Skip to Content
MilliporeSigma
All Photos(1)

Key Documents

View All Documentation

51455

Sigma-Aldrich

Vitamin K3 2,3-epoxide

≥98.5% (HPLC)

Synonym(s):

1a,7a-Dihydro-1a-methylnaphth[2,3-b]oxirene-2,7-dione, 2,3-Epoxy-2,3-dihydro-2-methyl-1,4-naphthoquinone, 2-Methyl-1,4-naphthoquinone epoxide, Menadione 2,3-epoxide, NSC 65669

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C11H8O3
CAS Number:
15448-59-6
Molecular Weight:
188.18
Beilstein/REAXYS Number:
144630
MDL number:
MFCD00022240
UNSPSC Code:
12352200
PubChem Substance ID:
329757691

assay

≥98.5% (HPLC)

form

powder

color

white

suitability

complies for H-NMR

application(s)

cell analysis

storage temp.

−20°C

SMILES string

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

InChI

1S/C11H8O3/c1-11-9(13)7-5-3-2-4-6(7)8(12)10(11)14-11/h2-5,10H,1H3

InChI key

NNUKDUBCRRYXDC-UHFFFAOYSA-N

Biochem/physiol Actions

Metabolite of vitamin K metabolism.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
STBG4659V
STBF3526V

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Customers Also Viewed

Slide 1 of 2

1 of 2

Retinyl Acetate (Vitamin A Acetate) Pharmaceutical Secondary Standard; Certified Reference Material

Supelco

PHR1236

Retinyl Acetate (Vitamin A Acetate)

Vitamin K1 viscous liquid

Sigma-Aldrich

V3501

Vitamin K1

A Brunmark et al.
Free radical biology & medicine, 5(3), 133-143 (1988-01-01)
The oxidation of various quinones by H2O2 results in quinone epoxide formation. The yield of epoxidation is inversely related to the degree of methyl substitution of the quinone and seems not to be dependent on the redox potential of the
Jender Wu et al.
Chemico-biological interactions, 193(1), 3-11 (2011-04-02)
2-Methyl-1,4-naphthoquinone (menadione or vitamin K3; EPO) and K3-2,3-epoxide (EPO1), but not vitamin K3-3-OH (EPO2), exhibited cytotoxicity that caused DNA fragmentation and chromatin condensation in U87 and C6 cells. EPO1 showed more-potent cytotoxicity than EPO, and the IC(50) values of EPO
2,3-Epoxy-2-methyl-1,4-naphthoquinone Microcapsule Emulsion: Preparation and Application in the Controlled-Release.
Qu, Y. and Zhang, S.
Asian Journal of Chemistry, 24, 4587-4590 (2012)
Nicole Jasmin Mueller et al.
Organic & biomolecular chemistry, 7(6), 1115-1119 (2009-03-06)
Three FMN-dependent oxidoreductases, YcnD and YhdA from Bacillus subtilis and Lot6p from Saccharomyces cerevisiae, oxidised alpha,beta-unsaturated carbonyl compounds and a thioether, respectively, to furnish the corresponding racemic epoxides or sulfoxide, respectively. The mechanism of this enzyme-mediated (rather than enzyme-catalysed) oxidation
Asymmetric Weitz-Scheffer epoxidation promoted by bovine serum albumin. Part III. Highly stereoselective synthesis of optically active epoxynaphthoquinones.
Colonna, S., et al.
Tetrahedron, 44, 5169-5178 (1988)
View All Related Papers

Questions

Reviews

No rating value

Active Filters

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service