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Home> Encyclopedia >Food Additives>Pharmaceutical Intermediates>Vitamins, Amino Acids and Coenzymes
DL-Phenylalanine structure
DL-Phenylalanine structure


Iupac Name:2-amino-3-phenylpropanoic acid
CAS No.: 150-30-1
Molecular Weight:165.192
Modify Date.: 2022-11-07 16:16
Introduction: As 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. View more+
1. Names and Identifiers
1.1 Name
1.2 Synonyms

(±)-3-Phenyl-2-aminopropanoic acid (±)-Phenylalanine (±)-β-Phenyl-α-alanine (2R)-2-azaniumyl-3-phenyl-propanoate 2-Amino-3-phenylpropanoic acid 2-Amino-3-phenylpropionic acid, dl- 2-Azaniumyl-3-phenylpropanoate Alanine, phenyl-, DL- Alanine, phenyl-, DL- (8CI) Alanine, β-phenyl- alpha-Aminohydrocinnamic acid, dl- DL-2-Amino-3-phenylpropanoic acid DL-2-Amino-3-phenylpropionic acid DL-3-Phenylalanine DL-alpha-Amino-beta-phenylpropionic acid DL-beta-Phenyl-alpha-alanine DLPA DL-α-Amino-β-phenylpropionic acid DL-β-Phenyl-α-alanine H-DL-Phe-OH NSC 9959 Phenylalanine DL-form

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1.3 CAS No.
1.4 CID
1.6 Molecular Formula
C9H11NO2 (isomer)
1.7 Inchi
1.8 InChIkey
1.9 Canonical Smiles
1.10 Isomers Smiles
2. Properties
2.1 Density
2.1 Melting point
2.1 Boiling point
307.5°C at 760mmHg
2.1 Refractive index
2.1 Flash Point
2.1 Precise Quality
2.1 PSA
2.1 logP
2.1 Solubility
14.11 g/L (25 ºC)
2.2 Appearance
White crystalline platelets; odourless
2.3 Storage
Ambient temperatures.
2.4 Chemical Properties
DL-Phenylalanine has a sweet taste. It is an essential amino acid that plays a key role in the biosynthesis of other aminoacids and some neurotransmitters.
2.5 Color/Form
Prisms form water
Monoclinic plates, leaflets from warm concentrated aqueous solution; hydrated needles from dilute solutions
2.6 pKa
pK1 2.58; pK2 9.24(at 25℃)
2.7 Water Solubility
14.11 g/L (25 oC)
2.8 Spectral Properties
Specific optical rotation: -35.1 deg at 20 deg C/D (c = 1.94)
Specific optical rotation: +70 deg at 18 deg C/D (water)
IR: 5556 (Sadtler Research Laboratories Prism Collection)
NMR: 16028 (Sadtler Research Laboratories Spectral Collection)
MASS: 107173 (NIST/EPA/MCDC Mass Spectral Database 1990 version)
2.9 Stability
Stable. Incompatible with strong oxidizing agents.
2.10 StorageTemp
Store at RT.
3. Use and Manufacturing
3.1 Definition
ChEBI: An aromatic amino acid that is alanine in which one of the methyl hydrogens is substituted by a phenyl group.
3.2 Purification Methods
dl-Phenylalanine crystallises from H2O or H2O/EtOH in large plates and is dried under vacuum over P2O5. S-Phenylalanine ethyl ester hydrochloride has m 156-158o and [ ] D -7.8o (c 2, H2O) after crystallisation from EtOH/Et2O [Billimoria & Cook J Chem Soc 2328 1949, Beilstein 14 IV 1556]. [Greenstein & Winitz The Chemistry of the Amino Acids J. Wiley, Vol 3 pp 2156-2175 1961, Beilstein 14 III 1229, 14 IV 1553.] DL-Phenylalanine Preparation Products And Raw materials Raw materials
3.3 Usage
Component of the artificial sweetner aspartame, q.v.; nutrient.
4. Safety and Handling
4.1 Hazard Codes
Xi; C
4.1 Risk Statements
4.1 Safety Statements
4.1 Exposure Standards and Regulations
L-Phenylalanine is a food additive permitted for direct addition to food for human consumption, as long as 1) the quantity of the substance added to food does not exceed the amount reasonably required to accomplish its intended physical, nutritive, or other technical effect in food, and 2) any substance intended for use in or on food is of appropriate food grade and is prepared and handled as a food ingredient.
Drug products containing certain active ingredients offered over-the-counter (OTC) for certain uses. A number of active ingredients have been present in OTC drug products for various uses, as described below. However, based on evidence currently available, there are inadequate data to establish general recognition of the safety and effectiveness of these ingredients for the specified uses: phenylalanine is included in weight control drug products.
Phenylalanine used as a nutrient and/or dietary supplement in animal drugs, feeds, and related products is generally recognized as safe when used in accordance with good manufacturing or feeding practice.
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4.2 Octanol/Water Partition Coefficient
log Kow = -1.38
4.3 DisposalMethods

SRP: Criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
SRP: At the time of review, regulatory criteria for small quantity disposal are subject to significant revision, however, household quantities of waste pharmaceuticals may be managed as follows: Mix with wet cat litter or coffee grounds, double bag in plastic, discard in trash.
SRP: Expired or waste pharmaceuticals shall carefully take into consideration applicable DEA, EPA, and FDA regulations. It is not appropriate to dispose by flushing the pharmaceutical down the toilet or discarding to trash. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.

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4.4 Formulations/Preparations
Grades: Technical, FCC [Lewis RJ Sr; Hawley's Condensed Chemical Dictionary 15th ed Wiley (2007)
Available commercially as DL-dihydroxyphenylalanine and as DL-phenylalanine. [Lewis RJ Sr; Hawley's Condensed Chemical Dictionary 15th ed Wiley (2007)
Available commercially as the naturally occurring L(+)-enantiomer
4.5 WGK Germany
4.5 Toxicity
Organic Compound; Amine; Drug; Food Toxin; Dietary Supplement; Micronutrient; Metabolite; Nutraceutical; Household Toxin; Animal Toxin; Natural Compound; Supplement; Amino Acid, Essential

2.Hazard identification

2.1 Classification of the substance or mixture

Not classified.

2.2 GHS label elements, including precautionary statements

Pictogram(s) No symbol.
Signal word

No signal word.

Hazard statement(s)


Precautionary statement(s)








2.3 Other hazards which do not result in classification


9. Other Information
9.0 Usage
DL-Phenylalanine is used to?relieve cases of minor depression?and other mood issues as well as and physical discomforts and pain. It is also used in acupuncture?anesthesia, alcohol withdrawal.
10. Computational chemical data
  • Molecular Weight: 165.192g/mol
  • Molecular Formula: C9H11NO2
  • Compound Is Canonicalized: True
  • XLogP3-AA: null
  • Exact Mass: 165.078978594
  • Monoisotopic Mass: 165.078978594
  • Complexity: 153
  • Rotatable Bond Count: 3
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 3
  • Topological Polar Surface Area: 63.3
  • Heavy Atom Count: 12
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count: 1
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 1
11. Question & Answer
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