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Merck
CN

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

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About This Item

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

Key Documents

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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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
STBG4659V
STBF3526V

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Toru Kitano et al.
Biological & pharmaceutical bulletin, 35(4), 617-623 (2012-04-03)
We investigated the cytotoxicity of eight vitamin K3 (VK3) analogs against neuroblastoma cell lines (IMR-32, LA-N-1, NB-39, and SK-N-SH) and normal cell lines (human umbilical vein endothelial cells (HUVEC) and human dermal fibroblasts (HDF)) using a 3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyltetrazolium bromide (MTT) assay.
Synthesis, thiol-mediated reactive oxygen species generation profiles and anti-proliferative activities of 2,3-epoxy-1,4-naphthoquinones.
Dharmaraja, A.T., et al
MedChemComm, 3, 219-224 (2012)
The Active Site of Vitamin K and the Role of the Vitamin K-Dependent Carboxylase.
Naganathan, S., et al.
Journal of the American Chemical Society, 116, 9831-9839 (1994)
Nan Chen et al.
Organic letters, 10(3), 381-384 (2008-01-11)
An efficient three-step construction of the highly oxygenated D-ring of the kinamycin antibiotics is reported for a simple model system. A comparison of the spectroscopic characteristics of the synthetic models with those of natural kinamycin F, which is suspected to
Xiao Lu et al.
ACS medicinal chemistry letters, 3(12), 1029-1033 (2012-12-13)
Cations of hydroxy-substituted 1,4-naphthoquinones were synthesized and evaluated as antiplasmodial agents against Plasmodium falciparum. The atovaquone analogues were found to be inactive as antagonists of parasite growth, which was attributed to ionization of the acidic hydroxyl moiety. Upon modification to
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