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.
It is found in olives.[1] It is found in the rumen of sheep fed with dried grass.[2] It is also a urinary metabolite of tyrosine in rats.[3]
Polyesters have been prepared from phloretic acid.[4]
It is one of the products of flavonoid metabolism performed by the bacterium Clostridium orbiscindens, a resident of some human intestinal tracts. [5]
Referencesedit
^Owen, R.W; Haubner, R.; Mier, W.; Giacosa, A.; Hull, W.E; Spiegelhalder, B.; Bartsch, H. (2003). "Isolation, structure elucidation and antioxidant potential of the major phenolic and flavonoid compounds in brined olive drupes". Food and Chemical Toxicology. 41 (5): 703–717. doi:10.1016/S0278-6915(03)00011-5. PMID 12659724.
^Chesson, A; Stewart, CS; Wallace, RJ (1982). "Influence of plant phenolic acids on growth and cellulolytic activity of rumen bacteria". Applied and Environmental Microbiology. 44 (3): 597–603. PMC242064. PMID 16346090.
^Booth AN, Masri MS, Robbins DJ, Emerson OH, Jones FT, Deeds F (1960). "Urinary phenolic acid metabolities of tyrosine". Journal of Biological Chemistry. 235 (9): 2649–2652.
^Reina, Antonio; Gerken, Andreas; Zemann, Uwe; Kricheldorf, Hans R. (1999). "New polymer syntheses, 101. Liquid-crystalline hyperbranched and potentially biodegradable polyesters based on phloretic acid and gallic acid". Macromolecular Chemistry and Physics. 200 (7): 1784–1791. doi:10.1002/(SICI)1521-3935(19990701)200:7<1784::AID-MACP1784>3.0.CO;2-B.
^Schoefer, Lilian; Mohan, Ruchika; Schwiertz, Andreas; Braune, Annett; Blaut, Michael (2003). "Anaerobic Degradation of Flavonoids by Clostridium orbiscindens". Applied and Environmental Microbiology. 69 (10): 5849–5854. doi:10.1128/AEM.69.10.5849-5854.2003. PMC201214. PMID 14532034.
External linksedit
Media related to Phloretic acid at Wikimedia Commons
April 12, 2024
phloretic, acid, organic, compound, with, formula, hoc6h4, 2co2h, white, solid, compound, contains, both, phenol, carboxylic, acid, functional, groups, sometimes, called, desaminotyrosine, because, identical, common, alpha, amino, acid, tyrosine, except, absen. 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 Phloretic acid NamesPreferred IUPAC name 3 4 Hydroxyphenyl propanoic acidOther names DesaminotyrosineHydro p coumaric acidPhloretateIdentifiersCAS Number 501 97 3 Y3D model JSmol Interactive imageChEBI CHEBI 32980ChemSpider 9965ECHA InfoCard 100 007 211EC Number 207 931 3KEGG C01744MeSH C008869PubChem CID 10394UNII 6QNC6P18SR YCompTox Dashboard EPA DTXSID2075427InChI InChI 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 Key NMHMNPHRMNGLLB UHFFFAOYSA NSMILES C1 CC CC C1CCC O O OPropertiesChemical formula C 9H 10O 3Molar mass 166 176 g mol 1Melting point 129 C 264 F 402 K Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox referencesProduction and occurrence editPhloretic 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 1 It is found in the rumen of sheep fed with dried grass 2 It is also a urinary metabolite of tyrosine in rats 3 Polyesters have been prepared from phloretic acid 4 It is one of the products of flavonoid metabolism performed by the bacterium Clostridium orbiscindens a resident of some human intestinal tracts 5 References edit Owen R W Haubner R Mier W Giacosa A Hull W E Spiegelhalder B Bartsch H 2003 Isolation structure elucidation and antioxidant potential of the major phenolic and flavonoid compounds in brined olive drupes Food and Chemical Toxicology 41 5 703 717 doi 10 1016 S0278 6915 03 00011 5 PMID 12659724 Chesson A Stewart CS Wallace RJ 1982 Influence of plant phenolic acids on growth and cellulolytic activity of rumen bacteria Applied and Environmental Microbiology 44 3 597 603 PMC 242064 PMID 16346090 Booth AN Masri MS Robbins DJ Emerson OH Jones FT Deeds F 1960 Urinary phenolic acid metabolities of tyrosine Journal of Biological Chemistry 235 9 2649 2652 Reina Antonio Gerken Andreas Zemann Uwe Kricheldorf Hans R 1999 New polymer syntheses 101 Liquid crystalline hyperbranched and potentially biodegradable polyesters based on phloretic acid and gallic acid Macromolecular Chemistry and Physics 200 7 1784 1791 doi 10 1002 SICI 1521 3935 19990701 200 7 lt 1784 AID MACP1784 gt 3 0 CO 2 B Schoefer Lilian Mohan Ruchika Schwiertz Andreas Braune Annett Blaut Michael 2003 Anaerobic Degradation of Flavonoids by Clostridium orbiscindens Applied and Environmental Microbiology 69 10 5849 5854 doi 10 1128 AEM 69 10 5849 5854 2003 PMC 201214 PMID 14532034 External links edit nbsp Media related to Phloretic acid at Wikimedia Commons Retrieved from https en wikipedia org w index php title Phloretic acid amp oldid 1214208013, wikipedia, wiki, book, books, library,
