Phylloquinone

Phylloquinone
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
3D model (Jmol) Interactive image
ChEBI CHEBI:18067 YesY
ChEMBL ChEMBL1550 YesY
ChemSpider 4447652 YesY
DrugBank DB01022 YesY
ECHA InfoCard 100.001.422
PubChem 4812
UNII A034SE7857 YesY
Properties
C31H46O2
Molar mass 450.70 g/mol
Pharmacology
B02BA01 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.

See also

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References

  1. ↑ "WHO Model List of Essential Medicines: 18th list" (PDF). World Health Organization. October 2013. Retrieved 22 April 2014.
  2. ↑ 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.
  3. ↑ "Vitamin K". Retrieved 2009-03-18.
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