25486-55-9 Usage
Description
Vitamin K is a dietary nutrient essential for the normal biosynthesis of factors that are required for blood clotting. It has also been shown to inhibit cell growth. Vitamin K1 2,3-epoxide is the inactive metabolite of vitamin K1. During clotting, vitamin K1 is converted to this epoxide form and then rapidly reduced back to the vitamin by a microsomal epoxide reductase. This is referred to as the vitamin K epoxide cycle. Certain anticoagulants target clotting factor synthesis by inhibiting the recycling of vitamin K1 from the inactive epoxide.
Uses
A metabolite of Vitamin K1 (V676080).
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.
Check Digit Verification of cas no
The CAS Registry Mumber 25486-55-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,5,4,8 and 6 respectively; the second part has 2 digits, 5 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 25486-55:
(7*2)+(6*5)+(5*4)+(4*8)+(3*6)+(2*5)+(1*5)=129
129 % 10 = 9
So 25486-55-9 is a valid CAS Registry Number.
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+
25486-55-9Relevant articles and documents
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Fieser,Tishler,Sampson
, p. 1628 (1940)
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Thermochemical investigation of the oxygenation of vitamin K
Flowers II, Robert A.,Naganathan, Sriram,Dowd, Paul,Arnett, Edward M.,Ham, Seung Wook
, p. 9409 - 9416 (2007/10/02)
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.).
Absolute configuration of vitamin K epoxide
Preusch,Suttie
, p. 2291 - 2293 (2007/10/02)
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