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Chemical and physical
properties of vitamin K
Domina Petric, MD
Derivative of 2-methyl-1,4-naphthoquinone.
Ring structure has a hydrophobic constituent
at the 3-position and can be alkylated with an
isoprenoid side chain.
April 11, 2018
Combs GF. The Vitamins. Fundamental Aspects
in Nutrition and Health. Elsevier Inc. 2008.
2
Essential features of the chemical
structure:
Phylloquinones
Menaquinones
Menadione
April 11, 2018
Combs GF. The Vitamins. Fundamental Aspects
in Nutrition and Health. Elsevier Inc. 2008.
3
Chemical structures of the vitamin K
group:
Sigmaaldrich.com
• Vitamin K is the generic descriptor for 2-
methyl-1,4-naphthoquinone and all of its
derivatives exhibiting qualitatively the
biological (antihemorrhagic) activity of
phylloquinone.
• Naturally occurring forms of the vitamin
have an unsaturated isoprenoid side chain
at C-3 of the naphthoquinone nucleus.
April 11, 2018
Combs GF. The Vitamins. Fundamental Aspects
in Nutrition and Health. Elsevier Inc. 2008.
4
Vitamin K nomenclature
The phylloquinone group includes forms with phytyl side
chains and side chains that are further alkylated, thus
consisting of several saturated isoprenoid units.
The vitamers of this group have only one double bond in
their side chains: on the proximal isoprene unit.
These vitamers are synthesized by green plants.
They are properly referred to as phylloquinones and are
abbreviated as K.
April 11, 2018
Combs GF. The Vitamins. Fundamental Aspects
in Nutrition and Health. Elsevier Inc. 2008.
5
Vitamin K nomenclature
• The menaquinone group also includes
vitamers with side chains consisting of
variable numbers of isoprenoid units.
• Each isoprene unit has a double bond.
• These vitamers are synthesized by
bacteria.
• They are abbreviated as MK13 and were
formerly referred to as vitamin K2.
April 11, 2018
Combs GF. The Vitamins. Fundamental Aspects
in Nutrition and Health. Elsevier Inc. 2008.
6
Vitamin K nomenclature
The compound 2-methyl-1,4-naphthoquinone (without a
side chain) is called menadione.
It does not exist naturally, but has biological activity by
virtue of the fact that animals can alkylate it to produce
such metabolites as MK-4.
Menadione is made in several forms: menadione sodium
bisulfite complex, menadione dimethylpyrimidinol bisulfite.
April 11, 2018
Combs GF. The Vitamins. Fundamental Aspects
in Nutrition and Health. Elsevier Inc. 2008.
7
Vitamin K nomenclature
The abbreviations K-n and MK-n
are used for the phylloquinones
and menaquinones to indicate
specific vitamers with side chains
consisting of n isoprenoid units.
April 11, 2018
Combs GF. The Vitamins. Fundamental Aspects
in Nutrition and Health. Elsevier Inc. 2008.
8
Vitamin K nomenclature
• Phylloquinone (K1) is a yellow oil at room
temperature, but the other vitamers K
are yellow crystals.
• The vitamers K, MK, and most forms of
menadione are insoluble in water, slightly
soluble in ethanol, and readily soluble in
ether, chloroform, fats and oils.
April 11, 2018
Combs GF. The Vitamins. Fundamental Aspects
in Nutrition and Health. Elsevier Inc. 2008.
9
Chemical and physical properties of
vitamin K
• The vitamers K are sensitive to
light and alkali, but are relatively
stable to heat and oxidizing
environments.
• Their oxidation proceeds to
produce the 2,3-epoxide form.
April 11, 2018
Combs GF. The Vitamins. Fundamental Aspects
in Nutrition and Health. Elsevier Inc. 2008.
10
Chemical and physical properties of
vitamin K
The biopotency of vitamers K depends on
both the nature and length of their
isoprenoid side chains.
The menaquinones (K-2) tend to have
greater biopotencies than the
corresponding phylloquinone analogs.
Members of each series with four or five
isoprenoid side chains are the most
biopotent.
April 11, 2018
Combs GF. The Vitamins. Fundamental Aspects
in Nutrition and Health. Elsevier Inc. 2008.
11
Vitamin K biopotency
• Combs GF. The Vitamins. Fundamental Aspects
in Nutrition and Health. Elsevier Inc. 2008.
Literature
April 11, 2018 12

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Chemical and physical properties of vitamin K

  • 1. Chemical and physical properties of vitamin K Domina Petric, MD
  • 2. Derivative of 2-methyl-1,4-naphthoquinone. Ring structure has a hydrophobic constituent at the 3-position and can be alkylated with an isoprenoid side chain. April 11, 2018 Combs GF. The Vitamins. Fundamental Aspects in Nutrition and Health. Elsevier Inc. 2008. 2 Essential features of the chemical structure:
  • 3. Phylloquinones Menaquinones Menadione April 11, 2018 Combs GF. The Vitamins. Fundamental Aspects in Nutrition and Health. Elsevier Inc. 2008. 3 Chemical structures of the vitamin K group: Sigmaaldrich.com
  • 4. • Vitamin K is the generic descriptor for 2- methyl-1,4-naphthoquinone and all of its derivatives exhibiting qualitatively the biological (antihemorrhagic) activity of phylloquinone. • Naturally occurring forms of the vitamin have an unsaturated isoprenoid side chain at C-3 of the naphthoquinone nucleus. April 11, 2018 Combs GF. The Vitamins. Fundamental Aspects in Nutrition and Health. Elsevier Inc. 2008. 4 Vitamin K nomenclature
  • 5. The phylloquinone group includes forms with phytyl side chains and side chains that are further alkylated, thus consisting of several saturated isoprenoid units. The vitamers of this group have only one double bond in their side chains: on the proximal isoprene unit. These vitamers are synthesized by green plants. They are properly referred to as phylloquinones and are abbreviated as K. April 11, 2018 Combs GF. The Vitamins. Fundamental Aspects in Nutrition and Health. Elsevier Inc. 2008. 5 Vitamin K nomenclature
  • 6. • The menaquinone group also includes vitamers with side chains consisting of variable numbers of isoprenoid units. • Each isoprene unit has a double bond. • These vitamers are synthesized by bacteria. • They are abbreviated as MK13 and were formerly referred to as vitamin K2. April 11, 2018 Combs GF. The Vitamins. Fundamental Aspects in Nutrition and Health. Elsevier Inc. 2008. 6 Vitamin K nomenclature
  • 7. The compound 2-methyl-1,4-naphthoquinone (without a side chain) is called menadione. It does not exist naturally, but has biological activity by virtue of the fact that animals can alkylate it to produce such metabolites as MK-4. Menadione is made in several forms: menadione sodium bisulfite complex, menadione dimethylpyrimidinol bisulfite. April 11, 2018 Combs GF. The Vitamins. Fundamental Aspects in Nutrition and Health. Elsevier Inc. 2008. 7 Vitamin K nomenclature
  • 8. The abbreviations K-n and MK-n are used for the phylloquinones and menaquinones to indicate specific vitamers with side chains consisting of n isoprenoid units. April 11, 2018 Combs GF. The Vitamins. Fundamental Aspects in Nutrition and Health. Elsevier Inc. 2008. 8 Vitamin K nomenclature
  • 9. • Phylloquinone (K1) is a yellow oil at room temperature, but the other vitamers K are yellow crystals. • The vitamers K, MK, and most forms of menadione are insoluble in water, slightly soluble in ethanol, and readily soluble in ether, chloroform, fats and oils. April 11, 2018 Combs GF. The Vitamins. Fundamental Aspects in Nutrition and Health. Elsevier Inc. 2008. 9 Chemical and physical properties of vitamin K
  • 10. • The vitamers K are sensitive to light and alkali, but are relatively stable to heat and oxidizing environments. • Their oxidation proceeds to produce the 2,3-epoxide form. April 11, 2018 Combs GF. The Vitamins. Fundamental Aspects in Nutrition and Health. Elsevier Inc. 2008. 10 Chemical and physical properties of vitamin K
  • 11. The biopotency of vitamers K depends on both the nature and length of their isoprenoid side chains. The menaquinones (K-2) tend to have greater biopotencies than the corresponding phylloquinone analogs. Members of each series with four or five isoprenoid side chains are the most biopotent. April 11, 2018 Combs GF. The Vitamins. Fundamental Aspects in Nutrition and Health. Elsevier Inc. 2008. 11 Vitamin K biopotency
  • 12. • Combs GF. The Vitamins. Fundamental Aspects in Nutrition and Health. Elsevier Inc. 2008. Literature April 11, 2018 12