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SMB00221

Sigma-Aldrich

4,5-Di-O-caffeoylquinic acid

≥85% (LC/MS-ELSD)

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Synonym(s):
4,5-DCQA, 4,5-Di-O-caffeoylquinate, 4,5-Dicaffeoylquinic acid, Isochlorogenate C, Isochlorogenic acid C
Empirical Formula (Hill Notation):
C25H24O12
CAS Number:
Molecular Weight:
516.45
MDL number:
PubChem Substance ID:
NACRES:
NA.25

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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This Item
SMB00224SMB00131PHL80425
vibrant-m

SMB00221

4,5-Di-O-caffeoylquinic acid

vibrant-m

SMB00224

3,4-Di-O-caffeoylquinic acid

vibrant-m

SMB00131

3,5-Di-caffeoylquinic acid

vibrant-m

PHL80425

3,4-Dicaffeoylquinic acid

assay

≥85% (LC/MS-ELSD)

assay

≥90% (LC/MS-ELSD)

assay

≥95% (LC/MS-ELSD)

assay

≥95.0% (HPLC)

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)

-

form

solid

form

solid

form

solid

form

solid

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

2-8°C

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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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)
Phenolic compounds and in vitro antioxidant, anti-inflammatory, antimicrobial activities of Scorzonera hieraciifolia Hayek roots
Sari A, et al.,
Asia-Pacific Journal of Molecular Biology and Biotechnology, 125, 116-119 (2019)
Yinku Liang et al.
Molecular medicine reports, 21(1), 229-239 (2019-11-21)
In this study, six compounds were isolated and purified from dandelion, and only sample I exhibited notable antifungal effect on Candida albicans (CA). high‑performance liquid chromatography‑diode‑array detector‑electrospray ionization‑tandem mass spectrometry analysis showed that sample I comprised 4‑coumaric acid, ferulic acid, quercetin
Phenolic compounds and in vitro antioxidant, anti-inflammatory, antimicrobial activities of Scorzonera hieraciifolia Hayek roots
Sari A, et al.,
South African Journal of botony, 125, 116-119 (2019)

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