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65969

Sigma-Aldrich

4-O-Caffeoylquinic acid

≥98.0%

Sinônimo(s):

4-O-(3,4-Dihydroxycinnamoyl)-D-quinic acid, Cryptochlorogenic acid

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About This Item

Fórmula empírica (Notação de Hill):
C16H18O9
Número CAS:
905-99-7
Peso molecular:
354.31
Número MDL:
MFCD10566638
Código UNSPSC:
12352204
ID de substância PubChem:
329760140
NACRES:
NA.28

Ensaio

≥98.0%

forma

powder or crystals

atividade óptica

[α]/D -76.0±5.0°, c = 0.5 in H2O

aplicação(ões)

metabolomics
vitamins, nutraceuticals, and natural products

temperatura de armazenamento

2-8°C

cadeia de caracteres SMILES

O[C@@H]1C[C@](O)(C[C@@H](O)[C@@H]1OC(=O)\C=C\c2ccc(O)c(O)c2)C(O)=O

InChI

1S/C16H18O9/c17-9-3-1-8(5-10(9)18)2-4-13(21)25-14-11(19)6-16(24,15(22)23)7-12(14)20/h1-5,11-12,14,17-20,24H,6-7H2,(H,22,23)/b4-2+/t11-,12-,14-,16+/m1/s1

chave InChI

GYFFKZTYYAFCTR-JUHZACGLSA-N

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Descrição geral

4-caffeoylquinic acid (4-CQA) is the derivative of caffeic acid (CA).
It is an ester of caffeic acid and quinic acid.

Aplicação

4-O-Caffeoylquinic acid has been used as a reference compound for the quantification in high performance liquid chromatography-diode array detector (HPLC-DAD).

Ações bioquímicas/fisiológicas

4-O-Caffeoylquinic acid (4-CQA) is a major active antioxidant marker in mulberry leaf extract. It is an inhibitor of ferroptosis hence, it is recognized as a potent anti-diabetic agent. 4-CQA plays an important role in the upregulation of nuclear factor (erythroid-derived 2)-like 2 (Nrf2) pathway.

Embalagem

Bottomless glass bottle. Contents are inside inserted fused cone.

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Certificados de análise (COA)

Busque Certificados de análise (COA) digitando o Número do Lote do produto. Os números de lote e remessa podem ser encontrados no rótulo de um produto após a palavra “Lot” ou “Batch”.

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Supelco

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3,4-Dicaffeoylquinic acid phyproof® Reference Substance

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Bioactive Phenolics of the Genus Artemisia (Asteraceae): HPLC-DAD-ESI-TQ-MS/MS Profile of the Siberian Species and Their Inhibitory Potential Against alpha-Amylase and alpha-Glucosidase
Olennikov D N, et al.
Frontiers in Pharmacology, 9 (2018)
Yi Zhou
Diabetes, metabolic syndrome and obesity : targets and therapy, 13, 1921-1931 (2020-07-02)
Mulberry leaf extract has exerted better antidiabetic activities, while the effects of major active components in mulberry leaf extract are still unclear. Cryptochlorogenic acid (CCA) as the major active component in mulberry leaf extracts was investigated herein. Rats were treated
Caffeic acid derivatives from Bupleurum chinense
Haghi G, et al.
Research in Pharmaceutical Sciences, 9(5), 323-323 (2014)
Gary R Takeoka et al.
Journal of agricultural and food chemistry, 51(2), 496-501 (2003-01-09)
Almond hulls (Nonpareil variety) were extracted with methanol and analyzed by reversed phase HPLC with diode array detection. The extract contained 5-O-caffeoylquinic acid (chlorogenic acid), 4-O-caffeoylquinic acid (cryptochlorogenic acid), and 3-O-caffeoylquinic acid (neochlorogenic acid) in the ratio 79.5:14.8:5.7. The chlorogenic
Liangmian Chen et al.
Chemical & pharmaceutical bulletin, 63(1), 25-32 (2015-03-07)
For the determination of seven caffeoylquinic acids [neochlorogenic acid (NcA), cryptochlorogenic acid (CcA), chlorogenic acid (CA), caffeic acid (CfA), isochlorogenic acid A (Ic A), isochlorogenic acid B (Ic B), isochlorogenic acid C (Ic C)] and two flavonoids [luteolin 7-O-glucoside (LtG) and luteolin (Lt)]
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