With an accout for my.chemeurope.com you can always see everything at a glance – and you can configure your own website and individual newsletter. [2] The transformation to ferulic acid is catalyzed by the enzyme caffeate O-methyltransferase. available from the NIST/EPA/NIH Mass Spectral Library. [14], This anti-inflammatory and anti-cancer property has also been shown to protect skin cells when exposed to ultraviolet (UV) radiation, in particular UVC radiation [15] and UVB radiation. These results confirm the therapeutic potential of the compounds and suggest that the anti-metastatic and anti-tumor effects of CA and CAPE are mediated through the selective suppression of MMP-9 enzyme activity and transcriptional down-regulation by the dual inhibition of NF-B as well as MMP-9 catalytic activity." [28] The developing chemistry is similar to that of catechol or pyrogallol. Caffeic acid and its derivative caffeic acid phenethyl ester (CAPE) are produced in many kinds of plants. the library and ChEBI CHEBI:36281 Caffeic acid phenethyl ester (CAPE) is an active component of propolis from honeybee hives. [29], It is also used as a matrix in MALDI mass spectrometry analyses.[30]. Caffeic acid View entire compound with free spectra: 22 NMR, 2 FTIR, and 1 UV-Vis. The studies are the first to show that oxidative stress that would otherwise trigger or enhance Aspergillus flavus aflatoxin production can be stymied by caffeic acid. It is also known as an antioxidant in vitro and also in vivo. click the mouse on the plot to revert to the orginal display. © 2018 by the U.S. Secretary of Commerce Chemical oxidation of caffeic acid in acidic conditions using sodium periodate leads to the formation of dimers with a furan structure (isomers of 2,5-(3′,4′-dihydroxyphenyl)tetrahydrofuran 3,4-dicarboxylic acid). Go To: Top, Mass spectrum (electron ionization), Notes, Go To: Top, Mass spectrum (electron ionization), References. 1.) Find out how LUMITOS supports you with online marketing. [19] Oral administration of high doses of caffeic acid in rats has caused stomach papillomas. The HardyDisk™ Caffeic Acid Disks are a modification of this rapid method and provide for the presumptive identification of Cryptococcus neoformans within four hours. [26] Caffeic acid can also be polymerized using the horseradish peroxidase/H2O2 oxidizing system. This anti-cancer effect was also seen when mice skin was treated with bee propolis and exposed to TPA (a chemical) that induced skin papillomas. This opens the door to using natural anti-fungicide methods by supplementing trees with antioxidants. Caffeate O-methyltransferase is an enzyme responsible for the transformation of caffeic acid into ferulic acid. Caffeic acid (3,4-hydroxycinnamic acid) is found in several grains, fruits, and vegetables 1.It also occurs in Coffea arabica (coffee beans), particularly in its esterified form, chlorogenic acid (5-caffeoylquinic acid). It is also known as an antioxidant in vitro and also in vivo. Overview Information Caffeic acid is a chemical found in many plants and foods. [9] and [10] There have been no known ill-effects of Caffeic Acid in humans. SRD Program Office of Data and Informatics About. Caffeic acid, C 9 H 8 O 4 is a naturally occurring phenolic compound, (formerly called a carbolic acid), which is found in many fruits, vegetables, and herbs, including coffee, although varying in amounts depending on the plant.. Caffeic acid has been shown to act as a carcinogenic inhibitor. ", "Carcinogenicity of antioxidants BHA, caffeic acid, sesamol, 4-methoxyphenol and catechol at low doses, either alone or in combination, and modulation of their effects in a rat medium-term multi-organ carcinogenesis model", "Agents Classified by the IARC Monographs", "Caffeic acid metabolism by gnotobiotic rats and their intestinal bacteria", "Chlorogenic acid bioavailability largely depends on its metabolism by the gut microflora in rats", "A Use for that Last Cup of Coffee: Film and Paper Development", https://en.wikipedia.org/w/index.php?title=Caffeic_acid&oldid=984962585, Creative Commons Attribution-ShareAlike License, 223 to 225 °C (433 to 437 °F; 496 to 498 K), 327 nm and a shoulder at c. 295 nm in acidified methanol, This page was last edited on 23 October 2020, at 03:56. [25] This browning is due to the conversion of o-diphenols into reactive o-quinones. [13], Another study also showed that CAPE suppresses acute immune and inflammatory responses and holds promise for therapeutic uses to reduce inflammation. [12] It is known to have antimitogenic, anticarcinogenic, anti-inflammatory, and immunomodulatory properties. View the Full Spectrum for FREE! [17], Caffeic acid is an antioxidant in vitro and also in vivo. [21] More recent data show that bacteria in the rats' guts may alter the formation of metabolites of caffeic acid. shall not be liable for any damage that may result from Stars Glutathione and thiol compounds (cysteine, thioglycolic acid or thiocresol) or ascorbic acid have a protective effect on browning and disappearance of caffeic acid. 3-O-caffeoylshikimic acid (dactylifric acid) and its isomers, are enzymic browning substrates found in dates (Phoenix dactylifera fruits). All rights reserved. CAPE significantly reduced the number of papillomas. View image of digitized "The subcutaneous and oral administrations of CA and CAPE significantly reduced liver metastasis. that these items are necessarily the best available for the purpose. )", "Dr. Duke's Phytochemical and Ethnobotanical Databases", "Chlorogenic acid and caffeic acid are absorbed in humans", "Nuts' New Aflatoxin Fighter: Caffeic Acid? the A hydroxycinnamic acid that is cinnamic acid in which the phenyl ring is substituted by hydroxy groups at positions 3 and 4. been selected on the basis of sound scientific judgment. The references in this article would be clearer with a different or consistent style of. Data compilation copyright The amount of caffeic acid is strongly dependent on the plant species. and HTML 5 enabled browser. Find out more about the company LUMITOS and our team.