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SMB00224

Sigma-Aldrich

3,4-Di-O-caffeoylquinic acid

≥90% (LC/MS-ELSD)

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Synonym(s):
3,4-DICQA, 3,4-Di-O-caffeoylquinate, 3,4-Dicaffeoylquinic acid, Isochlorogenate B, Isochlorogenic acid B
Empirical Formula (Hill Notation):
C25H24O12
CAS Number:
Molecular Weight:
516.45
MDL number:
PubChem Substance ID:
NACRES:
NA.25

Quality Level

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

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1 of 4

This Item
SMB00221SMB00131PHL80427
4,5-Dicaffeoylquinic acid phyproof® Reference Substance

PHL80427

4,5-Dicaffeoylquinic acid

form

solid

form

solid

form

solid

form

solid

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

application(s)

-

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

2-8°C

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

-

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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Xican Li et al.
Molecules (Basel, Switzerland), 23(1) (2018-01-25)
In this study, a series of di-O-caffeoylquinic acids (di-COQs) were systematically investigated for their antioxidant and cytoprotective effects towards •OH-damaged bone marrow-derived mesenchymal stem cells (bmMSCs). Five di-COQs were measured using a set of antioxidant assays. The results show that
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)
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)
Xican Li et al.
Molecules (Basel, Switzerland), 23(1) (2018-01-25)
In this study, a series of di-O-caffeoylquinic acids (di-COQs) were systematically investigated for their antioxidant and cytoprotective effects towards •OH-damaged bone marrow-derived mesenchymal stem cells (bmMSCs). Five di-COQs were measured using a set of antioxidant assays. The results show that
Daniil N Olennikov et al.
Frontiers in pharmacology, 9, 756-756 (2018-07-28)
Artemisia genus of Asteraceae family is a source of medicinal plants known worldwide and used as ethnopharmacological remedies for the treatment of diabetes in Northern Asia (Siberia). The aim of this study was to determine the phenolic profile of 12

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