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Chlorogenic acid information


Chlorogenic acid
Chlorogenic acid
Names
Preferred IUPAC name
(1S,3R,4R,5R)-3-{[(2E)-3-(3,4-Dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic acid
Other names
3-(3,4-Dihydroxycinnamoyl)quinate
3-(3,4-Dihydroxycinnamoyl)quinic acid
3-Caffeoylquinate
3-Caffeoylquinic acid
3-CQA
3-O-Caffeoylquinic acid
Chlorogenate
Chlorogenic acid
Heriguard
3-trans-Caffeoylquinic acid
5-O-Caffeoylquinic acid
Identifiers
CAS Number
  • 202650-88-2 checkY
  • 327-97-9 (E/Z)
3D model (JSmol)
  • Interactive image
3DMet
  • B01342
ChEBI
  • CHEBI:16112 ☒N
ChEMBL
  • ChEMBL284616 ☒N
ChemSpider
  • 1405788 checkY
KEGG
  • C00852
PubChem CID
  • 1794427
RTECS number
  • GU8480000
UNII
  • 318ADP12RI (E) checkY
InChI
  • 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 checkY
    Key: CWVRJTMFETXNAD-JUHZACGLSA-N checkY
  • InChI=1/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
    Key: CWVRJTMFETXNAD-JUHZACGLBD
SMILES
  • O=C(O)[C@]2(O)C[C@@H](O)[C@@H](O)[C@H](OC(=O)\C=C\c1ccc(O)c(O)c1)C2
Properties
Chemical formula
C16H18O9
Molar mass 354.311 g·mol−1
Density 1.28 g/cm3
Melting point 207 to 209 °C (405 to 408 °F; 480 to 482 K)
Hazards
GHS labelling:
Pictograms
GHS07: Exclamation mark
Signal word
Warning
Hazard statements
H315, H319, H335
Precautionary statements
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 0: Will not burn. E.g. waterInstability (yellow): no hazard codeSpecial hazards (white): no code
1
0
Safety data sheet (SDS) External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Chlorogenic acid (CGA) is the ester of caffeic acid and (−)-quinic acid, functioning as an intermediate in lignin biosynthesis.[1] The term "chlorogenic acids" refers to a related polyphenol family of esters, including hydroxycinnamic acids (caffeic acid, ferulic acid and p-coumaric acid) with quinic acid.[2]

Despite the "chloro" of the name, chlorogenic acids contain no chlorine. Instead, the name comes from the Greek χλωρός (khloros, light green) and -γένος (ghenos, a suffix meaning "giving rise to"), pertaining to the green color produced when chlorogenic acids are oxidized.

  1. ^ Boerjan, Wout; Ralph, John; Baucher, Marie (2003). "Lignin biosynthesis". Annual Review of Plant Biology. 54: 519–546. doi:10.1146/annurev.arplant.54.031902.134938. PMID 14503002.
  2. ^ Clifford, M. N.; Johnston, K. L.; Knight, S.; Kuhnert, N. (2003). "Hierarchical Scheme for LC-MSn Identification of Chlorogenic Acids". Journal of Agricultural and Food Chemistry. 51 (10): 2900–2911. doi:10.1021/jf026187q. PMID 12720369.

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Chlorogenic acid

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fatty acids. Chlorogenic acids belong to a group of compounds known as phenolic acids, which are antioxidants. The content of chlorogenic acids in dried...

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Hydroxycinnamic acid

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Cichoric acid Cinnamic acid – aloe Chlorogenic acid – echinacea, strawberries, pineapple, coffee, sunflower, blueberries Diferulic acids Coumaric acid Ferulic...

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Caffeic acid

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hydroxylation produces the caffeic acid ester of shikimic acid, which converts to chlorogenic acid. It is the precursor to ferulic acid, coniferyl alcohol, and sinapyl...

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Caffeoylquinic acid

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quinic acid and the rate of ATP production. Compounds of this class include: Chlorogenic acid (3-O-caffeoylquinic acid or 3-CQA) 4-O-caffeoylquinic acid (crypto-chlorogenic...

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Ferulic acid

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metabolites such as dihydroferulic acid, feruloylglycine and dihydroferulic acid sulfate are produced from chlorogenic acid in the large intestine by the action...

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Rosmarinic acid

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Bernd; Petersen, Maike (12 December 2008). "Occurrence of rosmarinic acid, chlorogenic acid and rutin in Marantaceae species". Phytochemistry Letters. 1 (4):...

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Cyclohexanecarboxylic acid

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cyclohexanecarboxylic acid include: abscisic acid buciclic acid chlorogenic acid chorismic acid dicyclomine quinic acid shikimic acid tranexamic acid Quinic acid Shikimic...

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Lonicera japonica

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caffeate, 3,4-di-O-caffeoylquinic acid, methyl 3,4-di-O-caffeoylquinate, protocatechuic acid, methyl chlorogenic acid, and luteolin. The two biflavonoids...

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5O

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ASL Airlines France (IATA airline code: 5O) 5-O-caffeoylquinic acid, see Chlorogenic acid 5-O-(4-coumaroyl)-D-quinate 3'-monooxygenase 5-O-Methylations...

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Hedera helix

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and β-hederin, falcarinol, didehydrofalcarinol, rutin, caffeic acid, chlorogenic acid, emetine, nicotiflorin, hederasaponin B and hederacoside C. However...

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Metal nitrosyl complex

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constituent polyphenols, including proanthocyanidins, quercetin, gallic acid, chlorogenic acid and kaempferol. Rhodiola rosea grows in cold regions of the world...

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Phyllostachys edulis

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Hydroxycinnamic acids p-coumaric acid caffeic acid ferulic acid Chlorogenic acids chlorogenic acid (3-(3,4-dihydroxycinnamoyl)quinic acid) 3-O-(3'-methylcaffeoyl)quinic...

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Nitrite

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to organic compounds having the –ONO group, which are esters of nitrous acid. Sodium nitrite is made industrially by passing a mixture of nitrogen oxides...

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Tanghulu

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pectin and chlorogenic acid, caffeic acid, maslinic acid, oleanolic acid, quercetin, ursolic acid, chrysin, epicatechin and other organic acids and nutritional...

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Green coffee extract

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the evidence was poor. A larger 2017 review assessed the effects of chlorogenic acid, the main phenolic compound in green coffee extract, determining that...

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List of phytochemicals in food

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olive oil. Chlorogenic acid echinacea, strawberries, pineapple, coffee, sunflower, blueberries. Cinnamic acid cinnamon, aloe. Ferulic acid oats, rice...

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Taphrina deformans

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to manage the spread and development of the disease. For example, chlorogenic acid, which is known to have antifungal activity in vitro, is present in...

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Apricot

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polyphenols, including catechins and chlorogenic acid. Taste and aroma compounds include sucrose, glucose, organic acids, terpenes, aldehydes and lactones...

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Maranta leuconeura

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erythroneura". Retrieved 3 January 2021. Occurrence of rosmarinic acid, chlorogenic acid and rutin in Marantaceae species. Yana Abdullah, Bernd Schneider...

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nitrating glycerol with white fuming nitric acid under conditions appropriate to the formation of the nitric acid ester. Chemically, the substance is an organic...

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Nitric oxide

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to produce nitric acid (HNO3): •NO + HO• 2 → •NO2 + •OH •NO2 + •OH → HNO3 Nitric acid, along with sulfuric acid, contributes to acid rain deposition. •NO...

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Cold brew coffee

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Effect of Time, Roasting Temperature, and Grind Size on Caffeine and Chlorogenic Acid Concentrations in Cold Brew Coffee". Scientific Reports. 7 (1): 17979...

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Quinic acid

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another common source. It is made synthetically by hydrolysis of chlorogenic acid. Quinic acid is also implicated in the perceived acidity of coffee. This...

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Polyphenol

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some reviews showing a minor effect of consuming polyphenols, such as chlorogenic acid or flavan-3-ols, on blood pressure. Higher intakes of soy isoflavones...

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Alkyl nitrite

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