Synonym
Menaquinone 7, MK-7, Vitamin K2(35), Vitamin MK-7
IUPAC/Chemical Name
2-(-3,7,11,15,19,23,27-heptamethyloctacosa-2E,6E,10E,14E,18E,22E,26-heptaen-1-yl)-3-methylnaphthalene-1,4-dione
InChi Key
RAKQPZMEYJZGPI-LJWNYQGCSA-N
InChi Code
InChI=1S/C46H64O2/c1-34(2)18-12-19-35(3)20-13-21-36(4)22-14-23-37(5)24-15-25-38(6)26-16-27-39(7)28-17-29-40(8)32-33-42-41(9)45(47)43-30-10-11-31-44(43)46(42)48/h10-11,18,20,22,24,26,28,30-32H,12-17,19,21,23,25,27,29,33H2,1-9H3/b35-20+,36-22+,37-24+,3
SMILES Code
O=C(C(C)=C(C/C=C(C)/CC/C=C(C)/CC/C=C(C)/CC/C=C(CC/C=C(C)/CC/C=C(C)/CC/C=C(C)\C)\C)C1=O)C2=C1C=CC=C2
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Menaquinone 7 (MK-7) is a vitamin K2 analog that has been shown to increase osteocalcin, osteoprotegerin, and RANKL mRNA expression in osteoblastic MC3T3E cells.
In vitro activity:
After 24 h of MK-7 administration, genes upregulated by MK-7 included tenascin C and BMP2. Genes downregulated by MK-7 administration included biglycan and butyrophilin. Western blot analysis showed that cells administered MK-7 displayed a higher phosphorylated Smad1 level than control cells.
Reference: Int J Mol Med. 2007 Feb;19(2):279-84. https://pubmed.ncbi.nlm.nih.gov/17203202/
In vivo activity:
OVX (ovariectomized) rats were freely given experimental diets containing menaquinone-4 (MK-4; 12mg/100g diet) or menaquinone-7 (MK-7; 18.1mg/100g diet) for 24 days; MK-4 and MK-7 were equal in molar concentrations. OVX-induced decreases in the femoral dry weight and femoral calcium content were significantly prevented by the feeding of diets containing natto with MK-7 added (37.6 microg/100g diets). This study demonstrates that the intake of dietary MK-7 has a preventive effect on bone loss caused by OVX.
Reference: J Bone Miner Metab. 1999;17(1):23-9. https://pubmed.ncbi.nlm.nih.gov/10084398/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
5.0 |
7.70 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
649.02
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Akbulut AC, Wasilewski GB, Rapp N, Forin F, Singer H, Czogalla-Nitsche KJ, Schurgers LJ. Menaquinone-7 Supplementation Improves Osteogenesis in Pluripotent Stem Cell Derived Mesenchymal Stem Cells. Front Cell Dev Biol. 2021 Jan 28;8:618760. doi: 10.3389/fcell.2020.618760. PMID: 33585456; PMCID: PMC7876270.
2. Katsuyama H, Saijoh K, Otsuki T, Tomita M, Fukunaga M, Sunami S. Menaquinone-7 regulates gene expression in osteoblastic MC3T3E1 cells. Int J Mol Med. 2007 Feb;19(2):279-84. PMID: 17203202.
3. Lee B, Choi GM, Hong JP, Cho DE, Kim Y, Yeom M, Han JJ, Kim SR, Hahm DH. Menaquinone-7 ameliorates cerebrovascular calcification-associated memory decline in aged mice. Life Sci. 2022 Oct 15;307:120912. doi: 10.1016/j.lfs.2022.120912. Epub 2022 Aug 26. PMID: 36037872.
4. Yamaguchi M, Taguchi H, Gao YH, Igarashi A, Tsukamoto Y. Effect of vitamin K2 (menaquinone-7) in fermented soybean (natto) on bone loss in ovariectomized rats. J Bone Miner Metab. 1999;17(1):23-9. doi: 10.1007/s007740050059. PMID: 10084398.
In vitro protocol:
1. Akbulut AC, Wasilewski GB, Rapp N, Forin F, Singer H, Czogalla-Nitsche KJ, Schurgers LJ. Menaquinone-7 Supplementation Improves Osteogenesis in Pluripotent Stem Cell Derived Mesenchymal Stem Cells. Front Cell Dev Biol. 2021 Jan 28;8:618760. doi: 10.3389/fcell.2020.618760. PMID: 33585456; PMCID: PMC7876270.
2. Katsuyama H, Saijoh K, Otsuki T, Tomita M, Fukunaga M, Sunami S. Menaquinone-7 regulates gene expression in osteoblastic MC3T3E1 cells. Int J Mol Med. 2007 Feb;19(2):279-84. PMID: 17203202.
In vivo protocol:
1. Lee B, Choi GM, Hong JP, Cho DE, Kim Y, Yeom M, Han JJ, Kim SR, Hahm DH. Menaquinone-7 ameliorates cerebrovascular calcification-associated memory decline in aged mice. Life Sci. 2022 Oct 15;307:120912. doi: 10.1016/j.lfs.2022.120912. Epub 2022 Aug 26. PMID: 36037872.
2. Yamaguchi M, Taguchi H, Gao YH, Igarashi A, Tsukamoto Y. Effect of vitamin K2 (menaquinone-7) in fermented soybean (natto) on bone loss in ovariectomized rats. J Bone Miner Metab. 1999;17(1):23-9. doi: 10.1007/s007740050059. PMID: 10084398.
1. Katsuyama, H., Otsuki, T., Tomita, M., et al. Menaquinone-7 regulates the expressions of osteocalcin, OPG, RANKL and RANK in osteoblastic MC3T3E1 cells. Int. J. Mol. Med. 15(2), 231-236 (2005).
2. Ehara, Y., Takahashi, H., Hanahisa, Y., et al. Effect of vitamin K2 (menaquinone-7) on bone metabolism in the femoral-metaphyseal tissues of normal and skeletal-unloaded rats: Enhancement with zinc. Res. Exp. Med. (Berl.) 196(3), 171-178 (1996).
3. Scheiber, D., Veulemans, V., Horn, P., et al. High-dose menaquinone-7 supplementation reduces cardiovascular calcification in a murine model of extraosseous calcification. Nutrients 7(8), 6991-7011 (2015).
4. Wu, W.-J., Lee, H.-Y., Lee, G.-H., et al. The antiosteoporotic effects of Cheonggukjang containing vitamin K2 (menaquinone-7) in ovariectomized rats. J. Med. Food 17(12), 1298-1305 (2014).
