Menaquinone-7

Base Information

• Chemical Name: Menaquinone-7
• CAS No.: 2124-57-4
• Molecular Formula: C46H64O2
• Molecular Weight: 649.013
• Hs Code.: 2936299055
• European Community (EC) Number: 870-176-9
• UNII: 8427BML8NY
• DSSTox Substance ID: DTXSID801317474
• Nikkaji Number: J141.747I,J16.269H
• Wikipedia: MK-7
• Wikidata: Q27120546
• Metabolomics Workbench ID: 56546
• ChEMBL ID: CHEMBL1230575
• Mol file: 2124-57-4.mol

Synonyms:1,4-naphthalenedione, 2-(3,7,11,15,19,23,27-heptamethyl-2,6,10,14,18,22,26-octacosaheptaenyl)-3-methyl-, (all-E)-;menaquinone 7;menaquinone K7;menaquinone-7;vitamin K2(35);vitamin MK 7

Chemical Property of Menaquinone-7

Chemical Property:

• Vapor Pressure: 1.38E-20mmHg at 25°C
• Melting Point: 54 °C
• Refractive Index: 1.532
• Boiling Point: 720.1 °C at 760mmHg
• Flash Point: 254.9 °C
• PSA: 34.14000
• Density: 0.961 g/cm³
• LogP: 14.09740
• Storage Temp.: -20°C
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• XLogP3: 14.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 20
• Exact Mass: 648.49063128
• Heavy Atom Count: 48
• Complexity: 1310

Purity/Quality:

10% ^*data from raw suppliers

Menaquinone7,Synthetic(90%) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Vitamins and Derivatives
• Canonical 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
• Isomeric SMILES: CC1=C(C(=O)C2=CC=CC=C2C1=O)C/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CCC=C(C)C
• Recent ClinicalTrials: Treatment to Reduce Vascular Calcification in Hemodialysis Patients Using Vitamin K
• Description: Menaquinone 7 (MK-7) 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. In vivo, MK-7 (100 μg/g diet) inhibits aortic and myocardial calcification and decreases aortic alkaline phosphatase tissue concentrations in a rat model of extraosseous calcification. It also increases trabecular number, bone mineral density, and bone mineral content in a rat model of ovariectomy-induced bone loss.
• Uses: Vitamin (prothrombogenic) Menaquinones are isoprenoid quinones of the naphthalene series and belongs to the K2 Vitamin homologs. Menaquinones were originally discovered as the anti-hemorrhagic factor and now encompasses a vari ety of physiological processes. Menaquinone 7 belongs to the class of K2-Vitamins homologs. Menaquinone 7 has been identified as the most bioactive cofactor for the carboxylation reaction of Gla-prote ins such as osteocalcin and matrix-Gla protein, which plays a crucial role in building and maintaining overall bone health. Vitamin K2 (MK-7)-(5,6,7,8-d4,2-methyl-d3) can be used as a stable isotope internal standard for data interpretation in specific biological samples.

Technology Process of Menaquinone-7

There total 61 articles about Menaquinone-7 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

2-(3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaenyl)-1,4-dimethoxy-3-methylnaphthalene (1218784-62-3) → menaquinone-7 (2124-57-4,27670-94-6)

Guidance literature:

With ammonium cerium (IV) nitrate; In water; acetonitrile; at 20 ℃; for 4.08333h;

Reference yield: 72.0%

C50H74O2 (1597486-88-8) → menaquinone-7 (2124-57-4,27670-94-6)

Guidance literature:

With ammonium cerium (IV) nitrate; In dichloromethane; water; acetonitrile; at 0 ℃; for 0.25h;

Reference yield: 65.0%

2-(chloromethyl)-3-methylnaphthalene-1,4-dione (31599-79-8) + C33H52 + trimethylaluminum (75-24-1) → menaquinone-7 (2124-57-4,27670-94-6)

Guidance literature:

C₃₃H₅₂; trimethylaluminum; With zirconocene dichloride; In toluene; at 0 ℃; for 1h;

2-(chloromethyl)-3-methylnaphthalene-1,4-dione; With bis(triphenylphosphine)nickel(II) chloride; n-butyllithium; In tetrahydrofuran; hexane; at -20 ℃; for 1h;

upstream raw materials:

(2E,6E)-farnesyl acetate

E,E,E-12-hydroxyfarnesyl acetate

(2E,6E,10E)-3,7,11-trimethyl-12-(phenylsulfonyl)-dodeca-2,6,10-trien-1-yl acetate

farnesyl bromide

Downstream raw materials:

menaquinol

2-((2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyl-octacosa-2,6,10,14,18,22,26-heptaen-1-yl)-3-methylnaphthalene-1,4-diyl dibenzoate

2-((2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-1-yl)-3-methylnaphthalene-1,4-diyl bis(4-(trifluoromethyl)benzoate)

2-((2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-1-yl)-4-hydroxy-3-methylnaphthalen-1-yl benzoate

Refernces

• 1、 -. "Menaquinol Compositions and Methods of Treatment". Paragraph 0129-0130. . Retrieved 2020/04/09.
• 2、 Baj, Aneta,Wa?ejko, Piotr,Kutner, Andrzej,Kaczmarek, ?ukasz,Morzycki, Jacek W.,Witkowski, Stanis?aw. "Convergent Synthesis of Menaquinone-7 (MK-7)". . p. 1026 - 1033. Retrieved 2016/11/11.