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
Show more names
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
- Formal charge
- 0
- Complexity
- 153
Experimental & physicochemical properties
Solubility
Soluble in water and dilute mineral acid and alkali hydroxide solutions
Slightly soluble (in ethanol)
Physical Description
Solid; [Merck Index] White powder; [Sigma-Aldrich MSDS]
White crystalline platelets; odourless
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
- storage temp.
- Store at RT.
- solubility
- Water (Sparingly, Sonicated)
- form
- Powder
- pka
- 1 · pK1 2.58; pK2 9.24(at 25℃)
- color
- White
- Odor
- odorless
- Odor Type
- odorless
- biological source
- synthetic
- Water Solubility
- 14.11 g/L · 14.11 g/L (25 ºC)
- Merck
- 14 · 14,7271
- JECFA Number
- 1432 · 1432
- BRN
- 1910407 · 1910407
- Stability
- Stable. Incompatible with strong oxidizing agents.
- Major Application
- peptide synthesis
- Cosmetics Ingredients Functions
- FRAGRANCESKIN CONDITIONINGHAIR CONDITIONING
- InChI
- 1S/C9H11NO2/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8H,6,10H2,(H,11,12)
- InChIKey
- COLNVLDHVKWLRT-UHFFFAOYSA-N
- SMILES
- NC(Cc1ccccc1)C(O)=O
- LogP
- 0.24 · 0.24
- CAS DataBase Reference
- 150 · 150-30-1(CAS DataBase Reference)
- Substances Added to Food (formerly EAFUS)
- DL-PHENYLALANINE
- FDA UNII
- 8 P946UF12S · 8P946UF12S
- NIST Chemistry Reference
- L-Phenylalanine(150-30-1)
- EPA Substance Registry System
- Phenylalanine (150-30-1)
- UNSPSC Code
- 12352209 · 12352209
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319
- Precautionary statements
- 264 · P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313
- PPE
- 95 · Eyeshields, Gloves, type N95 (US)
- Hazard Codes
- Xi,C
- Risk Statements
- 36 · 36/37/38-34
- Safety Statements
- 37 · 37/39-24/25-45-36/37/39-27-26
- WGK Germany
- 3 · 3
- Hazard Note
- Irritant
- TSCA
- TSCA listed
- HS Code
- 29224995 · 29224995
- Storage Class
- 11 · 11 - Combustible Solids
Safety & regulation
GHS classification
GHS Classification
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
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
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
- Symbol(GHS)
- GHS07
- hazard_code
- Xi,C
- hazard_note
- Irritant
- safety_code
- 37/39-24/25-45-36/37/39-27-26
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319
- Precautionary statements
- P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313
Chemistry & industry
Uses & manufacturing
Use Classification
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Applications
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.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
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
Linked notes
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