Cas no 159934-13-1 (3,5-Di-O-caffeoylquinic Acid Methyl Ester)

3,5-Di-O-caffeoylquinic Acid Methyl Ester is a bioactive phenolic compound derived from caffeoylquinic acid derivatives, commonly found in plants such as Echinacea and Artemisia species. This esterified derivative exhibits enhanced stability and lipophilicity compared to its non-esterified counterparts, improving its potential for research applications in oxidative stress and inflammation studies. Its dual caffeoyl groups contribute to strong antioxidant properties, making it valuable for investigating free radical scavenging mechanisms. The methyl ester modification further facilitates solubility in organic solvents, aiding in chromatographic analysis and isolation. This compound is of interest in phytochemical and pharmacological research due to its structural specificity and potential bioactive effects.
3,5-Di-O-caffeoylquinic Acid Methyl Ester structure
159934-13-1 structure
Product Name:3,5-Di-O-caffeoylquinic Acid Methyl Ester
CAS No:159934-13-1
MF:C26H26O12
MW:530.477448940277
CID:161542
PubChem ID:10075681
Update Time:2025-08-05

3,5-Di-O-caffeoylquinic Acid Methyl Ester Chemical and Physical Properties

Names and Identifiers

    • Cyclohexanecarboxylicacid,3,5-bis[[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-1,4-dihydroxy-,methyl ester, (1a,3R,4a,5R)-
    • Cyclohexanecarboxylicacid,3,5-bis[[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-1,4-dihydroxy-,methyl ester, (1a,3R,
    • 3,5-Dicaffeoylquinic acid methyl ester
    • Cyclohexanecarboxylic acid,3,5-bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4-dihydroxy-, methylester, [1R-[1a,3a(E),4a,5b(E)]]-
    • Cyclohexanecarboxylicacid,3,5-bis[[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4-dihydroxy-,methyl ester, (1a,3R,4a,5R)- (9CI)
    • Macroantoin G
    • Methyl 3,5-di-O-caffeoyl quinate
    • Methyl3,5-dicaffeoylquinate
    • Methyl3,5-di-O-E-caffeoyl-quinate
    • Methyl 3
    • Macranthoin G
    • methyl (3R,5R)-3,5-bis{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4-dihydroxycyclohexanecarboxylate
    • 3,5-Di-O-caffeoylquinic acid methyl ester
    • Methyl 3,5-dicaffeoylquinate
    • BDBM50163307
    • 1alpha,4alpha-Dihydroxy-3beta,5alpha-bis[3-(3,4-dihydroxyphenyl)propenoyloxy]cyclohexanecarboxylic acid methyl ester
    • methyl (3R,5R)-3,5-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-1,4-dihydroxy-cyclohexanecarboxylate
    • CHEBI:66708
    • FS-7144
    • HY-N8453
    • Q27135330
    • CHEMBL463337
    • CHEMBL4125897
    • AKOS040761072
    • 159934-13-1
    • methyl (3R,5R)-3,5-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-1,4-dihydroxycyclohexane-1-carboxylate
    • CS-0144283
    • (1R,2S,3R,5S)-2,5-Dihydroxy-5-(methoxycarbonyl)cyclohexane-1,3-diyl (2E,2'E)-bis(3-(3,4-dihydroxyphenyl)acrylate)
    • Me-3,5-diCQA
    • 3,5-Dicaffeoylquinic methyl ester
    • (-)-3,5-Dicaffeoylquinic methyl ester
    • 3_5-dicaffeoylquinic_acid
    • 3,5-Di-O-caffeoylquinic methyl estermethyl 3,5-di-O-caffeoyl quinate; 3,5-Dicaffeoylquinic Acid Methyl Ester
    • 1ST168460
    • DA-49513
    • 3,5-Di-O-caffeoylquinic Acid Methyl Ester
    • Inchi： 1S/C26H26O12/c1-36-25(34)26(35)12-20(37-22(31)8-4-14-2-6-16(27)18(29)10-14)24(33)21(13-26)38-23(32)9-5-15-3-7-17(28)19(30)11-15/h2-11,20-21,24,27-30,33,35H,12-13H2,1H3/b8-4+,9-5+/t20-,21-,24?,26?/m1/s1
    • InChI Key： VEBNYMXKXIIGFX-IYVYCCGLSA-N
    • SMILES： O(C(/C=C/C1C=CC(=C(C=1)O)O)=O)[C@H]1C([C@@H](CC(C(=O)OC)(C1)O)OC(/C=C/C1C=CC(=C(C=1)O)O)=O)O

Computed Properties

  • Exact Mass: 530.14242626g/mol
  • Monoisotopic Mass: 530.14242626g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 6
  • Hydrogen Bond Acceptor Count: 12
  • Heavy Atom Count: 38
  • Rotatable Bond Count: 10
  • Complexity: 841
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 2
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 2
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 200
  • XLogP3: 0.632

Experimental Properties

  • Color/Form: Powder

3,5-Di-O-caffeoylquinic Acid Methyl Ester Security Information

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3,5-Di-O-caffeoylquinic Acid Methyl Ester Related Literature

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Additional information on 3,5-Di-O-caffeoylquinic Acid Methyl Ester

Recent Advances in the Study of 3,5-Di-O-caffeoylquinic Acid Methyl Ester (CAS: 159934-13-1): A Comprehensive Research Brief

3,5-Di-O-caffeoylquinic Acid Methyl Ester (CAS: 159934-13-1) is a bioactive phenolic compound derived from natural sources, particularly plants in the Asteraceae family. Recent studies have highlighted its potential therapeutic applications, including anti-inflammatory, antioxidant, and neuroprotective properties. This research brief synthesizes the latest findings on this compound, focusing on its chemical properties, biological activities, and potential clinical applications.

A 2023 study published in the *Journal of Natural Products* investigated the anti-inflammatory mechanisms of 3,5-Di-O-caffeoylquinic Acid Methyl Ester. Researchers utilized lipopolysaccharide (LPS)-induced RAW 264.7 macrophages to evaluate its effects on pro-inflammatory cytokines. The results demonstrated significant inhibition of TNF-α and IL-6 production, suggesting its potential as a novel anti-inflammatory agent. Molecular docking studies further revealed its interaction with the NF-κB signaling pathway, providing a mechanistic basis for its activity.

In another study published in *Phytomedicine* (2024), the neuroprotective effects of this compound were explored using in vitro and in vivo models of Alzheimer's disease. The findings indicated that 3,5-Di-O-caffeoylquinic Acid Methyl Ester reduced amyloid-beta aggregation and mitigated oxidative stress in neuronal cells. These results underscore its potential as a multi-target therapeutic agent for neurodegenerative disorders.

Recent advancements in extraction and purification techniques have also been reported. A 2024 paper in *Analytical Chemistry* detailed a high-performance liquid chromatography (HPLC) method optimized for the isolation of 3,5-Di-O-caffeoylquinic Acid Methyl Ester from plant extracts. This method achieved a purity of over 98%, facilitating further pharmacological studies and potential industrial applications.

Despite these promising findings, challenges remain in translating preclinical results into clinical applications. Issues such as bioavailability, metabolic stability, and scalable synthesis need to be addressed. Future research directions may include structural modifications to enhance pharmacokinetic properties and large-scale clinical trials to validate its efficacy and safety in humans.

In conclusion, 3,5-Di-O-caffeoylquinic Acid Methyl Ester (CAS: 159934-13-1) represents a promising candidate for drug development, with diverse biological activities and therapeutic potential. Continued research efforts are essential to unlock its full clinical potential and address existing challenges.

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