Caffeic acid

Caffeic acid

Chembox new
Name = Caffeic acid
ImageFile = Caffeic acid.svg
ImageName = Caffeic acid
ImageFile1 = CaffeicAcid3d.png ImageName1 = Caffeic acid
IUPACName = 3-(3,4-Dihydroxyphenyl
3,4-Dihydroxy-cinnamic acid
2-propenoic acid
(E)-3-(3,4-dihydroxyphenyl)-2-propenoic acid
3-(3,4-Dihydroxyphenyl)-2-propenoic acid
Section1 = Chembox Identifiers
SMILES = Oc1ccc(/C=C/C(O)=O)cc1O
CASNo = 331-39-5

Section2 = Chembox Properties
Formula = C9H8O4
MolarMass = 180.16 g/mol
Density = 1.478 g/cm³
MeltingPt = 223-225 °C
BoilingPt =

Caffeic acid, C9H8O4 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. It is also known as an antioxidant in vitro and also in vivo.cite journal |author=Olthof MR, Hollman PC, Katan MB |title=Chlorogenic acid and caffeic acid are absorbed in humans |journal=J. Nutr. |volume=131 |issue=1 |pages=66–71 |year=2001 |month=January |pmid=11208940 |doi= |url=]

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.cite web |url= |title=CAFFEIC ACID (3,4-DIHYDROXY-TRANS-CINNAMATE), chemical properties |format= |work= |accessdate=]

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 MALDI mass spectroscopy analyses.cite journal |author=Beavis RC, Chait BT |title=Cinnamic acid derivatives as matrices for ultraviolet laser desorption mass spectrometry of proteins |journal=Rapid Commun. Mass Spectrom. |volume=3 |issue=12 |pages=432–5 |year=1989 |month=December |pmid=2520223 |doi=10.1002/rcm.1290031207 |url=]

Biological importance

Caffeic acid and its derivative caffeic acid phenethyl ester (CAPE) are produced in many plants including: pears, basil, thyme, verbena, tarragon, oregano, wood betony, burning bush, turmeric, dandelion, yarrow, horsetail, rosemary, hawthorn and coffee. The amount of caffeic acid is strongly dependent on the plant species.cite web |url= |title=Dr. Duke's Phytochemical and Ethnobotanical Databases |format= |work= |accessdate=]

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.

In laboratory experiments, colonies of a nut tree mould were grown on extracts of walnut and pistachio. Next, 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. cite web |url= |title=Nuts’New Aflatoxin Fighter: Caffeic Acid? |format= |work= |accessdate=]

Pharmaceutical Uses

Oral administration of high doses of caffeic acid in rats has caused stomach papillomas, 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 tumors in those same rats. No significant effect was noted otherwise. [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=|doi=10.1093/carcin/19.1.207|pmid=9472713] .

Caffeic Acid is still listed under older Hazard Data sheetscite web |url= |title=Caffeic Acid (IARC Summary & Evaluation, Volume 56, 1993) |format= |work= |accessdate=] 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 metabolites of Caffeic Acid [cite journal|journal=Proceedings of the National Acadamy of Sciences|volume=69|pages=1413-1415|year=1972|title=Caffeic acid metabolism by gnotobiotic rats and their intestinal bacteria|author=MA Peppercorn and P Goldman|url=|pmid=4504351] [cite journal|journal=Journal of Nutrition|volume=133|pages=1853-1859|year=2003|title=Chlorogenic acid bioavailability largely depends on its metabolism by the gut microflora in rats|author=M-P Gonthier, M-A Verny, C Besson, C Rémésy and A Scalbert|url=] . 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 subcutaneous and oral administrations of CA and CAPE significantly reduced liver metastasis. 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-kB as well as MMP-9 catalytic activity." cite journal |author=Chung TW, Moon SK, Chang YC, "et al" |title=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 |journal=FASEB J. |volume=18 |issue=14 |pages=1670–81 |year=2004 |month=November |pmid=15522912 |doi=10.1096/fj.04-2126com |url=] A study using the caffeic acid phenethyl ester (CAPE) showed a positive effect on reducing carcinogenic incidence. Caffeic acid phenethyl ester (CAPE) is an active component of propolis from honeybee hives. cite journal |author=Demestre M, Messerli SM, Celli N, "et al" |title=CAPE (caffeic acid phenethyl ester)-based propolis extract (Bio 30) suppresses the growth of human neurofibromatosis (NF) tumor xenografts in mice |journal=Phytother Res |volume= |issue= |pages= |year=2008 |month=August |pmid=18726924 |doi=10.1002/ptr.2594 |url=] It is known to have antimitogenic, anticarcinogenic, anti-inflammatory, and immunomodulatory properties.cite journal |author=Natarajan K, Singh S, Burke TR, Grunberger D, Aggarwal BB |title=Caffeic acid phenethyl ester is a potent and specific inhibitor of activation of nuclear transcription factor NF-kappa B |journal=Proc. Natl. Acad. Sci. U.S.A. |volume=93 |issue=17 |pages=9090–5 |year=1996 |month=August |pmid=8799159 |pmc=38600 |doi= |url=]

Another study also showed that CAPE suppresses acute immune and inflammatory responses and holds promise for therapeutic uses to reduce inflammation.cite journal |author=Orban Z, Mitsiades N, Burke TR, Tsokos M, Chrousos GP |title=Caffeic acid phenethyl ester induces leukocyte apoptosis, modulates nuclear factor-kappa B and suppresses acute inflammation |journal=Neuroimmunomodulation |volume=7 |issue=2 |pages=99–105 |year=2000 |pmid=10686520 |doi= |url=]

This anti-inflammatory and anti-cancer property has also been shown to protect skin cells when exposed to ultraviolet (UV) radiation, in particular UVC radiationcite journal |author=Neradil J, Veselská R, Slanina J |title=UVC-protective effect of caffeic acid on normal and transformed human skin cells in vitro |journal=Folia Biol. (Praha) |volume=49 |issue=5 |pages=197–202 |year=2003 |pmid=14680294 |doi= |url=] and UVB radiation. cite journal |author=Staniforth V, Chiu LT, Yang NS |title=Caffeic acid suppresses UVB radiation-induced expression of interleukin-10 and activation of mitogen-activated protein kinases in mouse |journal=Carcinogenesis |volume=27 |issue=9 |pages=1803–11 |year=2006 |month=September |pmid=16524889 |doi=10.1093/carcin/bgl006 |url=] 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. CAPE significantly reduced the number of papillomas. cite journal |author=Huang MT, Ma W, Yen P, "et al" |title=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 |journal=Carcinogenesis |volume=17 |issue=4 |pages=761–5 |year=1996 |month=April |pmid=8625488 |doi= |url=] cite journal |author=Huang MT, Smart RC, Wong CQ, Conney AH |title=Inhibitory effect of curcumin, chlorogenic acid, caffeic acid, and ferulic acid on tumor promotion in mouse skin by 12-O-tetradecanoylphorbol-13-acetate |journal=Cancer Res. |volume=48 |issue=21 |pages=5941–6 |year=1988 |month=November |pmid=3139287 |doi= |url=] 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.cite journal |author=Lee WJ, Zhu BT |title=Inhibition of DNA methylation by caffeic acid and chlorogenic acid, two common catechol-containing coffee polyphenols |journal=Carcinogenesis |volume=27 |issue=2 |pages=269–77 |year=2006 |month=February |pmid=16081510 |doi=10.1093/carcin/bgi206 |url=]

Caffeic acid has been shown to be an inhibitor of the lipoxygense enzyme that forms leukotrienes from arachadonic acid. This function has been useful in scientific experiments to elucidate the roles of the leukotrienes in various inflammatory responses.cite journal |author=Mirzoeva OK, Calder PC |title=The effect of propolis and its components on eicosanoid production during the inflammatory response |journal=Prostaglandins Leukot. Essent. Fatty Acids |volume=55 |issue=6 |pages=441–9 |year=1996 |month=December |pmid=9014224 |doi= |url=]


ee also

*Chlorogenic acid
*Coumaric acid
*Cinnamic acid
*Quinic acid

External links

*cite web|title=Chemical Land|work=Caffeic Acid as Carbocyclic Carboxylic Acid|url=

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Look at other dictionaries:

  • Caffeic acid — Caffeic Caf*fe ic, a. [See {Coffee}.] (Chem.) Pertaining to, or obtained from, coffee. [1913 Webster] {Caffeic acid}, an acid obtained from coffee tannin, as a yellow crystalline substance, {C9H8O4}. [1913 Webster] …   The Collaborative International Dictionary of English

  • caffeic acid — (ˈ)ka|fēik , fē.ēk noun Etymology: caffeic International Scientific Vocabulary caffe (from French café coffee) + ic : a yellow crystalline acid C6H3(OH)2CH . CHCOOH obtained by hydrolysis of chlorogenic acid; 3,4 dihydroxy cinnamic acid …   Useful english dictionary

  • caffeic acid — kavos rūgštis statusas T sritis chemija formulė (HO)₂C₆H₃CH=CHCOOH atitikmenys: angl. caffeic acid rus. кофейная кислота ryšiai: sinonimas – (E) 3 (3,4 dihidroksifenil)propeno rūgštis …   Chemijos terminų aiškinamasis žodynas

  • caffeic acid — caf·fe·ic acid (.)ka .fē ik n a yellow crystalline acid C9H8O4 obtained by hydrolysis of chlorogenic acid …   Medical dictionary

  • caffeic acid — noun The phenolic carboxylic acid 3 (3,4 dihydroxyphenyl 2 propenoic acid that is an intermediate in the biosynthesis of lignin …   Wiktionary

  • Caffeic — Caf*fe ic, a. [See {Coffee}.] (Chem.) Pertaining to, or obtained from, coffee. [1913 Webster] {Caffeic acid}, an acid obtained from coffee tannin, as a yellow crystalline substance, {C9H8O4}. [1913 Webster] …   The Collaborative International Dictionary of English

  • Chlorogenic acid — IUPAC name (1S,3R,4R,5R) 3 {[(2Z) 3 (3,4 dihydr …   Wikipedia

  • Ferulic acid — IUPAC name (E) 3 (4 hydroxy 3 methoxy phenyl)prop 2 enoic acid …   Wikipedia

  • Cichoric acid — IUPAC name (2R,3R) 2,3 bis{[(E) 3 (3,4 dihydroxyphenyl)prop 2 enoyl]oxy}butanedioic acid …   Wikipedia

  • Rosmarinic acid — Chembox new Name = Rosmarinic acid ImageFile = Rosmarinic acid.png ImageName = Rosmarinic acid IUPACName =(2 R ) 2 (2 E ) 3 (3,4 Dihydroxyphenyl) 1 oxo 2 propenyloxy] 3 (3,4 dihydroxyphenyl)propanoic acid Section1 = Chembox Identifiers SMILES =… …   Wikipedia

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