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SMB00221

Sigma-Aldrich

4,5-Di-O-caffeoylquinic acid

≥85% (LC/MS-ELSD)

Synonym(s):

4,5-DCQA, 4,5-Di-O-caffeoylquinate, 4,5-Dicaffeoylquinic acid, Isochlorogenate C, Isochlorogenic acid C

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About This Item

Empirical Formula (Hill Notation):
C25H24O12
CAS Number:
57378-72-0
Molecular Weight:
516.45
MDL number:
MFCD10566623
UNSPSC Code:
12352205
PubChem Substance ID:
329824879
NACRES:
NA.25

Quality Level

200

Assay

≥85% (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-RVXRWRFUSA-N

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General description

4,5-Di-O-caffeoylquinic acid (4,5-COQ) is a derivative of caffeoylquinic acid which is a bioactive phenylpropanoid.

Application

4,5-Di-O-caffeoylquinic acid has been used as a reference standard to detect phenolic compounds from Artemisia species using high-performance liquid chromatography with diode array detection (HPLC-DAD) It has also been used as a standard in high-performance liquid chromatography with diode array detection (HPLC-DAD) respectively.

Biochem/physiol Actions

4,5-Di-O-caffeoylquinic acid (4,5-COQ) is an excellent antioxidant, anti-inflammatory, antimicrobial, antifungal, and cytoprotective agent. It also shows neuroprotective and anti-amyloidogenic properties and can inhibit 42-mer amyloid β-protein (Aβ42). 4,5-COQ displays anti-human immunodeficiency virus (HIV) activity as its effectively inhibits HIV-1 reverse transcriptase.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Chlorogenic acid United States Pharmacopeia (USP) Reference Standard

USP

1115545

Chlorogenic acid

Chlorogenic acid European Pharmacopoeia (EP) Reference Standard

Y0000569

Chlorogenic acid

Caffeic acid ≥98.0% (HPLC)

Sigma-Aldrich

C0625

Caffeic acid

HIV-1 reverse transcriptase inhibitory activity of flavones and chlorogenic acid derivatives from Moquiniastrum floribundum (Asteraceae)
Tamayose CI, et al.,
South African Journal of botony, 123, 142-146 (2019)
HIV-1 reverse transcriptase inhibitory activity of flavones and chlorogenic acid derivatives from Moquiniastrum floribundum (Asteraceae)
Tamayose CI, et al.,
Asia-Pacific Journal of Molecular Biology and Biotechnology, 123, 142-146 (2019)
Jiu Liang Xu et al.
Food chemistry, 281, 261-268 (2019-01-20)
Green coffee extracted by pressurized liquid extraction (PLE) was found to undergo a roasting process similar to traditional roasting. Liquid chromatography-tandem mass spectrometry was used to investigate the chlorogenic acid (CGA) composition and profiling changes by PLE under different extraction

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