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Menaquinone

CAS No.:
11032-49-8
Catalog Number:
AG01EH3B
Molecular Formula:
Molecular Weight:
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Purity
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Product Description
Catalog Number:
AG01EH3B
Chemical Name:
Menaquinone
CAS Number:
11032-49-8
MDL Number:
MFCD00079646
IUPAC Name:
2-methyl-3-[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenyl]naphthalene-1,4-dione
InChI:
InChI=1S/C31H40O2/c1-22(2)12-9-13-23(3)14-10-15-24(4)16-11-17-25(5)20-21-27-26(6)30(32)28-18-7-8-19-29(28)31(27)33/h7-8,12,14,16,18-20H,9-11,13,15,17,21H2,1-6H3/b23-14+,24-16+,25-20+
InChI Key:
DKHGMERMDICWDU-GHDNBGIDSA-N
EC Number:
234-264-5
UNII:
27Y876D139
Properties
Complexity:
855  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
3  
Exact Mass:
444.303g/mol
Formal Charge:
0
Heavy Atom Count:
33  
Hydrogen Bond Acceptor Count:
2  
Hydrogen Bond Donor Count:
0
Isotope Atom Count:
0
Molecular Weight:
444.659g/mol
Monoisotopic Mass:
444.303g/mol
Rotatable Bond Count:
11  
Topological Polar Surface Area:
34.1A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
8.9  
Literature
Title Journal
Vitamin K2, a menaquinone present in dairy products targets castration-resistant prostate cancer cell-line by activating apoptosis signaling. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20180501
Biosynthesis and Regulation of Sulfomenaquinone, a Metabolite Associated with Virulence in Mycobacterium tuberculosis. ACS infectious diseases 20161111
Vitamin K2 regression aortic calcification induced by warfarin via Gas6/Axl survival pathway in rats. European journal of pharmacology 20160905
[A New Horizon in Vitamin K Research]. Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan 20160101
Plasma vitamin K concentrations depend on CYP4F2 polymorphism and influence on anticoagulation in Japanese patients with warfarin therapy. Thrombosis research 20150501
Cytochrome P450-dependent catabolism of vitamin K: ω-hydroxylation catalyzed by human CYP4F2 and CYP4F11. Biochemistry 20131119
Warfarin induces cardiovascular damage in mice. Arteriosclerosis, thrombosis, and vascular biology 20131101
The synergistic antitumor activity of arsenic trioxide and vitamin K2 in HL-60 cells involves increased ROS generation and regulation of the ROS-dependent MAPK signaling pathway. Die Pharmazie 20131001
UBIAD1-mediated vitamin K2 synthesis is required for vascular endothelial cell survival and development. Development (Cambridge, England) 20130415
Vitamin E decreases extra-hepatic menaquinone-4 concentrations in rats fed menadione or phylloquinone. Molecular nutrition & food research 20120601
Structure-activity relationship of novel menaquinone-4 analogues: modification of the side chain affects their biological activities. Journal of medicinal chemistry 20120223
Prevention of bone loss in children receiving long-term glucocorticoids with calcium and alfacalcidol or menatetrenone. Journal of pediatric endocrinology & metabolism : JPEM 20120101
PROX1 suppresses vitamin K-induced transcriptional activity of Steroid and Xenobiotic Receptor. Genes to cells : devoted to molecular & cellular mechanisms 20111101
Effect of GGCX gene polymorphism on the responses of serum undercarboxylated osteocalcin and bone turnover markers after treatment with vitamin K2 (menatetrenone) among postmenopausal Thai women. Journal of bone and mineral metabolism 20110901
Synthesis of new vitamin K analogues as steroid and xenobiotic receptor (SXR) agonists: insights into the biological role of the side chain part of vitamin K. Journal of medicinal chemistry 20110714
Cesiribacter andamanensis gen. nov., sp. nov., isolated from a soil sample from a mud volcano. International journal of systematic and evolutionary microbiology 20110701
Bone cell activity responsive drug release from biodegradable apatite/collagen nano-composite cements--in vitro dissolution medium responsive vitamin K2 release. Colloids and surfaces. B, Biointerfaces 20110701
Synthesis of novel vitamin K2 analogues with modification at the ω-terminal position and their biological evaluation as potent steroid and xenobiotic receptor (SXR) agonists. Journal of medicinal chemistry 20110623
Modelling the atypical absorption of menatetrenone and the metabolism to its epoxide: effect of VKORC1 polymorphism. Journal of clinical pharmacy and therapeutics 20110601
Effects of long-term vitamin K(1) (phylloquinone) or vitamin K(2) (menaquinone-4) supplementation on body composition and serum parameters in rats. Bone 20110501
Plasma vitamin K concentration in horses supplemented with several vitamin K homologs. Journal of animal science 20110401
A comparative effectiveness study of bone density changes in women over 40 following three bone health plans containing variations of the same novel plant-sourced calcium. International journal of medical sciences 20110101
Chemoprevention of chemically-induced biliary carcinogenesis in hamsters by vitamin K2. Hepato-gastroenterology 20110101
The prevention of hip fracture with menatetrenone and risedronate plus calcium supplementation in elderly patients with Alzheimer disease: a randomized controlled trial. The Kurume medical journal 20110101
Menaquinone-4 enhances testosterone production in rats and testis-derived tumor cells. Lipids in health and disease 20110101
Intraerythrocytic stages of Plasmodium falciparum biosynthesize menaquinone. FEBS letters 20101201
Identification of UBIAD1 as a novel human menaquinone-4 biosynthetic enzyme. Nature 20101104
Age- and brain region-specific effects of dietary vitamin K on myelin sulfatides. The Journal of nutritional biochemistry 20101101
[Dementia and fracture]. Clinical calcium 20100901
Colloid formation by drugs in simulated intestinal fluid. Journal of medicinal chemistry 20100527
Structure-activity relationships in the conversion of vitamin K analogues into menaquinone-4. Substrates essential to the synthesis of menaquinone-4 in cultured human cell lines. Bioorganic & medicinal chemistry 20100501
Inhibitory effect of vitamin K(2) on interleukin-1beta-stimulated proliferation of human osteoblasts. Biological & pharmaceutical bulletin 20100101
Vitamin K promotes mineralization, osteoblast-to-osteocyte transition, and an anticatabolic phenotype by {gamma}-carboxylation-dependent and -independent mechanisms. American journal of physiology. Cell physiology 20091201
[In vivo metabolism of vitamin K: in relation to the conversion of vitamin K1 to MK-4]. Clinical calcium 20091201
Phenobarbital (PB)-induced changes in blood coagulationrelated parameters in pregnant rats, lactating rats and pups. The Journal of toxicological sciences 20091201
Prior treatment with vitamin K(2) significantly improves the efficacy of risedronate. Osteoporosis international : a journal established as result of cooperation between the European Foundation for Osteoporosis and the National Osteoporosis Foundation of the USA 20091101
Enzymatic activity of the alternative complex III as a menaquinol:auracyanin oxidoreductase in the electron transfer chain of Chloroflexus aurantiacus. FEBS letters 20091006
Inhibition of matrix metalloproteinase expression by menatetrenone, a vitamin K2 analogue. Oncology reports 20090901
Vitamin K to prevent fractures in older women: systematic review and economic evaluation. Health technology assessment (Winchester, England) 20090901
Combination of vitamin K2 and angiotensin-converting enzyme inhibitor ameliorates cumulative recurrence of hepatocellular carcinoma. Journal of hepatology 20090801
Vitamin K prevents oxidative cell death by inhibiting activation of 12-lipoxygenase in developing oligodendrocytes. Journal of neuroscience research 20090701
Vitamin K treatment reduces undercarboxylated osteocalcin but does not alter bone turnover, density, or geometry in healthy postmenopausal North American women. Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research 20090601
Elucidation of the mechanism producing menaquinone-4 in osteoblastic cells. Bioorganic & medicinal chemistry letters 20090215
Short-term menatetrenone therapy increases gamma-carboxylation of osteocalcin with a moderate increase of bone turnover in postmenopausal osteoporosis: a randomized prospective study. Journal of bone and mineral metabolism 20090101
Collagen-related abnormalities, reduction in bone quality, and effects of menatetrenone in rats with a congenital ascorbic acid deficiency. Journal of bone and mineral metabolism 20090101
Vitamin K2 suppresses proliferation and motility of hepatocellular carcinoma cells by activating steroid and xenobiotic receptor. Endocrine journal 20090101
Prevention of hip fractures by exposure to sunlight and pharmacotherapy in patients with Alzheimer's disease. Aging clinical and experimental research 20090101
Effect of oxyethylene numbers on the pharmacokinetics of menatetrenone incorporated in oil-in-water lipid emulsions prepared with polyoxyethylene-polyoxypropylene block copolymers and soybean oil in rats. Biological & pharmaceutical bulletin 20081201
Vitamin E and K interactions--a 50-year-old problem. Nutrition reviews 20081101
Effect of oil-in-water lipid emulsions prepared with fish oil or soybean oil on the growth of MCF-7 cells and HepG2 cells. The Journal of pharmacy and pharmacology 20080801
Anticoagulant effect of sodium dehydroacetate (DHA-S) in rats. Journal of applied toxicology : JAT 20080501
Conversion of phylloquinone (Vitamin K1) into menaquinone-4 (Vitamin K2) in mice: two possible routes for menaquinone-4 accumulation in cerebra of mice. The Journal of biological chemistry 20080425
[Assessment of bone quality. Effects of bisphosphonates, raloxifene, alfacalcidol, and menatetrenone on bone quality: collagen cross-links, mineralization, and microdamage]. Clinical calcium 20080301
Low plasma phylloquinone concentration is associated with high incidence of vertebral fracture in Japanese women. Journal of bone and mineral metabolism 20080101
Effects of the blood coagulation vitamin K as an inhibitor of arterial calcification. Thrombosis research 20080101
Vitamin K content of foods and dietary vitamin K intake in Japanese young women. Journal of nutritional science and vitaminology 20071201
Vitamin K induces osteoblast differentiation through pregnane X receptor-mediated transcriptional control of the Msx2 gene. Molecular and cellular biology 20071101
[Vitamin K metabolism. Menaquinone-4 (MK-4) formation from ingested VK analogues and its potent relation to bone function]. Clinical calcium 20071101
Vitamin K2 induces phosphorylation of protein kinase A and expression of novel target genes in osteoblastic cells. Journal of molecular endocrinology 20071001
Simple and sensitive determination of menatetrenone and its epoxide metabolite in human plasma. Journal of pharmaceutical and biomedical analysis 20070903
Prevention of hepatocarcinogenesis with phosphatidylcholine and menaquinone-4: in vitro and in vivo experiments. Journal of hepatology 20070701
Determination of vitamin K homologues by high-performance liquid chromatography with on-line photoreactor and peroxyoxalate chemiluminescence detection. Analytica chimica acta 20070522
Menatetrenone, a vitamin K2 analogue, inhibits hepatocellular carcinoma cell growth by suppressing cyclin D1 expression through inhibition of nuclear factor kappaB activation. Clinical cancer research : an official journal of the American Association for Cancer Research 20070401
Synergistic growth inhibition by acyclic retinoid and vitamin K2 in human hepatocellular carcinoma cells. Cancer science 20070301
[Suspicious case of epidural hematoma due to coagulopathy caused by vitamin K deficiency associated with antibiotics]. Masui. The Japanese journal of anesthesiology 20070201
Comparative uptake, metabolism, and utilization of menaquinone-4 and phylloquinone in human cultured cell lines. Bioorganic & medicinal chemistry 20061001
Microsphere-based protease assays and screening application for lethal factor and factor Xa. Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501
Menadione is a metabolite of oral vitamin K. The British journal of nutrition 20060201
Pleiotropic actions of vitamin K: protector of bone health and beyond? Nutrition (Burbank, Los Angeles County, Calif.) 20060101
Geranylgeranylacetone inhibits formation and function of human osteoclasts and prevents bone loss in tail-suspended rats and ovariectomized rats. Calcified tissue international 20051201
Vitamins K2, K3 and K5 exert in vivo antitumor effects on hepatocellular carcinoma by regulating the expression of G1 phase-related cell cycle molecules. International journal of oncology 20050801
The secondary electron acceptor of photosystem I in Gloeobacter violaceus PCC 7421 is menaquinone-4 that is synthesized by a unique but unknown pathway. FEBS letters 20050704
Determination of plasma Vitamin K by high-performance liquid chromatography with fluorescence detection using Vitamin K analogs as internal standards. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20050225
Method for the determination of vitamin K homologues in human plasma using high-performance liquid chromatography-tandem mass spectrometry. Analytical chemistry 20050201
[Therapy for ROD and measurement of the bone mass]. Clinical calcium 20041201
Effects of vitamin K2 (menatetrenone) and alendronate on bone mineral density and bone strength in rats fed a low-magnesium diet. Bone 20041101
Histochemical evaluation for the biological effect of menatetrenone on metaphyseal trabeculae of ovariectomized rats. Bone 20041001
Quinones as antimycobacterial agents. Bioorganic & medicinal chemistry 20040915
Prolonged circulation of menatetrenone by emulsions with hydrogenated castor oils in rats. Journal of controlled release : official journal of the Controlled Release Society 20040220
Impaired gamma carboxylation of osteocalcin in elderly women with type II diabetes mellitus: relationship between increase in undercarboxylated osteocalcin levels and low bone mineral density. Journal of bone and mineral metabolism 20040101
High serum levels of menatetrenone in male patients with ossification of the posterior longitudinal ligament. Spine 20030815
Novel role of vitamin k in preventing oxidative injury to developing oligodendrocytes and neurons. The Journal of neuroscience : the official journal of the Society for Neuroscience 20030702
Effects of menatetrenone on the bone and serum levels of vitamin K2 (menaquinone derivatives) in osteopenia induced by phenytoin in growing rats. Nutrition (Burbank, Los Angeles County, Calif.) 20030501
Effect of particle size on the pharmacokinetics of menatetrenone incorporated in O/W lipid emulsions prepared with hydrogenated castor oils and soybean oil in rats. Journal of drug targeting 20030501
Vitamin K stimulates osteoblastogenesis and inhibits osteoclastogenesis in human bone marrow cell culture. The Journal of endocrinology 20030301
Effect of oxyethylene moieties in hydrogenated castor oil on the pharmacokinetics of menatetrenone incorporated in O/W lipid emulsions prepared with hydrogenated castor oil and soybean oil in rats. Journal of drug targeting 20030101
Tissue-specific utilization of menaquinone-4 results in the prevention of arterial calcification in warfarin-treated rats. Journal of vascular research 20030101
Effect of eicosapentaenoic acid in patients with refractory myelodysplastic syndrome. American journal of hematology 20021201
[Pharmacotherapy of osteoporosis]. Nihon yakurigaku zasshi. Folia pharmacologica Japonica 20021201
A calcium-deficient diet caused decreased bone mineral density and secondary elevation of estrogen in aged male rats-effect of menatetrenone and elcatonin. Metabolism: clinical and experimental 20021001
Effect of oxyethylene moiety in polyoxyethylene sorbitan esters on the pharmacokinetics of menatetrenone incorporated in O/W lipid emulsions prepared with polyoxyethylene sorbitan esters and soybean oil in rats. The Journal of pharmacy and pharmacology 20021001
A comparison of alfacalcidol and menatetrenone for the treatment of bone loss in an ovariectomized rat model of osteoporosis. Calcified tissue international 20020701
Vitamin K supplementation does not affect ovariectomy-induced bone loss in rats. Bone 20020601
Difference in the metabolism of vitamin K between liver and bone in vitamin K-deficient rats. The British journal of nutrition 20020401
[Comparative analyses on osteoporosis guidelines in Japan, EU and USA]. Nihon rinsho. Japanese journal of clinical medicine 20020301
Menaquinone-4 in breast milk is derived from dietary phylloquinone. The British journal of nutrition 20020301
Differential lipoprotein transport pathways of K-vitamins in healthy subjects. Biochimica et biophysica acta 20020215
Efficacy and safety of Menatetrenone-4 postmenopausal Thai women. Journal of the Medical Association of Thailand = Chotmaihet thangphaet 20011001
Inverse correlation between the changes of lumbar bone mineral density and serum undercarboxylated osteocalcin after vitamin K2 (menatetrenone) treatment in children treated with glucocorticoid and alfacalcidol. Endocrine journal 20010201
Supplementation of rats with a lutein mixture preserved with vitamin E reduces tissue phylloquinone and menaquinone-4. International journal for vitamin and nutrition research. Internationale Zeitschrift fur Vitamin- und Ernahrungsforschung. Journal international de vitaminologie et de nutrition 20010101
Effect of menatetrenone on bone mineral density and incidence of vertebral fractures in postmenopausal women with osteoporosis: a comparison with the effect of etidronate. Journal of orthopaedic science : official journal of the Japanese Orthopaedic Association 20010101
Vitamin K(2) inhibits adipogenesis, osteoclastogenesis, and ODF/RANK ligand expression in murine bone marrow cell cultures. Bone 20001201
Comparative effects of vitamin K2 and vitamin E on experimental arteriosclerosis. International journal for vitamin and nutrition research. Internationale Zeitschrift fur Vitamin- und Ernahrungsforschung. Journal international de vitaminologie et de nutrition 19990101
Mechanism of the abnormal vitamin K-dependent gamma-carboxylation process in human hepatocellular carcinomas. Cancer 19940901
Properties