paracoumaryl alcohol
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 399521780
| ImageFile=P-Coumaryl alcohol.svg
| ImageFile2 =
| ImageSize=200px
| PIN=4-[(1E)-3-Hydroxyprop-1-en-1-yl]phenol
| OtherNames=p-coumaryl alcohol, 4-coumaryl alcohol, 4-hydroxycinnamyl alcohol, 4-(3-hydroxy-1-propenyl)phenol
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|changed|??}}
| CASNo= 20649-40-5
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = 61POZ1QQ11
| PubChem=5280535
| SMILES= OC/C=C/c1ccc(O)cc1
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 4444166
| InChI = 1/C9H10O2/c10-7-1-2-8-3-5-9(11)6-4-8/h1-6,10-11H,7H2/b2-1+
| InChIKey = PTNLHDGQWUGONS-OWOJBTEDBL
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C9H10O2/c10-7-1-2-8-3-5-9(11)6-4-8/h1-6,10-11H,7H2/b2-1+
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = PTNLHDGQWUGONS-OWOJBTEDSA-N
| RTECS =
| MeSHName =
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 64555
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 109034
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = C02646
}}
|Section2={{Chembox Properties
| Formula = C9H10O2
| MolarMass = 150.1745
| Appearance = White solid
| Density =
| MeltingPtC = 114-116
| BoilingPt =
| Solubility =
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|Section3={{Chembox Hazards
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Paracoumaryl alcohol is a phytochemical, one of the monolignols. It is a white solid. p-Coumaryl alcohol is a major precursor to lignin or lignans.{{cite journal |doi=10.1074/jbc.M111.284497|title=Identification of Grass-specific Enzyme That Acylates Monolignols with p-Coumarate|year=2012|last1=Withers|first1=Saunia|last2=Lu|first2=Fachuang|last3=Kim|first3=Hoon|last4=Zhu|first4=Yimin|last5=Ralph|first5=John|last6=Wilkerson|first6=Curtis G.|journal=Journal of Biological Chemistry|volume=287|issue=11|pages=8347–8355|pmid=22267741|s2cid=24998478|doi-access=free|pmc=3318722}}
Biosynthesis and occurrence
It is synthesized via the phenylpropanoid biochemical pathway.
Esters of p-coumaryl alcohol and fatty acids are the basis of epicuticular waxes covering the surfaces of apples.
p-Coumaryl alcohol is an intermediate in biosynthesis of chavicol, stilbenoids, and coumarin.
External links
- [https://web.archive.org/web/20070929115202/http://www.acs.org/portal/a/c/s/1/acsdisplay.html?id=c373e9f77f6045088f6a4fd8fe800100 Molecule of the week: p-coumaryl alcohol]