Phenyllactic acid (YMDB01774)

Identification
YMDB IDYMDB01774
NamePhenyllactic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionPhenyllactic acid (PLA) is an antifungal metabolite produced by lactic acid bacteria (LAB). Lactic acid bacteria are naturally associated with many foods or their raw ingredients and are popularly used in food fermentation to enhance the sensory, aromatic, and textural properties of food. These microorganisms are well recognized for their biopreservative properties, which are achieved through the production of antimicrobial compounds such as lactic acid, diacetyl, bacteriocins, and other metabolites. [PMID 18724772]
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 2-Hydroxy-2-phenylpropanoic acid
  • 2-Hydroxy-2-phenylpropionic acid
  • 2-Phenyl-2-hydroxypropionic acid
  • 2-Phenyllactic acid
  • alpha-Hydroxy-alpha-phenylpropionic acid
  • alpha-Phenyllactic acid
  • dl-Atrolactic acid
  • Mandelic acid, .alpha.-methyl-
  • Mandelic acid, alpha-methyl-
  • Saeure
  • Saeuren
  • alpha-Hydroxy-alpha-methylbenzeneacetic acid
  • alpha-Methylmandelic acid
  • 2-Hydroxy-2-phenylpropionate
  • 2-Phenyllactate
  • a-Hydroxy-a-methylbenzeneacetate
  • a-Hydroxy-a-methylbenzeneacetic acid
  • alpha-Hydroxy-alpha-methylbenzeneacetate
  • Α-hydroxy-α-methylbenzeneacetate
  • Α-hydroxy-α-methylbenzeneacetic acid
  • a-Hydroxy-a-phenylpropionate
  • a-Hydroxy-a-phenylpropionic acid
  • alpha-Hydroxy-alpha-phenylpropionate
  • Α-hydroxy-α-phenylpropionate
  • Α-hydroxy-α-phenylpropionic acid
  • a-Methylmandelate
  • a-Methylmandelic acid
  • alpha-Methylmandelate
  • Α-methylmandelate
  • Α-methylmandelic acid
  • 2-Hydroxy-2-phenylpropanoate
CAS number515-30-0
WeightAverage: 166.1739
Monoisotopic: 166.062994186
InChI KeyNWCHELUCVWSRRS-UHFFFAOYSA-N
InChIInChI=1S/C9H10O3/c1-9(12,8(10)11)7-5-3-2-4-6-7/h2-6,12H,1H3,(H,10,11)
IUPAC Name2-hydroxy-2-phenylpropanoic acid
Traditional IUPAC Name(+-)-atrolactic acid
Chemical FormulaC9H10O3
SMILESCC(O)(C(O)=O)C1=CC=CC=C1
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassNot Available
Direct ParentBenzene and substituted derivatives
Alternative Parents
Substituents
  • Hydroxy acid
  • Monocyclic benzene moiety
  • Alpha-hydroxy acid
  • Tertiary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point98 °C
Experimental Properties
PropertyValueReference
Water Solubility21.2 mg/mL at 25 oC [MERCK INDEX (1996)]PhysProp
LogP1.83 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility19.7 g/LALOGPS
logP1.07ALOGPS
logP1.33ChemAxon
logS-0.93ALOGPS
pKa (Strongest Acidic)3.81ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity43.42 m³·mol⁻¹ChemAxon
Polarizability16.49 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dl-7900000000-509b9b053babfcf844f1JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00g3-6930000000-afa47fa6b30a3ed22ce4JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01b9-0900000000-8c9ece61417bc3e8797aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0100-3900000000-088af228b8e174205204JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-4900000000-ccc943c872291e1f6dcaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01b9-0900000000-4b021476072aad6093a6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0100-4900000000-c91b72f4b33d2faebe55JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9400000000-033a67da2a8599739c24JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-1900000000-7152b412eff38fd704ceJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-2900000000-a12b348e352a1dbe0c96JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-5900000000-1d00b97de5b408e1e0ebJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0pi0-0900000000-b90cbd23e326f78542e7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zi0-3900000000-5d10088081d7d30f8a05JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-5900000000-feee47e06a508c3d63a3JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Boer, V. M., Crutchfield, C. A., Bradley, P. H., Botstein, D., Rabinowitz, J. D. (2010). "Growth-limiting intracellular metabolites in yeast growing under diverse nutrient limitations." Mol Biol Cell 21:198-211.19889834
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID16684
HMDB IDHMDB00779
Pubchem Compound ID643327
Kegg IDC01479
ChemSpider ID1263
FOODB IDFDB093343
Wikipedia IDNot Available
BioCyc IDNot Available