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SMB00580

Sigma-Aldrich

Vitamin K4

≥98% (HPLC)

Synonym(s):

2-Methyl-1,4-naphthalenediol diacetate, Menadiol diacetate, Vitamin K diacetate, acetomenaphthone

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About This Item

Empirical Formula (Hill Notation):
C15H14O4
CAS Number:
573-20-6
Molecular Weight:
258.27
EC Number:
209-352-1
MDL number:
MFCD00021469
UNSPSC Code:
12352205
PubChem Substance ID:
329825069
NACRES:
NA.79

Quality Level

200

Assay

≥98% (HPLC)

form

powder

technique(s)

HPLC: suitable

color

white to off-white

storage temp.

2-8°C

SMILES string

CC(OC1=CC(C)=C(OC(C)=O)C2=CC=CC=C21)=O

InChI

1S/C15H14O4/c1-9-8-14(18-10(2)16)12-6-4-5-7-13(12)15(9)19-11(3)17/h4-8H,1-3H3

InChI key

RYWSYCQQUDFMAU-UHFFFAOYSA-N

General description

Vitamin K4 (VK4), also referred to as 2-methyl-1,4-naphthalenediyldiacetate, is a synthetic hydrophilic form of vitamin K that belongs to menadione family. It is a diacetate form of VK3.

Biochem/physiol Actions

Vitamin K4 elicits anti-cancer functionality and induces apoptosis in prostate carcinoma.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H318

Precautionary Statements

P280 - P305 + P351 + P338 + P310

Hazard Classifications

Eye Dam. 1

Storage Class Code

11 - Combustible Solids

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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Phytomenadione European Pharmacopoeia (EP) Reference Standard

P1609000

Phytomenadione

One-Pot Hydroacetylation of Menadione (Vitamin K3) to Menadiol Diacetate (Vitamin K4) by Heterogeneous Catalysis.
Dobrinescu C
Advanced Synthesis & Catalysis, 354, 1301-1306 (2012)
Vitamin K4 induces tumor cytotoxicity in human prostate carcinoma PC-3 cells via the mitochondria-related apoptotic pathway.
Jiang Y
Pharmazie, 68, 442-448 (2013)
Yu Jiang et al.
Die Pharmazie, 68(6), 442-448 (2013-07-24)
Vitamin K4 (VK4) is a synthetic hydrophilic menadione compound, which is clinically used as hemostasis medicine. It has been reported that several vitamin Ks had inhibitory effects on various cancer cells. However, there is no report about VK4s anticancer activity.

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