(2S)-2-amino-3-phenylpropanoic acid

• ChemBase ID: 7
• Molecular Formular: C9H11NO2
• Molecular Mass: 165.18914
• Monoisotopic Mass: 165.0789786
• SMILES: OC(=O)[C@@H](N)Cc1ccccc1
• Canonical SMILES: N[C@H](C(=O)O)Cc1ccccc1
• InChI: InChI=1S/C9H11NO2/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8H,6,10H2,(H,11,12)/t8-/m0/s1
• InChIKey: COLNVLDHVKWLRT-QMMMGPOBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-3-phenylpropanoic acid
• IUPAC Traditional name: L-phenylalanine
• Synonyms: (2S)-2-Amino-3-phenylpropanoic Acid; (S)-(-)-Phenylalanine; (S)-α-Amino-β-phenylpropionic Acid; (S)-α-Aminohydrocinnamic Acid; (S)-α-Amino-benzenepropanoic Acid; L-2-Amino-3-phenylpropanoic acid; L-PHENYLALANINE, U.S.P.; 2-Amino-3-phenylpropanoic acid; Phenylalanine; (S)-2-Amino-3-phenylpropionic acid; L-Phenylalanine; (S)-alpha-Amino-beta-phenylpropionic acid; L-Phenylalanine; D-Phenylalanine; L-2-Amino-3-phenyl propionic acid; H-Phe-OH; (S)-2-氨基-3-苯丙酸; L-苯基丙氨酸

Database IDs

• CAS Number: 150-30-1; 63-91-2
• EC Number: 200-568-1
• MDL Number: MFCD00004270; MFCD00064227
• Beilstein Number: 1910408
• Merck Index: 147271
• PubChem SID: 24887247; 24898657; 24898971; 46505708; 24901797; 24898274; 160963470
• PubChem CID: 994; 6140
• CHEBI ID: 58095
• CHEMBL: 301523
• Chemspider ID: 5910
• DrugBank ID: DB00120
• FEMA ID: 3585
• KEGG ID: D00021
• Unique Ingredient Identifier: 8P946UF12S
• Wikipedia Title: Phenylalanine
• Council of Europe Number: 10488
• Flavis Number: 17.018

CALCULATED PROPERTIES

JChem

• Acid pKa: 2.4692297
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -1.1845678
• LogD (pH = 7.4): -1.1878599
• Log P: -1.1844385
• Molar Refractivity: 45.1163 cm^3
• Polarizability: 17.887253 Å^3
• Polar Surface Area: 63.32 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -1.35
• LOG S: -1.6
• Solubility (Water): 4.14e+00 g/l

PROPERTIES

Physical Property

• Solubility: 1 M HCl: soluble50 mg/mL; H2O: soluble0.1 M at 20 °C, clear, colorless; H2O: soluble0.1 M, clear, colorless; Slight (0.1-1%); Water
• Apperance: powder; White to Off-White Solid
• Melting Point: 227°C dec.; 243-245°C; 270-275 °C (dec.)(lit.); 270-275°C; 273°C; 279-285°C
• Optical Rotation: [α]/D -34.0±0.5°, c = 2 in H2O; [α]20/D -34±0.5°, c = 2% in H2O; [α]20/D -34±1°, c = 2% in H2O; [α]25/D -32.7°, c = 2 in H2O; [α]25/D -33.5°, c = 2 in H2O; -34 (c=2 in water)
• Hydrophobicity(logP): -1.4
• pKa: 1.83 (carboxyl), 9.13 (amino)
• pH: 5.0-7.0 (25 °C, 0.1 M in H2O)

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• Storage Warning: IRRITANT; Irritant
• RTECS: AY7535000
• German water hazard class: 1
• TSCA Listed: false; 是
• NFPA704:
  

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• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Regulation Compliance: FCC; FDA 21 CFR (172.320)

Pharmacology Properties

• Gene Information: human ... CA1(759), CA14(23632), CA2(760), CA4(762), CA5A(763), CA7(766)

Product Information

• Purity: >99%; ≥98%; ≥98.5%; ≥99.0%; ≥99.0% (NT); 95+%; 97%; 98%; 98.5-101.0%; 99%
• Grade: analytical standard; certified reference material; EP; JP; Kosher; NI; PharmaGrade; reagent grade; SAJ special grade; TraceCERT®; USP
• Optical Purity: ee: 98% (GLC)
• Suitability: meets EP, JP, USP testing specifications; suitable for cell culture; suitable for manufacturing use
• Ignition Residue: ≤0.1% (as SO4)
• Impurities: ≤0.3% foreign amino acids; 8.5%±0.2% total nitrogen acc. to Kjeldahl; endotoxin, tested; insoluble matter, passes filter test
• Cation Traces: Al: ≤5 mg/kg; As: ≤0.1 mg/kg; Ba: ≤5 mg/kg; Bi: ≤5 mg/kg; Ca: ≤10 mg/kg; Cd: ≤5 mg/kg; Co: ≤5 mg/kg; Cr: ≤5 mg/kg; Cu: ≤5 mg/kg; Fe: ≤5 mg/kg; K: ≤50 mg/kg; Li: ≤5 mg/kg; Mg: ≤5 mg/kg; Mn: ≤5 mg/kg; Mo: ≤5 mg/kg; Na: ≤50 mg/kg; NH4+: ≤100 mg/kg; Ni: ≤5 mg/kg; Pb: ≤5 mg/kg; Sr: ≤5 mg/kg; Zn: ≤5 mg/kg
• Antion Traces: chloride (Cl-): ≤50 mg/kg; sulfate (SO42-): ≤100 mg/kg; sulfate (SO42-): ≤200 mg/kg
• Biological Source: from non-animal source
• Loss on Drying: ≤0.1% loss on drying; ≤0.1% loss on drying, 110°C; ≤0.2% loss on drying, 110 °C
• Quality Level: GMP-COMPENDIA; PREMIUM
• Product Line: BioUltra
• abs.: absorption0.1M/274 nm, H2O cut-off
• Linear Formula: C6H5CH2CH(NH2)CO2H

DETAILS

MP Biomedicals - 05220616

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02199540

White powder.

MP Biomedicals - 02102623

Crystalline
Purity: >99%

MP Biomedicals - 02194723

Cell Culture Reagent
Purity: >99%

DrugBank - DB00120

• Drug Groups: approved; nutraceutical
• Description: An essential aromatic amino acid that is a precursor of melanin; dopamine; noradrenalin (norepinephrine), and thyroxine. [PubChem]
• Indication: L-phenylalanine may be helpful in some with depression. It may also be useful in the treatment of vitiligo. There is some evidence that L-phenylalanine may exacerbate tardive dyskinesia in some schizophrenic patients and in some who have used neuroleptic drugs.
• Pharmacology: Used by the brain to produce Norepinephrine, a chemical that transmits signals between nerve cells and the brain; keeps you awake and alert; reduces hunger pains; functions as an antidepressant and helps improve memory.
• Toxicity: L-phenylalanine will exacerbate symptoms of phenylketonuria if used by phenylketonurics. L-phenylalanine was reported to exacerbate tardive dyskinesia when used by some with schizophrenia.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic. L-phenylalanine that is not metabolized in the liver is distributed via the systemic circulation to the various tissues of the body, where it undergoes metabolic reactions similar to those that take place in the liver.
• Absorption: Absorbed from the small intestine by a sodium dependent active transport process.
• External Links: Wikipedia; PDRhealth

Sigma Aldrich - P5482

Packaging
10 mg in autosmp vl

Sigma Aldrich - 78019

Other Notes
Growth requirement of various microorganisms1.

Sigma Aldrich - P8740

Packaging
Manufactured and Packaged under cGMP

Sigma Aldrich - W358509

Packaging
1 kg in poly bottle
1 sample in glass bottle
5, 10 kg in fiber drum

Sigma Aldrich - P2126

Packaging
1 kg in poly bottle
100, 500 g in poly bottle

Sigma Aldrich - 40541

Analysis Note
This certified reference material (CRM) is produced and certified in accordance with ISO/IEC 17025 and ISO Guide 34. This CRM is traceable to NIST SRM.
General description
Certified content by quantitative NMR incl. uncertainty and expiry are given in the certificate.Download your certificate at: http://www.sigma-aldrich.com.
Legal Information
TraceCERT is a registered trademark of Sigma-Aldrich Co. LLC

Toronto Research Chemicals - P319415

L-Phenylalanine is an essential amino acid. L-Phenylalanine is biologically converted into L-tyrosine, another one of the DNA-encoded amino acids, which in turn is converted to L-DOPA and further converted into dopamine, norepinephrine, and epinephrine. L

REFERENCES

• Hollunger, G. et al.: Acta Pharmacol. Toxicol., 34, 391 (1974)
• Bagchi, S.P. et al.: Biochem. Pharmacol., 26, 900 (1974)
• Other amino acids have been resolved by crystallization of their complexes with L-phenylalanine, and decomplexation with activated carbon: Chem. Lett., 113 (1984).
• Formation of the N,N-dibenzyl benzyl ester by reaction with benzyl bromide and base, followed by LAH reduction and Swern oxidation, lead to the N,N-dibenzyl (S)-ɑ-amino aldehyde, a useful chiral intermediate: Org. Synth., 76, 110 (1998).