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| {{DISPLAYTITLE:''p''-Coumaric acid}}
| | Ed is what people call me and my wife doesn't like it at all. He works as a bookkeeper. As a lady what she really likes is style and she's been doing it for fairly a whilst. Some time in the past he selected to live in North Carolina and he doesn't plan on changing it.<br><br>Also visit my blog post ... [http://kjhkkb.net/xe/notice/374835 best psychics] |
| {{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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Ed is what people call me and my wife doesn't like it at all. He works as a bookkeeper. As a lady what she really likes is style and she's been doing it for fairly a whilst. Some time in the past he selected to live in North Carolina and he doesn't plan on changing it.
Also visit my blog post ... best psychics