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SMB00224

3,4-Di-O-caffeoylquinic acid

≥90% (LC/MS-ELSD)

Synonym(s):

3,4-DICQA, 3,4-Di-O-caffeoylquinate, 3,4-Dicaffeoylquinic acid, Isochlorogenate B, Isochlorogenic acid B

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About This Item

Empirical Formula (Hill Notation):
C25H24O12
CAS Number:
14534-61-3
Molecular Weight:
516.45
NACRES:
NA.25
PubChem Substance ID:
329824881
UNSPSC Code:
12352205
MDL number:
MFCD22375481
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Quality Segment

assay

≥90% (LC/MS-ELSD)

form

solid

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

−20°C

SMILES string

O[C@@H]1C[C@](O)(C[C@@H](OC(=O)\C=C\c2ccc(O)c(O)c2)[C@@H]1OC(=O)\C=C\c3ccc(O)c(O)c3)C(O)=O

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

InChI key

UFCLZKMFXSILNL-PSEXTPKNSA-N

General 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

Biochem/physiol Actions

3,4-Di-O-caffeoylquinic acid, along with 3,5-dicaffeoylquinic acid and luteolin-7-O-glucoside, is a component of the medicinal herb Youngia japonica. It has known antiviral activity and along with 3,5,-dicaffeoylquinic acid, shows activity against respiratory syncyntial virus (RSV). 3,4-COQ elicits antioxidant effects which mediate its neuroprotective effects against in vitro retinal damage. It also exerts cytoprotective effects against oxidative damage in bone marrow-derived mesenchymal stem cells (bmMSCs).

Storage Class

11 - Combustible Solids

WGK

WGK 3

Flash Point (°F)

Not applicable

Flash Point (°C)

Not applicable

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