Caffeic acid
2629001
222688887
2008-06-30T17:03:35Z
Calvero JP
1361741
+ja
{{Chembox new
| Name = Caffeic acid
| ImageFile = Caffeic acid.svg
<!-- | ImageSize = 200px -->
| ImageName = Caffeic acid
| ImageFile1 = CaffeicAcid3d.png
<!-- | ImageSize1 = 200px -->
| ImageName1 = Caffeic acid
| IUPACName = 3-(3,4-Dihydroxyphenyl<br />3,4-Dihydroxy-cinnamic acid<br />trans-Caffeate<br />3,4-Dihydroxy-trans-cinnamate)<br />2-propenoic acid<br />(E)-3-(3,4-dihydroxyphenyl)-2-propenoic acid<br />3,4-Dihydroxybenzeneacrylicacid<br />3-(3,4-Dihydroxyphenyl)-2-propenoic acid
| Section1 = {{Chembox Identifiers
| SMILES = Oc1ccc(/C=C/C(O)=O)cc1O
}}
| Section2 = {{Chembox Properties
| Formula = C<sub>9</sub>H<sub>8</sub>O<sub>4</sub>
| MolarMass = 180.16 g/mol
| Density = 1.478 g/cm³
| MeltingPt = 223-225 °C
| BoilingPt =
}}
}}
'''Caffeic acid''', '''[[carbon|C]]<sub>9</sub>[[hydrogen|H]]<sub>8</sub>[[oxygen|O]]<sub>4</sub>''' is a naturally occurring [[phenol]]ic compound, (formerly called a carbolic acid), which is found in many [[fruit]]s, [[vegetable]]s, and [[herb]]s, including [[coffee]], although varying in amounts depending on the [[plant]].
Caffeic acid has been shown to act as a [[carcinogenic]] inhibitor. It is also known as an [[antioxidant]] [[in vitro]] and also [[in vivo]].[http://www.esi-topics.com/nhp/2003/january-03-MargreetOlthof.html]
Caffeic acid is a yellow crystalline acid that is [[soluble]] in hot water and [[alcohol]]. It is related to [[cinnamic acid]], but it has two [[hydroxyl]] groups not found in cinnamic acid. Both are part of the carbocyclic [[carboxylic acid]] group.[http://www.chemicalland21.com/fc/CARBOCYCLIC%20CARBOXYLIC%20ACIDS.htm]
Caffeic acid can be esterified with [[quinic acid]] to form [[chlorogenic acid]]. Both caffeic acid and chlorogenic acid are found in coffee beans. [[Caffeine]] is a different compound than caffeic acid. A derivative of caffeic acid is caffeic acid phenethyl ester (CAPE).
It is used as a matrix in [[Matrix-assisted laser desorption/ionization|MALDI]] [[mass spectroscopy]] analyses.[http://dx.doi.org/10.1002/rcm.1290031207]
==Biological importance==
Caffeic acid and its derivative caffeic acid phenethyl ester (CAPE) are produced in many plants including: [[pear]]s, [[basil]], [[thyme]], [[verbena]], [[tarragon]], [[oregano]], [[Stachys|wood betony]], [[burning bush]], [[turmeric]], [[dandelion]], [[yarrow]], [[horsetail]], [[rosemary]], [[Crataegus|hawthorn]] and [[coffee]]. The amount of caffeic acid is strongly dependent on the plant species.[http://www.ars-grin.gov/cgi-bin/duke/chemical.pl?CAFFEICACID]
Both caffeic acid and chlorogenic acid have been shown to be absorbed in humans. Caffeic acid absorption is hampered when it is esterified with quinic acid to form chlorogenic acid.[http://www.esi-topics.com/nhp/2003/january-03-MargreetOlthof.html]
In laboratory experiments, colonies of a [[Nut (fruit)|nut]] [[tree]] [[mold|mould]] were grown on extracts of [[walnut]] and [[pistachio]]. Next, [[fungus|fungal]] colonies were exposed to three compounds thought to be [[antioxidants]]: [[gallic acid]], which has [[aflatoxin]]-combating impacts in [[walnuts]], and chlorogenic acid and caffeic acid.
Caffeic acid outperformed the other antioxidants, reducing aflatoxin production by more than 95 percent. 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. This opens the door to using natural anti-[[fungicide]] methods by supplementing trees with antioxidants. [http://www.ars.usda.gov/is/AR/archive/oct06/nuts1006.htm]
==Pharmaceutical Uses==
[[Oral]] administration of high doses of caffeic acid in rats has caused [[stomach]] [[papilloma]]s, leading to the perception of caffeic acid as carcinogenic. In the same study, only high doses of combined antioxidants, including caffeic acid, showed a significant decrease in growth of [[Colon (anatomy)|colon]] [[tumor]]s in those same rats. No significant effect was noted otherwise.<ref>{{cite journal|journal=Carcinogenesis|volume=19|pages=207–212|year=1998|title=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|author=M Hirose, Y Takesada, H Tanaka, S Tamano, T Kato and T Shirai|url=http://carcin.oxfordjournals.org/cgi/reprint/19/1/207.pdf|doi=10.1093/carcin/19.1.207|pmid=9472713}}</ref>[http://carcin.oxfordjournals.org/cgi/content/abstract/19/1/207?maxtoshow=&HITS=10&hits=10&RESULTFORMAT=1&andorexacttitle=and&andorexacttitleabs=and&fulltext=caffeic+acid&andorexactfulltext=phrase&searchid=1&FIRSTINDEX=0&sortspec=relevance&resourcetype=HWCIT].
Caffeic Acid is still listed under older Hazard Data sheets [http://www.inchem.org/documents/iarc/vol56/03-caff.html] as a potential carcinogen because of two early experiments on rats and mice. More recent data show that [[bacteria]] in the rats' guts may alter the formation of [[metabolite]]s of Caffeic Acid. [http://www.pnas.org/cgi/content/abstract/69/6/1413] and [http://jn.nutrition.org/cgi/content/full/133/6/1853] There have been no known ill-effects of Caffeic Acid in humans.
Caffeic Acid and its derivative, Caffeic Acid Phenethyl Ester (CAPE) have shown tumor-shrinking properties. When an anti-[[cancer]] [[drug]] was being sought, Caffeic Acid and CAPE were derived from [[Burning Bush]] (''Euonymus alatus''). "The [[subcutis|subcutaneous]] and oral administrations of CA and CAPE significantly reduced [[liver]] [[metastasis]]. These results confirm the [[Pharmacotherapy|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 [[Matrix metalloproteinase|MMP]]-9 [[enzyme]] activity and [[transcription (genetics)|transcriptional]] down-[[regulation of gene expression|regulation]] by the dual [[enzyme inhibition|inhibition]] of [[NF-kB|NF-kB]] as well as MMP-9 [[catalysis|catalytic]] activity." [http://www.fasebj.org/cgi/content/abstract/18/14/1670]
A study using the caffeic acid phenethyl ester (CAPE) showed a positive effect on reducing [[carcinogen]]ic incidence. Caffeic acid phenethyl [[ester]] (CAPE) is an active component of [[propolis]] from [[honeybee]] [[hives]].[http://www.axxora.com/protein_synthesis_modification__degradation-ALX-270-244/opfa.1.1.ALX-270-244.1646.4.1.html] It is known to have [[mitosis|antimitogenic]], anticarcinogenic, [[anti-inflammatory]], and [[immunomodulator]]y properties.
[http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pubmed&pubmedid=8799159]
Another study also showed that CAPE suppresses [[acute (medical)|acute]] [[immune]] and [[inflammation|inflammatory]] responses and holds promise for therapeutic uses to reduce inflammation.
[http://content.karger.com/ProdukteDB/produkte.asp?Doi=26427]
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 [http://www.img.cas.cz/fb/pdf/2003-49-197-202.pdf] and UVB radiation. [http://carcin.oxfordjournals.org/cgi/content/abstract/27/9/1803?maxtoshow=&HITS=10&hits=10&RESULTFORMAT=1&andorexacttitle=and&andorexacttitleabs=and&fulltext=caffeic+acid&andorexactfulltext=phrase&searchid=1&FIRSTINDEX=0&sortspec=relevance&resourcetype=HWCIT]. This anti-cancer effect was also seen when mice skin was treated with bee propolis and exposed to TPA (a [[chemical]]) that induced skin [[papilloma]]s. CAPE significantly reduced the number of papillomas. [http://carcin.oxfordjournals.org/cgi/content/abstract/17/4/761?maxtoshow=&HITS=10&hits=10&RESULTFORMAT=1&andorexacttitle=and&andorexacttitleabs=and&fulltext=caffeic+acid&andorexactfulltext=phrase&searchid=1&FIRSTINDEX=0&sortspec=relevance&resourcetype=HWCIT] [http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=3139287&dopt=Abstract]
Caffeic Acid and chlorogenic acid from coffee beans both reduced [[DNA methylation]] [[in vitro]] in two lines of human cancer cells. DNA methylation contributes to the growth of tumors and regulates the [[epigenetics]] of cells that are passed along with [[DNA]] to future generations [http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=16081510&dopt=Abstract].
Caffeic acid has been shown to be an inhibitor of the lipoxygense enzyme that forms leukotrienes from the membrane-derived phospholipid arachadonic acid. this function has been useful in scientific experiments to elucidate the roles of the leukotrienes in various inflammatory responses.
==References==
{{Citationstyle|date=September 2007}}
<references/>
*{{cite web|title=Journal of Nutrition|work=Chlorogenic acid and caffeic acid are absorbed in humans. Jan. Margreet R. Olthof, P.C.H. Hollman, and M.B. Katan. Journal of Nutrition. 2001; 131:66-71|url=http://jn.nutrition.org/cgi/content/abstract/131/1/66}}
*{{cite web|title=PubMed: Rats|work=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. M Hirose, Y Takesada, H Tanaka, S Tamano, T Kato and T Shirai. Carcinogenesis. 1998; 19:207-212.|url=http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=9472713&dopt=Abstract}}
*{{cite web|title=FASEB Journal: Therapeutic Effects|work=Novel and therapeutic effect of caffeic acid and caffeic acid phenyl ester on hepatocarcinoma cells: complete regression of hepatoma growth and metastasis by dual mechanism. TAE-WOOK CHUNG, SUNG-KWON MOON, YOUNG-CHAE CHANG, JEONG-HEON KO, YOUNG-CHOON LEE, GUN CHO, SOO-HYUN KIM, JONG-GUK KIM and CHEORL-HO KIM. The FASEB Journal. 2004; 18:1670-681|url=http://www.fasebj.org/cgi/content/abstract/18/14/1670}}
*{{cite web|title=PubMed: Cancer Inhibitor|work=Caffeic acid phenethyl ester is a potent and specific inhibitor of activation of nuclear transcription factor NF-kappa. K Natarajan, S. Singh, T.R. Burke Jr, D. Grunberger, and B.B. Aggarwal. Proc Natl Acad Sci USA. 1996 August 20; 93(17): 9090–9095|url=http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pubmed&pubmedid=8799159}}
*{{cite web|title=Karger Online: Inflammation|work=Caffeic Acid Phenethyl Ester Induces Leukocyte Apoptosis, Modulates Nuclear Factor-Kappa B and Suppresses Acute Inflammation. 2000. Zsolt Orbana, N. Mitsiadesb, T.R. Burke Jr., M. Tsokosb, and G.P. Chrousosa. NeuroImmunoModulation. 2000; 7:99-105|url=http://content.karger.com/ProdukteDB/produkte.asp?Doi=26427}}
*{{cite web|title=Folia Biologica: Skin|work=UVC-Protective Effect of Caffeic Acid on Normal and Transformed Human Skin Cells in Vitro.J. NERADIL, R. VESELSK, J. SLANINA. Folia Biologica (Praha). 2003; 49:197-202|url=http://www.img.cas.cz/fb/pdf/2003-49-197-202.pdf}}
*{{cite web|title=Carcinogenesis: UVB|work=Caffeic acid suppresses UVB radiation-induced expression of interleukin-10 and activation of mitogen-activated protein kinases in mouse. Vanisree Staniforth, Lu-Tang Chiu and Ning-Sun Yang. Carcinogenesis. 2006; 27(9):1803-1811.|url=http://carcin.oxfordjournals.org/cgi/content/abstract/27/9/1803?maxtoshow=&HITS=10&hits=10&RESULTFORMAT=1&andorexacttitle=and&andorexacttitleabs=and&fulltext=caffeic+acid&andorexactfulltext=phrase&searchid=1&FIRSTINDEX=0&sortspec=relevance&resourcetype=HWCIT}}
*{{cite web|title=Carcinogenesis: Mice Skin|work=Inhibitory effects of caffeic acid phenethyl ester (CAPE) on 12-O-tetradecanoylphorbol-13-acetate-induced tumor promotion in mouse skin and the synthesis of DNA, RNA and protein in HeLa cells. Mou-Tuan Huang, Wei Ma, Patricia Yen, Jian-Guo Xie, Jingkang Han, Krystyna Frenkel, Dezider Grunberger and Allan H. Conney. 1996; 17(4):761-765.|url=http://carcin.oxfordjournals.org/cgi/content/abstract/17/4/761?maxtoshow=&HITS=10&hits=10&RESULTFORMAT=1&andorexacttitle=and&andorexacttitleabs=and&fulltext=caffeic+acid&andorexactfulltext=phrase&searchid=1&FIRSTINDEX=0&sortspec=relevance&resourcetype=HWCIT}}
*{{cite web|title=PubMed: Mice Skin|work=Inhibitory effect of curcumin, chlorogenic acid, caffeic acid, and ferulic acid on tumor promotion in mouse skin by 12-O-tetradecanoylphorbol-13-acetate. Huang MT, Smart RC, Wong CQ, Conney AH. Cancer Research. 1988 Nov 1;48(21):5941-6|url=http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=3139287&dopt=Abstract}}
*{{cite web|title=Agricultural Research: Nuts|work="Nuts’ New Aflatoxin Fighter: Caffeic Acid?" Bruce C. Campbell and Jong H. Kim. USDA-ARS Western Regional Research Center. Agricultural Research. Oct 2006.|url=http://www.ars.usda.gov/is/AR/archive/oct06/nuts1006.htm}}
*{{cite web|title=PubMed: DNA Methylation|work=Inhibition of DNA methylation by caffeic acid and chlorogenic acid, two common catechol-containing coffee polyphenols. Lee WJ, Zhu BT. Carcinogenesis. 2006 Feb;27(2):269-77. Epub 2005 Aug 4|url=http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=16081510&dopt=Abstract}}
==See also==
*[[Chlorogenic acid]]
*[[Coumaric acid]]
*[[Cinnamic acid]]
*[[Quinic acid]]
==External links==
*{{cite web|title=Chemical Land|work=Caffeic Acid as Carbocyclic Carboxylic Acid|url=http://www.chemicalland21.com/fc/CARBOCYCLIC%20CARBOXYLIC%20ACIDS.htm}}
[[Category:Carboxylic acids]]
[[Category:Aromatic compounds]]
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