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MedKoo Cat#: 576849 | Name: Malvidin chloride
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Description:

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

Malvidin chloride is an anti-inflammatory and antioxidant that has been shown to prevent inflammatory reactions caused by lipopolysaccharide (LPS) in peripheral blood mononuclear cells (PBMCs).

Chemical Structure

Malvidin chloride
Malvidin chloride
CAS#643-84-5

Theoretical Analysis

MedKoo Cat#: 576849

Name: Malvidin chloride

CAS#: 643-84-5

Chemical Formula: C17H15ClO7

Exact Mass: 366.0506

Molecular Weight: 366.75

Elemental Analysis: C, 55.67; H, 4.12; Cl, 9.67; O, 30.54

Price and Availability

Size Price Availability Quantity
5mg USD 465.00 2 Weeks
10mg USD 750.00 2 Weeks
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Related CAS #
No Data
Synonym
Malvidin chloride; Malvinidol chloride; Syringidin chloride
IUPAC/Chemical Name
3,5,7-Trihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-1-benzopyryliumchloride
InChi Key
KQIKOUUKQBTQBE-UHFFFAOYSA-N
InChi Code
InChI=1S/C17H14O7.ClH/c1-22-14-3-8(4-15(23-2)16(14)21)17-12(20)7-10-11(19)5-9(18)6-13(10)24-17;/h3-7H,1-2H3,(H3-,18,19,20,21);1H
SMILES Code
[Cl-].COc1cc(cc(OC)c1O)c2[o+]c3cc(O)cc(O)c3cc2O
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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:
Malvidin shows cytotoxicity through the arrest of the G2/M phase of cell cycle and induction of apoptosis.
In vitro activity:
In the present study, the protective effects and underlying mechanisms of malvidin-3-O-glucoside (M3G) against the toxicity of Cd on female reproduction in KGN cells (human ovarian granulosa-like tumor cells) were investigated. After treating cells with 10 µmol/L cadmium chloride, the results showed that M3G lessened Cd-induced KGN cell cytotoxicity better than malvidin and malvidin-3,5-O-diglucoside. Additionally, M3G significantly decreased the Cd-induced generation of reactive oxygen species, inhibited the Cd-induced arrest of the G2/M phase of the cell cycle, and increased estradiol (E2) production. Reference: Nutrients. 2023 Feb 2;15(3):753. https://pubmed.ncbi.nlm.nih.gov/36771459/
In vivo activity:
Moreover, dorsomorphin block assays verified that malvidin upregulated UCP2 expression through phosphorylating AMPK in SAE mouse models. Also, malvidin alleviated SAE progression through inhibition of ROS-dependent NLRP3 inflammasome activation mediated serum pro-inflammatory cytokines secretion and mitochondrial pathway mediated apoptosis with weakened apoptosis body formation and tunel positive signals, and decreased Bax, cytochrome C, caspase-3 and increased Bcl-2 protein levels. Reference: Front Pharmacol. 2023 Jan 9;13:1038802. https://pubmed.ncbi.nlm.nih.gov/36699054/
Solvent mg/mL mM
Solubility
DMF 25.0 68.17
DMF:PBS (pH 7.2) (1:9) 0.1 0.27
DMSO 16.0 43.63
Ethanol 16.0 43.63
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 366.75 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. Liang S, Li X, Liu R, Hu J, Li Y, Sun J, Bai W. Malvidin-3-O-Glucoside Ameliorates Cadmium-Mediated Cell Dysfunction in the Estradiol Generation of Human Granulosa Cells. Nutrients. 2023 Feb 2;15(3):753. doi: 10.3390/nu15030753. PMID: 36771459; PMCID: PMC9921828. 2. Silva S, Costa EM, Machado M, Morais R, Calhau C, Pintado M. Antiadhesive and Antibiofilm Effect of Malvidin-3-Glucoside and Malvidin-3-Glucoside/Neochlorogenic Acid Mixtures upon Staphylococcus. Metabolites. 2022 Nov 3;12(11):1062. doi: 10.3390/metabo12111062. PMID: 36355145; PMCID: PMC9694786. 3. Zhao P, Li X, Yang Q, Lu Y, Wang G, Yang H, Dong J, Zhang H. Malvidin alleviates mitochondrial dysfunction and ROS accumulation through activating AMPK-α/UCP2 axis, thereby resisting inflammation and apoptosis in SAE mice. Front Pharmacol. 2023 Jan 9;13:1038802. doi: 10.3389/fphar.2022.1038802. PMID: 36699054; PMCID: PMC9868257. 4. Liu F, Smith AD, Wang TTY, Pham Q, Cheung L, Yang H, Li RW. Biological pathways via which the anthocyanin malvidin alleviated the murine colitis induced by Citrobacter rodentium. Food Funct. 2023 Jan 23;14(2):1048-1061. doi: 10.1039/d2fo02873e. PMID: 36562464.
In vitro protocol:
1. Liang S, Li X, Liu R, Hu J, Li Y, Sun J, Bai W. Malvidin-3-O-Glucoside Ameliorates Cadmium-Mediated Cell Dysfunction in the Estradiol Generation of Human Granulosa Cells. Nutrients. 2023 Feb 2;15(3):753. doi: 10.3390/nu15030753. PMID: 36771459; PMCID: PMC9921828. 2. Silva S, Costa EM, Machado M, Morais R, Calhau C, Pintado M. Antiadhesive and Antibiofilm Effect of Malvidin-3-Glucoside and Malvidin-3-Glucoside/Neochlorogenic Acid Mixtures upon Staphylococcus. Metabolites. 2022 Nov 3;12(11):1062. doi: 10.3390/metabo12111062. PMID: 36355145; PMCID: PMC9694786.
In vivo protocol:
1. Zhao P, Li X, Yang Q, Lu Y, Wang G, Yang H, Dong J, Zhang H. Malvidin alleviates mitochondrial dysfunction and ROS accumulation through activating AMPK-α/UCP2 axis, thereby resisting inflammation and apoptosis in SAE mice. Front Pharmacol. 2023 Jan 9;13:1038802. doi: 10.3389/fphar.2022.1038802. PMID: 36699054; PMCID: PMC9868257. 2. Liu F, Smith AD, Wang TTY, Pham Q, Cheung L, Yang H, Li RW. Biological pathways via which the anthocyanin malvidin alleviated the murine colitis induced by Citrobacter rodentium. Food Funct. 2023 Jan 23;14(2):1048-1061. doi: 10.1039/d2fo02873e. PMID: 36562464.
1: Gilani SJ, Bin-Jumah MN, Al-Abbasi FA, Imam SS, Alshehri S, Ghoneim MM, Shahid Nadeem M, Afzal M, Alzarea SI, Sayyed N, Kazmi I. Antiamnesic Potential of Malvidin on Aluminum Chloride Activated by the Free Radical Scavenging Property. ACS Omega. 2022 Jul 1;7(28):24231-24240. doi: 10.1021/acsomega.2c01406. PMID: 35874261; PMCID: PMC9301734. 2: Zhao P, Li X, Yang Q, Lu Y, Wang G, Yang H, Dong J, Zhang H. Malvidin alleviates mitochondrial dysfunction and ROS accumulation through activating AMPK-α/UCP2 axis, thereby resisting inflammation and apoptosis in SAE mice. Front Pharmacol. 2023 Jan 9;13:1038802. doi: 10.3389/fphar.2022.1038802. PMID: 36699054; PMCID: PMC9868257. 3: Fan H, Cui J, Liu F, Zhang W, Yang H, He N, Dong Z, Dong J. Malvidin protects against lipopolysaccharide-induced acute liver injury in mice via regulating Nrf2 and NLRP3 pathways and suppressing apoptosis and autophagy. Eur J Pharmacol. 2022 Oct 15;933:175252. doi: 10.1016/j.ejphar.2022.175252. Epub 2022 Sep 2. PMID: 36063870. 4: Zarricueta ML, Fagundes FL, Pereira QC, Pantaleão SQ, Santos RCD. Relationship between Hormonal Modulation and Gastroprotective Activity of Malvidin and Cyanidin Chloride: In Vivo and In Silico Approach. Pharmaceutics. 2022 Mar 4;14(3):565. doi: 10.3390/pharmaceutics14030565. PMID: 35335941; PMCID: PMC8953580. 5: Merecz-Sadowska A, Sitarek P, Kowalczyk T, Zajdel K, Jęcek M, Nowak P, Zajdel R. Food Anthocyanins: Malvidin and Its Glycosides as Promising Antioxidant and Anti-Inflammatory Agents with Potential Health Benefits. Nutrients. 2023 Jul 1;15(13):3016. doi: 10.3390/nu15133016. PMID: 37447342; PMCID: PMC10346481. 6: Shi J, Wang Y, Zhang X, Fan H, Wang H, Li X, Xu B, Qiang J, Pan E, Chu M, Dong J, Dong Z. Ameliorative Effect of Malvidin on Spleen Injury in LPS-Induced Sepsis. Chem Biodivers. 2023 Aug;20(8):e202201161. doi: 10.1002/cbdv.202201161. Epub 2023 Jul 18. PMID: 37391875. 7: Fan H, Sun Y, Zhang X, Xu Y, Ming Y, Zhang L, Zhao P. Malvidin promotes PGC-1α/Nrf2 signaling to attenuate the inflammatory response and restore mitochondrial activity in septic acute kidney injury. Chem Biol Interact. 2024 Jan 25;388:110850. doi: 10.1016/j.cbi.2023.110850. Epub 2023 Dec 20. PMID: 38135199. 8: Liang S, Li X, Liu R, Hu J, Li Y, Sun J, Bai W. Malvidin-3-O-Glucoside Ameliorates Cadmium-Mediated Cell Dysfunction in the Estradiol Generation of Human Granulosa Cells. Nutrients. 2023 Feb 2;15(3):753. doi: 10.3390/nu15030753. PMID: 36771459; PMCID: PMC9921828. 9: Bastin AR, Sadeghi A, Abolhassani M, Doustimotlagh AH, Mohammadi A. Malvidin prevents lipopolysaccharide-induced oxidative stress and inflammation in human peripheral blood mononuclear cells. IUBMB Life. 2020 Jul;72(7):1504-1514. doi: 10.1002/iub.2286. Epub 2020 Apr 8. PMID: 32268009. 10: Silva S, Costa EM, Machado M, Morais R, Calhau C, Pintado M. Antiadhesive and Antibiofilm Effect of Malvidin-3-Glucoside and Malvidin-3-Glucoside/Neochlorogenic Acid Mixtures upon Staphylococcus. Metabolites. 2022 Nov 3;12(11):1062. doi: 10.3390/metabo12111062. PMID: 36355145; PMCID: PMC9694786. 11: Zhao X, He XM, Liu F, Duan CQ, He F. Intramolecular copigmentation in malvidin-3-O-(6-O-p-coumaryl)-glucoside: Insights from experimental and theoretical study. Food Chem. 2022 Oct 15;391:133255. doi: 10.1016/j.foodchem.2022.133255. Epub 2022 May 19. PMID: 35609464. 12: Bastin A, Sadeghi A, Nematollahi MH, Abolhassani M, Mohammadi A, Akbari H. The effects of malvidin on oxidative stress parameters and inflammatory cytokines in LPS-induced human THP-1 cells. J Cell Physiol. 2021 Apr;236(4):2790-2799. doi: 10.1002/jcp.30049. Epub 2020 Sep 10. PMID: 32914418. 13: Strugała-Danak P, Spiegel M, Gabrielska J. Malvidin and Its Mono- and Di- Glucosides Forms: A Study of Combining Both In Vitro and Molecular Docking Studies Focused on Cholinesterase, Butyrylcholinesterase, COX-1 and COX-2 Activities. Molecules. 2023 Nov 30;28(23):7872. doi: 10.3390/molecules28237872. PMID: 38067599; PMCID: PMC10708353. 14: Ma Y, Li Y, Zhang H, Wang Y, Wu C, Huang W. Malvidin induces hepatic stellate cell apoptosis via the endoplasmic reticulum stress pathway and mitochondrial pathway. Food Sci Nutr. 2020 Aug 10;8(9):5095-5106. doi: 10.1002/fsn3.1810. PMID: 32994970; PMCID: PMC7500790. 15: Forino M, Gambuti A, Luciano P, Moio L. Malvidin-3- O-glucoside Chemical Behavior in the Wine pH Range. J Agric Food Chem. 2019 Jan 30;67(4):1222-1229. doi: 10.1021/acs.jafc.8b05895. Epub 2019 Jan 14. PMID: 30604613. 16: Liobikas J, Skemiene K, Trumbeckaite S, Borutaite V. Anthocyanins in cardioprotection: A path through mitochondria. Pharmacol Res. 2016 Nov;113(Pt B):808-815. doi: 10.1016/j.phrs.2016.03.036. Epub 2016 Mar 30. PMID: 27038533. 17: Fagundes FL, Pereira QC, Zarricueta ML, Dos Santos RC. Malvidin Protects against and Repairs Peptic Ulcers in Mice by Alleviating Oxidative Stress and Inflammation. Nutrients. 2021 Sep 23;13(10):3312. doi: 10.3390/nu13103312. PMID: 34684313; PMCID: PMC8537945. 18: Singh CK, Siddiqui IA, El-Abd S, Mukhtar H, Ahmad N. Combination chemoprevention with grape antioxidants. Mol Nutr Food Res. 2016 Jun;60(6):1406-15. doi: 10.1002/mnfr.201500945. Epub 2016 Mar 3. PMID: 26829056; PMCID: PMC4911802. 19: Zhao X, Zhang X, He X, Duan C, He F. Acetylation of Malvidin-3-O-glucoside Impedes Intermolecular Copigmentation: Experimental and Theoretical Investigations. J Agric Food Chem. 2021 Jul 14;69(27):7733-7741. doi: 10.1021/acs.jafc.1c02378. Epub 2021 Jun 30. PMID: 34192464. 20: Sakthivel KM, Kokilavani K, Kathirvelan C, Brindha D. Malvidin Abrogates Oxidative Stress and Inflammatory Mediators to Inhibit Solid and Ascitic Tumor Development in Mice. J Environ Pathol Toxicol Oncol. 2020;39(3):247-260. doi: 10.1615/JEnvironPatholToxicolOncol.2020034430. PMID: 32865916.

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