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Merck

SMB00224

Sigma-Aldrich

3,4-Di-O-caffeoylquinic acid

≥90% (LC/MS-ELSD)

Synonym(e):

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

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About This Item

Empirische Formel (Hill-System):
C25H24O12
CAS-Nummer:
Molekulargewicht:
516.45
MDL-Nummer:
UNSPSC-Code:
12352205
PubChem Substanz-ID:
NACRES:
NA.25

Assay

≥90% (LC/MS-ELSD)

Form

solid

Anwendung(en)

metabolomics
vitamins, nutraceuticals, and natural products

Lagertemp.

−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

InChIKey

UFCLZKMFXSILNL-PSEXTPKNSA-N

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Allgemeine Beschreibung

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.

Anwendung

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. Wirkung

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).

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable


Analysenzertifikate (COA)

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Kunden haben sich ebenfalls angesehen

Slide 1 of 4

1 of 4

Esterification of the Free Carboxylic Group in 3,4-di-O-caffeoylquinic Acid Enhances the Inhibition Activity against Respiratory Syncytial Virus (RSV)
Wu D, et al.
Medicinal Chemistry (2015)
Antiviral activity and mode of action of caffeoylquinic acids from Schefflera heptaphylla (L.) Frodin.
Li Y, et al.
Antiviral Research, 68(1), 1-9 (2005)
Miki Hiemori-Kondo et al.
Bioscience, biotechnology, and biochemistry, 84(3), 621-632 (2019-11-26)
The antioxidant activity of Petasites japonicus flower buds cultivated in Tokushima, Japan, was examined in vitro and in vivo. The flower bud extracts were assayed using either oxygen radical absorbance capacity or 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity. Antioxidants in the
A comparative assessment of in vitro cytotoxic activity and phytochemical profiling of Andrographis nallamalayana JL Ellis and Andrographis paniculata (Burm. f.) Nees using UPLC-QTOF-MS/MS approach
Goel N, et al.,
Royal Society of Chemistry Advances, 11(57), 35918-35936 (2021)
Yoshimi Nakajima et al.
Life sciences, 80(4), 370-377 (2006-10-19)
We investigated whether water extract of Brazilian green propolis (WEP) and its main constituents [caffeoylquinic acid derivatives (3,4-di-O-caffeoylquinic acid, 3,5-di-O-caffeoylquinic acid, chlorogenic acid) and cinnamic acid derivatives (p-coumaric acid, artepillin C, drupanin, baccharin)] exert neuroprotective effects against the retinal damage

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