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3,4-Di-O-caffeoylquinic acid

SIGMA/SMB00224 - ≥90% (LC/MS-ELSD)

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

CAS Number: 14534-61-3
Empirical Formula (Hill Notation): C25H24O12
Molecular Weight: 516.45
MDL Number: MFCD22375481
Linear Formula: C25H24O12
Product Type: Chemical
Catalog Number PKG Qty. Price Quantity
45-SMB00224-1MG 1 mg
 $459.00
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assay ≥90% (LC/MS-ELSD)
form solid
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
Quality Level 200 
SMILES string O[C@@H]1C[C@](O)(C[C@@H](OC(=O)C=Cc2ccc(O)c(O)c2)[C@@H]1OC(=O)C=Cc3ccc(O)c(O)c3)C(O)=O
storage temp. −20°C
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).
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.
Packaging: 1 mg in glass bottle
RIDADR NONH for all modes of transport
WGK Germany WGK 3
Flash Point(F) Not applicable
Flash Point(C) Not applicable
Purity ≥90% (LC/MS-ELSD)
Storage Temp. −20°C
UNSPSC 12352200

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