Vitamin K2 Menaquinone-7 (MK-7)

• CAT Number: R007113
• CAS Number: 2124-57-4
• Molecular Formula: C46H64O2
• Molecular Weight: 649.016
• Purity: ≥95%
• Synonyms: (all-E)-2-(3,7,11,15,19,23,27-Heptamethyl-2,6,10,14,18,22,26-octacosaheptaenyl)-3-methyl-1,4-naphthalenedione; Vitamin K2(35); Menaquinone K7; Vitamin MK 7
• Storage: -20°C
• IUPAC Name: 2-[(2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaenyl]-3-methylnaphthalene-1,4-dione
• InChI: 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+,38-26+,39-28+,40-32+
• InChIKey: RAKQPZMEYJZGPI-LJWNYQGCSA-N
• SMILES: CC1=C(C(=O)C2=CC=CC=C2C1=O)CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C

Menaquinone 7 (MK-7; CAS 2124-57-4) is a vitamin K2 analog that has been found in a variety of fermented foods. It increases osteocalcin, osteoprotegerin, and RANKL mRNA expression in osteoblastic MC3T3E cells. MK-7 (1 µM) increases alkaline phosphatase activity and calcium content in femoral-metaphyseal tissues isolated from normal and skeletal-unloaded rats.

Reference

1. Nutr Rev. 2017 Jul 1;75(7):553-578. doi: 10.1093/nutrit/nux022.
US Pharmacopeial Convention safety evaluation of menaquinone-7, a form of vitamin K.
Marles RJ(1), Roe AL(1), Oketch-Rabah HA(1).
Author information:
(1)US Pharmacopeial Convention's Dietary Supplements Admission Evaluations Joint Standard Setting Subcommittee, US Pharmacopeial Convention, Rockville, Maryland, USA. US Pharmacopeial Convention, Rockville, Maryland, USA.
Vitamin K plays important biological roles in maintaining normal blood coagulation, bone mineralization, soft tissue physiology, and neurological development. Menaquinone-7 is a form of vitamin K2 that occurs naturally in some animal-derived and fermented foods. It is also available as an ingredient of dietary supplements. Menaquinone-7 has greater bioavailability than other forms of vitamin K, which has led to increasing sales and use of menaquinone-7 supplements. This special article reviews the chemistry, nomenclature, dietary sources, intake levels, and pharmacokinetics of menaquinones, along with the nonclinical toxicity data available and the data on clinical outcomes related to safety (adverse events). In conclusion, the data reviewed indicate that menaquinone-7, when ingested as a dietary supplement, is not associated with any serious risk to health or with other public health concerns. On the basis of this conclusion, US Pharmacopeia monographs have been developed to establish quality standards for menaquinone-7 as a dietary ingredient and as a dietary supplement in various dosage forms.

2. World J Microbiol Biotechnol. 2017 Jan;33(1):2. Epub 2016 Nov 10.
Production and application of menaquinone-7 (vitamin K2): a new perspective.
Mahdinia E(1), Demirci A(1), Berenjian A(2).
Author information:
(1)Department of Agricultural and Biological Engineering, The Pennsylvania State University, University Park, PA, 16802, USA. (2)Faculty of Science and Engineering, The University of Waikato, Hamilton, 3240, New Zealand. .
Menaquinone-7, a highly valuable member of the vitamin K series, has significant effects on preventing osteoporosis and cardiovascular disease besides its positive effects on blood coagulation. In this review, chemical and biological aspects of menaquinone-7 are briefly summarized followed by a critical review on upstream and downstream processing developments for its production and recovery, including solid versus liquid fermentations, static versus agitated fermentations and online versus post-production recovery. Latest research outcomes for improving industrial scale production of menaquinone-7 are summarized and recommendations are given for areas of future research.

3. Clin Calcium. 2006 Oct;16(10):1715-22.
[Prevention of osteoporosis by foods and dietary supplements. "Kinnotsubu honegenki": a fermented soybean (natto) with reinforced vitamin K2 (menaquinone-7)].
Takemura H(1).
Author information:
(1)Mizkan Co. Ltd, Chilled Foods Company, Marketing Department, Technical Division.
In recent years, it has been proven that vitamin K(2) has important roles not only in blood coagulation but also in bone metabolism. We developed a Bacillus subtilis (natto) strain with high productivity of vitamin K(2) (Menaquinone-7), and commercialized a natto with reinforced vitamin K(2) by use of the strain. The natto, named "Kinnotsubu honegenki", was granted a health claim based on our clinical studies which demonstrated that intake of the natto stimulated gamma-carboxylation of osteocalcin.