A homolog of of vitamin K2
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Labeled Version(s)
25709Menaquinone 4-d7
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Menaquinone 4

Item No. 18423

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-methyl-3-[(2E,6E,10E)-3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraen-1-yl]-1,4-naphthalenedione
CAS Number
863-61-6
Synonyms
  • MK-4
  • Vitamin K2(20)
Molecular Formula
C31H40O2
Formula Weight
444.7
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
Chloroform: 100 mg/ml
λmax
248, 269, 329 nm
SMILES
O=C1C(C/C=C(C)/CC/C=C(C)/CC/C=C(C)/CC/C=C(C)/C)=C(C)C(C2=CC=CC=C21)=O
InChi Code
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    100 mg

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    Product Description

    Menaquinone 4 (MK-4) is the predominant homolog of vitamin K2 and is composed of a naphthoquinone base with four isoprenoid units in the side chain.1 It is formed primarily via conversion of vitamin K1 (Item No. 21051) in vivo and accumulates in various tissues, including the brain.2,3 MK-4 halts the cell cycle at the G phase in HepG2, Hep3B, and Huh7 hepatocellular carcinoma cells in a concentration-dependent manner.4 It also inhibits IκB kinase (IKK) activity, IκBα phosphorylation, and the transcriptional activity of NF-κB. Vitamin K2 may have a role in bone metabolism.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Plaza, S.M., and Lamson, D.W. Vitamin K2 in bone metabolism and osteoporosis. Altern. Med. Rev. 10(1), 24-35 (2005).

    2. Shearer, M.J., and Newman, P. Metabolism and cell biology of vitamin K. Thromb. Haemost. 100(4), 530-547 (2008).

    3. Okano, T., Shimomura, Y., Yamane, M., et al. Conversion of phylloquinone (vitamin K1) into menaquinone-4 (vitamin K2) in mice: Two possible routes for menaquinone-4 accumulation in cerebra of mice. The Journal of Biological Chemisty 283(17), 11270-11279 (2008).

    4. Ozaki, I., Zhang, H., Mizuta, T., et al. Menatetrenone, a vitamin K2 analogue, inhibits hepatocellular carcinoma cell growth by suppressing cyclin D1 expression through inhibition of nuclear factor κB activation. Clin. Cancer Res. 13(7), 2236-2245 (2007).