1.0 2016-09-30 22:36:05 UTC 2020-05-11 20:47:57 UTC BMDB0000755 BMDB00755 Hydroxyphenyllactic acid 3-(4-Hydroxyphenyl)lactic acid, also known as 4-hydroxyphenyllactate or hpla, belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid. 3-(4-Hydroxyphenyl)lactic acid is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 3-(4-Hydroxyphenyl)lactic acid exists in all eukaryotes, ranging from yeast to humans. 3-(4-Hydroxyphenyl)lactic acid is a potentially toxic compound. 3-(4-Hydroxyphenyl)lactic acid has been found to be associated with several diseases known as eosinophilic esophagitis, colorectal cancer, and supradiaphragmatic malignancy; also 3-(4-hydroxyphenyl)lactic acid has been linked to the inborn metabolic disorders including phenylketonuria. 2-Hydroxy-3-(4-hydroxyphenyl)propanoate 2-Hydroxy-3-(p-hydroxyphenyl)propionic acid 4-Hydroxyphenyllactic acid beta-(4-Hydroxyphenyl)lactic acid beta-(p-Hydroxyphenyl)lactic acid DL-p-Hydroxyphenyllactic acid p-Hydroxyphenyl lactic acid 4-Hydroxyphenyllactate p-Hydroxyphenyllactate 2-Hydroxy-3-(4-hydroxyphenyl)propanoic acid 2-Hydroxy-3-(p-hydroxyphenyl)propionate b-(4-Hydroxyphenyl)lactate b-(4-Hydroxyphenyl)lactic acid beta-(4-Hydroxyphenyl)lactate Β-(4-hydroxyphenyl)lactate Β-(4-hydroxyphenyl)lactic acid b-(p-Hydroxyphenyl)lactate b-(p-Hydroxyphenyl)lactic acid beta-(p-Hydroxyphenyl)lactate Β-(p-hydroxyphenyl)lactate Β-(p-hydroxyphenyl)lactic acid DL-p-Hydroxyphenyllactate p-Hydroxyphenyl lactate p-Hydroxyphenyllactic acid Hydroxyphenyllactate (RS)-3-(4-Hydroxyphenyl)lactate (RS)-3-(4-Hydroxyphenyl)lactic acid 3-(4-Hydroxyphenyl)-DL-lactate 3-(4-Hydroxyphenyl)-DL-lactic acid 3-(4-Hydroxyphenyl)lactate 3-(p-Hydroxyphenyl)-lactate 3-(p-Hydroxyphenyl)-lactic acid a,4-Dihydroxybenzenepropanoate a,4-Dihydroxybenzenepropanoic acid b-(p-Hydroxyphenyl)-DL-lactate b-(p-Hydroxyphenyl)-DL-lactic acid beta-(p-Hydroxyphenyl)-DL-lactate beta-(p-Hydroxyphenyl)-DL-lactic acid DL-3-(4-Hydroxyphenyl)lactate DL-3-(4-Hydroxyphenyl)lactic acid HPLA 4-Hydroxyphenyllactic acid, (DL)-isomer Para-hydroxyphenyllactic acid 2-Hydroxyphloretate 2-Hydroxy-3-(4'-hydroxyphenyl)propanoic acid 2-Hydroxy-3-(4'-hydroxyphenyl)propanoic acid C9H10O4 182.1733 182.057908808 2-hydroxy-3-(4-hydroxyphenyl)propanoic acid hydroxyphenyllactic acid 306-23-0 OC(CC1=CC=C(O)C=C1)C(O)=O InChI=1S/C9H10O4/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,8,10-11H,5H2,(H,12,13) JVGVDSSUAVXRDY-UHFFFAOYSA-N belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid. Organic compounds Phenylpropanoids and polyketides Phenylpropanoic acids Phenylpropanoic acids 1-hydroxy-2-unsubstituted benzenoids Alpha hydroxy acids and derivatives Benzene and substituted derivatives Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Secondary alcohols 1-hydroxy-2-unsubstituted benzenoid 3-phenylpropanoic-acid Alcohol Alpha-hydroxy acid Aromatic homomonocyclic compound Benzenoid Carbonyl group Carboxylic acid Carboxylic acid derivative Hydrocarbon derivative Hydroxy acid Monocarboxylic acid or derivatives Monocyclic benzene moiety Organic oxide Organic oxygen compound Organooxygen compound Phenol Secondary alcohol Aromatic homomonocyclic compounds 2-hydroxy carboxylic acid phenols Solid water_solubility 12.9 mg/mL at 16 °C logp 0.87 ALOGPS logs -1.58 ALOGPS logp 0.88 ChemAxon pka_strongest_acidic 3.58 ChemAxon pka_strongest_basic -3.8 ChemAxon iupac 2-hydroxy-3-(4-hydroxyphenyl)propanoic acid ChemAxon average_mass 182.1733 ChemAxon mono_mass 182.057908808 ChemAxon smiles OC(CC1=CC=C(O)C=C1)C(O)=O ChemAxon formula C9H10O4 ChemAxon inchi InChI=1S/C9H10O4/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,8,10-11H,5H2,(H,12,13) ChemAxon inchikey JVGVDSSUAVXRDY-UHFFFAOYSA-N ChemAxon polar_surface_area 77.76 ChemAxon refractivity 45.44 ChemAxon polarizability 17.51 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 4 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Specdb::MsIr 834 Specdb::MsIr 835 Specdb::MsIr 836 Specdb::NmrTwoD 1470 Specdb::NmrOneD 1524 Specdb::NmrOneD 145230 Specdb::NmrOneD 145231 Specdb::NmrOneD 145232 Specdb::NmrOneD 145233 Specdb::NmrOneD 145234 Specdb::NmrOneD 145235 Specdb::NmrOneD 145236 Specdb::NmrOneD 145237 Specdb::NmrOneD 145238 Specdb::NmrOneD 145239 Specdb::NmrOneD 145240 Specdb::NmrOneD 145241 Specdb::NmrOneD 145242 Specdb::NmrOneD 145243 Specdb::NmrOneD 145244 Specdb::NmrOneD 145245 Specdb::NmrOneD 145246 Specdb::NmrOneD 145247 Specdb::NmrOneD 145248 Specdb::NmrOneD 145249 Specdb::CMs 1614 Specdb::CMs 3035 Specdb::CMs 31221 Specdb::CMs 31843 Specdb::CMs 37746 Specdb::CMs 150439 Specdb::CMs 1074729 Specdb::CMs 1074731 Specdb::CMs 1074733 Specdb::CMs 1074734 Specdb::CMs 1074736 Specdb::CMs 1074738 Specdb::CMs 1074740 Specdb::CMs 1074742 Specdb::CMs 1074744 Specdb::CMs 1074746 Specdb::CMs 1074747 Specdb::CMs 1074749 Specdb::CMs 1074751 Specdb::MsMs 1083 Specdb::MsMs 1084 Specdb::MsMs 1085 Specdb::MsMs 4625 Specdb::MsMs 179355 Specdb::MsMs 179356 Specdb::MsMs 179357 Specdb::MsMs 181680 Specdb::MsMs 181681 Specdb::MsMs 181682 Specdb::MsMs 438662 Specdb::MsMs 439230 Specdb::MsMs 440174 Specdb::MsMs 2227268 Specdb::MsMs 2227434 Specdb::MsMs 2229619 Specdb::MsMs 2229873 Specdb::MsMs 2232044 Specdb::MsMs 2232139 Specdb::MsMs 2234456 Specdb::MsMs 2234485 Specdb::MsMs 2236631 Specdb::MsMs 2236720 Specdb::MsMs 2242884 Specdb::MsMs 2242974 Epidermis Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Milk Commercial whole milk with 3.25% fat Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. 29291809 Milk Commercial milk, by CIL LC-MS Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. 28306241 Milk Raw milk, by UPLC-Q-TOF MS E Xi X, Kwok LY, Wang Y, Ma C, Mi Z, Zhang H: Ultra-performance liquid chromatography-quadrupole-time of flight mass spectrometry MS(E)-based untargeted milk metabolomics in dairy cows with subclinical or clinical mastitis. J Dairy Sci. 2017 Jun;100(6):4884-4896. doi: 10.3168/jds.2016-11939. Epub 2017 Mar 23. 28342601 Placenta Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Prostate Tissue Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 C03672 FDB017136 9010 9378 17385 C00050491 577 4-HYDROXYPHENYLLACTATE 2392410 5723 Deng, Xi-ling; Wang, Xin-bing; Xiang, Ying; Zhu, Shi-fa. Synthesis of b-(4-hydroxyphenyl)lactic acid. Shihezi Daxue Xuebao, Ziran Kexueban (2005), 23(1), 11-13. Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. 28306241 Xi X, Kwok LY, Wang Y, Ma C, Mi Z, Zhang H: Ultra-performance liquid chromatography-quadrupole-time of flight mass spectrometry MS(E)-based untargeted milk metabolomics in dairy cows with subclinical or clinical mastitis. J Dairy Sci. 2017 Jun;100(6):4884-4896. doi: 10.3168/jds.2016-11939. Epub 2017 Mar 23. 28342601 Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. 29291809