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| {{DISPLAYTITLE:''p''-Coumaric acid}}
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| {{chembox
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| | Name = ''p''-Coumaric acid
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| | ImageFile = Coumaric acid acsv.svg
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| | ImageName = Skeletal formula of ''p''-coumaric acid
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| | ImageFile1 = Coumaric-acid-3D-balls.png
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| | ImageName1 = Ball-and-stick model of ''p''-coumaric acid
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| | IUPACName = (E)-3-(4-hydroxyphenyl)-2-propenoic acid
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| | OtherNames = ''para''-coumaric acid,
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| 4-hydroxycinnamic acid,
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| β-(4-hydroxyphenyl)acrylic acid
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| | Section1 = {{Chembox Identifiers
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| | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
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| | ChemSpiderID = 553148
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| | InChI1 = 1/C9H8O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6,10H,(H,11,12)/b6-3+
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| | InChIKey1 = NGSWKAQJJWESNS-ZZXKWVIFBJ
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| | ChEMBL_Ref = {{ebicite|correct|EBI}}
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| | ChEMBL = 66879
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| | SMILES1 = c1cc(ccc1/C=C/C(=O)O)O
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| | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
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| | StdInChI = 1S/C9H8O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6,10H,(H,11,12)/b6-3+
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| | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
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| | StdInChIKey = NGSWKAQJJWESNS-ZZXKWVIFSA-N
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| | CASNo_Ref = {{cascite|changed|??}}
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| | CASNo = 7400-08-0
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| | ChEBI_Ref = {{ebicite|correct|EBI}}
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| | ChEBI = 32374
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| | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
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| | DrugBank = DB04066
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| | SMILES = C1=CC(=CC=C1\C=C\C(=O)O)O
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| | InChI = 1/C9H8O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6,10H,(H,11,
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| 12)/b6-3+/f/h11H
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| | PubChem = 637542
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| | EINECS = 231-000-0
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| }}
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| | Section2 = {{Chembox Properties
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| | C=9 | H=8 | O=3
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| | ExactMass = 164.047344
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| | MeltingPt = 210–213 °C
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| }}
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| | Section3 = {{Chembox Hazards
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| | RPhrases = {{R36/37/38}}
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| | SPhrases = {{S24/25}}
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| }}
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| }}
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| '''''p''-Coumaric acid''' is a [[hydroxycinnamic acid]], an organic compound that is a [[Hydroxyl|hydroxy]] derivative of [[cinnamic acid]]. There are three [[isomer]]s of [[coumaric acid]]- ''o''-coumaric acid, ''m''-coumaric acid, and ''p''-coumaric acid- that differ by the position of the hydroxy substitution of the phenyl group. ''p''-Coumaric acid is the most abundant isomer of the three in nature. ''p''-Coumaric acid exists in two forms ''trans-p''-coumaric acid and ''cis-p''-coumaric acid''.
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| It is a crystalline solid that is slightly soluble in water, but well soluble in [[ethanol]] and [[diethyl ether]].
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| Together with [[sinapyl alcohol]] and [[coniferyl alcohol]]s, ''p''-coumaric acid is a major component of [[lignin]].
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| == Natural occurrences ==
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| ''p''-Coumaric acid can be found in ''[[Gnetum cleistostachyum]]''.<ref>{{Cite journal|doi=10.1080/10286020310001625102|pmid=15621615|title=Stilbene derivatives from Gnetum cleistostachyum|year=2005|last1=Yao|first1=Chun-Suo|last2=Lin|first2=Mao|last3=Liu|first3=Xin|last4=Wang|first4=Ying-Hong|journal=Journal of Asian Natural Products Research|volume=7|issue=2|pages=131–7}}</ref>
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| === in food ===
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| ''p''-Coumaric acid can be found in a wide variety of edible plants such as [[peanut]]s, navy beans, [[tomato]]es, [[carrot]]s, and [[garlic]]. It is found in [[wine]] and [[vinegar]].<ref>{{Cite journal|doi=10.1007/BF01192948|title=Analysis of polyphenolic compounds of different vinegar samples|year=1994|last1=Gálvez|first1=Miguel Carrero|last2=Barroso|first2=Carmelo García|last3=Pérez-Bustamante|first3=Juan Antonio|journal=Zeitschrift für Lebensmittel-Untersuchung und -Forschung|volume=199|pages=29}}</ref> It is also found in [[barley]] grain.<ref>{{Cite journal|doi=10.1021/jf060974w|title=Phenolic Compounds of Barley Grain and Their Implication in Food Product Discoloration|year=2006|last1=Quinde-Axtell|first1=Zory|last2=Baik|first2=Byung-Kee|journal=Journal of Agricultural and Food Chemistry|volume=54|issue=26|pages=9978–84|pmid=17177530}}</ref>
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| ''p''-Coumaric acid from [[pollen]] is a constituent of [[honey]].<ref name=Berenbaum>{{cite journal | doi = 10.1073/pnas.1303884110 | title = Honey constituents up-regulate detoxification and immunity genes in the western honey bee Apis mellifera | year = 2013 | author = Mao W, Schuler M A, Berenbaum M R | journal = Proceedings of the National Academy of Sciences of the United States of America | issue = April 29 2013 | volume = 110 | pages = 8842}}</ref>
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| === Derivatives ===
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| [[p-Coumaric acid glucoside]] can also be found in commercial [[bread]]s containing [[flaxseed]].<ref>{{Cite journal|doi=10.1016/j.foodchem.2008.02.088|title=Phenolic glucosides in bread containing flaxseed|year=2008|last1=Strandås|first1=C.|last2=Kamal-Eldin|first2=A.|last3=Andersson|first3=R.|last4=Åman|first4=P.|journal=Food Chemistry|volume=110|issue=4|pages=997}}</ref>
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| Diesters of p-coumaric acid can be found in [[carnauba wax]].
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| == Metabolism ==
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| === Biosynthesis ===
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| It is biosynthesized from [[cinnamic acid]] by the action of the P450-dependent enzyme [[4-cinnamic acid hydroxylase]] (C4H).
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| : [[Image:Zimtsäure - Cinnamic acid.svg|100px|cinnamic acid]] <math>\xrightarrow{C4H}</math> [[Image:Coumaric acid acsv.svg|130px|para-coumaric acid]]
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| It is also produced from L-[[tyrosine]] by the action of [[tyrosine ammonia lyase]] (TAL).
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| : [[File:L-Tyrosin - L-Tyrosine.svg|130px|L-Tyrosine]] <math>\xrightarrow{TAL}</math> [[Image:Coumaric acid acsv.svg|130px|para-coumaric acid]] + [[Ammonia]] + H<sup>+</sup>
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| === Biochemistry ===
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| ''p''-Coumaric acid is the precursor of [[4-ethylphenol]] produced by the [[yeast (wine)|yeast]] ''[[Brettanomyces]]'' in wine. The yeast converts this to [[4-vinylphenol]] via the enzyme [[cinnamate decarboxylase]].<ref>[http://www.etslabs.com/scripts/ets/pagetemplate/blank.asp?pageid=193 Brettanomyces Monitoring by Analysis of 4-ethylphenol and 4-ethylguaiacol] at etslabs.com</ref> 4-Vinylphenol is further reduced to 4-ethylphenol by the enzyme [[vinyl phenol reductase]]. Coumaric acid is sometimes added to [[growth medium|microbiological media]], enabling the positive identification of ''Brettanomyces'' by smell.
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| :[[File:Coumaric acid to 4-ethyphenol.png|left|thumb|290px|The conversion of p-coumaric acid to 4-ethyphenol by Brettanomyces]]<br style="clear:left;"/>
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| [[cis-p-coumarate glucosyltransferase]] is an enzyme that uses UDP-glucose and cis-p-coumarate to produce [[4'-O-beta-D-glucosyl-cis-p-coumarate]] and UDP. This enzyme belongs to the family of glycosyltransferases, specifically the hexosyltransferases.<ref>{{Cite journal|doi=10.1016/S0031-9422(97)00337-3|title=Isolation, purification and characterization of UDP-glucose: Cis-p-coumaric acid-β-d-glucosyltransferase from sphagnum fallax|year=1997|last1=Rasmussen|first1=Susanne|last2=Rudolph|first2=Hansjörg|journal=Phytochemistry|volume=46|issue=3|pages=449}}</ref>
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| [[Phloretic acid]] is found in the rumen of sheep fed with dried grass and is produced by hydrogenation of the 2-propenoic side chain of p-coumaric acid.<ref>{{Cite journal|pmid=16346090|year=1982|last1=Chesson|first1=A|last2=Stewart|first2=CS|last3=Wallace|first3=RJ|title=Influence of plant phenolic acids on growth and cellulolytic activity of rumen bacteria|volume=44|issue=3|pages=597–603|pmc=242064|journal=Applied and environmental microbiology}}</ref>
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| == Medicinal uses ==
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| ''p''-Coumaric acid has [[antioxidant]] properties and is believed to reduce the risk of stomach [[cancer]]<ref name=Ferguson>{{cite journal | doi = 10.1002/mnfr.200500014 | title = Antioxidant and antigenotoxic effects of plant cell wall hydroxycinnamic acids in cultured HT-29 | year = 2005 | author = Ferguson LR, Shuo-tun Z, Harris PJ | journal = Molecular Nutrition & Food Research | pages = 585–693 | volume = 49 | issue = 6 | pmid = 15841493}}</ref> by reducing the formation of [[carcinogenic]] [[nitrosamine]]s.<ref name=Kikugawa>{{cite journal | doi = 10.1021/jf00118a025 | title = Reaction of ''p''-hydroxycinnamic acid derivatives with nitrite and its relevance to nitrosamine formation | year = 1983 | author = Kikugawa K, Hakamada T, Hasunuma M, Kurechi T | journal = Journal of Agricultural and Food Chemistry | pages = 780–785 | volume = 1 | issue = 4}}</ref>
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| == Biological Effects ==
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| ''p''-Coumeric acid is normally present in [[honey]], but not in the substitute nutrients based on [[high-fructose corn syrup]] that [[honey bee]] keepers feed to their colonies. This absence has been suggested as a possible contributor to [[Colony Collapse Disorder]] of honey bees because ''p''-coumeric acid has been found to help honey bees detoxify certain pesticides.<ref name="Berenbaum" />
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| == See also ==
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| * [[Coumaroyl-Coenzyme A]]
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| * [[Ferulic acid]]
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| * [[Cinnamic acid]]
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| * [[Phenolic content in wine]]
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| * [[p-Coumaroylated anthocyanin]]s
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| == References ==
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| {{Reflist}}
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| {{Hydroxycinnamic acid}}
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| [[Category:Hydroxycinnamic acids]]
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I would like to introduce myself to you, I am Jayson Simcox but I don't like when people use accurate psychic readings (appin.co.kr) my complete title. Distributing manufacturing is how he makes a living. best psychic, related web-site, What me and my family love is performing ballet but I've been using on new things recently. Ohio is exactly where my house is but my spouse wants us to move.
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