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19697

Sigma-Aldrich

Vitamin K1 2,3-epoxide

≥98.0% (HPLC)

Synonym(s):

(2,3-Epoxyphytyl)menaquinone, 1a,7a-Dihydro-1a-methyl-7a-(3,7,11,15-tetramethyl-2-hexadecenyl)naphth[2,3-b]oxirene-2,7-dione, 2,3-Epoxy-2,3-dihydro-2-methyl-3-phytyl-1,4-naphthoquinone, 2,3-Epoxyphylloquinone, Phylloquinone oxide

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About This Item

Empirical Formula (Hill Notation):
C31H46O3
CAS Number:
25486-55-9
Molecular Weight:
466.70
EC Number:
247-022-9
UNSPSC Code:
12352205
PubChem Substance ID:
329751934
NACRES:
NA.28

Quality Level

100

Assay

≥98.0% (HPLC)

form

(Liquid or Viscous Liquid)

color

colorless to green-yellow
 colorless to green
 colorless to yellow

storage temp.

−20°C

SMILES string

O=C1C2(C/C=C(C)/CCCC(C)CCCC(C)CCCC(C)C)C(O2)(C)C(C3=CC=CC=C31)=O

InChI

1S/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+

InChI key

KUTXFBIHPWIDJQ-LKUDQCMESA-N

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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.

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Metabolism of vitamin K1 (phylloquinone) in man
Barkhan P and Shearer MJ
Proceedings of the Royal Society of Medicine (1977)
Hereditary combined deficiency of the vitamin K-dependent clotting factors
Napolitano M, et al.
Orphanet Journal of Rare Diseases, 5(1), 21-21 (2010)
K Hirauchi et al.
Journal of chromatography, 430(1), 21-29 (1988-08-19)
A highly sensitive method for measuring endogenous vitamin K1, menaquinone-4 (which is one of the K2 vitamins) and vitamin K1 2,3-epoxide in human plasma was developed, based on high-performance liquid chromatography with coulometric reduction and fluorimetric detection, following extraction from
Changes in the urinary metabolites of phylloquinone (vitamin K1) in man following therapeutic anticoagulation with warfarin.
A McBurney et al.
Biochemical pharmacology, 27(3), 273-278 (1978-02-01)
D Trenk et al.
Journal of clinical pharmacology, 30(8), 737-742 (1990-08-01)
It seems that cephalosporins bearing a N-methyl-thio-tetrazole or a methyl-thiadiazole moiety in their molecule can cause hypoprothombinemia in patients via inhibition of the metabolism of vitamin K1 if they are in addition in a vitamin K1-deficient state. The authors therefore
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