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Caffeic acid information


Caffeic acid
2D diagram of caffeic acid
3D ball-and-stick model of caffeic acid
3D space filling model of caffeic acid
Names
IUPAC names
3-(3,4-Dihydroxyphenyl)-2-propenoic acid
3,4-Dihydroxycinnamic acid
trans-Caffeate
3,4-Dihydroxy-trans-cinnamate
(E)-3-(3,4-dihydroxyphenyl)-2-propenoic acid
3,4-Dihydroxybenzeneacrylicacid
3-(3,4-Dihydroxyphenyl)-2-propenoic acid
Preferred IUPAC name
(2E)-3-(3,4-Dihydroxyphenyl)prop-2-enoic acid
Identifiers
CAS Number
  • 501-16-6 checkY
  • 331-39-5 (non-specific) checkY
3D model (JSmol)
  • Interactive image
Beilstein Reference
1954563
ChEBI
  • CHEBI:16433 checkY
ChEMBL
  • ChEMBL145 checkY
ChemSpider
  • 600426 checkY
DrugBank
  • DB01880 checkY
ECHA InfoCard 100.005.784 Edit this at Wikidata
EC Number
  • 206-361-2
IUPHAR/BPS
  • 5155
KEGG
  • C01481 checkY
PubChem CID
  • 689043
UNII
  • U2S3A33KVM checkY
CompTox Dashboard (EPA)
  • DTXSID901316055 DTXSID5020231, DTXSID901316055 Edit this at Wikidata
InChI
  • InChI=1S/C9H8O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1-5,10-11H,(H,12,13)/b4-2+ checkY
    Key: QAIPRVGONGVQAS-DUXPYHPUSA-N checkY
  • InChI=1/C9H8O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1-5,10-11H,(H,12,13)/b4-2+
    Key: QAIPRVGONGVQAS-DUXPYHPUBE
SMILES
  • O=C(O)\C=C\c1cc(O)c(O)cc1
Properties
Chemical formula
C9H8O4
Molar mass 180.16 g/mol
Density 1.478 g/cm3
Melting point 223 to 225 °C (433 to 437 °F; 496 to 498 K)
UV-vis (λmax) 327 nm and a shoulder at c. 295 nm in acidified methanol[1]
Hazards
GHS labelling:
Pictograms
GHS07: Exclamation markGHS08: Health hazard
Signal word
Warning
Hazard statements
H315, H319, H335, H351, H361
Precautionary statements
P201, P202, P261, P264, P271, P280, P281, P302+P352, P304+P340, P305+P351+P338, P308+P313, 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 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
1
0
Related compounds
Related compounds
Chlorogenic acid
Cichoric acid
Coumaric acid
Quinic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references

Caffeic acid is an organic compound with the formula (HO)2C6H3CH=CHCO2H. It is a polyphenol. It is a yellow solid. Structurally, it is classified as a hydroxycinnamic acid. The molecule consists of both phenolic and acrylic functional groups. It is found in all plants as an intermediate in the biosynthesis of lignin, one of the principal components of biomass and its residues.[2] It is unrelated to caffeine.

  1. ^ Gould, Kevin S.; Markham, Kenneth R.; Smith, Richard H.; Goris, Jessica J. (2000). "Functional role of anthocyanins in the leaves of Quintinia serrata A. Cunn". Journal of Experimental Botany. 51 (347): 1107–1115. doi:10.1093/jexbot/51.347.1107. PMID 10948238.
  2. ^ Cite error: The named reference Boerjan was invoked but never defined (see the help page).

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Caffeic acid

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Caffeic acid is an organic compound with the formula (HO)2C6H3CH=CHCO2H. It is a polyphenol. It is a yellow solid. Structurally, it is classified as a...

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Caffeic acid phenethyl ester

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Caffeic acid phenethyl ester (CAPE) is a natural phenolic chemical compound. It is the ester of caffeic acid and phenethyl alcohol. CAPE is found in a...

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Chlorogenic acid

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Chlorogenic acid (CGA) is the ester of caffeic acid and (−)-quinic acid, functioning as an intermediate in lignin biosynthesis. The term "chlorogenic acids" refers...

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Ferulic acid

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acids in humans along with caffeic and isoferulic acid, and is absorbed in the small intestine, whereas other metabolites such as dihydroferulic acid...

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Hydroxycinnamic acid

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derivatives of cinnamic acid. In the category of phytochemicals that can be found in food, there are : α-Cyano-4-hydroxycinnamic acid Caffeic acid – burdock, hawthorn...

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Deoxycholic acid

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turmeric, and caffeic acid is a component high in some fruits and spices. Caffeic acid is also a digestive break-down product of chlorogenic acid, high in...

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Chicoric acid

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occurs in a variety of plant species. It is a derivative of both caffeic acid and tartaric acid. As a suitable marker for the distinction of Echinacea species...

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Caftaric acid

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esterified phenolic acid, composed of caffeic acid, a hydroxycinnamate produced by plants, and tartaric acid, the principal organic acid found in grape berries...

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Caffeic

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Caffeic is an adjective referring to coffee (see also: Caffè the Italian word for it, written with two "f"). It can be found in: Caffeic acid, a hydroxycinnamic...

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Cynarine

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Chemically, it is an ester formed from quinic acid and two units of caffeic acid. Chlorogenic acid Panizzi, Luigi; Scarpati, Maria Luisa (1954). "Constitution...

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Uric acid

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acid is a heterocyclic compound of carbon, nitrogen, oxygen, and hydrogen with the formula C5H4N4O3. It forms ions and salts known as urates and acid...

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phenolic acids with caffeic acid being the most numerous (38.57 mg/g). The next most common phenolic acids were ferulic acid (20.07 mg/g), p-coumaric acid (12...

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Rosmarinic acid

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the acid is named. Chemically, rosmarinic acid is a caffeic acid ester, with tyrosine providing another phenolic ring via dihydroxyphenyl-lactic acid. It...

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Caffenol

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Argan oil

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carotenes, squalene. Some trace phenols in argan oil include caffeic acid, oleuropein, vanillic acid, tyrosol, catechol, resorcinol, (−)-epicatechin and (+)-catechin...

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Vanillin

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removes CoA to afford caffeic acid. Caffeic acid then undergoes methylation by caffeic acid O-methyltransferase (COMT) to give ferulic acid. Finally, vanillin...

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Eugenol

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converted to caffeic acid by p-coumarate 3-hydroxylase using oxygen and NADPH. S-Adenosyl methionine (SAM) is then used to methylate caffeic acid, forming...

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Kalanchoe pinnata

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chalcones, taraxasterol, aurones, phenolic acid, caffeic acid, syringic acid, malic, oxalic and ferulic acid. Bufadienolides and phenanthrene are toxic...

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Antileukotriene

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Argyreia nervosa

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Adenosine diphosphate

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Linoleic acid

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List of antioxidants in food

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Vaccinium berries Examples: Chicoric acid - another caffeic acid derivative, is found in chicory and Echinacea. Chlorogenic acid - found in high concentration...

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Aronia

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quercetin-3-glycoside, epicatechin, caffeic acid, delphinidin, petunidin, pelargonidin, peonidin, and malvidin. All these except caffeic acid are members of the flavonoid...

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Propolis

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Jana, Snehasis (December 2014). "Evaluation of Inhibitory Effects of Caffeic acid and Quercetin on Human Liver Cytochrome P450 Activities". Phytotherapy...

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