Phylloquinone

Phylloquinone: Phylloquinone

IUPAC name

2-methyl-3-[(2E)-3,7,11,15-tetramethylhexadec-2-en-1-yl]naphthoquinone

Identifiers

CAS number 84-80-0

PubChem 4812

ChemSpider 4447652

UNII A034SE7857

DrugBank DB01022

ChEBI CHEBI:18067

ChEMBL CHEMBL1550^Y

Jmol-3D images Image 1

SMILES

CC1=C(C(=O)c2ccccc2C1=O)C/C=C(\C)/CCC[C@H](C)CCC[C@H](C)CCCC(C)C

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
Key: MBWXNTAXLNYFJB-NKFFZRIASA-NInChI=1/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
Key: MBWXNTAXLNYFJB-NKFFZRIABL

Properties

Molecular formula C₃₁H₄₆O₂

Molar mass 450.7 g mol⁻¹

Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Infobox references

Phylloquinone is a polycyclic aromatic ketone, based on 2-methyl-1,4-naphthoquinone, with a 3-phytyl substituent.

It is a fat-soluble vitamin that is stable to air and moisture but decomposes in sunlight. It is found naturally in a wide variety of green plants.

Contents

1 Terminology

2 Mechanism

3 See also

4 References

Terminology

It is often called vitamin K₁^[1] or phytonadione. Sometimes a distinction is made with phylloquinone considered natural and phytonadione considered synthetic.^[2]

A stereoisomer of phylloquinone is called vitamin k₁ (note the difference in capitalization).

Mechanism

Its best known mechanism of action is as a cofactor in the formation of coagulation factors II (prothrombin), VII, IX and X by the liver. Vitamin K₁ is commonly used to treat warfarin toxicity, and an antidote for coumatetralyl. It is also required for the formation of anticoagulant factors protein C and S. Vitamin K is also required for bone protein formation.

Phylloquinone is an electron acceptor in the electron transport chain of chloroplasts.

See also

Vitamin K

Menatetrenone

References

^ Haroon Y, Shearer MJ, Rahim S, Gunn WG, McEnery G, Barkhan P (June 1982). "The content of phylloquinone (vitamin K1) in human milk, cows' milk and infant formula foods determined by high-performance liquid chromatography". J. Nutr. 112 (6): 1105–17. PMID 7086539. http://jn.nutrition.org/cgi/pmidlookup?view=long&pmid=7086539.

^ "Vitamin K". http://www.umm.edu/altmed/articles/vitamin-k-000343.htm. Retrieved 2009-03-18.

v · d · eVitamins (A11)

Fat soluble

A

α-Carotene · β-Carotene · Retinol^# · Tretinoin

D

D₂ (Ergosterol, Ergocalciferol^#) · D₃ (7-Dehydrocholesterol, Previtamin D₃, Cholecalciferol, 25-hydroxycholecalciferol, Calcitriol (1,25-dihydroxycholecalciferol), Calcitroic acid) · D₄ (Dihydroergocalciferol) · D₅ · D analogues (Dihydrotachysterol, Calcipotriol, Tacalcitol, Paricalcitol)

E

Tocopherol (Alpha, Beta, Gamma, Delta) · Tocotrienol (Alpha, Beta, Gamma, Delta) · Tocofersolan

K

Naphthoquinone · Phylloquinone (K₁) · Menatetrenone (K₂) · Menadione (K₃) · Menadiol (K₄)

Water soluble

B

B₁ (Thiamine^#) · B₂ (Riboflavin^#) · B₃ (Niacin, Nicotinamide^#) · B₅ (Pantothenic acid, Dexpanthenol, Pantethine) · B₆ (Pyridoxine^#, Pyridoxal phosphate, Pyridoxamine) · B₇ (Biotin) · B₉ (Folic acid, Dihydrofolic acid, Folinic acid) · B₁₂ (Cyanocobalamin, Hydroxocobalamin, Methylcobalamin, Cobamamide) · Choline

C

Ascorbic acid^# · Dehydroascorbic acid

Combinations
Multivitamins

^#WHO-EM. ^‡Withdrawn from market. Clinical trials: ^†Phase III. ^§Never to phase III

M: NUT

cof, enz, met

noco, nuvi, sysi/epon, met

drug(A8/11/12)

v · d · eAntihemorrhagics (B02)

Hemostatics
(coagulation)

Systemic

Vitamin K

Phytomenadione (K₁) • Menadione (K₃)

Coagulation factors

intrinsic: IX/Nonacog alfa • VIII

extrinsic: VII/Eptacog alfa
common: X • II/Thrombin • I/Fibrinogen

Other systemic

Etamsylate • Carbazochrome • Batroxobin • thrombopoietin receptor agonist (Romiplostim, Eltrombopag)

Local

Absorbable gelatin sponge • Oxidized cellulose • Tetragalacturonic acid hydroxymethylester • Thrombin • Collagen • Calcium alginate • Epinephrine/Adrenalone

Antifibrinolytics
amino acids (Aminocaproic acid, Tranexamic acid, Aminomethylbenzoic acid)
serpins (Aprotinin, Alfa1 antitrypsin, C1-inhibitor, Camostat)

M: MYL

cell/phys (coag, heme, immu, gran), csfs

rbmg/mogr/tumr/hist, sysi/epon, btst

drug (B1/2/3+5+6), btst, trns

Categories:
Naphthoquinones
Vitamers
Vitamin K

Phylloquinone

IUPAC name 2-methyl-3-[(2E)-3,7,11,15-tetramethylhexadec-2-en-1-yl]naphthoquinone
Identifiers
CAS number	84-80-0
PubChem	4812
ChemSpider	4447652
UNII	A034SE7857
DrugBank	DB01022
ChEBI	CHEBI:18067
ChEMBL	CHEMBL1550^Y
Jmol-3D images	Image 1
SMILES CC1=C(C(=O)c2ccccc2C1=O)C/C=C(\C)/CCC[C@H](C)CCC[C@H](C)CCCC(C)C
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 Key: MBWXNTAXLNYFJB-NKFFZRIASA-NInChI=1/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 Key: MBWXNTAXLNYFJB-NKFFZRIABL
Properties
Molecular formula	C₃₁H₄₆O₂
Molar mass	450.7 g mol⁻¹
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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Look at other dictionaries:

Phylloquinone — Structure de la phylloquinone Général Nom IUPAC 2 méthyl 3 [(2E) 3,7,11,15 tétramethylhexadéc … Wikipédia en Français
phylloquinone — ● phylloquinone nom féminin Naphtoquinone C31H46O2, qui est la vitamine K1 antihémorragique … Encyclopédie Universelle
phylloquinone — filochinonas statusas T sritis chemija apibrėžtis 2 metil 1,4 naftochinono darinys su izoprenoidine grandine trečiojoje padėtyje. atitikmenys: angl. phylloquinone; vitamin K rus. витамин K; филлохинон ryšiai: sinonimas – vitaminas K … Chemijos terminų aiškinamasis žodynas
Phylloquinone monooxygenase (2,3-epoxidizing) — In enzymology, a phylloquinone monooxygenase (2,3 epoxidizing) (EC number|1.14.99.20) is an enzyme that catalyzes the chemical reaction:phylloquinone + AH2 + O2 ightleftharpoons 2,3 epoxyphylloquinone + A + H2OThe 3 substrates of this enzyme are… … Wikipedia
phylloquinone — /fil oh kwi nohn , kwin ohn/, n. Biochem. See vitamin K1. [1935 40; PHYLLO + QUINONE] * * * … Universalium
phylloquinone — noun a) A polycyclic aromatic ketone, based on 2 methyl 1,4 naphthoquinone. b) Vitamin K Syn: phytonadione, phytomenadione See Also: naphthoquinone … Wiktionary
phylloquinone — Isolated from alfalfa; also prepared synthetically; major form of vitamin K found in plants. SYN: phytomenadione, phytonadione, vitamin K1, vitamin K1(20). p. reductase SYN: NADPH dehydrogenase (quinone). * * * phyl·lo·qui·none .fil ō kwin ōn,… … Medical dictionary
phylloquinone — n. vitamin K 1 … English contemporary dictionary
phylloquinone — [ˌfɪlə(ʊ) kwɪnəʊn] noun Biochemistry vitamin K1, a compound found in cabbage, spinach, and other leafy green vegetables, and essential for the blood clotting process … English new terms dictionary
phylloquinone — phyl·lo·quinone … English syllables

Academic Dictionaries and Encyclopedias

Phylloquinone

Contents

Terminology

Mechanism

See also

References

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Academic Dictionaries and Encyclopedias

Wikipedia

Phylloquinone

Contents

Terminology

Mechanism

See also

References

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