Menaquinone 4(Mixture of cis-trans isomers)

• CAT Number: R007114
• CAS Number: 863-61-6
• Molecular Formula: C31H40O2
• Molecular Weight: 444.659
• Purity: ≥95%
• Storage: -20°C
• IUPAC Name: 2-methyl-3-[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenyl]naphthalene-1,4-dione
• InChI: 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+
• InChIKey: DKHGMERMDICWDU-GHDNBGIDSA-N
• SMILES: CC1=C(C(=O)C2=CC=CC=C2C1=O)CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C

Menaquinone 4(Mixture of cis-trans isomers)(CAT: R007114) is a form of Vitamin K that is found naturally in certain foods, including fermented foods like natto and cheese. It is also available in supplement form. Menaquinone 4 has been studied for its potential health benefits, particularly for bone health. Some studies suggest that it may help to prevent bone loss and reduce the risk of fractures. It has also been studied for its potential role in reducing the risk of cardiovascular disease and certain types of cancer.

Reference

1: Jiang Y, Zhang ZL, Zhang ZL, Zhu HM, Wu YY, Cheng Q, Wu FL, Xing XP, Liu JL, Yu W, Meng XW. Menatetrenone versus alfacalcidol in the treatment of Chinese postmenopausal women with osteoporosis: a multicenter, randomized, double-blinded, double-dummy, positive drug-controlled clinical trial. Clin Interv Aging. 2014;9:121-7. doi: 10.2147/CIA.S54107. Epub 2014 Jan 8. PubMed PMID: 24426779; PubMed Central PMCID: PMC3890406.2: Iwamoto J, Sato Y. Menatetrenone for the treatment of osteoporosis. Expert Opin Pharmacother. 2013 Mar;14(4):449-58. doi: 10.1517/14656566.2013.763796. Epub 2013 Jan 25. Review. PubMed PMID: 23346882.3: Suzuki K, Tsuji S, Fukushima Y, Nakase T, Hamada M, Tomita T, Yoshikawa H. Clinical results of alendronate monotherapy and combined therapy with menatetrenone (VitK₂) in postmenopausal RA patients. Mod Rheumatol. 2013 May;23(3):450-5. doi: 10.1007/s10165-012-0678-x. Epub 2012 Jun 13. PubMed PMID: 22692649.4: Rianthavorn P, Pisutikul K, Deekajorndech T, Tepmongkol S, Suphapeetiporn K. Prevention of bone loss in children receiving long-term glucocorticoids with calcium and alfacalcidol or menatetrenone. J Pediatr Endocrinol Metab. 2012;25(3-4):307-12. PubMed PMID: 22768661.5: Ishizuka M, Kubota K, Shimoda M, Kita J, Kato M, Park KH, Shiraki T. Effect of menatetrenone, a vitamin k2 analog, on recurrence of hepatocellular carcinoma after surgical resection: a prospective randomized controlled trial. Anticancer Res. 2012 Dec;32(12):5415-20. PubMed PMID: 23225445.6: Baek IH, Kang W, Yun HY, Lee SS, Kwon KI. Modelling the atypical absorption of menatetrenone and the metabolism to its epoxide: effect of VKORC1 polymorphism. J Clin Pharm Ther. 2011 Jun;36(3):390-8. doi: 10.1111/j.1365-2710.2010.01183.x. Epub 2010 Aug 24. PubMed PMID: 21545618.7: Songpatanasilp T, Chailurkit LO, Chantprasertyothin S, Ongphiphadhanakul B, Taechakraichana N. Effect of GGCX gene polymorphism on the responses of serum undercarboxylated osteocalcin and bone turnover markers after treatment with vitamin K2 (menatetrenone) among postmenopausal Thai women. J Bone Miner Metab. 2011 Sep;29(5):606-14. doi: 10.1007/s00774-011-0263-y. Epub 2011 Feb 23. PubMed PMID: 21344298.8: Iwamoto J. Vitamin K₂ therapy for postmenopausal osteoporosis. Nutrients. 2014 May 16;6(5):1971-80. doi: 10.3390/nu6051971. Review. PubMed PMID: 24841104; PubMed Central PMCID: PMC4042573.9: Sato Y, Honda Y, Umeno K, Hayashida N, Iwamoto J, Takeda T, Matsumoto H. The prevention of hip fracture with menatetrenone and risedronate plus calcium supplementation in elderly patients with Alzheimer disease: a randomized controlled trial. Kurume Med J. 2011;57(4):117-24. PubMed PMID: 21778673.10: Mizuta T, Ozaki I, Eguchi Y, Yasutake T, Kawazoe S, Fujimoto K, Yamamoto K. The effect of menatetrenone, a vitamin K2 analog, on disease recurrence and survival in patients with hepatocellular carcinoma after curative treatment: a pilot study. Cancer. 2006 Feb 15;106(4):867-72. PubMed PMID: 16400650.11: Hara K, Akiyama Y, Nakamura T, Murota S, Morita I. The inhibitory effect of vitamin K2 (menatetrenone) on bone resorption may be related to its side chain. Bone. 1995 Feb;16(2):179-84. PubMed PMID: 7756045.12: Koshihara Y, Hoshi K, Shiraki M. Vitamin K2 (menatetrenone) inhibits prostaglandin synthesis in cultured human osteoblast-like periosteal cells by inhibiting prostaglandin H synthase activity. Biochem Pharmacol. 1993 Oct 19;46(8):1355-62. PubMed PMID: 8240383.13: Shiraki M, Itabashi A. Short-term menatetrenone therapy increases gamma-carboxylation of osteocalcin with a moderate increase of bone turnover in postmenopausal osteoporosis: a randomized prospective study. J Bone Miner Metab. 2009;27(3):333-40. doi: 10.1007/s00774-008-0034-6. Epub 2009 Jan 27. PubMed PMID: 19172219.14: Ueda K, Fujimoto M, Noto H, Sakaeda T, Iwakawa S. Effect of acyl chains of phosphatidylcholines on the pharmacokinetics of menatetrenone incorporated in O/W lipid emulsions prepared with phosphatidylcholines and soybean oil in rats. J Pharm Pharmacol. 2004 Jul;56(7):855-9. PubMed PMID: 15233863.15: Ueda K, Yamazaki Y, Noto H, Teshima Y, Yamashita C, Sakaeda T, Iwakawa S. Effect of oxyethylene moieties in hydrogenated castor oil on the pharmacokinetics of menatetrenone incorporated in O/W lipid emulsions prepared with hydrogenated castor oil and soybean oil in rats. J Drug Target. 2003 Jan;11(1):37-43. PubMed PMID: 12852439.