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65969

Sigma-Aldrich

4-O-Caffeoylquinic acid

≥98.0%

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Synonym(s):
4-O-(3,4-Dihydroxycinnamoyl)-D-quinic acid, Cryptochlorogenic acid
Empirical Formula (Hill Notation):
C16H18O9
CAS Number:
Molecular Weight:
354.31
MDL number:
PubChem Substance ID:

Assay

≥98.0%

form

powder or crystals

optical activity

[α]/D -76.0±5.0°, c = 0.5 in H2O

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

2-8°C

SMILES string

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

Inchi Key

GYFFKZTYYAFCTR-JUHZACGLSA-N

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This Item
SMB00221SMB00224SMB00131
form

powder or crystals

form

solid

form

solid

form

solid

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)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

Quality Level

100

Quality Level

200

Quality Level

200

Quality Level

200

optical activity

[α]/D -76.0±5.0°, c = 0.5 in H2O

optical activity

-

optical activity

-

optical activity

-

General description

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

Application

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

Biochem/physiol Actions

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.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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Jerome G Ganzon et al.
Journal of food and drug analysis, 26(3), 985-993 (2018-07-07)
Mulberry (Morus alba L.) leaves are widely used as herbal tea to prevent heat stroke. Potential chemical markers of the antioxidant properties and its correlation with harvesting times and leaf location were explored in this study. A 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical-scavenging
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
Caffeic acid derivatives from Bupleurum chinense
Haghi G, et al.
Research in Pharmaceutical Sciences, 9(5), 323-323 (2014)
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

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