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84-80-0,MFCD00214063
Catalog No.:AA003AC6

84-80-0 | 1,4-Naphthalenedione,2-methyl-3-[(2E,7R,11R)-3,7,11,15-tetramethyl-2-hexadecen-1-yl]-

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250mg
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA003AC6
Chemical Name:
1,4-Naphthalenedione,2-methyl-3-[(2E,7R,11R)-3,7,11,15-tetramethyl-2-hexadecen-1-yl]-
CAS Number:
84-80-0
Molecular Formula:
C31H46O2
Molecular Weight:
450.6957
MDL Number:
MFCD00214063
SMILES:
C[C@H](CCC[C@@H](CCCC(C)C)C)CCC/C(=C/CC1=C(C)C(=O)c2c(C1=O)cccc2)/C
NSC Number:
760373
Properties
Computed Properties
 
Complexity:
696  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
2  
Defined Bond Stereocenter Count:
1  
Heavy Atom Count:
33  
Hydrogen Bond Acceptor Count:
2  
Rotatable Bond Count:
14  
XLogP3:
10.9  

Downstream Synthesis Route

[1]Hirschmann;Miller;Wendler[JournaloftheAmericanChemicalSociety,1954,vol.76,p.4592]Isler;Doebel[HelveticaChimicaActa,1954,vol.37,p.225,229]

84-80-0   
vitaminK12,3epoxide 

[1]CurrentPatentAssignee:RESEARCHCORPORATIONFORSCIENCEADVANCEMENT(RCSA)-US2312504,1942,AFieser;Tishler;Sampson[JournaloftheAmericanChemicalSociety,1940,vol.62,p.1628]

[1]Kvitaetal.[CollectionofCzechoslovakChemicalCommunications,1957,vol.22,p.583,586]

84-80-0   
1,4-bis-diphenylcarbamoyloxy-2-methyl-3-((7<i>R</i>,11<i>R</i>)-<i>trans</i>-phytyl)-naphthalene 

[1]Martius;Esser[BiochemischeZeitschrift,1959,vol.331,p.1,2]

[1]Tishler;Fieser;Wendler[JournaloftheAmericanChemicalSociety,1940,vol.62,p.1982,1990]Wagneretal.[JournaloftheAmericanChemicalSociety,1963,vol.85,p.1178]

Literature

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Title: c-Met-Akt pathway-mediated enhancement of inhibitory c-Raf phosphorylation is involved in vitamin K1 and sorafenib synergy on HCC growth inhibition.

Journal: Cancer biology & therapy 20110915

Title: Elevated international normalized ratio values associated with concomitant use of warfarin and ceftriaxone.

Journal: American journal of health-system pharmacy : AJHP : official journal of the American Society of Health-System Pharmacists 20110901

Title: Matrix Gla protein metabolism in vascular smooth muscle and role in uremic vascular calcification.

Journal: The Journal of biological chemistry 20110819

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Journal: JPEN. Journal of parenteral and enteral nutrition 20110701

Title: Elevated International Normalized Ratio associated with long-term azithromycin therapy in a child with cerebral palsy.

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Title: Effect of hydrogen bond strength on the redox properties of phylloquinones: a two-dimensional hyperfine sublevel correlation spectroscopy study of photosystem I.

Journal: Biochemistry 20110503

Title: Effects of long-term vitamin K(1) (phylloquinone) or vitamin K(2) (menaquinone-4) supplementation on body composition and serum parameters in rats.

Journal: Bone 20110501

Title: Moxifloxacin-acetaminophen-warfarin interaction during bacille Calmette-Guerin treatment for bladder cancer.

Journal: American journal of health-system pharmacy : AJHP : official journal of the American Society of Health-System Pharmacists 20110501

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Title: Human vitamin K 2,3-epoxide reductase complex subunit 1-like 1 (VKORC1L1) mediates vitamin K-dependent intracellular antioxidant function.

Journal: The Journal of biological chemistry 20110429

Title: Vitamin K, bone fractures, and vascular calcifications in chronic kidney disease: an important but poorly studied relationship.

Journal: Journal of endocrinological investigation 20110401

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Journal: Journal of animal science 20110401

Title: Functional study of the vitamin K cycle in mammalian cells.

Journal: Blood 20110310

Title: Novel insight into the mechanism of the vitamin K oxidoreductase (VKOR): electron relay through Cys43 and Cys51 reduces VKOR to allow vitamin K reduction and facilitation of vitamin K-dependent protein carboxylation.

Journal: The Journal of biological chemistry 20110304

Title: Alteration of the H-bond to the A(1A) phylloquinone in Photosystem I: influence on the kinetics and energetics of electron transfer.

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Title: Eicosapentaenoic acid reduces warfarin-induced arterial calcification in rats.

Journal: Atherosclerosis 20110301

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Title: High prevalence of hypovitaminosis D and K in patients with hip fracture.

Journal: Asia Pacific journal of clinical nutrition 20110101

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Journal: Lipids in health and disease 20110101

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Journal: Journal of Korean medical science 20101201

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Journal: British journal of clinical pharmacology 20101201

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Title: Dietary phylloquinone and menaquinones intakes and risk of type 2 diabetes.

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Title: Small intestinal bacterial overgrowth and warfarin dose requirement variability.

Journal: Thrombosis research 20100701

Title: Sorafenib combined vitamin K induces apoptosis in human pancreatic cancer cell lines through RAF/MEK/ERK and c-Jun NH2-terminal kinase pathways.

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Title: Hop rho iso-alpha acids, berberine, vitamin D3 and vitamin K1 favorably impact biomarkers of bone turnover in postmenopausal women in a 14-week trial.

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Title: A high menaquinone intake reduces the incidence of coronary heart disease.

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Journal: The journal of physical chemistry. B 20090730

Title: Measurement of deuterium-labeled phylloquinone in plasma by high-performance liquid chromatography/mass spectrometry.

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Title: CYP4F2 is a vitamin K1 oxidase: An explanation for altered warfarin dose in carriers of the V433M variant.

Journal: Molecular pharmacology 20090601

Title: Role of the hydrogen bond from Leu722 to the A1A phylloquinone in photosystem I.

Journal: Biochemistry 20090421

Title: Genetic and non-genetic correlates of vitamins K and D.

Journal: European journal of clinical nutrition 20090401

Title: Effect of cell differentiation for neuroblastoma by vitamin k analogs.

Journal: Japanese journal of clinical oncology 20090401

Title: Association of sequence variations in vitamin K epoxide reductase and gamma-glutamyl carboxylase genes with biochemical measures of vitamin K status.

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Title: Glutamate receptor mGlu2 and mGlu3 knockout striata are dopamine supersensitive, with elevated D2(High) receptors and marked supersensitivity to the dopamine agonist (+)PHNO.

Journal: Synapse (New York, N.Y.) 20090301

Title: Management of prehospital antiplatelet and anticoagulant therapy in traumatic head injury: a review.

Journal: The Journal of trauma 20090301

Title: Surface immobilization of PSI using vitamin K1-like molecular wires for fabrication of a bio-photoelectrode.

Journal: Journal of nanoscience and nanotechnology 20090301

Title: Elucidation of the mechanism producing menaquinone-4 in osteoblastic cells.

Journal: Bioorganic & medicinal chemistry letters 20090215

Title: Hydrogen-bonding interactions between water and the one- and two-electron-reduced forms of vitamin K1: applying quinone electrochemistry to determine the moisture content of non-aqueous solvents.

Journal: Journal of the American Chemical Society 20090204

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Journal: European journal of pediatrics 20090201

Title: An oral vitamin K protocol to reverse over-anticoagulation in patients presenting with an International Normalised Ratio above 10.0.

Journal: Thrombosis and haemostasis 20090201

Title: Effect of low dose vitamin K2 (MK-4) supplementation on bio-indices in postmenopausal Japanese women.

Journal: Journal of nutritional science and vitaminology 20090201

Title: Biological and pharmacological activities of squalene and related compounds: potential uses in cosmetic dermatology.

Journal: Molecules (Basel, Switzerland) 20090123

Title: Serum undercarboxylated osteocalcin as biomarker of vitamin K intake and risk of prostate cancer: a nested case-control study in the Heidelberg cohort of the European prospective investigation into cancer and nutrition.

Journal: Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20090101

Title: A possible ethanol-catalyzed rearrangement of vitamin K(1) detected by gas chromatography/mass spectrometry.

Journal: Rapid communications in mass spectrometry : RCM 20081201

Title: A stable isotope method for the simultaneous measurement of vitamin K1 (phylloquinone) kinetics and absorption.

Journal: European journal of clinical nutrition 20081101

Title: Vitamin K in hand osteoarthritis: results from a randomised clinical trial.

Journal: Annals of the rheumatic diseases 20081101

Title: Detection and quantification of vitamin K(1) quinol in leaf tissues.

Journal: Phytochemistry 20081001

Title: Six weeks phylloquinone supplementation produces undesirable effects on blood lipids with no changes in inflammatory and fibrinolytic markers in postmenopausal women.

Journal: European journal of nutrition 20081001

Title: Update on the role of vitamin K in skeletal health.

Journal: Nutrition reviews 20081001

Title: Metabolism and cell biology of vitamin K.

Journal: Thrombosis and haemostasis 20081001

Title: Vitamin K supplementation in postmenopausal women with osteopenia (ECKO trial): a randomized controlled trial.

Journal: PLoS medicine 20081001

Title: Efficacy of high dose phylloquinone in correcting vitamin K deficiency in cystic fibrosis.

Journal: Journal of cystic fibrosis : official journal of the European Cystic Fibrosis Society 20080901

Title: Does high vitamin K1 intake protect against bone loss in later life?

Journal: Nutrition reviews 20080901

Title: Vitamin K supplementation does not significantly impact bone mineral density and biochemical markers of bone in pre- and perimenopausal women.

Journal: Nutrition research (New York, N.Y.) 20080901

Title: Bromadiolone toxicokinetics: diagnosis and treatment implications.

Journal: Clinical toxicology (Philadelphia, Pa.) 20080901

Title: Vitamin K, circulating cytokines, and bone mineral density in older men and women.

Journal: The American journal of clinical nutrition 20080801

Title: Characterization and biological function of the ISOCHORISMATE SYNTHASE2 gene of Arabidopsis.

Journal: Plant physiology 20080701

Title: Mechanisms underlying the biphasic effect of vitamin K1 (phylloquinone) on arterial blood pressure.

Journal: The Journal of pharmacy and pharmacology 20080701

Title: Intoxication with three different superwarfarin compounds in an adult woman.

Journal: Thrombosis and haemostasis 20080701

Title: Conversion of phylloquinone (Vitamin K1) into menaquinone-4 (Vitamin K2) in mice: two possible routes for menaquinone-4 accumulation in cerebra of mice.

Journal: The Journal of biological chemistry 20080425

Title: The AAE14 gene encodes the Arabidopsis o-succinylbenzoyl-CoA ligase that is essential for phylloquinone synthesis and photosystem-I function.

Journal: The Plant journal : for cell and molecular biology 20080401

Title: Effect of vitamin K supplementation on bone loss in elderly men and women.

Journal: The Journal of clinical endocrinology and metabolism 20080401

Title: The vibrational spectrum of the secondary electron acceptor, A1, in photosystem I.

Journal: The journal of physical chemistry. B 20080327

Title: Indoleamine 2,3-dioxygenase is the anticancer target for a novel series of potent naphthoquinone-based inhibitors.

Journal: Journal of medicinal chemistry 20080327

Title: Low plasma phylloquinone concentration is associated with high incidence of vertebral fracture in Japanese women.

Journal: Journal of bone and mineral metabolism 20080101

Title: The vitamin K cycle.

Journal: Vitamins and hormones 20080101

Title: Structure and function of vitamin K epoxide reductase.

Journal: Vitamins and hormones 20080101

Title: Vitamin K-dependent carboxylation.

Journal: Vitamins and hormones 20080101

Title: Vitamin K and bone health in adult humans.

Journal: Vitamins and hormones 20080101

Title: Additive effect of mutations affecting the rate of phylloquinone reoxidation and directionality of electron transfer within photosystem I.

Journal: Photochemistry and photobiology 20080101

Title: Identification and quantitation of vitamins K1 and K3 in cosmetic products for facial skin protection.

Journal: Journal of cosmetic science 20080101

Title: Post-translational modifications regulate matrix Gla protein function: importance for inhibition of vascular smooth muscle cell calcification.

Journal: Journal of thrombosis and haemostasis : JTH 20071201

Title: Vitamin K content of foods and dietary vitamin K intake in Japanese young women.

Journal: Journal of nutritional science and vitaminology 20071201

Title: Determination of processing effects and of storage stability on vitamin K1 (Phylloquinone) in Sea Buckthorn Berries (Hippophaë rhamnoides L. ssp. rhamnoides) and related products.

Journal: Journal of food science 20071101

Title: Vitamin K1 versus vitamin K3 for prevention of subclinical vitamin deficiency: a randomized controlled trial.

Journal: Indian pediatrics 20071101

Title: HPLC method for plasma vitamin K1: effect of plasma triglyceride and acute-phase response on circulating concentrations.

Journal: Clinical chemistry 20070901

Title: [Vitamin K epoxide reductase complex 1 gene polymorphism and warfarin dose requirement in Chinese patients].

Journal: Zhonghua xin xue guan bing za zhi 20070701

Title: The conversion of vitamin K epoxide to vitamin K quinone and vitamin K quinone to vitamin K hydroquinone uses the same active site cysteines.

Journal: Biochemistry 20070619

Title: Bio-photosensor: Cyanobacterial photosystem I coupled with transistor via molecular wire.

Journal: Biochimica et biophysica acta 20070601

Title: Enhancement effects of vitamin K1 (phylloquinone) or vitamin K2 (menaquinone-4) on intestinal alkaline phosphatase activity in rats.

Journal: Journal of nutritional science and vitaminology 20070601

Title: Determination of vitamin K homologues by high-performance liquid chromatography with on-line photoreactor and peroxyoxalate chemiluminescence detection.

Journal: Analytica chimica acta 20070522

Title: Loss of phylloquinone in Chlamydomonas affects plastoquinone pool size and photosystem II synthesis.

Journal: The Journal of biological chemistry 20070504

Title: Two-year randomized controlled trial of vitamin K1 (phylloquinone) and vitamin D3 plus calcium on the bone health of older women.

Journal: Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research 20070401

Title: Relationship between diet and anticoagulant response to warfarin: a factor analysis.

Journal: European journal of nutrition 20070401

Title: Comparison of various phytonadione (vitamin K1) administration routes in achieving warfarin reversal.

Journal: South Dakota medicine : the journal of the South Dakota State Medical Association 20070401

Title: Subclinical vitamin K deficiency in hemodialysis patients.

Journal: American journal of kidney diseases : the official journal of the National Kidney Foundation 20070301

Title: High-performance liquid chromatography: photochemical reduction in aerobic conditions for determination of K vitamins using fluorescence detection.

Journal: Journal of chromatography. A 20070202

Title: Effect of phylloquinone supplementation on biochemical markers of vitamin K status and bone turnover in postmenopausal women.

Journal: The British journal of nutrition 20070201

Title: Vitamin K1 accumulation in tobacco plants overexpressing bacterial genes involved in the biosynthesis of salicylic acid.

Journal: Journal of biotechnology 20070130

Title: Disulfide-dependent protein folding is linked to operation of the vitamin K cycle in the endoplasmic reticulum. A protein disulfide isomerase-VKORC1 redox enzyme complex appears to be responsible for vitamin K1 2,3-epoxide reduction.

Journal: The Journal of biological chemistry 20070126

Title: Phylloquinone intake and risk of cardiovascular diseases in men.

Journal: Nutrition, metabolism, and cardiovascular diseases : NMCD 20070101

Title: Effects of vitamin K1 supplementation on vascular responsiveness and oxidative stress in a rat femoral osteotomy model.

Journal: Cell biochemistry and function 20070101

Title: Deficiency in phylloquinone (vitamin K1) methylation affects prenyl quinone distribution, photosystem I abundance, and anthocyanin accumulation in the Arabidopsis AtmenG mutant.

Journal: The Journal of biological chemistry 20061229

Title: Purified vitamin K epoxide reductase alone is sufficient for conversion of vitamin K epoxide to vitamin K and vitamin K to vitamin KH2.

Journal: Proceedings of the National Academy of Sciences of the United States of America 20061219

Title: Bidirectional electron transfer in photosystem I: replacement of the symmetry-breaking tryptophan close to the PsaB-bound phylloquinone A1B with a glycine residue alters the redox properties of A1B and blocks forward electron transfer at cryogenic temperatures.

Journal: Biochimica et biophysica acta 20061201

Title: Comparative dietary intake and sources of phylloquinone (vitamin K1) among British adults in 1986-7 and 2000-1.

Journal: The British journal of nutrition 20061201

Title: Plasma phylloquinone (vitamin K1) concentration and its relationship to intake in British adults aged 19-64 years.

Journal: The British journal of nutrition 20061201

Title: Determination of phylloquinone and cholecalciferol encapsulated in granulates formed by melt extrusion.

Journal: Journal of biochemical and biophysical methods 20061130

Title: Effect of calcium, vitamins K1 and D3 on bone in galactosemia.

Journal: Bone 20061101

Title: Reversal of asymptomatic over-anticoagulation with oral vitamin K.

Journal: British journal of haematology 20061101

Title: Time-resolved FTIR difference spectroscopy for the study of photosystem I particles with plastoquinone-9 occupying the A1 binding site.

Journal: Biochemistry 20061024

Title: Comparative uptake, metabolism, and utilization of menaquinone-4 and phylloquinone in human cultured cell lines.

Journal: Bioorganic & medicinal chemistry 20061001

Title: [Protective effects of vitamin K against osteoporosis and its pleiotropic actions].

Journal: Clinical calcium 20060901

Title: Vitamin K and the prevention of fractures: systematic review and meta-analysis of randomized controlled trials.

Journal: Archives of internal medicine 20060626

Title: A plant locus essential for phylloquinone (vitamin K1) biosynthesis originated from a fusion of four eubacterial genes.

Journal: The Journal of biological chemistry 20060623

Title: Phylloquinone and related radical anions studied by pulse electron nuclear double resonance spectroscopy at 34 GHz and density functional theory.

Journal: The journal of physical chemistry. B 20060615

Title: Fat-soluble vitamins in breast-fed preterm and term infants.

Journal: European journal of clinical nutrition 20060601

Title: Vitamin K1 (phylloquinone) induces vascular endothelial dysfunction: role of oxidative stress.

Journal: Toxicology and applied pharmacology 20060515

Title: Microsphere-based protease assays and screening application for lethal factor and factor Xa.

Journal: Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501

Title: Phylloquinone (vitamin K1) intakes and serum undercarboxylated osteocalcin levels in Irish postmenopausal women.

Journal: The British journal of nutrition 20060501

Title: Reversal of asymptomatic over-anticoagulation by orally administered vitamin K.

Journal: British journal of haematology 20060501

Title: Modification of the phylloquinone in the A1 binding site in photosystem I studied using time-resolved FTIR difference spectroscopy and density functional theory.

Journal: Biochemistry 20060404

Title: Vitamin K suppresses lipopolysaccharide-induced inflammation in the rat.

Journal: Bioscience, biotechnology, and biochemistry 20060401

Title: [Determination of vitamin K in aojiru (green juice) products by HPLC].

Journal: Shokuhin eiseigaku zasshi. Journal of the Food Hygienic Society of Japan 20060401

Title: [Hemorrhagic complications during warfarin treatment].

Journal: Vnitrni lekarstvi 20060301

Title: Treatment of excessive anticoagulation with phytonadione (vitamin K): a meta-analysis.

Journal: Archives of internal medicine 20060227

Title: Menadione is a metabolite of oral vitamin K.

Journal: The British journal of nutrition 20060201

Title: Oxandrolone steroid use and impaired coagulation.

Journal: Archives of internal medicine 20060109

Title: Subclinical hypervitaminosis A in rat: measurements of bone mineral density (BMD) do not reveal adverse skeletal changes.

Journal: Chemico-biological interactions 20060105

Title: Automatic determination of phylloquinone in vegetables and fruits using on-line photochemical reduction and fluorescence detection via solid phase extraction and flow injection.

Journal: Analytical and bioanalytical chemistry 20060101

Title: Association of dietary and biochemical measures of vitamin K with quantitative ultrasound of the heel in men and women.

Journal: Osteoporosis international : a journal established as result of cooperation between the European Foundation for Osteoporosis and the National Osteoporosis Foundation of the USA 20060101

Title: Dietary phylloquinone depletion and repletion in postmenopausal women: effects on bone and mineral metabolism.

Journal: Osteoporosis international : a journal established as result of cooperation between the European Foundation for Osteoporosis and the National Osteoporosis Foundation of the USA 20060101

Title: No effect of vitamin K1 intake on bone mineral density and fracture risk in perimenopausal women.

Journal: Osteoporosis international : a journal established as result of cooperation between the European Foundation for Osteoporosis and the National Osteoporosis Foundation of the USA 20060101

Title: Analysis of isotope ratios in vitamin K1 (phylloquinone) from human plasma by gas chromatography/mass spectrometry.

Journal: Rapid communications in mass spectrometry : RCM 20060101

Title: Pleiotropic actions of vitamin K: protector of bone health and beyond?

Journal: Nutrition (Burbank, Los Angeles County, Calif.) 20060101

Title: Effect of calcium fortified milk supplementation with or without vitamin K on biochemical markers of bone turnover in premenopausal women.

Journal: Nutrition (Burbank, Los Angeles County, Calif.) 20060101

Title: Surgical delay in acute admissions on warfarin: are we doing enough?

Journal: International journal of clinical practice 20051101

Title: Site-directed mutagenesis of coumarin-type anticoagulant-sensitive VKORC1: evidence that highly conserved amino acids define structural requirements for enzymatic activity and inhibition by warfarin.

Journal: Thrombosis and haemostasis 20051001

Title: Regression of medial elastocalcinosis in rat aorta: a new vascular function for carbonic anhydrase.

Journal: Circulation 20050913

Title: [Isolation and structure identification of the main photolysis product in vitamin K1].

Journal: Sichuan da xue xue bao. Yi xue ban = Journal of Sichuan University. Medical science edition 20050901

Title: Vitamin K in the treatment and prevention of osteoporosis and arterial calcification.

Journal: American journal of health-system pharmacy : AJHP : official journal of the American Society of Health-System Pharmacists 20050801

Title: Significant effect of capecitabine on the pharmacokinetics and pharmacodynamics of warfarin in patients with cancer.

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20050720

Title: Modelling of the electron transfer reactions in Photosystem I by electron tunnelling theory: the phylloquinones bound to the PsaA and the PsaB reaction centre subunits of PS I are almost isoenergetic to the iron-sulfur cluster F(X).

Journal: Biochimica et biophysica acta 20050715

Title: The secondary electron acceptor of photosystem I in Gloeobacter violaceus PCC 7421 is menaquinone-4 that is synthesized by a unique but unknown pathway.

Journal: FEBS letters 20050704

Title: Prediction of genotoxicity of chemical compounds by statistical learning methods.

Journal: Chemical research in toxicology 20050601

Title: Immediate cutaneous hypersensitivity response to phytomenadione induced by vitamin K in skin diagnostic procedure.

Journal: Contact dermatitis 20050501

Title: Determinants of plasma dihydrophylloquinone in men and women.

Journal: The British journal of nutrition 20050501

Title: Intake and sources of phylloquinone (vitamin K(1)) in 4-year-old British children: comparison between 1950 and the 1990s.

Journal: Public health nutrition 20050401

Title: Pharmacokinetics and efficacy of oral versus intravenous mixed-micellar phylloquinone (vitamin K1) in severe acute liver disease.

Journal: Journal of hepatology 20050301

Title: Phylloquinone intake as a marker for coronary heart disease risk but not stroke in women.

Journal: European journal of clinical nutrition 20050201

Title: Expression of LRP1 by human osteoblasts: a mechanism for the delivery of lipoproteins and vitamin K1 to bone.

Journal: Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research 20050201

Title: Method for the determination of vitamin K homologues in human plasma using high-performance liquid chromatography-tandem mass spectrometry.

Journal: Analytical chemistry 20050201

Title: Inactivation and deficiency of core proteins of photosystems I and II caused by genetical phylloquinone and plastoquinone deficiency but retained lamellar structure in a T-DNA mutant of Arabidopsis.

Journal: The Plant journal : for cell and molecular biology 20050201

Title: Ethnic differences in osteocalcin gamma-carboxylation, plasma phylloquinone (vitamin K1) and apolipoprotein E genotype.

Journal: European journal of clinical nutrition 20050101

Title: Vitamin K status of older individuals in northern China is superior to that of older individuals in the UK.

Journal: The British journal of nutrition 20041201

Title: Influence of plasma total antioxidant ability on lipid and protein oxidation products in plasma and erythrocyte ghost obtained from developing and adult rats pretreated with two vitamin K formulations.

Journal: Molecular and cellular biochemistry 20041201

Title: Warfarin reversal: consensus guidelines, on behalf of the Australasian Society of Thrombosis and Haemostasis.

Journal: The Medical journal of Australia 20041101

Title: Over-the-counter vitamin K1-containing multivitamin supplements disrupt warfarin anticoagulation in vitamin K1-depleted patients. A prospective, controlled trial.

Journal: Thrombosis and haemostasis 20041101

Title: Vitamin K status in patients with Crohn's disease and relationship to bone turnover.

Journal: The American journal of gastroenterology 20041101

Title: Phenotypic modulation of vascular smooth muscle cells during medial arterial calcification: a role for endothelin?

Journal: Journal of cardiovascular pharmacology 20041101

Title: Associations between vitamin K biochemical measures and bone mineral density in men and women.

Journal: The Journal of clinical endocrinology and metabolism 20041001

Title: Determination of phylloquinone (vitamin K1) in plasma and serum by HPLC with fluorescence detection.

Journal: Clinica chimica acta; international journal of clinical chemistry 20040901

Title: Comparison of oral versus intravenous phytonadione in patients with excessive anticoagulation.

Journal: Current hematology reports 20040901

Title: Dietary phylloquinone intake as a potential marker for a heart-healthy dietary pattern in the Framingham Offspring cohort.

Journal: Journal of the American Dietetic Association 20040901

Title: [Analysis of vitamins and inorganic elements in the water extracts of Radix Changii].

Journal: Zhong xi yi jie he xue bao = Journal of Chinese integrative medicine 20040901

Title: Phylloquinone (vitamin K1) intakes and food sources in 18-64-year-old Irish adults.

Journal: The British journal of nutrition 20040701

Title: On the alcohol- and water-catalyzed tautomerization of vitamins K1- and K2-derived quinone methide intermediates.

Journal: The Journal of organic chemistry 20040430

Title: Quinones facilitate the self-assembly of the phosphorylated tubulin binding region of tau into fibrillar polymers.

Journal: Biochemistry 20040316

Title: Effect of supplementary feeding of vitamin K1 on difethialone treated Indian gerbil, Tatera indica Hardwicke in laboratory.

Journal: Indian journal of experimental biology 20040301

Title: Skin reaction to subcutaneous phytonadione injections.

Journal: American journal of health-system pharmacy : AJHP : official journal of the American Society of Health-System Pharmacists 20040215

Title: Removal of PsaF alters forward electron transfer in photosystem I: evidence for fast reoxidation of QK-A in subunit deletion mutants of Synechococcus sp. PCC 7002.

Journal: Biochemistry 20040210

Title: Beneficial effects of vitamins D and K on the elastic properties of the vessel wall in postmenopausal women: a follow-up study.

Journal: Thrombosis and haemostasis 20040201

Title: Indirect identification of isoprenoid quinones in Escherichia coli by LC-MS with atmospheric pressure chemical ionization in negative mode.

Journal: Journal of basic microbiology 20040101

Title: Observations on possible effects of daily vitamin K replacement, especially upon warfarin therapy.

Journal: JPEN. Journal of parenteral and enteral nutrition 20040101

Title: [A model of the quinone-binding site of photosystem I: investigation of charge transfer complexes of phylloquinone and its derivatives with tryptophan].

Journal: Biofizika 20040101

Title: Prevention of vitamin K deficiency bleeding with oral mixed micellar phylloquinone: results of a 6-year surveillance in Switzerland.

Journal: European journal of pediatrics 20031201

Title: Vitamin K content of nuts and fruits in the US diet.

Journal: Journal of the American Dietetic Association 20031201

Title: Effects of dietary particulate limestone, vitamin K3 and fluoride and photostimulation on skeletal morphology and osteoporosis in laying hens.

Journal: British poultry science 20031201

Title: Comparison of oral vs intravenous phytonadione (vitamin K1) in patients with excessive anticoagulation: a prospective randomized controlled study.

Journal: Archives of internal medicine 20031110

Title: Multivitamin supplements may affect warfarin anticoagulation in susceptible patients.

Journal: The Annals of pharmacotherapy 20031101

Title: A retrospective evaluation of vitamin K1 therapy to reverse the anticoagulant effect of warfarin.

Journal: Pharmacotherapy 20031001

Title: Electrochemical studies of vitamin K1 microdroplets: electrocatalytic hydrogen evolution.

Journal: Chemphyschem : a European journal of chemical physics and physical chemistry 20030915

Title: Superwarfarin and glass ingestion with prolonged coagulopathy requiring high-dose vitamin K1 therapy.

Journal: Pharmacotherapy 20030901

Title: The biological activity and tissue distribution of 2',3'-dihydrophylloquinone in rats.

Journal: Biochimica et biophysica acta 20030822

Title: Isotopic labeling and LC-APCI-MS quantification for investigating absorption of carotenoids and phylloquinone from kale (Brassica oleracea).

Journal: Journal of agricultural and food chemistry 20030813

Title: Species comparison of vitamin K1 2,3-epoxide reductase activity in vitro: kinetics and warfarin inhibition.

Journal: Toxicology 20030801

Title: Asymptomatic excessive coumarin anticoagulation is a risk factor for thrombotic and bleeding complications of oral anticoagulant therapy.

Journal: Journal of thrombosis and haemostasis : JTH 20030801

Title: The anticancer effects of vitamin K.

Journal: Alternative medicine review : a journal of clinical therapeutic 20030801

Title: Electron transfer in cyanobacterial photosystem I: II. Determination of forward electron transfer rates of site-directed mutants in a putative electron transfer pathway from A0 through A1 to FX.

Journal: The Journal of biological chemistry 20030725

Title: Novel role of vitamin k in preventing oxidative injury to developing oligodendrocytes and neurons.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20030702

Title: Weekly oral vitamin K prophylaxis in Denmark.

Journal: Acta paediatrica (Oslo, Norway : 1992) 20030701

Title: Menatetrenone (vitamin K2) acts directly on circulating human osteoclast precursors.

Journal: Calcified tissue international 20030701

Title: Control of electron transport in photosystem I by the iron-sulfur cluster FX in response to intra- and intersubunit interactions.

Journal: The Journal of biological chemistry 20030523

Title: Differential effects of two growth inhibitory K vitamin analogs on cell cycle regulating proteins in human hepatoma cells.

Journal: Life sciences 20030502

Title: Primary photoreactions of phylloquinone (vitamin K1) and plastoquinone-1 in solution.

Journal: Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology 20030501

Title: Genome organization in Arabidopsis thaliana: a survey for genes involved in isoprenoid and chlorophyll metabolism.

Journal: Plant molecular biology 20030401

Title: The menD and menE homologs code for 2-succinyl-6-hydroxyl-2,4-cyclohexadiene-1-carboxylate synthase and O-succinylbenzoic acid-CoA synthase in the phylloquinone biosynthetic pathway of Synechocystis sp. PCC 6803.

Journal: Biochimica et biophysica acta 20030306

Title: Intestinal absorption of mixed micellar phylloquinone (vitamin K1) is unreliable in infants with conjugated hyperbilirubinaemia: implications for oral prophylaxis of vitamin K deficiency bleeding.

Journal: Archives of disease in childhood. Fetal and neonatal edition 20030301

Title: A new model of isolated systolic hypertension induced by chronic warfarin and vitamin K1 treatment.

Journal: American journal of hypertension 20030201

Title: Safety and effectiveness of low dose oral vitamin K1 administration in asymptomatic out-patients on warfarin or acenocoumarol with excessive anticoagulation.

Journal: Haematologica 20030201

Title: Simultaneous determination of vitamin K analogs in human serum by sensitive and selective high-performance liquid chromatography with electrochemical detection.

Journal: Nutrition (Burbank, Los Angeles County, Calif.) 20030101

Title: [Intermolecular interactions of dipeptide triterpene derivatives and natural quinones with alpha-tocopherol].

Journal: Biomeditsinskaia khimiia 20030101

Title: Tissue-specific utilization of menaquinone-4 results in the prevention of arterial calcification in warfarin-treated rats.

Journal: Journal of vascular research 20030101

Title: Phylloquinone, what can we learn from plants?

Journal: BioFactors (Oxford, England) 20030101

Title: Vitamin K1 attenuates hypoxia-induced relaxation of rat carotid artery.

Journal: Pharmacological research 20021201

Title: Modeling of the P700+ charge recombination kinetics with phylloquinone and plastoquinone-9 in the A1 site of photosystem I.

Journal: Biophysical journal 20021201

Title: Homozygosity mapping of a second gene locus for hereditary combined deficiency of vitamin K-dependent clotting factors to the centromeric region of chromosome 16.

Journal: Blood 20021101

Title: Shift of serum osteocalcin components between cord blood and blood at day 5 of life.

Journal: Pediatric research 20021101

Title: The incidence of anaphylaxis following intravenous phytonadione (vitamin K1): a 5-year retrospective review.

Journal: Annals of allergy, asthma & immunology : official publication of the American College of Allergy, Asthma, & Immunology 20021001

Title: Vitamin K(1) prevents the effect of hypoxia on phenylephrine-induced contraction in the carotid artery.

Journal: Pharmacology 20020901

Title: Multilaboratory comparison of anaerobe susceptibility results using 3 different agar media.

Journal: Clinical infectious diseases : an official publication of the Infectious Diseases Society of America 20020901

Title: Pharmacological prevention and regression of arterial remodeling in a rat model of isolated systolic hypertension.

Journal: Journal of hypertension 20020801

Title: Vitamin K supplementation does not affect ovariectomy-induced bone loss in rats.

Journal: Bone 20020601

Title: Total body phylloquinone and its turnover in human subjects at two levels of vitamin K intake.

Journal: The British journal of nutrition 20020601

Title: Intake and sources of phylloquinone (vitamin K1): variation with socio-demographic and lifestyle factors in a national sample of British elderly people.

Journal: The British journal of nutrition 20020601

Title: Plasma phylloquinone (vitamin K1) concentration and its relationship to intake in a national sample of British elderly people.

Journal: The British journal of nutrition 20020601

Title: Difference in the metabolism of vitamin K between liver and bone in vitamin K-deficient rats.

Journal: The British journal of nutrition 20020401

Title: Menaquinone-4 in breast milk is derived from dietary phylloquinone.

Journal: The British journal of nutrition 20020301

Title: Differential lipoprotein transport pathways of K-vitamins in healthy subjects.

Journal: Biochimica et biophysica acta 20020215

Title: [Effects of riboxin, essentiale, and phylloquinone on the immunomodulating and antioxidant effect of laser and magneto-laser irradiation in liver toxicosis induced by gentamycin].

Journal: Eksperimental'naia i klinicheskaia farmakologiia 20020101

Title: Determination of vitamin K1 isomers in foods by liquid chromatography with C30 bonded-phase column.

Journal: Journal of AOAC International 20020101

Title: Measurement of cis and trans isomers of vitamin K1 in rat tissues by liquid chromatography with a C30 column.

Journal: Journal of AOAC International 20020101

Title: A patient with anaphylactoid hypersensitivity to intravenous cyclosporine and subcutaneous phytonadione (vitamin K(1)).

Journal: Bone marrow transplantation 20011201

Title: Modification of photosystem I reaction center by the extraction and exchange of chlorophylls and quinones.

Journal: Biochimica et biophysica acta 20011030

Title: Electron spin echo envelope modulation spectroscopy in photosystem I.

Journal: Biochimica et biophysica acta 20011030

Title: Recruitment of a foreign quinone into the A1 site of photosystem I. In vivo replacement of plastoquinone-9 by media-supplemented naphthoquinones in phylloquinone biosynthetic pathway mutants of Synechocystis sp. PCC 6803.

Journal: The Journal of biological chemistry 20011026

Title: Mutations in both sides of the photosystem I reaction center identify the phylloquinone observed by electron paramagnetic resonance spectroscopy.

Journal: The Journal of biological chemistry 20011005

Title: Clinical predictors of prolonged delay in return of the international normalized ratio to within the therapeutic range after excessive anticoagulation with warfarin.

Journal: Annals of internal medicine 20010918

Title: Summaries for patients. Predicting risk for prolonged high INR after too much anticoagulation.

Journal: Annals of internal medicine 20010918

Title: Quantitative effects of interacting variables on vitamin K1, phylloquinone, entrapment in liposomes.

Journal: African journal of medicine and medical sciences 20010901

Title: Oxygen free radical generating mechanisms in the colon: do the semiquinones of vitamin K play a role in the aetiology of colon cancer?

Journal: Biochimica et biophysica acta 20010815

Title: Off-center fold: indurated plaques on the arms of a 52-year-old man. Diagnosis: Cutaneous reaction to phytonadione injection.

Journal: Archives of dermatology 20010701

Title: Practitioner report involving intravenous use of vitamin K1 prompts label review and revision.

Journal: Journal of the American Veterinary Medical Association 20010601

Title: Effect of dietary vitamin K1 on selected plasma characteristics and bone ash in young turkeys fed diets adequate or deficient in vitamin D3.

Journal: Poultry science 20010501

Title: Dietary vitamin K1 requirement and comparison of biopotency of different vitamin K sources for young turkeys.

Journal: Poultry science 20010501

Title: Characterization and purification of the vitamin K1 2,3 epoxide reductases system from rat liver.

Journal: The Journal of pharmacy and pharmacology 20010401

Title: Content of phylloquinone and menaquinone in the tissues of mummichog Fundulus heteroclitus fed diets containing different forms of vitamin K.

Journal: Journal of nutritional science and vitaminology 20010401

Title: Separation and determination of minor photosynthetic pigments by reversed-phase HPLC with minimal alteration of chlorophylls.

Journal: Analytical sciences : the international journal of the Japan Society for Analytical Chemistry 20010401

Title: A Fourier transform infrared absorption difference spectrum associated with the reduction of A1 in photosystem I: are both phylloquinones involved in electron transfer?

Journal: Biochemistry 20010327

Title: Efficacy and safety of intravenous phytonadione (vitamin K1) in patients on long-term oral anticoagulant therapy.

Journal: Mayo Clinic proceedings 20010301

Title: The association of vitamin K status with warfarin sensitivity at the onset of treatment.

Journal: British journal of haematology 20010301

Title: Site-directed mutagenesis of PsaA residue W693 affects phylloquinone binding and function in the photosystem I reaction center of Chlamydomonas reinhardtii.

Journal: Biochemistry 20010220

Title: Reversal of excessive oral anticoagulation with a low oral dose of vitamin K1 compared with acenocoumarine discontinuation. A prospective, randomized, open study.

Journal: Blood coagulation & fibrinolysis : an international journal in haemostasis and thrombosis 20010101

Title: Supplementation of rats with a lutein mixture preserved with vitamin E reduces tissue phylloquinone and menaquinone-4.

Journal: International journal for vitamin and nutrition research. Internationale Zeitschrift fur Vitamin- und Ernahrungsforschung. Journal international de vitaminologie et de nutrition 20010101

Title: Role of vitamin K and vitamin K-dependent proteins in vascular calcification.

Journal: Zeitschrift fur Kardiologie 20010101

Title: Cytotoxic activity of vitamins K1, K2 and K3 against human oral tumor cell lines.

Journal: Anticancer research 20010101

Title: Pseudoscleroderma secondary to phytomenadione (vitamin K1) injections: Texier's disease.

Journal: The Australasian journal of dermatology 19960201

Title: Mutagenesis of vitamin K-dependent carboxylase demonstrates a carboxyl terminus-mediated interaction with vitamin K hydroquinone.

Journal: The Journal of biological chemistry 19950310

Title: Mechanism of the abnormal vitamin K-dependent gamma-carboxylation process in human hepatocellular carcinomas.

Journal: Cancer 19940901

Title: Anticoagulant-related intracerebral hemorrhage in patients with prosthetic heart valves--report of two cases.

Journal: Neurologia medico-chirurgica 19911101

Title: Exposure of the pregnant rat to warfarin and vitamin K1: an animal model of intraventricular hemorrhage in the fetus.

Journal: Teratology 19901001

Title: Patulin biosynthesis: epoxidation of toluquinol and gentisyl alcohol by particulate preparations from Penicillium patulum.

Journal: Biochemistry 19891114

Title: Specificity of increased des-gamma-carboxyprothrombin in hepatocellular carcinoma after vitamin K1 injection.

Journal: Journal of hepatology 19870801

Title: Vitamin K-dependent carboxylase: evidence for a semiquinone radical intermediate.

Journal: Archives of biochemistry and biophysics 19840501

Title: Drug-induced convulsions. Report from Boston Collaborative Drug Surveillance Program.

Journal: Lancet (London, England) 19720930

Title: [Clinical use of vitamin K-1 in hearing disorders caused by kanamycin].

Journal: Jibi inkoka Otolaryngology 19660401

Title: Basset GJ, et al. Phylloquinone (Vitamin K1): Occurrence, Biosynthesis and Functions. Mini Rev Med Chem. 2016 Jun 22.

Title: Orlando A, et al. Vitamin K1 exerts antiproliferative effects and induces apoptosis in three differently graded human colon cancer cell lines. Biomed Res Int. 2015;2015:296721.

Title: Ibarrola-Jurado N, et al. Dietary phylloquinone intake and risk of type 2 diabetes in elderly subjects at high risk of cardiovascular disease. Am J Clin Nutr. 2012 Nov;96(5):1113-8.

Title: Kim M, et al. Vitamin K1 (phylloquinone) and K2 (menaquinone-4) supplementation improves bone formation in a high-fat diet-induced obese mice. J Clin Biochem Nutr. 2013 Sep;53(2):108-13.

Title: Hemmati AA, et al. Topical vitamin K1 promotes repair of full thickness wound in rat. Indian J Pharmacol. 2014 Jul-Aug;46(4):409-12.

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Tags:84-80-0 Molecular Formula|84-80-0 MDL|84-80-0 SMILES|84-80-0 1,4-Naphthalenedione,2-methyl-3-[(2E,7R,11R)-3,7,11,15-tetramethyl-2-hexadecen-1-yl]-