25486-55-9

Usage

Uses

Used in Pharmaceutical Industry:
(2,3-epoxyphytyl)menaquinone is used as an essential component in the study and understanding of blood clotting mechanisms. Its role in the vitamin K epoxide cycle helps researchers develop new therapeutic approaches for managing blood clotting disorders and improving the efficacy of anticoagulant drugs.
Additionally, Vitamin K1 and its metabolites, including (2,3-epoxyphytyl)menaquinone, have been shown to inhibit cell growth, making them potential candidates for further research in cancer treatment and other related applications.

Biochem/physiol Actions

Vitamin K1 2,3-epoxide is a vitamin K derivative. It is a fat soluble vitamin produced by plants. Vitamin K is essential for blood coagulation. Vitamin K is rarely deficient in a human diet since it is continually recycled in our cells. Vitamin K 2,3-epoxide acts as a substrate for vitamin K 2,3-epoxide reductase (VKOR) complex. Elevated levels of serum vitamin K epoxide in patients is associated with familial multiple coagulation factor deficiency.

InChI:InChI=1/C31H46O3/c1-22(2)12-9-13-23(3)14-10-15-24(4)16-11-17-25(5)20-21-31-29(33)27-19-8-7-18-26(27)28(32)30(31,6)34-31/h7-8,18-20,22-24H,9-17,21H2,1-6H3/b25-20+

Upstream product

• 81818-54-4 2-methyl-3-(3,7,11,15-tetramethyl-hexadec-2-enyl)-[1,4]naphthoquinone 
• 16869-68-4 trans-1,4-Dihydro-vitamin K₁⁽²⁰⁾ 
• 84-80-0 phytomenadione 
• 84-80-0 vitamin K₁ 

Downstream Products

• 84-80-0 vitamin K₁ 
• 16869-68-4 trans-1,4-Dihydro-vitamin K₁⁽²⁰⁾ 
• 85873-38-7 2-Hydroxy-2-methyl-3-phytyl-2,3-dihydro-1,4-naphthoquinone 
• 86631-62-1 3-Hydroxy-2-methyl-3-phytyl-2,3-dihydro-1,4-naphthoquinone 
• 81818-54-4 2-methyl-3-(3,7,11,15-tetramethyl-hexadec-2-enyl)-[1,4]naphthoquinone 
• 84-80-0 vitamin K 

Relevant academic research and scientific papers

Immunomodulating compositions for treatment of immune system disorders

The present invention relates to a composition for use as an immunomodulator comprising small molecular weight components of less than 3000 daltons, and having the following properties: a) is extractable from bile of animals; b) is capable of stimulating monocytes and macrophages in vitro and in vivo; c) is capable of modulating tumor necrosis factor production; d) contains no measurable IL-1α, IL-1β, TNF, IL-6, IL-8, IL-4, GM-CSF or IFN-γ; e) has an anti-proliferative effect in a malignant mouse hybridoma cell line; f) shows no cytotoxicity to human peripheral blood mononuclear cells or lymphocytes; and g) is not an endotoxin. The invention also relates to a method of preparing the composition, its use as an immunomodulator, and its use in the treatment of diseases and conditions having an immunological component.

Thermochemical investigation of the oxygenation of vitamin K

Discovery of a new oxygenation reaction of naphthohydroquinone anions makes possible a determination of the heat of reaction (ΔHox) of oxygen with the potassium salt derived from deprotonation of the hydroquinone form of vitamin K. From that value (-33.52 ± 0.60 kcal/mol), the heat of deprotonation of vitamin KH2 (-30.03 ± 1.20 kcal/mol), and the heat of deprotonation of water (-6.05 ± 0.3 kcal/mol), the enthalpy change for converting vitamin KH2 to vitamin K oxide is established to be -57.5 kcal/mol, in reasonable agreement with our previous estimate of -62.4 kcal/mol for the oxygenation of the parent naphthohydroquinone. Indeed, in similar fashion the heat of oxygenation of the parent naphthohydroquinone was determined to be -58.47 kcal/mol, and this permits the assignment of a heat of formation to naphthoquinone epoxide of ΔHf° = -47.6 kcal/mol. Heats of oxygenation and deprotonation of a variety of related phenols and naphthols provide perspective on cation and substitution effects. These data provide strong support for the base strength amplification mechanism for the biological action of vitamin K proposed by two of us (P.D. and S.W.H.).