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Merck

SMB00221

Sigma-Aldrich

4,5-Di-O-caffeoylquinic acid

≥85% (LC/MS-ELSD)

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C25H24O12
Número de CAS:
Peso molecular:
516.45
MDL number:
UNSPSC Code:
12352205
PubChem Substance ID:
NACRES:
NA.25

Quality Level

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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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)
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)
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)
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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