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phytonadione epoxide
(2,3-epoxyphytyl)menaquinone; phylloquinine 2,3-epoxide; vitamin K1 oxide

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CAS Number: 25486-55-9Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:247-022-9
XlogP3-AA:10.10 (est)
Molecular Weight:466.70522000
Formula:C31 H46 O3
NMR Predictor:Predict (works with chrome, Edge or firefox)
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Soluble in:
 water, 1.067e-006 mg/L @ 25 °C (est)
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
Cosmetic Information:
CosIng:cosmetic data
Cosmetic Uses: astringents
BOC Sciences
For experimental / research use only.
2,3-Epoxide Vitamin K1 (Mixture of Diastereomers)
Odor: characteristic
Use: One of the impurities of Vitamin K1, which could be found commonly in green plants and photosynthetic bacteria, and has been found to be related to osteoporosis.
Santa Cruz Biotechnology
For experimental / research use only.
Vitamin K1 2,3-Epoxide
Sigma-Aldrich: Sigma
For experimental / research use only.
Vitamin K1 2,3-epoxide ≥98.0% (HPLC)
Safety Information:
Preferred SDS: View
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
Safety in Use Information:
Recommendation for phytonadione epoxide usage levels up to:
 not for fragrance use.
Recommendation for phytonadione epoxide flavor usage levels up to:
 not for flavor use.
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :91577
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):91577
Pubchem (sid):135048513
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
KEGG (GenomeNet):C05849
HMDB (The Human Metabolome Database):HMDB02972
Potential Blenders and core components note
None Found
Potential Uses:
None Found
Occurrence (nature, food, other):note
 not found in nature
1a,7a-dihydro-1a-methyl-7a-(3,7,11,15-tetramethyl-2-hexadecenyl)naphth(2,3-b) oxirene-2,7-dione
(2,3-epoxyphytyl)menaquinone; phylloquinine 2,3-epoxide; vitamin K1 oxide
 vitamin K1 oxide
Vitamin K1 2,3-epoxide is a vitamin K derivative. Vitamin K needed for the posttranslational modification of certain proteins, mostly required for blood coagulation. Within the cell, Vitamin K undergoes electron reduction to a reduced form of Vitamin K (called Vitamin K hydroquinone) by the enzyme Vitamin K epoxide reductase (or VKOR). Another enzyme then oxidizes Vitamin K hydroquinone to allow carboxylation of Glutamate to Gamma-cabroxygluatmate (Gla); this enzyme is called the gamma-glutamyl carboxylase or the Vitamin K-dependent carboxylase. The carboxylation reaction will only proceed if the carboxylase enzyme is able to oxidize Vitamin K hydroquinone to vitamin K epoxide at the same time; the carboxylation and epoxidation reactions are said to be coupled reactions. Vitamin K epoxide is then re-converted to Vitamin K by the Vitamin K epoxide reductase. These two enzymes comprise the so-called Vitamin K cycle. One of the reasons why Vitamin K is rarely deficient in a human diet is because Vitamin K is continually recycled in our cells. Vitamin K 2,3-epoxide is the substrate for vitamin K 2,3-epoxide reductase (VKOR) complex. Significantly increased level of serum vitamin K epoxide has been found in patients with familial multiple coagulation factor deficiency. (PMID 12384421) Accumulation of vitamin K1-2,3-epoxide in plasma is also a sensitive marker of coumarin-like activity of drugs. (PMID 2401753) [HMDB]
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