Isochlorogenic acid B - analytical standard, ≥98% , Channel blocker of TRPV3, CAS No.14534-61-3, Channel blocker of TRPV3

CAS: 14534-61-3 Cat. No.: I111373 Molecular Weight: 516.46 EC Number: 874-682-0

GRADE & PURITY Analytical standard, ≥98%

Synonyms

CHEBI:5995 | 4,5-Dicaffeoylquinic acid | 4,5-Dicqa | Isochlorogenic acid b | UNII-45777W94HK | (1S,3R,4R,5R)-3,4-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-1,5-dihydroxycyclohexane-1-carboxylic acid | 3,4-Di-O-Caffeoylquinic acid

Storage

Store at 2-8°C

Shipped In

Wet ice

Overview

3,4-Di-O-caffeoylquinic acid (3,4-COQ) is a component of the medicinal herb Youngia japonica.It has a caffeoyl moiety attached with a hexacyclic quinic acid in its structure.

Application：
3,4-Di-O-caffeoylquinic acid has been used as a reference standard:
to quantify the caffeoylquinic acids of Artemisia frigida Willd. (Fringed sagewort) using high-performance liquid chromatography with diode array detection and electrospray ionization triple quadrupole mass spectrometric detection (HPLC-DAD-ESI-QQQ-MS)
to quantify the phenolic compounds of Artemisia species using high-performance liquid chromatography with diode array detection (HPLC-DAD) technique
for metabolic profiling of methanolic leaf extract of A. nallamalayana and to identify the phenolic acids using High-Performance Liquid Chromatography-Ultraviolet (HPLC-UV) analysis

Specifications

Synonyms

CHEBI:5995 | 4, 5-Dicaffeoylquinic acid | 4, 5-Dicqa | Isochlorogenic acid b | UNII-45777W94HK | (1S, 3R, 4R, 5R)-3, 4-bis[[(E)-3-(3, 4-dihydroxyphenyl)prop-2-enoyl]oxy]-1, 5-dihydroxycyclohexane-1-carboxylic acid | 3, 4-Di-O-Caffeoylquinic acid

Specifications & Purity

analytical standard, ≥98%

Storage

Store at 2-8°C

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Analytical standard

Action Type

CHANNEL BLOCKER

Mechanism of action

Channel blocker of TRPV3

Purity

≥98%

Names and Identifiers

• Canonical Smiles: C1C(C(C(CC1(C(=O)O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O)OC(=O)C=CC3=CC(=C(C=C3)O)O)O
• IUPAC Name: (1S,3R,4R,5R)-3,4-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-1,5-dihydroxycyclohexane-1-carboxylic acid
• InChIKey: UFCLZKMFXSILNL-PSEXTPKNSA-N
• INCHI: 1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(31)36-20-12-25(35,24(33)34)11-19(30)23(20)37-22(32)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-30,35H,11-12H2,(H,33,34)/b7-3+,8-4+/t19-,20-,23-,25+/m1/s1
• Isomeric SMILES: C1[C@H]([C@H]([C@@H](C[C@@]1(C(=O)O)O)OC(=O)/C=C/C2=CC(=C(C=C2)O)O)OC(=O)/C=C/C3=CC(=C(C=C3)O)O)O
• Alternate CAS: 14534-61-3,32451-88-0,89886-31-7
• MeSH Entry Terms: 3,4-di-O-caffeoylquinic acid;3,4-dicaffeoylquinic acid;3,4-DICQA;isochlorogenic acid B;methyl 3,5-di-O-caffeoyl quinate;methyl-3,5-di-O-caffeoylquinate
• Molecular Weight: 516.46
• Reaxy-Rn: 11340191
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=11340191&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Class Organooxygen compounds
      • Subclass Alcohols and polyols
        • Level5 Cyclic alcohols and derivatives
          • Level6 Cyclitols and derivatives
            • Level7 Quinic acids and derivatives

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Class: Organooxygen compounds
• Subclass: Alcohols and polyols
• Intermediate Tree Nodes: Cyclic alcohols and derivatives - Cyclitols and derivatives
• Direct Parent: Quinic acids and derivatives
• Alternative Parents: Coumaric acids and derivatives Cinnamic acid esters Tricarboxylic acids and derivatives Styrenes Catechols 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Fatty acid esters Cyclohexanols Alpha hydroxy acids and derivatives Tertiary alcohols Enoate esters Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Quinic acid - Cinnamic acid or derivatives - Coumaric acid or derivatives - Hydroxycinnamic acid or derivatives - Cinnamic acid ester - Tricarboxylic acid or derivatives - Catechol - Styrene - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Cyclohexanol - Fatty acid ester - Phenol - Fatty acyl - Hydroxy acid - Monocyclic benzene moiety - Alpha-hydroxy acid - Benzenoid - Tertiary alcohol - Alpha,beta-unsaturated carboxylic ester - Enoate ester - Carboxylic acid ester - Secondary alcohol - Carboxylic acid derivative - Carboxylic acid - Hydrocarbon derivative - Carbonyl group - Organic oxide - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as quinic acids and derivatives. These are compounds containing a quinic acid moiety (or a derivative thereof), which is a cyclitol made up of a cyclohexane ring that bears four hydroxyl groups at positions 1,3.4, and 5, as well as a carboxylic acid at position 1.
• External Descriptors: Caffeate derivatives

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

TRPV3 Tchem Transient receptor potential cation channel subfamily V member 3 (0 Activities)

Discover Target: TRPV3

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

AKR1B10 Tchem Aldo-keto reductase family 1 member B10 (1 Activities)

Discover Target: AKR1B10

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

AKR1B1 Tclin Aldose reductase (1 Activities)

Discover Target: AKR1B1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

TYR Tclin Tyrosinase (717 Activities)

Discover Target: TYR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ACHE Tclin Acetylcholinesterase (18204 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

AKR1B1 Tclin Aldose reductase (1404 Activities)

Discover Target: AKR1B1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

APP Tclin Amyloid-beta A4 protein (8510 Activities)

Discover Target: APP

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

BACE1 Tchem Beta-secretase 1 (15641 Activities)

Discover Target: BACE1

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MCF7 (126967 Activities)

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SH-SY5Y (11521 Activities)

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A549 (127892 Activities)

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Jurkat (10389 Activities)

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KETR3 (279 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

AKR1B10 Tchem Aldo-keto reductase family 1 member B10 (300 Activities)

Discover Target: AKR1B10

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

Ptpn1 Protein-tyrosine phosphatase 1B (270 Activities)

Discover Target: Ptpn1

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Staphylococcus aureus (210822 Activities)

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Escherichia coli (133304 Activities)

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Trypanosoma cruzi (99888 Activities)

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Hepatitis B virus (7925 Activities)

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Human immunodeficiency virus 1 (70413 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

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Influenza A virus H3N2 (588 Activities)

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DHODH Dihydroorotate dehydrogenase (fumarate) (195 Activities)

Discover Target: DHODH

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

B16-F1 (104 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Molecular Weight: 516.400 g/mol
• XLogP3: 1.500
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 9
• Exact Mass: 516.127 Da
• Monoisotopic Mass: 516.127 Da
• Topological Polar Surface Area: 211.000 Ų
• Heavy Atom Count: 37
• Formal Charge: 0
• Complexity: 887.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 4
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 2
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 2
• Covalently-Bonded Unit Count: 1

References

1. Yu-Mei Zhao, Lv-Huan Wang, Si-Fan Luo, Qi-Qin Wang, Ruin Moaddel, Ting-Ting Zhang, Zheng-Jin Jiang.  (2018)  Magnetic beads-based neuraminidase enzyme microreactor as a drug discovery tool for screening inhibitors from compound libraries and fishing ligands from natural products.  JOURNAL OF CHROMATOGRAPHY A,      [PMID:30005943] [10.1016/j.chroma.2018.07.031]

2. Ziyu Zhang, Xiaoying Yang, Chang Liu, Xianfa Zeng, Zhigang Yin, Yulong Liu, Jiangli Luo, Ying Zhou.  (2025)  Serum pharmacochemistry profiling combined with molecular docking analysis to reveal the pharmacodynamic material basis of Lonicerae japonicae flos against acute lung injury.  Journal of Functional Foods,      [PMID:] [10.1016/j.jff.2025.106858]