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Showing Compound (±)-Phenylalanine (FDB013245)

Record Information
Version1.0
Creation date2010-04-08 22:10:36 UTC
Update date2025-11-18 23:42:41 UTC
Primary IDFDB013245
Secondary Accession Numbers
  • FDB014705
Chemical Information
FooDB Name(±)-Phenylalanine
Description(±)-Phenylalanine, also known as F, belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom (±)-Phenylalanine is an odorless tasting compound (±)-Phenylalanine is found, on average, in the highest concentration within a few different foods, such as red bell peppers (Capsicum annuum), wheats (Triticum), and oats (Avena sativa) and in a lower concentration in dills (Anethum graveolens), greater sturgeons (Acipenser), and gadiformes (Gadiformes) (±)-Phenylalanine has also been detected, but not quantified in, several different foods, such as tallow, sesame oil, sunflower oil, rapeseed oil, and lard. This could make (±)-phenylalanine a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on (±)-Phenylalanine.
CAS Number150-30-1
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
alpha-Amino-beta-phenylpropionic acidChEBI
DL-PhenylalanineChEBI
FChEBI
FenilalaninaChEBI
PHEChEBI
PhenylalaninChEBI
a-Amino-b-phenylpropionateGenerator
a-Amino-b-phenylpropionic acidGenerator
alpha-Amino-beta-phenylpropionateGenerator
Α-amino-β-phenylpropionateGenerator
Α-amino-β-phenylpropionic acidGenerator
L-Isomer phenylalanineMeSH
EndorphenylMeSH
L-PhenylalanineMeSH
PhenylalanineMeSH
Phenylalanine, L isomerMeSH
Phenylalanine, L-isomerMeSH
(.+/-.)-phenylalaninebiospider
(+/-)-2-Amino-3-phenylpropionic acidbiospider
(2R)-2-amino-3-phenylpropanoic acidbiospider
α-amino-α-alaninebiospider
β-phenylalanine, DL-biospider
2-amino-3-phenylpropanoic acidbiospider
2-Amino-3-phenylpropionic acid, dl-biospider
Alanine, phenyl-, d-biospider
Alanine, phenyl-, DL-biospider
Alanine, phenyl-, DL- (8CI)biospider
Alpha-aminohydrocinnamic acid, DL-biospider
D -alpha-amino- beta-phenyl- propionic acidbiospider
D-beta-phenyl-alpha-alaninebiospider
D-phenylalaninebiospider
DL-α-amino-β-phenylpropionic acidbiospider
DL-β-phenyl-α-alaninebiospider
DL-β-phenylalaninebiospider
DL-2-Amino-3-phenylpropanoic acidbiospider
DL-3-Phenylalaninebiospider
DL-alpha-amino-beta-phenylpropionic acidbiospider
DL-phenylalaninebiospider
DL-phenylalanine, homopolymerbiospider
FEMA 3726db_source
L -2-Amino-3-phenylpropanoic acidbiospider
L-Phenylalanine-[ring-2,6-3H(N)biospider
L-phenylalanine, u.s.p.biospider
Phenylalanine DL-formbiospider
Phenylalanine, DL-biospider
Phenylalanine, homopolymerbiospider
Polyphenylalaninebiospider
Sabidenbiospider
Predicted Properties
PropertyValueSource
Water Solubility4.14 g/LALOGPS
logP-1.4ALOGPS
logP-1.2ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)2.47ChemAxon
pKa (Strongest Basic)9.45ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity45.12 m³·mol⁻¹ChemAxon
Polarizability17.2 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC9H11NO2
IUPAC name2-amino-3-phenylpropanoic acid
InChI IdentifierInChI=1S/C9H11NO2/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8H,6,10H2,(H,11,12)
InChI KeyCOLNVLDHVKWLRT-UHFFFAOYSA-N
Isomeric SMILESNC(CC1=CC=CC=C1)C(O)=O
Average Molecular Weight165.1891
Monoisotopic Molecular Weight165.078978601
Classification
Description Belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentPhenylalanine and derivatives
Alternative Parents
Substituents
  • Phenylalanine or derivatives
  • 3-phenylpropanoic-acid
  • Alpha-amino acid
  • Amphetamine or derivatives
  • Aralkylamine
  • Monocyclic benzene moiety
  • Benzenoid
  • Amino acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic nitrogen compound
  • Primary amine
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 65.44%; H 6.71%; N 8.48%; O 19.37%DFC
Melting PointMp 318-320° dec.DFC
Boiling PointNot Available
Experimental Water Solubility14.2 mg/mL at 25 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP-1.44HANSCH,C ET AL. (1995)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-00dl-9300000000-4782928378caea601f9b2014-09-20View Spectrum
Predicted GC-MS(±)-Phenylalanine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9400000000-1880f5dae4360fab4947Spectrum
Predicted GC-MS(±)-Phenylalanine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(±)-Phenylalanine, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(±)-Phenylalanine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(±)-Phenylalanine, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(±)-Phenylalanine, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-00di-0900000000-58b3e0504dfeb61254e82021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-00di-0900000000-3cc5d610e74436c96c192021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-23ba76644ba103a54f612021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Negativesplash10-01ot-0900000000-73ddf7eb5a4bdf9750832021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00di-0900000000-0ddf3e263974f732a55e2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00di-0900000000-b92f5a299928b72a0c152021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0fb9-9300000000-a9cd15dd22c7c4c675492021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-00di-0900000000-a7383573a0010855fafa2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-00di-0900000000-c990ee531fa1fddaad6c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-cf6d59da738657f88ea62021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00di-2900000000-1a69a7a4025aa0ee4c772021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 25V, Positivesplash10-00di-0900000000-6528c07eab2c79fd47e62021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-00di-0900000000-e98ddf2ca45f030195912021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 25V, Positivesplash10-00di-0900000000-ceb4bd7dd8e1f71d56032021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0udi-2900000000-00e5545144646ccd72e62021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-00di-0900000000-4858dd4ae63964321d5f2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-00di-0900000000-8819a69344a55991578f2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-00di-0900000000-259adf768bdd45a62a932021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-00di-1900000000-3436f16ff1c07507e6132021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00xs-0900000000-ff1b3ddc479e700847862015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-1900000000-fc318d4d3cde828334e42015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9400000000-866eeb88a50bd575fa092015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-407406ada2082438a5792015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dj-1900000000-347dc84ca7da32c5c1762015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dl-9600000000-a608d60e21d3beb49b122015-05-27View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, D2O, experimental)Spectrum
ChemSpider ID969
ChEMBL IDCHEMBL25080
KEGG Compound IDC02057
Pubchem Compound ID994
Pubchem Substance IDNot Available
ChEBI ID28044
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDJVC81-S:HQC15-W
EAFUS ID2994
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1037691
SuperScent IDNot Available
Wikipedia IDPhenylalanine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
odorless
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).