Phloretic acid
{{Chembox
| Name =
| ImageFile = Phloretic acid.svg
| ImageSize = 200px
| ImageAlt = Chemical structure of phloretic acid
| PIN = 3-(4-Hydroxyphenyl)propanoic acid
| OtherNames = Desaminotyrosine
Hydro-p-coumaric acid
Phloretate
| Section1 = {{Chembox Identifiers
| CASNo = 501-97-3
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 6QNC6P18SR
| PubChem = 10394
| SMILES = C1=CC(=CC=C1CCC(=O)O)O
| EINECS = 207-931-3
| ChemSpiderID = 9965
| StdInChI = 1S/C9H10O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-2,4-5,10H,3,6H2,(H,11,12)
| StdInChIKey = NMHMNPHRMNGLLB-UHFFFAOYSA-N
| RTECS =
| MeSHName = C008869
| ChEBI = 32980
| KEGG = C01744
}}
| Section2 = {{Chembox Properties
| C=9 | H=10 | O=3
| Appearance =
| Density =
| MeltingPtC =129
| BoilingPt =
| Solubility =
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| Section3 = {{Chembox Hazards
| MainHazards =
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Phloretic acid is an organic compound with the formula HOC6H4(CH2)2CO2H. It is a white solid. The compound contains both phenol and carboxylic acid functional groups. It is sometimes called Desaminotyrosine (DAT) because it is identical to the common alpha amino acid tyrosine except for the absence of the amino functional group on the alpha carbon.
Production and occurrence
Phloretic acid is produced by reduction of the unsaturated side chain of p-coumaric acid. Together with phloroglucinol, it is produced by the action of the enzyme phloretin hydrolase on phloretin.
It is found in olives.{{cite journal|doi=10.1016/S0278-6915(03)00011-5|pmid=12659724|title=Isolation, structure elucidation and antioxidant potential of the major phenolic and flavonoid compounds in brined olive drupes|journal=Food and Chemical Toxicology|volume=41|issue=5|pages=703–717|year=2003|last1=Owen|first1=R.W|last2=Haubner|first2=R.|last3=Mier|first3=W.|last4=Giacosa|first4=A.|last5=Hull|first5=W.E|last6=Spiegelhalder|first6=B.|last7=Bartsch|first7=H.}} It is found in the rumen of sheep fed with dried grass.{{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}} It is also a urinary metabolite of tyrosine in rats.{{cite journal | title = Urinary phenolic acid metabolities of tyrosine|vauthors=Booth AN, Masri MS, Robbins DJ, Emerson OH, Jones FT, Deeds F | journal = Journal of Biological Chemistry | year = 1960 | volume = 235 | pages = 2649–2652 | url = http://www.jbc.org/content/235/9/2649.citation | issue = 9}}
Polyesters have been prepared from phloretic acid.{{cite journal | doi = 10.1002/(SICI)1521-3935(19990701)200:7<1784::AID-MACP1784>3.0.CO;2-B | title = New polymer syntheses, 101. Liquid-crystalline hyperbranched and potentially biodegradable polyesters based on phloretic acid and gallic acid | year = 1999 | last1 = Reina | first1 = Antonio | last2 = Gerken | first2 = Andreas | last3 = Zemann | first3 = Uwe | last4 = Kricheldorf | first4 = Hans R. | journal = Macromolecular Chemistry and Physics | volume = 200 | issue = 7 | pages = 1784–1791}}
It is one of the products of flavonoid metabolism performed by the bacterium Clostridium orbiscindens, a resident of some human intestinal tracts.
Drug uses
Phloretic acid is used in the synthesis of Esmolol.
References
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External links
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