An internal standard for the quantification of menaquinone 4
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Unlabeled Version(s)
18423Menaquinone 4
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Menaquinone 4-d7

Item No. 25709

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-(methyl-d3)-3-[(2E,6E,10E)-3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraen-1-yl]-1,4-naphthalenedione-5,6,7,8-d4
CAS Number
1233937-25-1
Synonyms
  • MK-4-d7
  • Vitamin K2(20)-d7
Molecular Formula
C31H33D7O2
Formula Weight
451.7
Purity
≥99% deuterated forms (d1-d7)
Formulation
An oil
Solubility(Learn about Variance in Solubility)
Chloroform: Slightly Soluble
SMILES
[2H]C1=C2C(C(C(C([2H])([2H])[2H])=C(C/C=C(C)/CC/C=C(C)/CC/C=C(C)/CC/C=C(C)/C)C2=O)=O)=C([2H])C([2H])=C1[2H]
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+/i6D3,7D,8D,18D,19D
InChi Key
DKHGMERMDICWDU-CKBRGKTGSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    250 µg

    $769

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    Product Description

    Menaquinone 4-d7 (MK-4-d7) is intended for use as an internal standard for the quantification of MK-4 (Item No. 18423) by GC- or LC-MS. 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 G1 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).

    Product Citations

    Mishima, E., Ito, J., Wu, Z., et al. A non-canonical vitamin K cycle is a potent ferroptosis suppressor. Nature 608(7924), 778-783 (2022).