Record Information
Version1.0
Creation date2015-10-09 22:27:54 UTC
Update date2017-01-19 02:36:11 UTC
FoodComEx IDPC000067
FoodDB RecordNot Available
Chemical Information
NameL-Phenylalanine
DescriptionFound in many foods. It is used in cocoa substitutes. Flavouring ingredient; dietary supplement L-phenylalanine can also be converted into L-tyrosine, another one of the DNA-encoded amino acids. L-tyrosine in turn is converted into L-DOPA, which is further converted into dopamine, norepinephrine (noradrenaline), and epinephrine (adrenaline). The latter three are known as the catecholamines.; Phenylalanine (abbreviated as Phe or F) is an ?-amino acid with the formula HO2CCH(NH2)CH2C6H5, which is found naturally in the breast milk of mammals and manufactured for food and drink products and are also sold as nutritional supplements for their reputed analgesic and antidepressant effects. Phenylalanine is structurally closely related to dopamine, epinephrine (adrenaline) and tyrosine. It is a direct precursor to the neuromodulator phenylethylamine, a commonly used dietary supplement.; Phenylalanine is an essential amino acid and the precursor for the amino acid tyrosine. Like tyrosine, it is the precursor of catecholamines in the body (tyramine, dopamine, epinephrine and norepinephrine). The psychotropic drugs (mescaline, morphine, codeine, and papaverine) also have phenylalanine as a constituent. Phenylalanine is a precursor of the neurotransmitters called catecholamines, which are adrenalin-like substances. Phenylalanine is highly concentrated in the human brain and plasma. Normal metabolism of phenylalanine requires biopterin, iron, niacin, vitamin B6, copper and vitamin C. An average adult ingests 5 g of phenylalanine per day and may optimally need up to 8 g daily. Phenylalanine is highly concentrated in high protein foods, such as meat, cottage cheese and wheat germ. A new dietary source of phenylalanine is artificial sweeteners containing aspartame. Aspartame appears to be nutritious except in hot beverages; This essential amino acid is classified as nonpolar because of the hydrophobic nature of the benzyl side chain. The codons for L-phenylalanine are UUU and UUC. It is a white, powdery solid. L-Phenylalanine (LPA) is an electrically-neutral amino acid, one of the twenty common amino acids used to biochemically form proteins, coded for by DNA.; It is used by the brain to produce Norepinephrine, a chemical that transmits signals between nerve cells and the brain; however, it should be avoided by phenylketonurics and pregnant women. Phenylketonurics, who have a genetic error of phenylalanine metabolism, have elevated serum plasma levels of phenylalanine up to 400 times normal. Mild phenylketonuria can be an unsuspected cause of hyperactivity, learning problems, and other developmental problems in children. Phenylalanine can be an effective pain reliever. Its use in premenstrual syndrome and Parkinson's may enhance the effects of acupuncture and electric transcutaneous nerve stimulation (TENS). Phenylalanine and tyrosine, like L-dopa, produce a catecholamine effect. Phenylalanine is better absorbed than tyrosine and may cause fewer headaches. Low phenylalanine diets have been prescribed for certain cancers with mixed results. Some tumors use more phenylalanine (particularly melatonin-producing tumors called melanoma). One strategy is to exclude this amino acid from the diet, i.e., a Phenylketonuria (PKU) diet (compliance is a difficult issue; it is hard to quantify and is under-researched). The other strategy is just to increase phenylalanine's competing amino acids, i.e., tryptophan, valine, isoleucine and leucine, but not tyrosine. (http://www.dcnutrition.com)
CAS Number63-91-2
Structure
Thumb
Synonyms
SynonymSource
(-)-β-phenylalaninebiospider
(-)-beta-phenylalaninebiospider
(2S)-2-amino-3-phenylpropanoic acidbiospider
(l)-phenylalaninebiospider
(s)-(-)-phenylalaninebiospider
(s)-α-aminobenzenepropanoic acidbiospider
(S)-2-amino-3-phenylpropanoatebiospider
(S)-2-amino-3-phenylpropanoic acidbiospider
(S)-2-Amino-3-phenylpropionatebiospider
(S)-2-Amino-3-phenylpropionic acidbiospider
(S)-a-amino-b-PhenylpropionateGenerator
(S)-a-amino-b-Phenylpropionic acidGenerator
(s)-alpha-amino-benzenepropanoatebiospider
(s)-alpha-amino-benzenepropanoic acidbiospider
(s)-alpha-amino-beta-phenylpropionatebiospider
(s)-alpha-amino-beta-phenylpropionic acidbiospider
(s)-alpha-aminobenzenepropanoatebiospider
(s)-alpha-aminobenzenepropanoic acidbiospider
(s)-alpha-aminohydrocinnamatebiospider
(s)-alpha-aminohydrocinnamic acidbiospider
(S)-PhenylalanineHMDB
(S)-α-amino-β-phenylpropionateGenerator
(S)-α-amino-β-phenylpropionic acidGenerator
α-alanine, l-biospider
α-amino-, (s)-biospider
α-amino-α-aminohydrocinnamic acidbiospider
α-amino-β-phenylpropionic acidbiospider
α-aminohydrocinnamic acidbiospider
β-phenyl-α-alaninebiospider
β-phenyl-α-alanine, l-biospider
β-phenyl-l-alaninebiospider
β-phenylalaninebiospider
1usibiospider
2-Amino-3-phenylpropionic acid, L-biospider
3-Phenyl-L-alanineChEBI
Alpha-amino-beta-phenylpropionic acid, l-biospider
Alpha-aminohydrocinnamatebiospider
Alpha-aminohydrocinnamic acidbiospider
Alpha-aminohydrocinnamic acid, l-biospider
b-Phenyl-L-alanineGenerator
Benzenepropanoic acid, α-amino-, (s)-biospider
Benzenepropanoic acid, alpha-amino-, (s)-biospider
Beta-phenyl-alpha-alaninebiospider
Beta-phenyl-l-alaninebiospider
Beta-phenylalaninebiospider
Beta-phenylalnine, (-)-biospider
Endophenylbiospider
FChEBI
FEMA 3585db_source
Hydrocinnamic acid, α-amino-biospider
Hydrocinnamic acid, alpha-amino-biospider
L-α-alanine (van)biospider
L-β-phenylalaninebiospider
L-2-Amino-3-phenylpropionatebiospider
L-2-Amino-3-phenylpropionic acidbiospider
L-Alanine, 3-phenyl-biospider
L-Phenylalanine (JP15)biospider
L-Phenylalanine, JANdb_source
L-phenylalininebiospider
PALbiospider
PHEbiospider
Phenyl-α-alaninebiospider
Phenyl-alaninebiospider
PhenylalamineHMDB
PHENYLALANINEChEBI
Phenylalanine (usp/inn)biospider
Phenylalanine (van)biospider
Phenylalanine [usan:inn:jan]biospider
Phenylalanine, 9CI, USAN; L-formdb_source
Phenylalanine, l-biospider
Phenylalaninumbiospider
β-phenyl-L-alanineGenerator
Chemical FormulaNot Available
IUPAC nameNot Available
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
Chemical Taxonomy
ClassificationNot classified
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logP-1.38AVDEEF,A (1997)
Experimental Water Solubility26.9 mg/mL at 25 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Melting PointMp 283-284° (rapid heat)DFC
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 4 g
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
AKSci J93620
AKSci K018
Glentham GM4385
Glentham GM7895
MetaSci HMDB0000159
National Biochemicals Corporation HMDB0000159
Toronto Research Chemicals P319415