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V9378

Sigma-Aldrich

Vitamin K2

Synonym(s):

Menaquinone 4, Menatetrenone

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About This Item

Empirical Formula (Hill Notation):
C31H40O2
CAS Number:
863-61-6
Molecular Weight:
444.65
MDL number:
MFCD00079646
UNSPSC Code:
12352205
PubChem Substance ID:
329830240
NACRES:
NA.79

form

powder

color

yellow

storage temp.

−20°C

SMILES string

C\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC1=C(C)C(=O)c2ccccc2C1=O

InChI

1S/C31H40O2/c1-22(2)12-9-13-23(3)14-10-15-24(4)16-11-17-25(5)20-21-27-26(6)30(32)28-18-7-8-19-29(28)31(27)33/h7-8,12,14,16,18-20H,9-11,13,15,17,21H2,1-6H3/b23-14+,24-16+,25-20+

InChI key

DKHGMERMDICWDU-GHDNBGIDSA-N

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Application

  • Vitamin K2 ameliorates osteoarthritis by suppressing ferroptosis and extracellular matrix degradation through activation GPX4′s dual functions.: Vitamin K₂ is shown to have protective effects in osteoarthritis by inhibiting ferroptosis and preventing the degradation of the extracellular matrix. The study emphasizes the therapeutic potential of vitamin K₂ in managing joint health and reducing the progression of osteoarthritis (He et al., 2024).

Biochem/physiol Actions

Menatetrenone (MK-4) is one of nine forms of vitamin K2 which is ubiquitously present in extrahepatic tissues. MK-4 has a number of metabolic and anti-neoplastic activities.

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Product No.
Description
Pricing

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Jonna Weisell et al.
Scientific reports, 11(1), 3014-3014 (2021-02-06)
In calcific aortic valve disease (CAVD) progressive valvular calcification causes aortic valve dysfunction. CAVD has several risk factors such as age and dyslipidemia. Vitamin K was shown to inhibit vascular calcification in mice and valvular calcification in patients with CAVD.
Ala Al Rajabi et al.
The Journal of nutrition, 142(5), 841-845 (2012-03-23)
Phylloquinone (PK) is converted into menaquinone-4 (MK-4) via side chain removal-addition. Stable isotope use is an effective approach to identify the tissue location of this conversion, which is currently unknown. Following a 14-d PK-deficient diet, male Fischer 344 rats (8
Xi Gu et al.
Plant physiology, 185(4), 1443-1456 (2021-04-02)
Nonphotosynthetic holoparasites exploit flexible targeting of phylloquinone biosynthesis to facilitate plasma membrane redox signaling. Phylloquinone is a lipophilic naphthoquinone found predominantly in chloroplasts and best known for its function in photosystem I electron transport and disulfide bridge formation of photosystem
Carla A F Portela et al.
Journal of bacteriology, 196(11), 2012-2022 (2014-03-25)
Oxygen and oxidative stress have become relevant components in clarifying the mechanism that weakens bacterial cells in parallel to the mode of action of bactericidal antibiotics. Given the importance of oxidative stress in the overall defense mechanism of bacteria and
Renata Tonhosolo et al.
FEBS letters, 584(23), 4761-4768 (2010-11-03)
Herein, we show that intraerythrocytic stages of Plasmodium falciparum have an active pathway for biosynthesis of menaquinone. Kinetic assays confirmed that plasmodial menaquinone acts at least in the electron transport. Similarly to Escherichia coli, we observed increased levels of menaquinone
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