FComEx: L-Phenylalanine (PC000067)

Record Information

Version

1.0

Creation date

2015-10-09 22:27:54 UTC

Update date

2017-01-19 02:36:11 UTC

FoodComEx ID

PC000067

FoodDB Record

Not Available

Chemical Information

Name

L-Phenylalanine

Description

Found 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 Number

63-91-2

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(-)-β-phenylalanine	biospider
(-)-beta-phenylalanine	biospider
(2S)-2-amino-3-phenylpropanoic acid	biospider
(l)-phenylalanine	biospider
(s)-(-)-phenylalanine	biospider
(s)-α-aminobenzenepropanoic acid	biospider
(S)-2-amino-3-phenylpropanoate	biospider
(S)-2-amino-3-phenylpropanoic acid	biospider
(S)-2-Amino-3-phenylpropionate	biospider
(S)-2-Amino-3-phenylpropionic acid	biospider
(S)-a-amino-b-Phenylpropionate	Generator
(S)-a-amino-b-Phenylpropionic acid	Generator
(s)-alpha-amino-benzenepropanoate	biospider
(s)-alpha-amino-benzenepropanoic acid	biospider
(s)-alpha-amino-beta-phenylpropionate	biospider
(s)-alpha-amino-beta-phenylpropionic acid	biospider
(s)-alpha-aminobenzenepropanoate	biospider
(s)-alpha-aminobenzenepropanoic acid	biospider
(s)-alpha-aminohydrocinnamate	biospider
(s)-alpha-aminohydrocinnamic acid	biospider
(S)-Phenylalanine	HMDB
(S)-α-amino-β-phenylpropionate	Generator
(S)-α-amino-β-phenylpropionic acid	Generator
α-alanine, l-	biospider
α-amino-, (s)-	biospider
α-amino-α-aminohydrocinnamic acid	biospider
α-amino-β-phenylpropionic acid	biospider
α-aminohydrocinnamic acid	biospider
β-phenyl-α-alanine	biospider
β-phenyl-α-alanine, l-	biospider
β-phenyl-l-alanine	biospider
β-phenylalanine	biospider
1usi	biospider
2-Amino-3-phenylpropionic acid, L-	biospider
3-Phenyl-L-alanine	ChEBI
Alpha-amino-beta-phenylpropionic acid, l-	biospider
Alpha-aminohydrocinnamate	biospider
Alpha-aminohydrocinnamic acid	biospider
Alpha-aminohydrocinnamic acid, l-	biospider
b-Phenyl-L-alanine	Generator
Benzenepropanoic acid, α-amino-, (s)-	biospider
Benzenepropanoic acid, alpha-amino-, (s)-	biospider
Beta-phenyl-alpha-alanine	biospider
Beta-phenyl-l-alanine	biospider
Beta-phenylalanine	biospider
Beta-phenylalnine, (-)-	biospider
Endophenyl	biospider
F	ChEBI
FEMA 3585	db_source
Hydrocinnamic acid, α-amino-	biospider
Hydrocinnamic acid, alpha-amino-	biospider
L-α-alanine (van)	biospider
L-β-phenylalanine	biospider
L-2-Amino-3-phenylpropionate	biospider
L-2-Amino-3-phenylpropionic acid	biospider
L-Alanine, 3-phenyl-	biospider
L-Phenylalanine (JP15)	biospider
L-Phenylalanine, JAN	db_source
L-phenylalinine	biospider
PAL	biospider
PHE	biospider
Phenyl-α-alanine	biospider
Phenyl-alanine	biospider
Phenylalamine	HMDB
PHENYLALANINE	ChEBI
Phenylalanine (usp/inn)	biospider
Phenylalanine (van)	biospider
Phenylalanine [usan:inn:jan]	biospider
Phenylalanine, 9CI, USAN; L-form	db_source
Phenylalanine, l-	biospider
Phenylalaninum	biospider
β-phenyl-L-alanine	Generator

Chemical Formula

Not Available

IUPAC name

Not Available

InChI Identifier

InChI=1S/C9H11NO2/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8H,6,10H2,(H,11,12)

InChI Key

COLNVLDHVKWLRT-UHFFFAOYSA-N

Isomeric SMILES

NC(CC1=CC=CC=C1)C(O)=O

Average Molecular Weight

165.1891

Monoisotopic Molecular Weight

165.078978601

Chemical Taxonomy

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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Phenylalanine 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 Framework

Aromatic homomonocyclic compounds

External Descriptors

alpha-amino acid (CHEBI:28044 )
aromatic amino acid (CHEBI:28044 )

Physico-Chemical Properties - Experimental

Property	Value	Reference
Experimental logP	-1.38	AVDEEF,A (1997)
Experimental Water Solubility	26.9 mg/mL at 25 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Melting Point	Mp 283-284° (rapid heat)	DFC

Foods of Origin