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Phylloquinone

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Phylloquinone
280px
Names
IUPAC name
2-methyl-3-[(2E)-3,7,11,15-tetramethylhexadec-2-en-1-yl]naphthoquinone
Other names
Vitamin K1; phytomenadione; phytonadione
Identifiers
84-80-0 YesY
ChEBI CHEBI:18067 YesY
ChEMBL ChEMBL1550 YesY
ChemSpider 4447652 YesY
DrugBank DB01022 YesY
Jmol 3D model Interactive image
PubChem 4812
UNII A034SE7857 YesY
  • 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 YesY
    Key: MBWXNTAXLNYFJB-NKFFZRIASA-N YesY
  • InChI=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
  • CC1=C(C(=O)c2ccccc2C1=O)C/C=C(\C)/CCC[C@H](C)CCC[C@H](C)CCCC(C)C
Properties
C31H46O2
Molar mass 450.70 g/mol
Pharmacology
ATC code B02BA01
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY verify (what is YesYN ?)
Infobox references

Phylloquinone, also Vitamin K1, 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, particularly leaves, since it functions as an electron acceptor during photosynthesis, forming part of the electron transport chain of Photosystem I.

It is on the World Health Organization's List of Essential Medicines, a list of the most important medication needed in a basic health system.[1]

Terminology

It is often called vitamin K,[2] phytomenadione or phytonadione. Sometimes a distinction is made with phylloquinone considered natural and phytonadione considered synthetic.[3]

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

Biochemistry

Phylloquinone is an electron acceptor during photosynthesis, forming part of the electron transport chain of Photosystem I.

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

Vitamin K is required for bone protein formation.[4]

See also

External links

References

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