SMB00224
3,4-Di-O-caffeoylquinic acid
别名:
3,4-DICQA, 3,4-Di-O-caffeoylquinate, 3,4-Dicaffeoylquinic acid, Isochlorogenate B, Isochlorogenic acid B
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关于此项目
经验公式（希尔记法）:
C25H24O12
化学文摘社编号:
分子量:
516.45
NACRES:
NA.25
PubChem Substance ID:
UNSPSC Code:
12352205
MDL number:
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
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 key
UFCLZKMFXSILNL-PSEXTPKNSA-N
Quality Level
form
solid
application(s)
metabolomics
vitamins, nutraceuticals, and natural products
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).
存储类别
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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)
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)
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
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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