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84-80-0

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

CAS No: 84-80-0 Catalog No: AG003AEY MDL No:MFCD00214063

Product Description

Catalog Number:
AG003AEY
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
IUPAC Name:
2-methyl-3-[(E,7R,11R)-3,7,11,15-tetramethylhexadec-2-enyl]naphthalene-1,4-dione
InChI:
InChI=1S/C31H46O2/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/h7-8,18-20,22-24H,9-17,21H2,1-6H3/b25-20+/t23-,24-/m1/s1
InChI Key:
MBWXNTAXLNYFJB-NKFFZRIASA-N
SMILES:
C[C@H](CCC[C@@H](CCCC(C)C)C)CCC/C(=C/CC1=C(C)C(=O)c2c(C1=O)cccc2)/C
UNII:
S5Z3U87QHF
NSC Number:
760373

Properties

Complexity:
696  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
2  
Defined Bond Stereocenter Count:
1  
Exact Mass:
450.35g/mol
Formal Charge:
0
Heavy Atom Count:
33  
Hydrogen Bond Acceptor Count:
2  
Hydrogen Bond Donor Count:
0
Isotope Atom Count:
0
Molecular Weight:
450.707g/mol
Monoisotopic Mass:
450.35g/mol
Rotatable Bond Count:
14  
Topological Polar Surface Area:
34.1A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
10.9  

Literature

Title Journal
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A Dedicated Type II NADPH Dehydrogenase Performs the Penultimate Step in the Biosynthesis of Vitamin K1 in Synechocystis and Arabidopsis. The Plant cell 20150601
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A novel mutation in VKORC1 and its effect on enzymatic activity in Japanese warfarin-resistant rats. The Journal of veterinary medical science 20130201
Influence of CYP4F2 polymorphisms and plasma vitamin K levels on warfarin sensitivity in Japanese pediatric patients. Drug metabolism and pharmacokinetics 20130101
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Measurement of menadione in urine by HPLC. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20100915
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A stable isotope method for the simultaneous measurement of vitamin K1 (phylloquinone) kinetics and absorption. European journal of clinical nutrition 20081101
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Detection and quantification of vitamin K(1) quinol in leaf tissues. Phytochemistry 20081001
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Mechanisms underlying the biphasic effect of vitamin K1 (phylloquinone) on arterial blood pressure. The Journal of pharmacy and pharmacology 20080701
Intoxication with three different superwarfarin compounds in an adult woman. Thrombosis and haemostasis 20080701
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The AAE14 gene encodes the Arabidopsis o-succinylbenzoyl-CoA ligase that is essential for phylloquinone synthesis and photosystem-I function. The Plant journal : for cell and molecular biology 20080401
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Additive effect of mutations affecting the rate of phylloquinone reoxidation and directionality of electron transfer within photosystem I. Photochemistry and photobiology 20080101
Identification and quantitation of vitamins K1 and K3 in cosmetic products for facial skin protection. Journal of cosmetic science 20080101
Post-translational modifications regulate matrix Gla protein function: importance for inhibition of vascular smooth muscle cell calcification. Journal of thrombosis and haemostasis : JTH 20071201
Vitamin K content of foods and dietary vitamin K intake in Japanese young women. Journal of nutritional science and vitaminology 20071201
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 of food science 20071101
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Bio-photosensor: Cyanobacterial photosystem I coupled with transistor via molecular wire. Biochimica et biophysica acta 20070601
Enhancement effects of vitamin K1 (phylloquinone) or vitamin K2 (menaquinone-4) on intestinal alkaline phosphatase activity in rats. Journal of nutritional science and vitaminology 20070601
Determination of vitamin K homologues by high-performance liquid chromatography with on-line photoreactor and peroxyoxalate chemiluminescence detection. Analytica chimica acta 20070522
Loss of phylloquinone in Chlamydomonas affects plastoquinone pool size and photosystem II synthesis. The Journal of biological chemistry 20070504
Two-year randomized controlled trial of vitamin K1 (phylloquinone) and vitamin D3 plus calcium on the bone health of older women. Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research 20070401
Relationship between diet and anticoagulant response to warfarin: a factor analysis. European journal of nutrition 20070401
Comparison of various phytonadione (vitamin K1) administration routes in achieving warfarin reversal. South Dakota medicine : the journal of the South Dakota State Medical Association 20070401
Subclinical vitamin K deficiency in hemodialysis patients. American journal of kidney diseases : the official journal of the National Kidney Foundation 20070301
High-performance liquid chromatography: photochemical reduction in aerobic conditions for determination of K vitamins using fluorescence detection. Journal of chromatography. A 20070202
Effect of phylloquinone supplementation on biochemical markers of vitamin K status and bone turnover in postmenopausal women. The British journal of nutrition 20070201
Vitamin K1 accumulation in tobacco plants overexpressing bacterial genes involved in the biosynthesis of salicylic acid. Journal of biotechnology 20070130
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. The Journal of biological chemistry 20070126
Phylloquinone intake and risk of cardiovascular diseases in men. Nutrition, metabolism, and cardiovascular diseases : NMCD 20070101
Effects of vitamin K1 supplementation on vascular responsiveness and oxidative stress in a rat femoral osteotomy model. Cell biochemistry and function 20070101
Deficiency in phylloquinone (vitamin K1) methylation affects prenyl quinone distribution, photosystem I abundance, and anthocyanin accumulation in the Arabidopsis AtmenG mutant. The Journal of biological chemistry 20061229
Purified vitamin K epoxide reductase alone is sufficient for conversion of vitamin K epoxide to vitamin K and vitamin K to vitamin KH2. Proceedings of the National Academy of Sciences of the United States of America 20061219
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. Biochimica et biophysica acta 20061201
Comparative dietary intake and sources of phylloquinone (vitamin K1) among British adults in 1986-7 and 2000-1. The British journal of nutrition 20061201
Plasma phylloquinone (vitamin K1) concentration and its relationship to intake in British adults aged 19-64 years. The British journal of nutrition 20061201
Determination of phylloquinone and cholecalciferol encapsulated in granulates formed by melt extrusion. Journal of biochemical and biophysical methods 20061130
Effect of calcium, vitamins K1 and D3 on bone in galactosemia. Bone 20061101
Reversal of asymptomatic over-anticoagulation with oral vitamin K. British journal of haematology 20061101
Time-resolved FTIR difference spectroscopy for the study of photosystem I particles with plastoquinone-9 occupying the A1 binding site. Biochemistry 20061024
Comparative uptake, metabolism, and utilization of menaquinone-4 and phylloquinone in human cultured cell lines. Bioorganic & medicinal chemistry 20061001
[Protective effects of vitamin K against osteoporosis and its pleiotropic actions]. Clinical calcium 20060901
Vitamin K and the prevention of fractures: systematic review and meta-analysis of randomized controlled trials. Archives of internal medicine 20060626
A plant locus essential for phylloquinone (vitamin K1) biosynthesis originated from a fusion of four eubacterial genes. The Journal of biological chemistry 20060623
Phylloquinone and related radical anions studied by pulse electron nuclear double resonance spectroscopy at 34 GHz and density functional theory. The journal of physical chemistry. B 20060615
Fat-soluble vitamins in breast-fed preterm and term infants. European journal of clinical nutrition 20060601
Vitamin K1 (phylloquinone) induces vascular endothelial dysfunction: role of oxidative stress. Toxicology and applied pharmacology 20060515
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
Phylloquinone (vitamin K1) intakes and serum undercarboxylated osteocalcin levels in Irish postmenopausal women. The British journal of nutrition 20060501
Reversal of asymptomatic over-anticoagulation by orally administered vitamin K. British journal of haematology 20060501
Modification of the phylloquinone in the A1 binding site in photosystem I studied using time-resolved FTIR difference spectroscopy and density functional theory. Biochemistry 20060404
Vitamin K suppresses lipopolysaccharide-induced inflammation in the rat. Bioscience, biotechnology, and biochemistry 20060401
[Determination of vitamin K in aojiru (green juice) products by HPLC]. Shokuhin eiseigaku zasshi. Journal of the Food Hygienic Society of Japan 20060401
[Hemorrhagic complications during warfarin treatment]. Vnitrni lekarstvi 20060301
Treatment of excessive anticoagulation with phytonadione (vitamin K): a meta-analysis. Archives of internal medicine 20060227
Menadione is a metabolite of oral vitamin K. The British journal of nutrition 20060201
Oxandrolone steroid use and impaired coagulation. Archives of internal medicine 20060109
Subclinical hypervitaminosis A in rat: measurements of bone mineral density (BMD) do not reveal adverse skeletal changes. Chemico-biological interactions 20060105
Automatic determination of phylloquinone in vegetables and fruits using on-line photochemical reduction and fluorescence detection via solid phase extraction and flow injection. Analytical and bioanalytical chemistry 20060101
Association of dietary and biochemical measures of vitamin K with quantitative ultrasound of the heel in men and women. Osteoporosis international : a journal established as result of cooperation between the European Foundation for Osteoporosis and the National Osteoporosis Foundation of the USA 20060101
Dietary phylloquinone depletion and repletion in postmenopausal women: effects on bone and mineral metabolism. Osteoporosis international : a journal established as result of cooperation between the European Foundation for Osteoporosis and the National Osteoporosis Foundation of the USA 20060101
No effect of vitamin K1 intake on bone mineral density and fracture risk in perimenopausal women. Osteoporosis international : a journal established as result of cooperation between the European Foundation for Osteoporosis and the National Osteoporosis Foundation of the USA 20060101
Analysis of isotope ratios in vitamin K1 (phylloquinone) from human plasma by gas chromatography/mass spectrometry. Rapid communications in mass spectrometry : RCM 20060101
Pleiotropic actions of vitamin K: protector of bone health and beyond? Nutrition (Burbank, Los Angeles County, Calif.) 20060101
Effect of calcium fortified milk supplementation with or without vitamin K on biochemical markers of bone turnover in premenopausal women. Nutrition (Burbank, Los Angeles County, Calif.) 20060101
Surgical delay in acute admissions on warfarin: are we doing enough? International journal of clinical practice 20051101
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. Thrombosis and haemostasis 20051001
Regression of medial elastocalcinosis in rat aorta: a new vascular function for carbonic anhydrase. Circulation 20050913
[Isolation and structure identification of the main photolysis product in vitamin K1]. Sichuan da xue xue bao. Yi xue ban = Journal of Sichuan University. Medical science edition 20050901
Vitamin K in the treatment and prevention of osteoporosis and arterial calcification. American journal of health-system pharmacy : AJHP : official journal of the American Society of Health-System Pharmacists 20050801
Significant effect of capecitabine on the pharmacokinetics and pharmacodynamics of warfarin in patients with cancer. Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20050720
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). Biochimica et biophysica acta 20050715
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
Prediction of genotoxicity of chemical compounds by statistical learning methods. Chemical research in toxicology 20050601
Immediate cutaneous hypersensitivity response to phytomenadione induced by vitamin K in skin diagnostic procedure. Contact dermatitis 20050501
Determinants of plasma dihydrophylloquinone in men and women. The British journal of nutrition 20050501
Intake and sources of phylloquinone (vitamin K(1)) in 4-year-old British children: comparison between 1950 and the 1990s. Public health nutrition 20050401
Pharmacokinetics and efficacy of oral versus intravenous mixed-micellar phylloquinone (vitamin K1) in severe acute liver disease. Journal of hepatology 20050301
Phylloquinone intake as a marker for coronary heart disease risk but not stroke in women. European journal of clinical nutrition 20050201
Expression of LRP1 by human osteoblasts: a mechanism for the delivery of lipoproteins and vitamin K1 to bone. Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research 20050201
Method for the determination of vitamin K homologues in human plasma using high-performance liquid chromatography-tandem mass spectrometry. Analytical chemistry 20050201
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. The Plant journal : for cell and molecular biology 20050201
Ethnic differences in osteocalcin gamma-carboxylation, plasma phylloquinone (vitamin K1) and apolipoprotein E genotype. European journal of clinical nutrition 20050101
Vitamin K status of older individuals in northern China is superior to that of older individuals in the UK. The British journal of nutrition 20041201
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. Molecular and cellular biochemistry 20041201
Warfarin reversal: consensus guidelines, on behalf of the Australasian Society of Thrombosis and Haemostasis. The Medical journal of Australia 20041101
Over-the-counter vitamin K1-containing multivitamin supplements disrupt warfarin anticoagulation in vitamin K1-depleted patients. A prospective, controlled trial. Thrombosis and haemostasis 20041101
Vitamin K status in patients with Crohn's disease and relationship to bone turnover. The American journal of gastroenterology 20041101
Phenotypic modulation of vascular smooth muscle cells during medial arterial calcification: a role for endothelin? Journal of cardiovascular pharmacology 20041101
Associations between vitamin K biochemical measures and bone mineral density in men and women. The Journal of clinical endocrinology and metabolism 20041001
Determination of phylloquinone (vitamin K1) in plasma and serum by HPLC with fluorescence detection. Clinica chimica acta; international journal of clinical chemistry 20040901
Comparison of oral versus intravenous phytonadione in patients with excessive anticoagulation. Current hematology reports 20040901
Dietary phylloquinone intake as a potential marker for a heart-healthy dietary pattern in the Framingham Offspring cohort. Journal of the American Dietetic Association 20040901
[Analysis of vitamins and inorganic elements in the water extracts of Radix Changii]. Zhong xi yi jie he xue bao = Journal of Chinese integrative medicine 20040901
Phylloquinone (vitamin K1) intakes and food sources in 18-64-year-old Irish adults. The British journal of nutrition 20040701
On the alcohol- and water-catalyzed tautomerization of vitamins K1- and K2-derived quinone methide intermediates. The Journal of organic chemistry 20040430
Quinones facilitate the self-assembly of the phosphorylated tubulin binding region of tau into fibrillar polymers. Biochemistry 20040316
Effect of supplementary feeding of vitamin K1 on difethialone treated Indian gerbil, Tatera indica Hardwicke in laboratory. Indian journal of experimental biology 20040301
Skin reaction to subcutaneous phytonadione injections. American journal of health-system pharmacy : AJHP : official journal of the American Society of Health-System Pharmacists 20040215
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. Biochemistry 20040210
Beneficial effects of vitamins D and K on the elastic properties of the vessel wall in postmenopausal women: a follow-up study. Thrombosis and haemostasis 20040201
Indirect identification of isoprenoid quinones in Escherichia coli by LC-MS with atmospheric pressure chemical ionization in negative mode. Journal of basic microbiology 20040101
Observations on possible effects of daily vitamin K replacement, especially upon warfarin therapy. JPEN. Journal of parenteral and enteral nutrition 20040101
[A model of the quinone-binding site of photosystem I: investigation of charge transfer complexes of phylloquinone and its derivatives with tryptophan]. Biofizika 20040101
Prevention of vitamin K deficiency bleeding with oral mixed micellar phylloquinone: results of a 6-year surveillance in Switzerland. European journal of pediatrics 20031201
Vitamin K content of nuts and fruits in the US diet. Journal of the American Dietetic Association 20031201
Effects of dietary particulate limestone, vitamin K3 and fluoride and photostimulation on skeletal morphology and osteoporosis in laying hens. British poultry science 20031201
Comparison of oral vs intravenous phytonadione (vitamin K1) in patients with excessive anticoagulation: a prospective randomized controlled study. Archives of internal medicine 20031110
Multivitamin supplements may affect warfarin anticoagulation in susceptible patients. The Annals of pharmacotherapy 20031101
A retrospective evaluation of vitamin K1 therapy to reverse the anticoagulant effect of warfarin. Pharmacotherapy 20031001
Electrochemical studies of vitamin K1 microdroplets: electrocatalytic hydrogen evolution. Chemphyschem : a European journal of chemical physics and physical chemistry 20030915
Superwarfarin and glass ingestion with prolonged coagulopathy requiring high-dose vitamin K1 therapy. Pharmacotherapy 20030901
The biological activity and tissue distribution of 2',3'-dihydrophylloquinone in rats. Biochimica et biophysica acta 20030822
Isotopic labeling and LC-APCI-MS quantification for investigating absorption of carotenoids and phylloquinone from kale (Brassica oleracea). Journal of agricultural and food chemistry 20030813
Species comparison of vitamin K1 2,3-epoxide reductase activity in vitro: kinetics and warfarin inhibition. Toxicology 20030801
Asymptomatic excessive coumarin anticoagulation is a risk factor for thrombotic and bleeding complications of oral anticoagulant therapy. Journal of thrombosis and haemostasis : JTH 20030801
The anticancer effects of vitamin K. Alternative medicine review : a journal of clinical therapeutic 20030801
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. The Journal of biological chemistry 20030725
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
Weekly oral vitamin K prophylaxis in Denmark. Acta paediatrica (Oslo, Norway : 1992) 20030701
Menatetrenone (vitamin K2) acts directly on circulating human osteoclast precursors. Calcified tissue international 20030701
Control of electron transport in photosystem I by the iron-sulfur cluster FX in response to intra- and intersubunit interactions. The Journal of biological chemistry 20030523
Differential effects of two growth inhibitory K vitamin analogs on cell cycle regulating proteins in human hepatoma cells. Life sciences 20030502
Primary photoreactions of phylloquinone (vitamin K1) and plastoquinone-1 in solution. Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology 20030501
Genome organization in Arabidopsis thaliana: a survey for genes involved in isoprenoid and chlorophyll metabolism. Plant molecular biology 20030401
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. Biochimica et biophysica acta 20030306
Intestinal absorption of mixed micellar phylloquinone (vitamin K1) is unreliable in infants with conjugated hyperbilirubinaemia: implications for oral prophylaxis of vitamin K deficiency bleeding. Archives of disease in childhood. Fetal and neonatal edition 20030301
A new model of isolated systolic hypertension induced by chronic warfarin and vitamin K1 treatment. American journal of hypertension 20030201
Safety and effectiveness of low dose oral vitamin K1 administration in asymptomatic out-patients on warfarin or acenocoumarol with excessive anticoagulation. Haematologica 20030201
Simultaneous determination of vitamin K analogs in human serum by sensitive and selective high-performance liquid chromatography with electrochemical detection. Nutrition (Burbank, Los Angeles County, Calif.) 20030101
[Intermolecular interactions of dipeptide triterpene derivatives and natural quinones with alpha-tocopherol]. Biomeditsinskaia khimiia 20030101
Tissue-specific utilization of menaquinone-4 results in the prevention of arterial calcification in warfarin-treated rats. Journal of vascular research 20030101
Phylloquinone, what can we learn from plants? BioFactors (Oxford, England) 20030101
Vitamin K1 attenuates hypoxia-induced relaxation of rat carotid artery. Pharmacological research 20021201
Modeling of the P700+ charge recombination kinetics with phylloquinone and plastoquinone-9 in the A1 site of photosystem I. Biophysical journal 20021201
Homozygosity mapping of a second gene locus for hereditary combined deficiency of vitamin K-dependent clotting factors to the centromeric region of chromosome 16. Blood 20021101
Shift of serum osteocalcin components between cord blood and blood at day 5 of life. Pediatric research 20021101
The incidence of anaphylaxis following intravenous phytonadione (vitamin K1): a 5-year retrospective review. Annals of allergy, asthma & immunology : official publication of the American College of Allergy, Asthma, & Immunology 20021001
Vitamin K(1) prevents the effect of hypoxia on phenylephrine-induced contraction in the carotid artery. Pharmacology 20020901
Multilaboratory comparison of anaerobe susceptibility results using 3 different agar media. Clinical infectious diseases : an official publication of the Infectious Diseases Society of America 20020901
Pharmacological prevention and regression of arterial remodeling in a rat model of isolated systolic hypertension. Journal of hypertension 20020801
Vitamin K supplementation does not affect ovariectomy-induced bone loss in rats. Bone 20020601
Total body phylloquinone and its turnover in human subjects at two levels of vitamin K intake. The British journal of nutrition 20020601
Intake and sources of phylloquinone (vitamin K1): variation with socio-demographic and lifestyle factors in a national sample of British elderly people. The British journal of nutrition 20020601
Plasma phylloquinone (vitamin K1) concentration and its relationship to intake in a national sample of British elderly people. The British journal of nutrition 20020601
Difference in the metabolism of vitamin K between liver and bone in vitamin K-deficient rats. The British journal of nutrition 20020401
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
[Effects of riboxin, essentiale, and phylloquinone on the immunomodulating and antioxidant effect of laser and magneto-laser irradiation in liver toxicosis induced by gentamycin]. Eksperimental'naia i klinicheskaia farmakologiia 20020101
Determination of vitamin K1 isomers in foods by liquid chromatography with C30 bonded-phase column. Journal of AOAC International 20020101
Measurement of cis and trans isomers of vitamin K1 in rat tissues by liquid chromatography with a C30 column. Journal of AOAC International 20020101
A patient with anaphylactoid hypersensitivity to intravenous cyclosporine and subcutaneous phytonadione (vitamin K(1)). Bone marrow transplantation 20011201
Modification of photosystem I reaction center by the extraction and exchange of chlorophylls and quinones. Biochimica et biophysica acta 20011030
Electron spin echo envelope modulation spectroscopy in photosystem I. Biochimica et biophysica acta 20011030
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. The Journal of biological chemistry 20011026
Mutations in both sides of the photosystem I reaction center identify the phylloquinone observed by electron paramagnetic resonance spectroscopy. The Journal of biological chemistry 20011005
Clinical predictors of prolonged delay in return of the international normalized ratio to within the therapeutic range after excessive anticoagulation with warfarin. Annals of internal medicine 20010918
Summaries for patients. Predicting risk for prolonged high INR after too much anticoagulation. Annals of internal medicine 20010918
Quantitative effects of interacting variables on vitamin K1, phylloquinone, entrapment in liposomes. African journal of medicine and medical sciences 20010901
Oxygen free radical generating mechanisms in the colon: do the semiquinones of vitamin K play a role in the aetiology of colon cancer? Biochimica et biophysica acta 20010815
Off-center fold: indurated plaques on the arms of a 52-year-old man. Diagnosis: Cutaneous reaction to phytonadione injection. Archives of dermatology 20010701
Practitioner report involving intravenous use of vitamin K1 prompts label review and revision. Journal of the American Veterinary Medical Association 20010601
Effect of dietary vitamin K1 on selected plasma characteristics and bone ash in young turkeys fed diets adequate or deficient in vitamin D3. Poultry science 20010501
Dietary vitamin K1 requirement and comparison of biopotency of different vitamin K sources for young turkeys. Poultry science 20010501
Characterization and purification of the vitamin K1 2,3 epoxide reductases system from rat liver. The Journal of pharmacy and pharmacology 20010401
Content of phylloquinone and menaquinone in the tissues of mummichog Fundulus heteroclitus fed diets containing different forms of vitamin K. Journal of nutritional science and vitaminology 20010401
Separation and determination of minor photosynthetic pigments by reversed-phase HPLC with minimal alteration of chlorophylls. Analytical sciences : the international journal of the Japan Society for Analytical Chemistry 20010401
A Fourier transform infrared absorption difference spectrum associated with the reduction of A1 in photosystem I: are both phylloquinones involved in electron transfer? Biochemistry 20010327
Efficacy and safety of intravenous phytonadione (vitamin K1) in patients on long-term oral anticoagulant therapy. Mayo Clinic proceedings 20010301
The association of vitamin K status with warfarin sensitivity at the onset of treatment. British journal of haematology 20010301
Site-directed mutagenesis of PsaA residue W693 affects phylloquinone binding and function in the photosystem I reaction center of Chlamydomonas reinhardtii. Biochemistry 20010220
Reversal of excessive oral anticoagulation with a low oral dose of vitamin K1 compared with acenocoumarine discontinuation. A prospective, randomized, open study. Blood coagulation & fibrinolysis : an international journal in haemostasis and thrombosis 20010101
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
Role of vitamin K and vitamin K-dependent proteins in vascular calcification. Zeitschrift fur Kardiologie 20010101
Cytotoxic activity of vitamins K1, K2 and K3 against human oral tumor cell lines. Anticancer research 20010101
Pseudoscleroderma secondary to phytomenadione (vitamin K1) injections: Texier's disease. The Australasian journal of dermatology 19960201
Mutagenesis of vitamin K-dependent carboxylase demonstrates a carboxyl terminus-mediated interaction with vitamin K hydroquinone. The Journal of biological chemistry 19950310
Mechanism of the abnormal vitamin K-dependent gamma-carboxylation process in human hepatocellular carcinomas. Cancer 19940901
Anticoagulant-related intracerebral hemorrhage in patients with prosthetic heart valves--report of two cases. Neurologia medico-chirurgica 19911101
Exposure of the pregnant rat to warfarin and vitamin K1: an animal model of intraventricular hemorrhage in the fetus. Teratology 19901001
Patulin biosynthesis: epoxidation of toluquinol and gentisyl alcohol by particulate preparations from Penicillium patulum. Biochemistry 19891114
Specificity of increased des-gamma-carboxyprothrombin in hepatocellular carcinoma after vitamin K1 injection. Journal of hepatology 19870801
Vitamin K-dependent carboxylase: evidence for a semiquinone radical intermediate. Archives of biochemistry and biophysics 19840501
Drug-induced convulsions. Report from Boston Collaborative Drug Surveillance Program. Lancet (London, England) 19720930
[Clinical use of vitamin K-1 in hearing disorders caused by kanamycin]. Jibi inkoka Otolaryngology 19660401

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