Malvidin chloride | CAS# 643-84-5 | Biochemical

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

MedKoo CAT#: 576849

CAS#: 643-84-5

Description: 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

CAS# 643-84-5

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 576849
Name: Malvidin chloride
CAS#: 643-84-5
Chemical Formula: C17H15ClO7
Exact Mass: 366.05
Molecular Weight: 366.750
Elemental Analysis: C, 55.67; H, 4.12; Cl, 9.67; O, 30.54

Price and Availability

Size	Price	Availability
5mg	USD 465	2 Weeks
10mg	USD 750	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

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

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Product Data:

Product Data

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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/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. 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

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.

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.

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1. 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.

2. 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.

3. 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.

4. 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.

5. Dai T, Shi K, Chen G, Shen Y, Pan T. Malvidin attenuates pain and inflammation in rats with osteoarthritis by suppressing NF-κB signaling pathway. Inflamm Res. 2017 Dec;66(12):1075-1084. doi: 10.1007/s00011-017-1087-6. Epub 2017 Aug 29. PMID: 28852776.

6. Seo HR, Choi MJ, Choi JM, Ko JC, Ko JY, Cho EJ. Malvidin Protects WI-38 Human Fibroblast Cells Against Stress-induced Premature Senescence. J Cancer Prev. 2016 Mar;21(1):32-40. doi: 10.15430/JCP.2016.21.1.32. Epub 2016 Mar 30. PMID: 27051647; PMCID: PMC4819664.

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