Dl-Phenylalanine

HCID 994CAS 150-30-1

Basic information

Standard SMILES
NC(Cc1ccccc1)C(=O)O
InChIKey
COLNVLDHVKWLRT-UHFFFAOYSA-N
Molecular formula
C9H11NO2
Average molar mass
165.19 g/mol
Monoisotopic mass
165.07897859

Overview

Phenylalanine is an aromatic amino acid that is alanine in which one of the methyl hydrogens is substituted by a phenyl group. It has a role as a Daphnia magna metabolite. It is an alpha-amino acid and an aromatic amino acid. It contains a benzyl group. It is a conjugate base of a phenylalaninium. It is a conjugate acid of a phenylalaninate.

Names & identifiers

Preferred name
Dl-Phenylalanine
IUPAC
2-amino-3-phenylpropanoic acid
English name
DL-Phenylalanine
Molecular formula
C9H11NO2
Molecular weight
165.19

Names & synonyms

DL-PHENYLALANINE150-30-1DL-3-PhenylalaninePhenylalanine DL-formPhenylalanine, dl-DL-2-Amino-3-phenylpropanoic acidFEMA No. 3726NSC 9959DTXSID9023463d,l-phenylalanineEINECS 205-756-7CCRIS 8601
Show more names
3-AMINO-3-PHENYLPROPANOIC ACIDH-DL-PHE-OHDL-PHENYALANINE3 AMINO-PHENYLPROPIONIC ACIDD,L-PHEDLPA 375FEMA 3726DL-Phenylalani
AI3-18436PHENYLALANINE DL8P946UF12SNSC-9959DL-PHENYLALANINE [FCC]DTXCID103463DL-PHENYLALANINE [FHFI]DL-PHENYLALANINE [WHO-DD]

Database identifiers

CAS
150-30-1、30394-07-1、63-91-2、673-06-3
PubChem CID
994
DTXSID
DTXSID9023463
ChEMBL
CHEMBL25080
ChEBI
CHEBI:28044
UNII
8P946UF12S
EC Number
205-756-7
Nikkaji
J1.258K

Properties

Computed structural properties

XLogP
-1.5
Topological polar surface area
63.3 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
3
Rotatable bonds
3
Heavy atoms
12

Experimental & physicochemical properties

Chemical ClassesBiological Agents -> Amino Acids and Derivatives
DrugsPharmaceuticals
Food AdditivesFLAVOR ENHANCER, FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Flavoring AgentsEU Flavoring substances
Solubility · 2 items

Soluble in water and dilute mineral acid and alkali hydroxide solutions

Slightly soluble (in ethanol)

Vapor Pressure0.00000005 [mmHg]

Physicochemical properties

Melting point
266 · 266-267 °C (dec.) (lit.)
Boiling point
293.03 °C · 293.03°C (rough estimate)
Density
1.1603 · 1.1603 (rough estimate)
refractive index
1.52 · 1.5200 (estimate)
FEMA
3726 · 3726 | D,L-PHENYLALANINE
FLAVIS Number
17.017 · 17.017 | D,L-Phenylalanine

Safety & regulation

GHS classification

GHS Classification · 3 items

This chemical does not meet GHS hazard criteria for 99.1% (112 of 113) of all reports.

Not Classified

Aggregated GHS information provided per 113 reports by companies from 2 notifications to the ECHA C&L Inventory.

Hazard information

Regulatory Information · 3 items

Chemical: DL-Phenylalanine

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

Phenylalanine: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - DL-Phenylalanine: Human health tier I assessment
Hazards SummarySafe when used as a flavoring agent in food; [EFSA] Not considered hazardous by GHS classification; [Sigma-Aldrich MSDS] See Phenylalanine.
Hazard Classes and CategoriesNot Classified

Safety data

PPE
Eyeshields, Gloves, type N95 (US)
wgk
3
tsca
TSCA listed
hs_code
29224995
risk_code
36/37/38-34
Signal word
Warning

Chemistry & industry

Uses & manufacturing

UsesUsed as a component of aspartame and as a nutrient; [Merck Index] Used as a flavoring agent; [FDA]
Use Classification · 2 items

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

General Manufacturing InformationPhenylalanine: ACTIVE
Applications · 6 items

DescriptionAs an essential amino acid, phenylalanine is necessary for the production of tyrosine in human body, which cannot be synthesized from more basic substances in humans and other animals, meaning that it is obtained only by ingestion of phenylalanine or phenylalanine- containing proteins, which is particularly rich in eggs, chicken, liver, beef, breast milk of mammals, and soybeans, etc. There are three forms of phenylalanine: L-phenylalanine, the natural form found in protein-rich foods, D-phenylalanine, the synthetic mirror image and DL-Phenylalanine (DLPA), the mixture of both forms made in the laboratory that can maximize benefits. DLPA is manufactured for medical, feed, and nutritional applications, which can be used to produce food and drink products. It is marketed as a nutritional supplement due to its reputed analgesic and antidepressant effects. Besides, it can be applied for depression, attention deficit-hyperactivity disorder (ADHD), Parkinson's disease, chronic pain, osteoarthritis, rheumatoid arthritis, alcohol withdrawal symptoms, and a skin disease called vitiligo.

OccurrencePhenylalanine is the most commonly found aromatic amino acid in proteins and enzymes with a molar ratio of 3.5% compared to the other amino acids, about double the amount of any other aromatic amino acid. Reported found in white bread, macaroni, egg noodles, corn flakes, corn grits, oatmeal, wheat bran, wheat flakes, shredded wheat, barley, brown rice, rye flour, whole grain wheat flour, buttermilk, blue cheese, cheddar cheese, cottage cheese, cream cheese, parmesan cheese, bacon, cured ham, frankfurters, pork sausage, canned red kidney beans, canned sweet corn, canned peas, canned lima beans, canned potatoes, canned asparagus, canned snap beans, canned beets, beef, lamb, fresh ham, veal round, beef liver, chicken, chicken liver, turkey and other natural sources.

UsesDL-Phenylalanine may be used in the synthesis of ternary piroxicam (Pir; 4-hydroxy-2-methyl-N-(2-pyridyl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide) complexes of Fe(II), Fe(III), Co(II), Ni(II), Cu(II) and Zn(II).

UsesComponent of the artificial sweetner aspartame, q.v.; nutrient.

UsesDL-Phenylalanine is used torelieve cases of minor depressionand other mood issues as well as and physical discomforts and pain. It is also used in acupunctureanesthesia, alcohol withdrawal.

General DescriptionPhenylalanine is an amino acid. It participates in the preparation of ternary piroxicam complexes of Fe(II), Fe(III), Co(II), Ni(II), Cu(II) and Zn(II). Characterization of these complexes by elemental analyses, molar conductance, IR, UV-Vis, magnetic moment, diffuse reflectance and X-ray powder diffraction methods has been conducted. Crystalline DL-phenylalanine was prepared by its reduction in silica gel by solubility method.

Preparation methods

PreparationBy microbial bioengineered process.

Suppliers50 total

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北京华美互利生物化工010-56205725 · [email protected]
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上海如吉生物科技发展有限公司+86-21-65211385-8001 36031160 · [email protected]

Additional notes

DefinitionChEBI: An aromatic amino acid that is alanine in which one of the methyl hydrogens is substituted by a phenyl group.

Related reactions

140 records

Linked notes

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