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:
Molecular Weight:
354.31
NACRES:
NA.28
PubChem Substance ID:
UNSPSC Code:
12352204
MDL number:
Quality Segment
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
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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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
Caffeic acid derivatives from Bupleurum chinense
Haghi G, et al.
Research in Pharmaceutical Sciences, 9(5), 323-323 (2014)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 65969-10MG | 04061832733821 |
| 65969-50MG | 04061832404844 |