5-caffeoyl quinic acid
3-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy] 1,4,5-trihydroxycyclohexanecarboxylic acid
Identification
| Name | 5-caffeoyl quinic acid |
| CAS Number | 906-33-2 |
| EINECS | 212-997-1 |
| FDA UNII | O4601UER1Z |
| Molecular Formula | C16 H18 O9 |
| Molecular Weight | 354.31226000 |
| MDL Number | MFCD10566639 |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 664.95 °C. @ 760.00 mm Hg (est) |
| Flash Point | 474.00 °F. TCC ( 245.50 °C. ) (est) |
| logP (o/w) | 0.370 (est) |
| Soluble in | water, 4.047e+005 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for 5-caffeoyl quinic acid usage levels up to | not for fragrance use. |
| Recommendation for 5-caffeoyl quinic acid flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
5-
caffeoylquinic acid
neo
chlorogenic acid
3-[[3-(3,4-
dihydroxyphenyl)-1-oxo-2-propenyl]oxy] 1,4,5-trihydroxycyclohexanecarboxylic acid
3-[3-(3,4-
dihydroxyphenyl)prop-2-enoyloxy]-1,4,5-trihydroxycyclohexane-1-carboxylic acid
PubMed:
Influence of the Stage of Ripeness on the Composition of Iridoids and Phenolic Compounds in Genipap (Genipa americana L.).
PubMed:
Estimated dietary intake and major food sources of polyphenols in the Polish arm of the HAPIEE study.
PubMed:
Effect of Chlorogenic Acid (5-Caffeoylquinic Acid) Isolated from Baccharis oxyodonta on the Structure and Pharmacological Activities of Secretory Phospholipase A2 from Crotalus durissus terrificus.
PubMed:
Metabolomic fingerprinting of primed tobacco cells provide the first evidence for the biological origin of cis-chlorogenic acid.
PubMed:
5-Caffeoylquinic acid decreases diet-induced obesity in rats by modulating PPARα and LXRα transcription.
PubMed:
Precursor ion scan driven fast untargeted screening and semi-determination of caffeoylquinic acid derivatives in Cynara scolymus L.
PubMed:
Isolation and identification of colourless caffeoyl compounds in purple sweet potato by HPLC-DAD-ESI/MS and their antioxidant activities.
PubMed:
Decaffeinated green coffee bean extract attenuates diet-induced obesity and insulin resistance in mice.
PubMed:
Coffee polyphenols improve peripheral endothelial function after glucose loading in healthy male adults.
PubMed:
Inhibition of the β-Catenin/Tcf Signaling by Caffeoylquinic Acids in Sweet Potato Leaf through down Regulation of the Tcf-4 Transcription.
PubMed:
Investigation of the in vivo antioxidative activity of Cynara scolymus (artichoke) leaf extract in the streptozotocin-induced diabetic rat.
PubMed:
Sugar cane stillage: a potential source of natural antioxidants.
PubMed:
Impact of chemical changes on the sensory characteristics of coffee beans during storage.
PubMed:
Qualitative and quantitative analysis of phenolics in Tetrastigma hemsleyanum and their antioxidant and antiproliferative activities.
PubMed:
A new method for the preparative isolation of chlorogenic acid lactones from coffee and model roasts of 5-caffeoylquinic acid.
PubMed:
Development and validation of methods for the extraction of phenolic acids from plasma, urine, and liver and analysis by UPLC-MS.
PubMed:
Biotransformation of caffeoyl quinic acids from green coffee extracts by Lactobacillus johnsonii NCC 533.
PubMed:
Detection of a plant enzyme exhibiting chlorogenate-dependant caffeoyltransferase activity in methanolic extracts of arbuscular mycorrhizal tomato roots.
PubMed:
Carotenoids and phenolic compounds from Solanum sessiliflorum, an unexploited Amazonian fruit, and their scavenging capacities against reactive oxygen and nitrogen species.
PubMed:
Analysis of hydroxycinnamic acids derivatives in calafate (Berberis microphylla G. Forst) berries by liquid chromatography with photodiode array and mass spectrometry detection.
PubMed:
Phenolic profile and antioxidant capacity of the principal apples produced in Brazil.
PubMed:
Dietary intake and major food sources of polyphenols in a Spanish population at high cardiovascular risk: the PREDIMED study.
PubMed:
Degradation kinetics of chlorogenic acid at various pH values and effects of ascorbic acid and epigallocatechin gallate on its stability under alkaline conditions.
PubMed:
Qualitative and quantitative analysis of phenylpropanoids in cell culture, regenerated plantlets and herbs of Saussurea involucrata.
PubMed:
Gastrointestinal absorption and metabolism of apple polyphenols ex vivo by the pig intestinal mucosa in the Ussing chamber.
PubMed:
The type and concentration of milk increase the in vitro bioaccessibility of coffee chlorogenic acids.
PubMed:
Coupling lipophilization and amylose complexation to encapsulate chlorogenic acid.
PubMed:
Looking for the physiological role of anthocyanins in the leaves of Coffea arabica.
PubMed:
Standardised herbal extract of chlorogenic acid from leaves of Etlingera elatior (Zingiberaceae).
PubMed:
Phenolic composition and antioxidant activity of aqueous infusions from Capparis spinosa L. and Crithmum maritimum L. before and after submission to a two-step in vitro digestion model.
PubMed:
Investigation of isomeric transformations of chlorogenic acid in buffers and biological matrixes by ultraperformance liquid chromatography coupled with hybrid quadrupole/ion mobility/orthogonal acceleration time-of-flight mass spectrometry.
PubMed:
Rapid identification and evaluation of antioxidant compounds from extracts of Petasites japonicus by hyphenated-HPLC techniques.
PubMed:
Chemical composition and antioxidant activity of yerba-mate (Ilex paraguariensis A.St.-Hil., Aquifoliaceae) extract as obtained by spray drying.
PubMed:
Identification and characterization of two new derivatives of chlorogenic acids in Arnica (Arnica montana L.) flowers by high-performance liquid chromatography/tandem mass spectrometry.
PubMed:
The antioxidant and chlorogenic acid profiles of whole coffee fruits are influenced by the extraction procedures.
PubMed:
Colonic availability of polyphenols and D-(-)-quinic acid after apple smoothie consumption.
PubMed:
Phenolic compounds of mountain tea from the Balkans: LC/DAD/ESI/MSn profile and content.
PubMed:
Chemometric models for the quantitative descriptive sensory analysis of Arabica coffee beverages using near infrared spectroscopy.
PubMed:
Intestinal transit and systemic metabolism of apple polyphenols.
PubMed:
Profile and characterization of the chlorogenic acids in green Robusta coffee beans by LC-MS(n): identification of seven new classes of compounds.
PubMed:
Hierarchical scheme for liquid chromatography/multi-stage spectrometric identification of 3,4,5-triacyl chlorogenic acids in green Robusta coffee beans.
PubMed:
Polyphenols and phenolic acids from strawberry and apple decrease glucose uptake and transport by human intestinal Caco-2 cells.
PubMed:
Novel hydroxycinnamoyl-coenzyme A quinate transferase genes from artichoke are involved in the synthesis of chlorogenic acid.
PubMed:
Preparative separation of chlorogenic acid by centrifugal partition chromatography from highbush blueberry leaves (Vaccinium corymbosum L.).
PubMed:
Kinetic analysis and mechanism on the inhibition of chlorogenic acid and its components against porcine pancreas alpha-amylase isozymes I and II.
PubMed:
Influence of silicon on resistance of Zinnia elegans to Myzus persicae (Hemiptera: Aphididae).
PubMed:
Antioxidative phenylpropanoid-substituted epicatechin glycosides from Parabarium huaitingii.
PubMed:
Caffeic and chlorogenic acids in Ilex paraguariensis extracts are the main inhibitors of AGE generation by methylglyoxal in model proteins.
PubMed:
Isolation and mapping of a C3'H gene (CYP98A49) from globe artichoke, and its expression upon UV-C stress.
PubMed:
Chlorogenic acid protects paraoxonase 1 activity in high density lipoprotein from inactivation caused by physiological concentrations of hypochlorite.
PubMed:
Salting-out gradients in centrifugal partition chromatography for the isolation of chlorogenic acids from green coffee beans.
PubMed:
Caffeic acid derivatives from Eupatorium perfoliatum L.
PubMed:
Activity of elaeochytrin A from Ferula elaeochytris on leukemia cell lines.
PubMed:
5-Caffeoylquinic acid and caffeic acid orally administered suppress P-selectin expression on mouse platelets.
PubMed:
Stress-induced biosynthesis of dicaffeoylquinic acids in globe artichoke.
PubMed:
Quinic acid derivatives from Saussurea triangulata attenuates glutamate-induced neurotoxicity in primary cultured rat cortical cells.
PubMed:
Low molecular weight melanoidins in coffee brew.
PubMed:
5-caffeoylquinic acid and caffeic acid down-regulate the oxidative stress- and TNF-alpha-induced secretion of interleukin-8 from Caco-2 cells.
PubMed:
Human glycemic response and phenolic content of unsweetened cranberry juice.
PubMed:
Hydroxyhydroquinone interferes with the chlorogenic acid-induced restoration of endothelial function in spontaneously hypertensive rats.
PubMed:
Profiling the phenolic compounds of Artemisia pectinata by HPLC-PAD-MSn.
PubMed:
Abnormal accumulation of sugars and phenolics in tobacco roots expressing the Agrobacterium T-6b oncogene and the role of these compounds in 6b-induced growth.
PubMed:
Phenol contents, oxidase activities, and the resistance of coffee to the leaf miner Leucoptera coffeella.
PubMed:
Quantitation of volatiles and nonvolatile acids in an extract from coffee beverages: correlation with antioxidant activity.
PubMed:
Characterization by LC-MS(n) of four new classes of p-coumaric acid-containing diacyl chlorogenic acids in green coffee beans.
PubMed:
NMR metabolomics to revisit the tobacco mosaic virus infection in Nicotiana tabacum leaves.
PubMed:
Chlorogenic acid attenuates hypertension and improves endothelial function in spontaneously hypertensive rats.
PubMed:
Antioxidant and antiulcerative properties of phenolics from Chinese quince, quince, and apple fruits.
PubMed:
Polyphenoloxidase activity in coffee leaves and its role in resistance against the coffee leaf miner and coffee leaf rust.
PubMed:
A phenolic compound, 5-caffeoylquinic acid (chlorogenic acid), is a new type and strong matrix metalloproteinase-9 inhibitor: isolation and identification from methanol extract of Euonymus alatus.
PubMed:
Discriminating between the six isomers of dicaffeoylquinic acid by LC-MS(n).
PubMed:
Phenolic profile of hazelnut (Corylus avellana L.) leaves cultivars grown in Portugal.
PubMed:
Phenolic profile, antioxidant property, and anti-influenza viral activity of Chinese quince (Pseudocydonia sinensis Schneid.), quince (Cydonia oblonga Mill.), and apple (Malus domestica Mill.) fruits.
PubMed:
In vitro antioxidative effects and tyrosinase inhibitory activities of seven hydroxycinnamoyl derivatives in green coffee beans.
PubMed:
LC-MS investigation of oxidation products of phenolic antioxidants.
PubMed:
Profiling glucosinolates and phenolics in vegetative and reproductive tissues of the multi-purpose trees Moringa oleifera L. (horseradish tree) and Moringa stenopetala L.
PubMed:
Quantitative changes in phenolic content during physiological development of the olive (Olea europaea) cultivar Hardy's Mammoth.
PubMed:
Construction and application of a mass spectral and retention time index database generated from plant GC/EI-TOF-MS metabolite profiles.
PubMed:
Green coffee bean extract and its metabolites have a hypotensive effect in spontaneously hypertensive rats.
PubMed:
Metabolism of phenolic compounds during loquat fruit development.
PubMed:
Absorption of chlorogenic acid and caffeic acid in rats after oral administration.
PubMed:
Stabilization of soybean oil with heated quercetin and 5-caffeoylquinic acid in the presence of ferric ion.
PubMed:
Phenolic antioxidants from the leaves of Corchorus olitorius L.
PubMed:
Phytochemical and pharmacological studies of Guettarda acreana.
PubMed:
Inhibition in vitro linoleic acid peroxidation and haemolysis by caffeoyltryptophan.
PubMed:
Isolation and identification of compounds from Brazilian propolis which enhance macrophage spreading and mobility.
PubMed:
Phenylpropanoid esters from Lamium album flowers.
PubMed:
Developmental inhibition ofSpodoptera litura (Fab.) larvae by a novel caffeoylquinic acid from the wild groundnut,Arachis paraguariensis (Chod et Hassl.).
PubMed:
[Hydroxycinnamic acid esters in brassicaceous vegetables and garden cress].