Vitamin K

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Id	Image	COMMON NAME	NAME	DATA No	Lipid class	INFORMANT	SYMBOL	FORMULA	MOL.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
Id	Image	COMMON NAME	NAME	DATA No	Lipid class	INFORMANT	SYMBOL	FORMULA	MOL.WT(average)	Download cdx file / Mol format file	BIOOGICAL ACTIVITY	MELTING POINT	BOILING POINT	DENSITY	REFRACTIVE INDEX	OPTICAL ROTATION	SOLUBILITY	UV SPECTRA	IR SPECTRA	NMR SPECTRA	MASS SPECTRA	OTHER SPECTRA	CHROMATOGRAM DATA	SOURCE	CHEMICAL SYNTHESIS	METABOLISM	GENETIC INFORMATION	NOTE	REFERENCES
1		vitamin 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	VVK0001	Vitamin K	Tetsuya Nakamura	VK₁	C₃₁H₄₆O₂	450.696	Download 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 (II_a) 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 V_a and VIII_a [Table 0007] << Ref. 0006>>.	Yellow viscous oil << Ref. 0001>>			n²⁰_D=1.5263<< Ref. 0010>>	[a]²⁵_D=-28<< 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^%₁_c_m396, 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 C. 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)
2		Menaquinone 1.	1,4-Naphthalenedione, 2-methyl-3-(3-methyl-2-butenyl)- / 1,4-Naphthoquinone, 2-methyl-3-(3-methyl-2-butenyl)-	VVK0002	Vitamin K	Tetsuya Nakamura	MK-1	C₁₆H₁₆O₂	240.297	Download ChemDraw structure data					n²⁰_D=1.5840<< Ref. 0010>>			lmax, 248.5 mm, ¹^%₁_c_m =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 50. 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 -50. 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)
3		Menaquinone 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-	VVK0003	Vitamin K	Tetsuya Nakamura	MK-2	C₂₁H₂₄O₂	308.414	Download ChemDraw structure data		53<< Ref. 0010>>						E¹^%₁_c_m (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 50. 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 -50. 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)
4		Menaquinone 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)-	VVK0004	Vitamin K	Tetsuya Nakamura	MK-3	C₂₆H₃₂O₂	376.531	Download ChemDraw structure data		35C<< Ref. 0010>>			n²⁰_D=1.5588<< Ref. 0010>>			E¹^%₁_c_m (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 50. 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 -50. 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)
5		Menaquinone 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)-	VVK0005	Vitamin K	Tetsuya Nakamura	MK-4	C₃₁H₄₀O₂	444.648	Download 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>>	35C<< Ref. 0001>>						E¹^%₁_c_m (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 50. 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 -50. 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)
6		Menaquinone 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)-	VVK0006	Vitamin K	Tetsuya Nakamura	MK-5	C₃₆H₄₈O₂	512.765	Download ChemDraw structure data		39C << Ref. 0010>>						E¹^%₁_c_m (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 50. 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 -50. 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)
7		Menaquinone 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)-	VVK0007	Vitamin K	Tetsuya Nakamura	MK-6	C₄₁H₅₆O₂	580.882	Download ChemDraw structure data		50C<< Ref. 0010>>						E¹^%₁_c_m (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 50. 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 -50. 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)
8		Menaquinone 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)-	VVK0008	Vitamin K	Tetsuya Nakamura	MK-7	C₄₆H₆₄O₂	648.999	Download ChemDraw structure data		54C<< Ref. 0010>>						E¹^%₁_c_m (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 50. 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 -50. 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)
9		Menaquinone 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)-	VVK0009	Vitamin K	Tetsuya Nakamura	MK-8	C₅₁H₇₂O₂	717.116	Download ChemDraw structure data		56C<< Ref. 0010>>						E¹^%₁_c_m (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 50. 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 -50. 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)
10		Menaquinone 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)-	VVK0010	Vitamin K	Tetsuya Nakamura	MK-9	C₅₆H₈₀O₂	785.233	Download ChemDraw structure data		56-57C<< Ref. 0017>>						E¹^%₁_c_m (248mm) =246, in petroleum ether, 80-105<< 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 55 - 60 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. 56-57. << 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)-	VVK0011	Vitamin K	Tetsuya Nakamura	MK10	C₆₁H₈₈O₂	853.350	Download ChemDraw structure data								E¹^%₁_c_m (248mm) =224, in petroleum ether, b.p. 80-105.<< 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 55 - 60 under nitrogen. The crude product, m.p. 56., is chromatographed on Hostalen, yielding pure menaquinone-10 as fine yellow crystals, melting at 62. << 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.		VVK0012	Vitamin K	Tetsuya Nakamura	MK11	C₆₆H₉₆O₂	921.467	Download 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)
13		Menaquinone 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)-	VVK0013	Vitamin K	Tetsuya Nakamura	MK12	C₇₁H₁₀₄O₂	989.584	Download 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)
14		Menaquinone 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)-	VVK0014	Vitamin K	Tetsuya Nakamura	MK13	C₇₆H₁₁₂O₂	1057.701	Download 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)
15		Menaquinone 14/ Menaquinone MK14 / Vitamin K₂₍₇₀₎ / Vitamin MK14.		VVK0015	Vitamin K	Tetsuya Nakamura	MK14	C₈₁H₁₂₀O₂	1125.818	Download ChemDraw structure data
16		Vitamin 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	VVK0016	Vitamin K	Tetsuya Nakamura		C₃₁H₄₆O₃	466.695	Download ChemDraw structure data								uv max (95% alc): 259, 305 nm (log E_M 3.79, 3.31)<< Ref. 0026>>.