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Merck
CN

65969

4-O-Caffeoylquinic acid

≥98.0%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C16H18O9
CAS Number:
905-99-7
Molecular Weight:
354.31
NACRES:
NA.28
PubChem Substance ID:
329760140
UNSPSC Code:
12352204
MDL number:
MFCD10566638

Key Documents

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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

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 key

GYFFKZTYYAFCTR-JUHZACGLSA-N

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

Quality Level

100

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

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
WXBF8245V
WXBF7581V
WXBF6134V
WXBF5552V
BCCJ9701

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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
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
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)
Caffeic acid derivatives from Bupleurum chinense
Haghi G, et al.
Research in Pharmaceutical Sciences, 9(5), 323-323 (2014)
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
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