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150-30-1 molecular structure
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(2S)-2-amino-3-phenylpropanoic acid

ChemBase ID: 7
Molecular Formular: C9H11NO2
Molecular Mass: 165.18914
Monoisotopic Mass: 165.0789786
SMILES and InChIs

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

Cite this record

CBID:7 http://www.chembase.cn/molecule-7.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(2S)-2-amino-3-phenylpropanoic acid
IUPAC Traditional name
L-phenylalanine
Synonyms
(S)-alpha-Amino-beta-phenylpropionic acid
L-Phenylalanine
D-Phenylalanine
2-Amino-3-phenylpropanoic acid
Phenylalanine
L-2-Amino-3-phenylpropanoic acid
(S)-2-Amino-3-phenylpropionic acid
L-Phenylalanine
L-PHENYLALANINE, U.S.P.
(2S)-2-Amino-3-phenylpropanoic Acid
(S)-(-)-Phenylalanine
(S)-α-Amino-β-phenylpropionic Acid
(S)-α-Aminohydrocinnamic Acid
(S)-α-Amino-benzenepropanoic Acid
H-Phe-OH
L-2-Amino-3-phenyl propionic acid
(S)-2-氨基-3-苯丙酸
L-苯基丙氨酸
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
46505708
24898657
160963470
24898971
24901797
24898274
PubChem CID
6140
994
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

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 2.4692297  H Acceptors
H Donor LogD (pH = 5.5) -1.1845678 
LogD (pH = 7.4) -1.1878599  Log P -1.1844385 
Molar Refractivity 45.1163 cm3 Polarizability 17.887253 Å3
Polar Surface Area 63.32 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P -1.35  LOG S -1.6 
Solubility (Water) 4.14e+00 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
1 M HCl: soluble50 mg/mL expand Show data source
H2O: soluble0.1 M at 20 °C, clear, colorless expand Show data source
H2O: soluble0.1 M, clear, colorless expand Show data source
Slight (0.1-1%) expand Show data source
Water expand Show data source
Apperance
powder expand Show data source
White to Off-White Solid expand Show data source
Melting Point
227°C dec. expand Show data source
243-245°C expand Show data source
270-275 °C (dec.)(lit.) expand Show data source
270-275°C expand Show data source
273°C expand Show data source
279-285°C expand Show data source
Optical Rotation
[α]/D -34.0±0.5°, c = 2 in H2O expand Show data source
[α]20/D -34±0.5°, c = 2% in H2O expand Show data source
[α]20/D -34±1°, c = 2% in H2O expand Show data source
[α]25/D -32.7°, c = 2 in H2O expand Show data source
[α]25/D -33.5°, c = 2 in H2O expand Show data source
-34 (c=2 in water) expand Show data source
Hydrophobicity(logP)
-1.4 expand Show data source
pKa
1.83 (carboxyl), 9.13 (amino) expand Show data source
pH
5.0-7.0 (25 °C, 0.1 M in H2O) expand Show data source
Storage Condition
Room Temperature (15-30°C) expand Show data source
Storage Warning
IRRITANT expand Show data source
Irritant expand Show data source
RTECS
AY7535000 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
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German water hazard class
1 expand Show data source
TSCA Listed
false expand Show data source
expand Show data source
NFPA704
NFPA 704 diagram
1
2
0
expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Regulation Compliance
FCC expand Show data source
FDA 21 CFR (172.320) expand Show data source
Gene Information
human ... CA1(759), CA14(23632), CA2(760), CA4(762), CA5A(763), CA7(766) expand Show data source
Purity
>99% expand Show data source
≥98% expand Show data source
≥98.5% expand Show data source
≥99.0% expand Show data source
≥99.0% (NT) expand Show data source
95+% expand Show data source
97% expand Show data source
98% expand Show data source
98.5-101.0% expand Show data source
99% expand Show data source
Grade
analytical standard expand Show data source
certified reference material expand Show data source
EP expand Show data source
JP expand Show data source
Kosher expand Show data source
NI expand Show data source
PharmaGrade expand Show data source
reagent grade expand Show data source
SAJ special grade expand Show data source
TraceCERT® expand Show data source
USP expand Show data source
Optical Purity
ee: 98% (GLC) expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
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Suitability
meets EP, JP, USP testing specifications expand Show data source
suitable for cell culture expand Show data source
suitable for manufacturing use expand Show data source
Ignition Residue
≤0.1% (as SO4) expand Show data source
Impurities
≤0.3% foreign amino acids expand Show data source
8.5%±0.2% total nitrogen acc. to Kjeldahl expand Show data source
endotoxin, tested expand Show data source
insoluble matter, passes filter test expand Show data source
Cation Traces
Al: ≤5 mg/kg expand Show data source
As: ≤0.1 mg/kg expand Show data source
Ba: ≤5 mg/kg expand Show data source
Bi: ≤5 mg/kg expand Show data source
Ca: ≤10 mg/kg expand Show data source
Cd: ≤5 mg/kg expand Show data source
Co: ≤5 mg/kg expand Show data source
Cr: ≤5 mg/kg expand Show data source
Cu: ≤5 mg/kg expand Show data source
Fe: ≤5 mg/kg expand Show data source
K: ≤50 mg/kg expand Show data source
Li: ≤5 mg/kg expand Show data source
Mg: ≤5 mg/kg expand Show data source
Mn: ≤5 mg/kg expand Show data source
Mo: ≤5 mg/kg expand Show data source
Na: ≤50 mg/kg expand Show data source
NH4+: ≤100 mg/kg expand Show data source
Ni: ≤5 mg/kg expand Show data source
Pb: ≤5 mg/kg expand Show data source
Sr: ≤5 mg/kg expand Show data source
Zn: ≤5 mg/kg expand Show data source
Antion Traces
chloride (Cl-): ≤50 mg/kg expand Show data source
sulfate (SO42-): ≤100 mg/kg expand Show data source
sulfate (SO42-): ≤200 mg/kg expand Show data source
Biological Source
from non-animal source expand Show data source
Loss on Drying
≤0.1% loss on drying expand Show data source
≤0.1% loss on drying, 110°C expand Show data source
≤0.2% loss on drying, 110 °C expand Show data source
Quality Level
GMP-COMPENDIA expand Show data source
PREMIUM expand Show data source
Product Line
BioUltra expand Show data source
abs.
absorption0.1M/274 nm, H2O cut-off expand Show data source
Linear Formula
C6H5CH2CH(NH2)CO2H expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC DrugBank DrugBank
MP Biomedicals - 02194723 external link
Cell Culture Reagent
Purity: >99%
MP Biomedicals - 02199540 external link
White powder.
MP Biomedicals - 02102623 external link
Crystalline
Purity: >99%
MP Biomedicals - 05220616 external link
MP Biomedicals Rare Chemical collection
Sigma Aldrich - 78019 external link
Other Notes
Growth requirement of various microorganisms1.
Sigma Aldrich - W358509 external link
Packaging
1 kg in poly bottle
1 sample in glass bottle
5, 10 kg in fiber drum
Sigma Aldrich - P8740 external link
Packaging
Manufactured and Packaged under cGMP
Sigma Aldrich - P5482 external link
Packaging
10 mg in autosmp vl
Sigma Aldrich - 40541 external link
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
Sigma Aldrich - P2126 external link
Packaging
1 kg in poly bottle
100, 500 g in poly bottle
Toronto Research Chemicals - P319415 external link
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
DrugBank - DB00120 external link
Item Information
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

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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).
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PATENTS

PATENTS

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INTERNET

INTERNET

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