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MedKoo Cat#: 328611 | Name: Menatetrenone
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Menatetrenone (also known as Vitamin K-2[20], Vitamin MK-4, and E-3100) is a vitamin K compound used as a hemostatic agent, and also as adjunctive therapy for the pain of osteoporosis.

Chemical Structure

Menatetrenone
Menatetrenone
CAS#863-61-6

Theoretical Analysis

MedKoo Cat#: 328611

Name: Menatetrenone

CAS#: 863-61-6

Chemical Formula: C31H40O2

Exact Mass: 444.3028

Molecular Weight: 444.66

Elemental Analysis: C, 83.74; H, 9.07; O, 7.20

Price and Availability

Size Price Availability Quantity
100mg USD 250.00 2 Weeks
250mg USD 450.00 2 Weeks
500mg USD 750.00 2 Weeks
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Related CAS #
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Synonym
Menatetrenone; E-3100; Ea-0167; MK-4; Vitamin K-2(20); Vitamin MK-4; E 3100; Ea 0167; MK 4; Vitamin K 2(20); Vitamin MK 4; E3100; Ea0167; MK4; Vitamin K2(20); Vitamin MK4
IUPAC/Chemical Name
2-methyl-3-((2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl)naphthalene-1,4-dione
InChi Key
DKHGMERMDICWDU-GHDNBGIDSA-N
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+
SMILES Code
O=C(C1=C2C=CC=C1)C(C/C=C(C)/CC/C=C(C)/CC/C=C(C)/CC/C=C(C)\C)=C(C)C2=O
Appearance
Solid powder
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
>2 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
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Menaquinone-4 is a vitamin K, used as a hemostatic agent, and also a adjunctive therapy for the pain of osteoporosis.
In vitro activity:
This study investigated the effects of MK-4 on the level of ALP activity and expression of ALP messenger RNA in the human colon carcinoma cell line Caco-2, which is known to differentiate into small intestinal epithelial cells in vitro. After treatment with MK-4, there were significant increases in the ALP activities of Caco-2 cells. Reference: Nutr Res. 2016 Nov;36(11):1269-1276. https://pubmed.ncbi.nlm.nih.gov/27865621/
In vivo activity:
This study studied the effects of MK-4 in vivo in ovariectomized mice, a postmenopausal osteoporosis murine model. MK-4 inhibited osteoclast differentiation, decreased the mRNA expression of nuclear factor of activated T cells c1 (NFATc1), osteoclast-associated receptor (OSCAR), and cathepsin K (CTSK), and inhibited bone loss in ovariectomized mice. Reference: J Med Food. 2023 Feb;26(2):128-134. https://pubmed.ncbi.nlm.nih.gov/36724309/
Solvent mg/mL mM
Solubility
DMSO 54.0 121.44
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 444.66 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.

Recalculate based on batch purity %
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. Bai H, Kawahara M, Takahashi M. Identification of menaquinone-4 (vitamin K2) target genes in bovine endometrial epithelial cells in vitro. Theriogenology. 2023 Mar 1;198:183-193. doi: 10.1016/j.theriogenology.2022.12.033. Epub 2022 Dec 28. PMID: 36592516. 2. Noda S, Yamada A, Tanabe R, Nakaoka K, Hosoi T, Goseki-Sone M. Menaquinone-4 (vitamin K2) up-regulates expression of human intestinal alkaline phosphatase in Caco-2 cells. Nutr Res. 2016 Nov;36(11):1269-1276. doi: 10.1016/j.nutres.2016.10.001. Epub 2016 Oct 14. PMID: 27865621. 3. Lee AS, Sung MJ, Son SJ, Han AR, Hong SM, Lee SH. Effect of Menaquinone-4 on Receptor Activator of Nuclear Factor κB Ligand-Induced Osteoclast Differentiation and Ovariectomy-Induced Bone Loss. J Med Food. 2023 Feb;26(2):128-134. doi: 10.1089/jmf.2022.K.0078. Epub 2023 Feb 1. PMID: 36724309. 4. Wang H, Zhang N, Li L, Yang P, Ma Y. Menaquinone 4 Reduces Bone Loss in Ovariectomized Mice through Dual Regulation of Bone Remodeling. Nutrients. 2021 Jul 27;13(8):2570. doi: 10.3390/nu13082570. PMID: 34444729; PMCID: PMC8398915.
In vitro protocol:
1. Bai H, Kawahara M, Takahashi M. Identification of menaquinone-4 (vitamin K2) target genes in bovine endometrial epithelial cells in vitro. Theriogenology. 2023 Mar 1;198:183-193. doi: 10.1016/j.theriogenology.2022.12.033. Epub 2022 Dec 28. PMID: 36592516. 2. Noda S, Yamada A, Tanabe R, Nakaoka K, Hosoi T, Goseki-Sone M. Menaquinone-4 (vitamin K2) up-regulates expression of human intestinal alkaline phosphatase in Caco-2 cells. Nutr Res. 2016 Nov;36(11):1269-1276. doi: 10.1016/j.nutres.2016.10.001. Epub 2016 Oct 14. PMID: 27865621.
In vivo protocol:
1. Lee AS, Sung MJ, Son SJ, Han AR, Hong SM, Lee SH. Effect of Menaquinone-4 on Receptor Activator of Nuclear Factor κB Ligand-Induced Osteoclast Differentiation and Ovariectomy-Induced Bone Loss. J Med Food. 2023 Feb;26(2):128-134. doi: 10.1089/jmf.2022.K.0078. Epub 2023 Feb 1. PMID: 36724309. 2. Wang H, Zhang N, Li L, Yang P, Ma Y. Menaquinone 4 Reduces Bone Loss in Ovariectomized Mice through Dual Regulation of Bone Remodeling. Nutrients. 2021 Jul 27;13(8):2570. doi: 10.3390/nu13082570. PMID: 34444729; PMCID: PMC8398915.
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.

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