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Isochlorogenic acid B - 10mM in DMSO, high purity , CAS No.14534-61-3, Channel blocker of TRPV3

    Grade & Purity:
  • 10mM in DMSO
In stock
Item Number
I421670
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I421670-1ml
1ml
Available within 8-12 weeks(?)
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$241.90

Basic Description

Synonyms 3,4-Dicaffeoylquinic acid | Isochlorogenic acid b | 14534-61-3 | 4,5-Dicqa | 4,5-Dicaffeoylquinic acid | (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 | 45777W94HK | CHEBI:599
Specifications & Purity 10mM in DMSO
Storage Temp Store at -80°C
Shipped In
Ice chest + Ice pads
This product requires cold chain shipping. Ground and other economy services are not available.
Action Type CHANNEL BLOCKER
Mechanism of action Channel blocker of TRPV3
Product Description

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

Taxonomic Classification

Taxonomy Tree

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

Associated Targets(Human)

AKR1B10 Tchem Aldo-keto reductase family 1 member B10 (1 Activities)
Activity Type Activity Value -log(M) Mechanism of Action Activity Reference Publications (PubMed IDs)
AKR1B1 Tclin Aldose reductase (1 Activities)
Activity Type Activity Value -log(M) Mechanism of Action Activity Reference Publications (PubMed IDs)
TYR Tclin Tyrosinase (717 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
ACHE Tclin Acetylcholinesterase (18204 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
AKR1B1 Tclin Aldose reductase (1404 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
APP Tclin Amyloid-beta A4 protein (8510 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
BACE1 Tchem Beta-secretase 1 (15641 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
MCF7 (126967 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
SH-SY5Y (11521 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
A549 (127892 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Jurkat (10389 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
KETR3 (279 Activities)
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)
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)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Staphylococcus aureus (210822 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Escherichia coli (133304 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Trypanosoma cruzi (99888 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Hepatitis B virus (7925 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Human immunodeficiency virus 1 (70413 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
rep Replicase polyprotein 1ab (378 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Influenza A virus H3N2 (588 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
DHODH Dihydroorotate dehydrogenase (fumarate) (195 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
B16-F1 (104 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID

Mechanisms of Action

Mechanism of Action Action Type target ID Target Name Target Type Target Organism Binding Site Name References

Names and Identifiers

IUPAC Name (1S,3R,4R,5R)-3,4-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-1,5-dihydroxycyclohexane-1-carboxylic acid
INCHI 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
InChIKey UFCLZKMFXSILNL-PSEXTPKNSA-N
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
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=

Certificates(CoA,COO,BSE/TSE and Analysis Chart)

C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:

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

Citations of This Product

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,  1568  (123). 

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