Cas no 89919-62-0 (3,5-O-Dicaffeoylquinic acid)

3,5-O-Dicaffeoylquinic acid is a naturally occurring polyphenolic compound classified as a hydroxycinnamic acid derivative. It is characterized by the esterification of quinic acid with two caffeoyl groups at the 3 and 5 positions, contributing to its notable antioxidant and anti-inflammatory properties. This compound is commonly found in plants such as artichoke, burdock, and Echinacea species. Its structural configuration enhances free radical scavenging activity and metal chelation, making it valuable in research applications related to oxidative stress and cellular protection. Additionally, 3,5-O-Dicaffeoylquinic acid exhibits potential bioactive effects, including antiviral and neuroprotective properties, underscoring its relevance in pharmacological and nutraceutical studies.
3,5-O-Dicaffeoylquinic acid structure
3,5-O-Dicaffeoylquinic acid structure
Product Name:3,5-O-Dicaffeoylquinic acid
CAS No:89919-62-0
MF:C25H24O12
MW:516.450868606567
CID:61329
PubChem ID:6474310
Update Time:2025-06-08

3,5-O-Dicaffeoylquinic acid Chemical and Physical Properties

Names and Identifiers

    • (-)-3,5-Dicaffeoyl quinic acid
    • (E,E)-3,5-Di-O-caffeoylquinic acid
    • (1S,3R,4S,5R)-3,5-Bis(((E)-3-(3,4-dihydroxyphenyl)acryloyl)-oxy)-1,4-dihydroxycyclohexanecarboxylic acid
    • 3,5-Di-O-caffeoylquinic acid
    • Isochlorogenic acid A
    • 3,5-DCQA
    • 3,5-di-O-trans-caffeoyl-D-quinic acid
    • Rel-3,5-Dicaffeoylquinic Acid
    • (1α,3R,4α,5R)-3,5-Bis[[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-1,4-dihydroxycyclohexanecarboxylic acid (ACI)
    • Cyclohexanecarboxylic acid, 3,5-bis[[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4-dihydroxy-, (1α,3R,4α,5R)- (9CI)
    • Cyclohexanecarboxylic acid, 3,5-bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4-dihydroxy-, [1R-[1α,3α(E),4α,5β(E)]]- (ZCI)
    • (-)-3,5-Dicaffeoylquinic acid
    • 3,5-Di-O-(E)-caffeoylquinic acid
    • 3,5-Dicaffeoylquininic acid
    • Trans 3,5-O-dicaffeoylquinic acid
    • 3,5-O-Dicaffeoylquinic acid
    • Methylhydrogenphthalate
    • CHEMBL4466054
    • (1S,3R,4S,5R)-3,5-BIS(((E)-3-(3,4-DIHYDROXYPHENYL)ACRYLOYL)OXY)-1,5-DIHYDROXYCYCLOHEXANE-1-CARBOXYLIC ACID
    • CYCLOHEXANECARBOXYLIC ACID, 3,5-BIS((3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPENYL)OXY)-1,4-DIHYDROXY-, (1R-(1.ALPHA.,3.ALPHA.(E),4.ALPHA.,5.BETA.(E)))-
    • 3,5-Di-caffeoylquinic acid, >=95% (LC/MS-ELSD)
    • DTXSID00424282
    • (1R,3R,4S,5R)-3,5-Bis[[(e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-1,4-dihydroxycyclohexane-1-carboxylic acid
    • 3,5-dicaffeoylquinate
    • ACon1_002290
    • 89919-62-0
    • CS-3768
    • A,5R)-3,5-Bis(((E)-3-(3,4-dihydroxyphenyl)acryloyl)oxy)-1,4-dihydroxycyclohexanecarboxylic acid
    • (1
    • Dicaffeoylquinic acid
    • Isochlorogenic acid A
    • BS-42212
    • Q27134233
    • CJ-4-16-4
    • 3,5-DICQA
    • 3,5-H56:H75dicaffeoyl-epi-quinic acid
    • (3R,5R)-3,5-bis(((2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl))-1,4-dihydroxy-cyclohexanecarboxylic acid
    • 3,5-Dicaffeoyl-epi-quinic acid
    • (3R,5R)-3,5-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-1,4-dihydroxy-cyclohexanecarboxylic acid
    • NCGC00390251-01
    • 2450-53-5
    • CJ 4-16-4
    • 3,5-dicaffeoyl quinic acid
    • (1S,3R,4R,5R)-3,5-Bis[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-1,4-dihydroxycyclohexanecarboxylic acid
    • NCGC00169984-03
    • (1S,3R,4S,5R)-1,3,4,5-tetrahydroxy-1-carboxycyclohexane3,5-di-3-(3,4-dihydroxyphenyl)propenoate
    • (1S,3R,4S,5R)-3,5-Bis(((E)-3-(3,4-dihydroxyphenyl)acryloyl)oxy)-1,4-dihydroxycyclohexanecarboxylicacid
    • UNII-ND94C5E75K
    • AKOS016007890
    • 3,5-CQA
    • 1ST40155
    • NCGC00169984-01
    • CYCLOHEXANECARBOXYLIC ACID, 1,4-DIHYDROXY-3,5-BIS(((2E)-3-(4-HYDROXYPHENYL)-1-OXO-2-PROPEN-1-YL)OXY)-, (1.ALPHA.,3R,4.ALPHA.,5R)-
    • CCG-269821
    • SCHEMBL20339739
    • AKOS032948323
    • CHEMBL4289566
    • PD197614
    • BDBM50466107
    • s9282
    • (3R,5R)-3,5-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-1,4-dihydroxycyclohexane-1-carboxylic acid
    • 3,5-di-O-caffeoyl quinic acid
    • Isochlorogenic-acid-A
    • HY-N0056
    • CS-0204164
    • 3,5-Di-o-caffeoylquinic acid/Isochlorogenic acid A
    • MFCD00951290
    • 3,5-Dicaffeoylquinic acid
    • (1.ALPHA.,3R,4.ALPHA.,5R)-3,5-BIS(((2E)-3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPEN-1-YL)OXY)-1,4-DIHYDROXYCYCLOHEXANECARBOXYLIC ACID
    • Quinic acid 3,5-di-O-caffeate
    • ND94C5E75K
    • A,3R,4
    • SCHEMBL13567304
    • 3,5-di-O-Aaffeoylquinic acid
    • HY-N9895
    • A877898
    • (E,E)-3,5-O-dicaffeoylquinic acid
    • CHEBI:65751
    • AKOS015903388
    • Q-100315
    • (3R,5R)-3,5-bis{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4-dihydroxycyclohexanecarboxylic acid
    • BDBM50362839
    • (1S,3R,4S,5R)-3,5-Bis(((E)-3-(3,4-dihydroxyphenyl)acryloyl)oxy)-1,4-dihydroxycyclohexanecarboxylic acid
    • CHEMBL249447
    • CYCLOHEXANECARBOXYLIC ACID, 3,5-BIS(((2E)-3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPEN-1-YL)OXY)-1,4-DIHYDROXY-, (1.ALPHA.,3R,4.ALPHA.,5R)-
    • GTPL12548
    • 879305-14-3
    • 3,5-Caffeoyl quinic acid
    • 3,5-Di-caffeoylquinic acid
    • 3,5-di-O-caffeate
    • sochlorogenic acid a
    • 3_5-di-O-caffeoylquinic_acid
    • DA-74544
    • DA-49507
    • 3,5-Dicaffeoylquinicacid
    • DA-60222
    • Inchi： 1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(30)36-19-11-25(35,24(33)34)12-20(23(19)32)37-22(31)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-29,32,35H,11-12H2,(H,33,34)/b7-3+,8-4+/t19-,20-,23-,25+/m1/s1
    • InChI Key： KRZBCHWVBQOTNZ-PSEXTPKNSA-N
    • SMILES： O([C@@H]1C[C@@](O)(C(=O)O)C[C@@H](OC(=O)/C=C/C2C=CC(O)=C(O)C=2)[C@@H]1O)C(=O)/C=C/C1C=CC(O)=C(O)C=1

Computed Properties

  • Exact Mass: 516.12700
  • Monoisotopic Mass: 516.12677620 g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 7
  • Hydrogen Bond Acceptor Count: 12
  • Heavy Atom Count: 37
  • Rotatable Bond Count: 9
  • Complexity: 825
  • 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
  • Molecular Weight: 516.4
  • XLogP3: 1.5
  • Topological Polar Surface Area: 211?2

Experimental Properties

  • Color/Form: Powder
  • Density: 1.64
  • Melting Point: No data available
  • Boiling Point: 826.2±65.0 °C at 760 mmHg
  • Flash Point: 280.4±27.8 °C
  • PSA: 211.28000
  • LogP: 1.02960
  • Vapor Pressure: No data available

3,5-O-Dicaffeoylquinic acid Security Information

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3,5-O-Dicaffeoylquinic acid Production Method

Production Method 1

Reaction Conditions
1.1 Catalysts: Iodine Solvents: Methanol-d4 ;  2 min, 50 °C
Reference
A highly efficient transformation of cis- to trans-cinnamic acid derivatives by iodine
Li, Zhen-Jie; Cai, Le; Mei, Rui-Feng; Dong, Jian-Wei; Li, Shu-Quan; et al, Tetrahedron Letters, 2015, 56(52), 7197-7200

Production Method 2

Reaction Conditions
1.1 Catalysts: Piperidine ,  4-(Dimethylamino)pyridine Solvents: Dimethylformamide ;  8 d, rt
Reference
Total synthesis of 3,5-O-dicaffeoylquinic acid and its derivatives
Raheem, K. Saki; Botting, Nigel P.; Williamson, Gary; Barron, Denis, Tetrahedron Letters, 2011, 52(52), 7175-7177

Production Method 3

Reaction Conditions
1.1 Reagents: Water Solvents: Water ;  10 min, 100 °C
Reference
Investigating the Chemical Changes of Chlorogenic Acids during Coffee Brewing: Conjugate Addition of Water to the Olefinic Moiety of Chlorogenic Acids and Their Quinides
Matei, Marius Febi; Jaiswal, Rakesh; Kuhnert, Nikolai, Journal of Agricultural and Food Chemistry, 2012, 60(49), 12105-12115

3,5-O-Dicaffeoylquinic acid Raw materials

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Amadis Chemical Company Limited
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Quantity:50mg
Purity:99%
Pricing Information Last Updated:Friday, 30 August 2024 03:42
Price ($):241.0
Tiancheng Chemical (Jiangsu) Co., Ltd
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(CAS:89919-62-0)3,5-O-Dicaffeoylquinic acid
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Purity:99%
Pricing Information Last Updated:Friday, 20 June 2025 12:04
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3,5-O-Dicaffeoylquinic acid Related Literature

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Additional information on 3,5-O-Dicaffeoylquinic acid

3,5-O-Dicaffeoylquinic Acid (CAS No. 89919-62-0): A Comprehensive Guide to Its Properties and Health Benefits

3,5-O-Dicaffeoylquinic acid (CAS No. 89919-62-0) is a naturally occurring polyphenolic compound belonging to the class of chlorogenic acids. This bioactive molecule is widely studied for its potential health benefits, including antioxidant, anti-inflammatory, and neuroprotective properties. As interest in natural antioxidants and plant-derived bioactive compounds grows, 3,5-O-Dicaffeoylquinic acid has emerged as a key focus in nutritional and pharmaceutical research.

The compound is structurally characterized by the presence of two caffeoyl groups attached to a quinic acid backbone, which enhances its biological activity. Its unique structure contributes to its ability to scavenge free radicals and modulate cellular signaling pathways. Researchers have identified 3,5-O-Dicaffeoylquinic acid in various medicinal plants, including Echinacea purpurea and Artemisia annua, which are traditionally used for their immune-boosting and anti-malarial properties, respectively.

In recent years, the demand for natural health supplements and functional foods has surged, driven by consumer awareness of oxidative stress and chronic inflammation. 3,5-O-Dicaffeoylquinic acid aligns with these trends, as studies suggest it may support cardiovascular health, metabolic balance, and cognitive function. Its potential role in gut microbiota modulation has also attracted attention, given the growing focus on gut-brain axis research.

From a technical perspective, 3,5-O-Dicaffeoylquinic acid is often extracted using advanced techniques such as ultrasound-assisted extraction or supercritical fluid extraction to ensure high purity. Analytical methods like HPLC-MS and NMR spectroscopy are employed to verify its structural integrity and quantify its presence in complex matrices. These methodologies are critical for quality control in the production of dietary supplements and cosmeceuticals.

Another area of interest is the compound's potential synergy with other polyphenols, such as quercetin and resveratrol, in multi-component formulations. This synergy could enhance bioavailability and efficacy, addressing common challenges in nutraceutical delivery systems. As the functional ingredient market expands, 3,5-O-Dicaffeoylquinic acid is poised to play a significant role in innovative product development.

In conclusion, 3,5-O-Dicaffeoylquinic acid (CAS No. 89919-62-0) represents a promising bioactive compound with multifaceted applications in health and wellness. Its antioxidant capacity, anti-inflammatory effects, and metabolic benefits make it a valuable subject for ongoing research. As consumers increasingly seek evidence-based natural remedies, this compound is likely to gain further prominence in both scientific and commercial spheres.

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Amadis Chemical Company Limited
(CAS:89919-62-0)3,5-O-Dicaffeoylquinic acid
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Purity:99%
Quantity:50mg
Price ($):241.0
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Tiancheng Chemical (Jiangsu) Co., Ltd
(CAS:89919-62-0)3,5-O-Dicaffeoylquinic acid
LE11177
Purity:99%
Quantity:25KG,200KG,1000KG
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