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Chemical Structure| 863-61-6 Chemical Structure| 863-61-6

Structure of Menaquinone-4
CAS No.: 863-61-6

Chemical Structure| 863-61-6

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CAS No.: 863-61-6

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Menaquinone-4 is the most important member of short-chain menaquinones in Vitamine K2.

Synonyms: Vitamin K2(MK-4); Menaquinone K4; Vitamin MK-4

4.5 *For Research Use Only !

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Product Details of Menaquinone-4

CAS No. :863-61-6
Formula : C31H40O2
M.W : 444.65
SMILES Code : O=C1C(C)=C(C/C=C(C)/CC/C=C(C)/CC/C=C(C)/CCC=C(C)C)C(C2=C1C=CC=C2)=O
Synonyms :
Vitamin K2(MK-4); Menaquinone K4; Vitamin MK-4
MDL No. :MFCD00079646
InChI Key :DKHGMERMDICWDU-GHDNBGIDSA-N
Pubchem ID :5282367

Safety of Menaquinone-4

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302+H312+H332-H319
Precautionary Statements:P280-P305+P351+P338

Isoform Comparison

Biological Activity

In Vitro:

Cell Line
Concentration Treated Time Description References
SH-SY5Y cells 5–20 μM 24 h MK-4 significantly attenuated the rotenone-activated BV2 cell-mediated death of SH-SY5Y cells. PMC5022102
BV2 cells 0.5–20 μM 24 h MK-4 suppressed the rotenone-induced upregulation of iNOS and COX-2 expression in BV2 cells, as well as the production of TNF-α and IL-1β. PMC5022102
Bacillus subtilis 50 μM 12 h To investigate the rescue effect of MK-4 on Bacillus subtilis growth inhibition, results showed that MK-4 significantly increased the ED50 value PMC6427912
SK-N-BE neuroblastoma cells 50 μM 48 h To evaluate the effect of Menaquinone-4 on the expression of genes involved in neurodegeneration and neuroinflammation. Results showed that Menaquinone-4 treatment decreased the expression of PSEN1 and BACE1 and increased the expression of ADAM10 and ADAM17. PMC10778373
Endothelial cells 1 μM 48 h To evaluate the effect of MK-4 on endothelial cell function under high glucose conditions, results showed that MK-4 could alleviate endothelial cell dysfunction induced by high glucose. PMC11954476
Human hepatocarcinoma HepG2 cells 30 μM 24 h To investigate the effects of MK-4 on the expression of bile acid synthesis genes CYP7A1 and CYP8B1, the results showed that MK-4 significantly suppressed the expression of both genes. PMC6116188

In Vivo:

Species
Animal Model
Administration Dosage Frequency Description References
Actinomyces oris UbiE mutant Culture medium 0.1 mM 16 hours Supplementation of Menaquinone-4 rescues the cell growth and pilus assembly defects of the ubiE mutant. PMC5478893
C57BL/6 mice Ovariectomized model Gavage 20 and 40 mg/kg Every other day for 12 weeks To evaluate the effect of MK-4 on the expression of critical genes related to bone formation and bone resorption pathways, the results showed that MK-4 increased bone density, improved bone microstructure, and enhanced serum bone metabolism indicators PMC8398915
Mice Type 2 diabetic osteoporosis model Oral 30 mg/kg 5 times per week for 8 weeks To evaluate the effect of MK-4 on bone mass and angiogenesis in a type 2 diabetic osteoporosis mouse model, results showed that MK-4 could alleviate bone loss and angiogenesis impairment. PMC11954476
Mice Transgenic mice expressing human PXR Oral gavage 10, 50, or 100 mg/kg Single dose, sacrificed after 6 hours To investigate the effects of MK-4 on the expression of bile acid synthesis and energy metabolism-related genes, the results showed that MK-4 significantly suppressed the expression of Cyp7a1 and Cyp8b1 in hPXR mice, but had a weaker effect in wild-type mice. PMC6116188
C57BL/6N mice Sepsis model Intraperitoneal injection 200 mg/kg Once daily for 3 days MK-4 alleviates sepsis-associated acute lung injury by upregulating Sirt3 expression, inhibiting the p53/SLC7A11 signaling pathway, and reducing oxidative stress and inflammatory responses PMC11514946
Mice Hepatocyte-specific Gpx4 knockout mice Intraperitoneal injection 200 mg/kg/day Once daily until the end of the study To evaluate the protective effect of MK4 on hepatocyte-specific Gpx4 knockout mice, results showed that MK4 significantly extended survival time and reduced liver pathological changes and lipid peroxidation. PMC9402432

Clinical Trial:

NCT Number Conditions Phases Recruitment Completion Date Locations
NCT06707909 Socket Preservation PHASE4 RECRUITING 2025-11-24 Cairo, Cairo, Egypt
NCT02876354 Vascular Calcifications PHASE4 COMPLETED 2025-09-16 Saint-Georges Hospital, Ajalto... More >>un, Keserwan, Lebanon Less <<

Protocol

Bio Calculators
Preparing Stock Solutions 1mg 5mg 10mg

1 mM

5 mM

10 mM

2.25mL

0.45mL

0.22mL

11.24mL

2.25mL

1.12mL

22.49mL

4.50mL

2.25mL

References

[1]Torii S, Ikari Y, et al. Plasma phylloquinone, menaquinone-4 and menaquinone-7 levels and coronary artery calcification. J Nutr Sci. 2016 Dec 29;5:e48.

[2]Nakamura E, Aoki M, et al. Low-dose menaquinone-4 improves γ-carboxylation of osteocalcin in young males: a non-placebo-controlled dose-response study. Nutr J. 2014 Aug 27;13:85.

[3]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

[4]Farhadi Moghadam B, Fereidoni M. Neuroprotective effect of menaquinone-4 (MK-4) on transient global cerebral ischemia/reperfusion injury in rat. PLoS One. 2020 Mar 9;15(3):e0229769

[5]Ho HJ, Shirakawa H, Hirahara K, Sone H, Kamiyama S, Komai M. Menaquinone-4 Amplified Glucose-Stimulated Insulin Secretion in Isolated Mouse Pancreatic Islets and INS-1 Rat Insulinoma Cells. Int J Mol Sci. 2019 Apr 23;20(8):1995

[6]Cui L, Xu J, Zhang J, Zhang M, Zhang S, Bai Y. Menaquinone-4 modulates the expression levels of calcification-associated factors to inhibit calcification of rat aortic vascular smooth muscle cells in a dose-dependent manner. Exp Ther Med. 2018 Oct;16(4):3172-3178

[7]Saputra WD, Aoyama N, Komai M, Shirakawa H. Menaquinone-4 Suppresses Lipopolysaccharide-Induced Inflammation in MG6 Mouse Microglia-Derived Cells by Inhibiting the NF-κB Signaling Pathway. Int J Mol Sci. 2019 May 10;20(9):2317

[8]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

 

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