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C3878

Sigma-Aldrich

Chlorogenic acid

≥95% (titration)

Synonym(s):

CGA, 1,4,5-Trihydroxycyclohexanecarboxylic acid 3-(3,4-dihydroxycinnamate), 3-(3,4-Dihydroxycinnamoyl)quinic acid

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About This Item

Empirical Formula (Hill Notation):
C16H18O9
CAS Number:
Molecular Weight:
354.31
EC Number:
MDL number:
UNSPSC Code:
12352106
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

≥95% (titration)

form

powder

mp

210 °C (dec.) (lit.)

SMILES string

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

InChI

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

InChI key

CWVRJTMFETXNAD-JUHZACGLSA-N

Gene Information

rat ... G6pc(25634)

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General description

Chlorogenic acid is a bioactive polyphenolic compound mainly found in many plants, such as coffee. It is a potent neuroprotectant and also possesses antiviral, antifungal, antioxidant and antitumor properties. CGA may also be involved in regulating glucose and lipid metabolism and improving insulin sensitivity.
Chlorogenic acid is a cinnamate ester used as a reducing agent and stabilizer in bimetallic nanoparticle synthesis.

Application

  • Antioxidant and Phenolic Profiles: A study detailed the antioxidant and phenolic profiles of Thai medicinal plants, including chlorogenic acid, to support functional food and pharmaceutical development, highlighting its potential applications in enhancing food functionality and health benefits (Wanyo et al., 2024).
  • Intravesical Therapy for Cystitis: Research demonstrated the use of chlorogenic acid in intravesical therapy to modify acute voiding behavior in mice with systemic lipopolysaccharide inflammation-induced cystitis, suggesting therapeutic potential in bladder disorders (Yeh et al., 2024).
  • Cardioprotection in Chemotherapy: A hydroethanolic extract containing chlorogenic acid was investigated for its role in mitigating doxorubicin-induced cardiotoxicity through mitochondrial protection mediated by AMPK-PGC-1α-SOD, underscoring its potential in protective strategies against chemotherapy-induced cardiac damage (Song et al., 2024).
  • Nutritional Delivery and Food Industry: A review discussed chlorogenic acid′s role in nutrition delivery and its implications in the food industry, proposing its use as nanoparticles for active food packaging application. (Hu et al., 2024).

Caution

May yield a hazy solution in ethanol

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Chlorogenic acid and caffeic acid are absorbed in humans
Olthof MR
The Journal of Nutrition, 131(1), 66-71 (2001)
Shp2 regulates chlorogenic acid-induced proliferation and adipogenic differentiation of bone marrow-derived mesenchymal stem cells in adipogenesis
Zhou RP
Molecular Medicine Reports, 11(6), 4489-4495 (2015)
Alexandros Priftis et al.
Mechanisms of ageing and development, 172, 115-122 (2017-11-28)
Coffee and grape contain various bioactive compounds like polyphenols that may exert beneficial effects, especially antioxidant activity, on human health upon consumption. However, the molecular mechanisms through which these effects are achieved are not fully elucidated. Thus, in the present
Roles of chlorogenic acid on regulating glucose and lipids metabolism: a review
Meng S
Evidence-Based Complementary and Alternative Medicine : ECAM (2013)
Computational screen and experimental validation of anti-influenza effects of quercetin and chlorogenic acid from traditional Chinese medicine
Liu Z
Scientific Reports, 6, 19095-19095 (2016)

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