref. 0010>> E1%1cm (248mm) =363, in petroleum ether<< Ref. 0010>> Condensation of 2-methyl-1,4-naphthohydroquinone (I) with farnesyllinalool (II). I (27.5g) is dissolved in 65 ml of dry dioxane, 1.5 g of zinc chloride, and 3.5 ml of borontrifluoride etherate are added with stirring, and the mixture is heated to 50deg. A solution of 0.87 mole of II per mole of I in 25 ml of dry dioxane is added, and the reaction mixture is stirred for 20 min longer. After cooling water and ether are added, the layers were separated and the etheral layer is washed. The ether solution is evaporated. The residue is dissolved in 200 ml of petroleum ether, the solution cooled to -50deg. The precipitate centrifuged. The precipitate dissolved in 100 ml of ether, 20 g of dry silver oxide is added and the mixture shaken for 30 min. After filtration the etheral solution is evaporated in vacuo, the residue dissolved in petroleum ether and chramatogphed. << Ref. 0017>> << Ref.0010 >> AUTHOR: Sommer,P., and Kofler,M. TITLE: Physicochemical Properties and Methods of Analysis of Phylloquinones, Menaquinones, Ubiquinones, and Related Compounds. PubMed ID:5340867 JOURNAL: Vitamins and Hormones VOLUME: 24 PAGE: 349 -399 (1966)
<< Ref.0017 >> AUTHOR: Mayer,H., and Isler,O. TITLE: Synthesis of vitamin K. JOURNAL: Methods in Enzymology VOLUME: 18 PAGE: 491 -547 (1971)
7Menaquinone 6 / Vitamin K2(30)/ Vitamin MK6 / Menaquinone K6 / Farnoquinone. 1,4-Naphthalenedione,2-methyl-3-(3,7,11,15,19,23-hexamethyl-2,6,10,14,18,22-tetracosahexaenyl)- / 1,4-Naphthoquinone,2-methyl-3-(3,7,11,15,19,23--hexamethyl-2,6,10,14,18,22-tetracosahexaenyl)- VVK0007Vitamin KTetsuya NakamuraMK-6 C41H56O2 580.882Download ChemDraw structure data 50degC<< Ref. 0010>> E1%1cm (248mm) =320-321, in petroleum ether<< Ref. 0010>> Condensation of 2-methyl-1,4-naphthohydroquinone (I) with farnesylnerolidol (II). I (27.5g) is dissolved in 65 ml of dry dioxane, 1.5 g of zinc chloride, and 3.5 ml of borontrifluoride etherate are added with stirring, and the mixture is heated to 50deg. A solution of 0.87 mole of II per mole of I in 25 ml of dry dioxane is added, and the reaction mixture is stirred for 20 min longer. After cooling water and ether are added, the layers were separated and the etheral layer is washed. The ether solution is evaporated. The residue is dissolved in 200 ml of petroleum ether, the solution cooled to -50deg. The precipitate centrifuged. The precipitate dissolved in 100 ml of ether, 20 g of dry silver oxide is added and the mixture shaken for 30 min. After filtration the etheral solution is evaporated in vacuo, the residue dissolved in petroleum ether and chramatogphed. << Ref. 0017>> << Ref.0010 >> AUTHOR: Sommer,P., and Kofler,M. TITLE: Physicochemical Properties and Methods of Analysis of Phylloquinones, Menaquinones, Ubiquinones, and Related Compounds. PubMed ID:5340867 JOURNAL: Vitamins and Hormones VOLUME: 24 PAGE: 349 -399 (1966)
<< Ref.0017 >> AUTHOR: Mayer,H., and Isler,O. TITLE: Synthesis of vitamin K. JOURNAL: Methods in Enzymology VOLUME: 18 PAGE: 491 -547 (1971)
8Menaquinone 7 / Vitamin K2 (35)/ Vitamin MK7 / Menaquinone K7. 1,4-Naphthalenedione,2-methyl-3-(3,7,11,15,19,23,27-heptamethyl-2,6,10,14,18,22,26-octacosaheptaenyl)- / 1,4-Naphthoquinone,2-methyl-3-(3,7,11,15,19,23,27-heptamethyl-2,6,10,14,18,22,26-octacosaheptaenyl)- VVK0008Vitamin KTetsuya NakamuraMK-7 C46H64O2 648.999Download ChemDraw structure data 54degC<< Ref. 0010>> E1%1cm (248mm) =292-295, in petroleum ether<< Ref. 0010>>
UV [Spectrum 0001] << Ref. 0010>>
[Spectrum 0002] << Ref. 0010>> [Spectrum 0003] << Ref. 0010>> UV specra [Table 0001], IR spectra [Table 0002], NMR spectra [Table 0003]. [Table 0001] << Ref. 0022>> Condensation of 2-methyl-1,4-naphthohydroquinone (I) with farnesylgeranyllinalool (II). I (27.5g) is dissolved in 65 ml of dry dioxane, 1.5 g of zinc chloride, and 3.5 ml of borontrifluoride etherate are added with stirring, and the mixture is heated to 50deg. A solution of 0.87 mole of II per mole of I in 25 ml of dry dioxane is added, and the reaction mixture is stirred for 20 min longer. After cooling water and ether are added, the layers were separated and the etheral layer is washed. The ether solution is evaporated. The residue is dissolved in 200 ml of petroleum ether, the solution cooled to -50deg. The precipitate centrifuged. The precipitate dissolved in 100 ml of ether, 20 g of dry silver oxide is added and the mixture shaken for 30 min. After filtration the etheral solution is evaporated in vacuo, the residue dissolved in petroleum ether and chramatogphed. << Ref. 0017>> << Ref.0010 >> AUTHOR: Sommer,P., and Kofler,M. TITLE: Physicochemical Properties and Methods of Analysis of Phylloquinones, Menaquinones, Ubiquinones, and Related Compounds. PubMed ID:5340867 JOURNAL: Vitamins and Hormones VOLUME: 24 PAGE: 349 -399 (1966)
<< Ref.0017 >> AUTHOR: Mayer,H., and Isler,O. TITLE: Synthesis of vitamin K. JOURNAL: Methods in Enzymology VOLUME: 18 PAGE: 491 -547 (1971)
<< Ref.0022 >> AUTHOR: Usui, Y., Nishimura, N., Kobayashi, N., Okanoue, T., Kimoto, M., and Ozawa, K. TITLE: Measurement of vitamin K in human liver by gradient elution high-performance liquid chromatography using platinum-black catalyst reduction and fluorimetric detection PubMed ID:2753953 JOURNAL: J Chromatogr. VOLUME: 489 PAGE: 291-301(1989)
9Menaquinone 8 / Menaquinone MK8/ Vitamin K2(40)/ Vitamin MK8. 1,4-Naphthalenedione,2-methyl-3-(3,7,11,15,19,23,27,31-octamethyl-2,6,10,14,18,22,26,30-dotriacontaoctaenyl)- / 1,4-Naphthoquinone,2-methyl-3-(3,7,11,15,19,23,27,31-octamethyl-2,6,10,14,18,22,26,30-dotriacontaoctaenyl)- VVK0009Vitamin KTetsuya NakamuraMK-8 C51H72O2 717.116Download ChemDraw structure data 56degC<< Ref. 0010>> E1%1cm (248mm)= 268, in petroleum ether<< Ref. 0010>> [Table 0001] << Ref. 0022>>
[Table 0002] << Ref. 0022>>
Condensation of 2-methyl-1,4-naphthohydroquinone (I) with farnesylfarnesyllinalool (II). I (27.5g) is dissolved in 65 ml of dry dioxane, 1.5 g of zinc chloride, and 3.5 ml of borontrifluoride etherate are added with stirring, and the mixture is heated to 50deg. A solution of 0.87 mole of II per mole of I in 25 ml of dry dioxane is added, and the reaction mixture is stirred for 20 min longer. After cooling water and ether are added, the layers were separated and the etheral layer is washed. The ether solution is evaporated. The residue is dissolved in 200 ml of petroleum ether, the solution cooled to -50deg. The precipitate centrifuged. The precipitate dissolved in 100 ml of ether, 20 g of dry silver oxide is added and the mixture shaken for 30 min. After filtration the etheral solution is evaporated in vacuo, the residue dissolved in petroleum ether and chramatogphed. << Ref. 0017>> [Table 0001] << Ref.0010 >> AUTHOR: Sommer,P., and Kofler,M. TITLE: Physicochemical Properties and Methods of Analysis of Phylloquinones, Menaquinones, Ubiquinones, and Related Compounds. PubMed ID:5340867 JOURNAL: Vitamins and Hormones VOLUME: 24 PAGE: 349 -399 (1966)
<< Ref.0017 >> AUTHOR: Mayer,H., and Isler,O. TITLE: Synthesis of vitamin K. JOURNAL: Methods in Enzymology VOLUME: 18 PAGE: 491 -547 (1971)
<< Ref.0022 >> AUTHOR: Usui, Y., Nishimura, N., Kobayashi, N., Okanoue, T., Kimoto, M., and Ozawa, K. TITLE: Measurement of vitamin K in human liver by gradient elution high-performance liquid chromatography using platinum-black catalyst reduction and fluorimetric detection PubMed ID:2753953 JOURNAL: J Chromatogr. VOLUME: 489 PAGE: 291-301(1989)
10Menaquinone 9 / Menaquinone MK9 / Vitamin K2 (45) / Vitamin MK9. 1,4-Naphthalenedione,2-methyl-3-(3,7,11,15,19,23,27,31,35-nonamethyl-2,6,10,14,18,22,26,30,34-hexatriacontanonaenyl)- / 1,4-Naphthoquinone,2-methyl-3-(3,7,11,15,19,23,27,31,35-nonamethyl-2,6,10,14,18,22,26,30,34-hexatriacontanonaenyl)- VVK0010Vitamin KTetsuya NakamuraMK-9 C56H80O2 785.233Download ChemDraw structure data 56-57degC<< Ref. 0017>> E1%1cm (248mm) =246, in petroleum ether, 80deg-105deg<< Ref. 0017>> [Table 0001] << Ref. 0022>>
[Table 0002] << Ref. 0022>>
Seven grams of 2-methyl-1,4-naphthohydroquinone (I) is dissolved in 50 ml of dry dioxane, 0.5 g of zinc chloride and 1 ml of boron trifluoride etherate in 65 ml of dry dioxane, 1.5 g of zinc chloride of borontrifluoride etherate are added with stirring, and the mixture is heated to 55deg - 60deg under nitrogen. A solution of 7.5 g of solanesol in 30 ml of dry dioxane is added, and the reaction mixture is stirred for 1 hour longer. After cooling water and ether are added, the layers were separated and the etheral layer is washed. The ether solution is evaporated. The residue is dissolved in 200 ml of ether, 10 g of dry silver oxide is added and the mixture shaken for 30 min. After filtration the etheral solution is evaporated in vacuo, the residue dissolved in petroleum ether and chramatogphed through a colum of aluminum oxide. Yield : 120 mg. m.p. 56deg-57deg. << Ref. 0017>> Rats were made vitamin K-deficiency by feeding them diet devoid of vitamin K. after one week, circulating prothrombin concentrations were between 5 and 10% of initial values and various amounts of phylloquinone, menaquinone-4, and menaquinone-9 were given in a single dose either subcutaneously, orally, or colorectally. The relative 'vitamin K acitivties' of these compounds were assessed by comparing their activity to support prothrombin synthesis after subcutaneous injection. The stimulation of prothormbin synthesis by menaquinone-9 lasted much longer than that by the two other K-vitamers, resulting in a substantially higher 'vitamin K activity' of menaquinone-9.<< Ref. 0032>> [Table 0003] << Ref. 0032>> << Ref.0017 >> AUTHOR: Mayer,H., and Isler,O. TITLE: Synthesis of vitamin K. JOURNAL: Methods in Enzymology VOLUME: 18 PAGE: 491 -547 (1971)
<< Ref.0022 >> AUTHOR: Usui, Y., Nishimura, N., Kobayashi, N., Okanoue, T., Kimoto, M., and Ozawa, K. TITLE: Measurement of vitamin K in human liver by gradient elution high-performance liquid chromatography using platinum-black catalyst reduction and fluorimetric detection PubMed ID:2753953 JOURNAL: J Chromatogr. VOLUME: 489 PAGE: 291-301(1989)
<< Ref.0032 >> AUTHOR: Groenen-van Dooren, M. M., Ronden, J. E., Soute, B. A., and Vermeer, C. TITLE: Bioavailability of phylloquinone and menaquinones after oral and colorectal administration in vitamin K-deficient rats PubMed ID:7575640 JOURNAL: Biochem Pharmacol. VOLUME: 50 PAGE: 797-801(1995)
11 Menaquinone 10 / Menaquinone MK10 / Vitamin K2(50) / Vitamin MK10. 1,4-Naphthalenedione,2-methyl-3-(3,7,11,15,19,23,27,31,35,39-decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecaenyl)- / 1,4-Naphthoquinone,2-methyl-3-(3,7,11,15,19,23,27,31,35,39-decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecaenyl)- VVK0011Vitamin KTetsuya NakamuraMK10 C61H88O2 853.350Download ChemDraw structure data E1%1cm (248mm) =224, in petroleum ether, b.p. 80deg-105deg.<< Ref. 0017>> Concentration in human liver [Table 0001] << Ref. 0022>>.
Distribution in human mitochondrial and microsomal fractions [Table 0002] << Ref. 0022>>.
Menaquinone-10 << Ref. 0011>> is prepared in analogy to menaquinone-9 << Ref. 0010>> from 7g of farnesylfarnesylgeranyllinalool, 7 g of 2-methyl-1,4-naphthohydroquinone (I) is dissolved in 50 ml of dry dioxane, 0.5 g of zinc chloride and 1 ml of boron trifluoride etherate in 65 ml of dry dioxane, 1.5 g of zinc chloride of borontrifluoride etherate are added with stirring, and the mixture is heated to 55deg - 60deg under nitrogen. The crude product, m.p. 56deg., is chromatographed on Hostalen, yielding pure menaquinone-10 as fine yellow crystals, melting at 62deg. << Ref. 0017>> << Ref.0010 >> AUTHOR: Sommer,P., and Kofler,M. TITLE: Physicochemical Properties and Methods of Analysis of Phylloquinones, Menaquinones, Ubiquinones, and Related Compounds. PubMed ID:5340867 JOURNAL: Vitamins and Hormones VOLUME: 24 PAGE: 349 -399 (1966)
<< Ref.0011 >> AUTHOR: Bristol, J. A., Ratcliffe, J. V., Roth, D. A., Jacobs, M. A., Furie, B. C., and Furie, B. TITLE: Biosynthesis of prothrombin: intracellular localization of the vitamin K-dependent carboxylase and the sites of gamma-carboxylation PubMed ID:8839851 JOURNAL: Blood. VOLUME: 88 PAGE: 2585-2593(1996)
<< Ref.0017 >> AUTHOR: Mayer,H., and Isler,O. TITLE: Synthesis of vitamin K. JOURNAL: Methods in Enzymology VOLUME: 18 PAGE: 491 -547 (1971)
<< Ref.0022 >> AUTHOR: Usui, Y., Nishimura, N., Kobayashi, N., Okanoue, T., Kimoto, M., and Ozawa, K. TITLE: Measurement of vitamin K in human liver by gradient elution high-performance liquid chromatography using platinum-black catalyst reduction and fluorimetric detection PubMed ID:2753953 JOURNAL: J Chromatogr. VOLUME: 489 PAGE: 291-301(1989)
12 Menaquinone 11/ Menaquinone MK11 / Vitamin K2(55) / Vitamin MK11. VVK0012Vitamin KTetsuya NakamuraMK11 C66H96O2 921.467Download ChemDraw structure data Concentration in human liver [Table 0001] << Ref. 0022>>.
Distribution in human mitochondrial and microsomal fractions [Table 0002] << Ref. 0022>>.
<< Ref.0022 >> AUTHOR: Usui, Y., Nishimura, N., Kobayashi, N., Okanoue, T., Kimoto, M., and Ozawa, K. TITLE: Measurement of vitamin K in human liver by gradient elution high-performance liquid chromatography using platinum-black catalyst reduction and fluorimetric detection PubMed ID:2753953 JOURNAL: J Chromatogr. VOLUME: 489 PAGE: 291-301(1989)
13Menaquinone 12/ Menaquinone MK12 / Vitamin K2(60) / Vitamin MK12. 1,4-Naphthalenedione, 2-methyl-3-2-(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)-/ 1,4-Naphthoquinone, 2-methyl-3-2-(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)- VVK0013Vitamin KTetsuya NakamuraMK12 C71H104O2 989.584Download ChemDraw structure data Concentration in human liver [Table 0001] << Ref. 0022>>.
Distribution in human mitochondrial and microsomal fractions [Table 0002] << Ref. 0022>>.
<< Ref.0022 >> AUTHOR: Usui, Y., Nishimura, N., Kobayashi, N., Okanoue, T., Kimoto, M., and Ozawa, K. TITLE: Measurement of vitamin K in human liver by gradient elution high-performance liquid chromatography using platinum-black catalyst reduction and fluorimetric detection PubMed ID:2753953 JOURNAL: J Chromatogr. VOLUME: 489 PAGE: 291-301(1989)
14Menaquinone 13/ Menaquinone MK13 / Vitamin K2(65) / Vitamin MK13. 1,4-Naphthalenedione, 2-methyl-3-2-(3,7,11,15,19,23,27,31,35,39,43,47,51-tridecamethyl- 2,6,10,14,18, 22,26,30,34,38,42,46-octatetracontadodecaenyl)-/ 1,4-Naphthoquinone, 2-methyl-3-2-(3,7,11,15,19,23,27,31,35,39,43,47,51-tridecamethyl- 2,6,10,14,18, 22,26,30,34,38,42,46,50-dopentacontatridecaenyl)- VVK0014Vitamin KTetsuya NakamuraMK13 C76H112O2 1057.701Download ChemDraw structure data Human liver MK-13 concentration was determined by HPLC using platinum-back catalyst reduction and fluorimetric detection [Table 0001] << Ref. 0022>>. MK-13 concentrations in human mitochondrial and microsomal fractions were analyzed by the same procedure [Table 0002] << Ref. 0022>>. << Ref.0022 >> AUTHOR: Usui, Y., Nishimura, N., Kobayashi, N., Okanoue, T., Kimoto, M., and Ozawa, K. TITLE: Measurement of vitamin K in human liver by gradient elution high-performance liquid chromatography using platinum-black catalyst reduction and fluorimetric detection PubMed ID:2753953 JOURNAL: J Chromatogr. VOLUME: 489 PAGE: 291-301(1989)
15Menaquinone 14/ Menaquinone MK14 / Vitamin K2(70) / Vitamin MK14. VVK0015Vitamin KTetsuya NakamuraMK14 C81H120O2 1125.818Download ChemDraw structure data
16Vitamin K1 2,3-oxide / Vitamin K1 2,3-epoxide / 1,4-Naphthoquinone, 2,3-epoxy2,3-dihydro-2-methyl-3-phytyl- / 2,3-Epoxyphylloquinone / Phylloquinone oxide / Phylloquinone, epoxide / Phylloquinone-2,3-epoxide. 1a, 7a-Dihydro-7a-methyl-1a-(3,7,11,15-tetramethyl-2-hexadecyl)naphth[2,3-b]oxirene-2,7-dione / 2-methyl-3-phytyl1,4-naphthoquinone 2,3-oxide VVK0016Vitamin KTetsuya Nakamura C31H46O3 466.695Download ChemDraw structure data uv max (95% alc): 259, 305 nm (log EM 3.79, 3.31)<< Ref. 0026>>.