CAS 63-91-2|L-Phenylalanine

Introduction：Basic information about CAS 63-91-2|L-Phenylalanine, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. L-Phenylalanine BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
MUTATION DATA
5. Safety Information
6. Customs
7. Articles233
8. Synonyms

Common Name	L-Phenylalanine
CAS Number	63-91-2	Molecular Weight	165.189
Density	1.2±0.1 g/cm3	Boiling Point	307.5±30.0 °C at 760 mmHg
Molecular Formula	C₉H₁₁NO₂	Melting Point	270-275ºC (dec.)(lit.)
MSDS	USA	Flash Point	139.8±24.6 °C

Names

Name	L-phenylalanine
Synonym	More Synonyms

L-Phenylalanine BiologicalActivity

Description	L-Phenylalanine is an antagonist at α2δ calcium channels with a Ki of 980 nM. IC50 Value: 980 nM [1]Target: Calcium ChannelL-Phenylalanine (LPA) is an electrically neutral amino acid, one of the twenty common amino acids used to biochemically form proteins. In the brain, L-phenylalanine is a competitive antagonist at the glycine binding site of NMDA receptor and at the glutamate binding site of AMPA receptor [2, 3]. At the glycine binding site of NMDA receptor L-phenylalanine has an apparent equilibrium dissociation constant (KB) of 573 ?M estimated by Schild regression [4] which is considerably lower than brain L-phenylalanine concentration observed in untreated human phenylketonuria [5]. L-Phenylalanine also inhibits neurotransmitter release at glutamatergic synapses in hippocampus and cortex with IC50 of 980 nM, a brain concentration seen in classical phenylketonuria, whereas D-phenylalanine has a significantly smaller effect [3].
Related Catalog	Signaling Pathways >>Membrane Transporter/Ion Channel >>Calcium ChannelResearch Areas >>Metabolic DiseaseNatural Products >>Phenylpropanoids
References	[1]. Mortell, K.H., et al., Structure-activity relationships of alpha-amino acid ligands for the alpha2delta subunit of voltage-gated calcium channels. Bioorg Med Chem Lett, 2006. 16(5): p. 1138-41. [2]. Glushakov, A.V., et al., Specific inhibition of N-methyl-D-aspartate receptor function in rat hippocampal neurons by L-phenylalanine at concentrations observed during phenylketonuria. Mol Psychiatry, 2002. 7(4): p. 359-67. [3]. Glushakov, A.V., et al., L-phenylalanine selectively depresses currents at glutamatergic excitatory synapses. J Neurosci Res, 2003. 72(1): p. 116-24. [4]. Glushakov, A.V., et al., Long-term changes in glutamatergic synaptic transmission in phenylketonuria. Brain, 2005. 128(Pt 2): p. 300-7. [5]. Moller, H.E., et al., Brain imaging and proton magnetic resonance spectroscopy in patients with phenylketonuria. Pediatrics, 2003. 112(6 Pt 2): p. 1580-3.

Description

L-Phenylalanine is an antagonist at α2δ calcium channels with a Ki of 980 nM. IC50 Value: 980 nM [1]Target: Calcium ChannelL-Phenylalanine (LPA) is an electrically neutral amino acid, one of the twenty common amino acids used to biochemically form proteins. In the brain, L-phenylalanine is a competitive antagonist at the glycine binding site of NMDA receptor and at the glutamate binding site of AMPA receptor [2, 3]. At the glycine binding site of NMDA receptor L-phenylalanine has an apparent equilibrium dissociation constant (KB) of 573 ?M estimated by Schild regression [4] which is considerably lower than brain L-phenylalanine concentration observed in untreated human phenylketonuria [5]. L-Phenylalanine also inhibits neurotransmitter release at glutamatergic synapses in hippocampus and cortex with IC50 of 980 nM, a brain concentration seen in classical phenylketonuria, whereas D-phenylalanine has a significantly smaller effect [3].

Related Catalog

Signaling Pathways >>Membrane Transporter/Ion Channel >>Calcium ChannelResearch Areas >>Metabolic DiseaseNatural Products >>Phenylpropanoids

References

[1]. Mortell, K.H., et al., Structure-activity relationships of alpha-amino acid ligands for the alpha2delta subunit of voltage-gated calcium channels. Bioorg Med Chem Lett, 2006. 16(5): p. 1138-41.

[2]. Glushakov, A.V., et al., Specific inhibition of N-methyl-D-aspartate receptor function in rat hippocampal neurons by L-phenylalanine at concentrations observed during phenylketonuria. Mol Psychiatry, 2002. 7(4): p. 359-67.

[3]. Glushakov, A.V., et al., L-phenylalanine selectively depresses currents at glutamatergic excitatory synapses. J Neurosci Res, 2003. 72(1): p. 116-24.

[4]. Glushakov, A.V., et al., Long-term changes in glutamatergic synaptic transmission in phenylketonuria. Brain, 2005. 128(Pt 2): p. 300-7.

[5]. Moller, H.E., et al., Brain imaging and proton magnetic resonance spectroscopy in patients with phenylketonuria. Pediatrics, 2003. 112(6 Pt 2): p. 1580-3.

Chemical & Physical Properties

Density	1.2±0.1 g/cm3
Boiling Point	307.5±30.0 °C at 760 mmHg
Melting Point	270-275ºC (dec.)(lit.)
Molecular Formula	C₉H₁₁NO₂
Molecular Weight	165.189
Flash Point	139.8±24.6 °C
Exact Mass	165.078979
PSA	63.32000
LogP	1.11
Vapour Pressure	0.0±0.7 mmHg at 25°C
Index of Refraction	1.576
InChIKey	COLNVLDHVKWLRT-QMMMGPOBSA-N
SMILES	NC(Cc1ccccc1)C(=O)O

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: AY7535000

CHEMICAL NAME :: Alanine, phenyl-, L-

CAS REGISTRY NUMBER :: 63-91-2

LAST UPDATED :: 199706

DATA ITEMS CITED :: 18

MOLECULAR FORMULA :: C9-H11-N-O2

MOLECULAR WEIGHT :: 165.21

WISWESSER LINE NOTATION :: QVYZ1R -L

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 5287 mg/kg

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - dyspnea Nutritional and Gross Metabolic - body temperature decrease

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >1322 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 276 gm/kg/13W-C

TOXIC EFFECTS :: Behavioral - alteration of operant conditioning Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 220 gm/kg

SEX/DURATION :: male 2 week(s) pre-mating female 2 week(s) pre-mating - 3 week(s) post-birth

TOXIC EFFECTS :: Reproductive - Effects on Newborn - weaning or lactation index (e.g., # alive at weaning per # alive at day 4) Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 160 gm/kg

SEX/DURATION :: male 2 week(s) pre-mating female 2 week(s) pre-mating - 8 day(s) post-birth

TOXIC EFFECTS :: Reproductive - Effects on Newborn - behavioral

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 192 gm/kg

SEX/DURATION :: male 2 week(s) pre-mating female 2 week(s) pre-mating - 15 day(s) post-birth

TOXIC EFFECTS :: Reproductive - Effects on Newborn - physical

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 21750 mg/kg

SEX/DURATION :: female 15-19 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - other effects to embryo

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 30 gm/kg

SEX/DURATION :: female 10-14 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Effects on Newborn - behavioral

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 7930 mg/kg

SEX/DURATION :: female 8-11 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 1980 mg/kg

SEX/DURATION :: female 9 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - cardiovascular (circulatory) system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 2640 mg/kg

SEX/DURATION :: female 10 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - other effects to embryo

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 6048 mg/kg

SEX/DURATION :: female 8-11 day(s) after conception

TOXIC EFFECTS :: Reproductive - Maternal Effects - other effects Reproductive - Specific Developmental Abnormalities - cardiovascular (circulatory) system Reproductive - Effects on Newborn - biochemical and metabolic

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 30 mg/kg

SEX/DURATION :: female 3 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Maternal Effects - uterus, cervix, vagina

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 33600 mg/kg

SEX/DURATION :: female 1-24 week(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Newborn - behavioral

MUTATION DATA

TYPE OF TEST :: Sister chromatid exchange

TEST SYSTEM :: Human Lymphocyte

DOSE/DURATION :: 10 mg/L

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 280,279,1992 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X5534 No. of Facilities: 792 (estimated) No. of Industries: 4 No. of Occupations: 14 No. of Employees: 19901 (estimated) No. of Female Employees: 14903 (estimated)

Safety Information

Personal Protective Equipment	Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Hazard Codes	C: Corrosive;
Risk Phrases	R36/37/38
Safety Phrases	22-24/25-37/39-45-36/37/39-27-26
RIDADR	NONH for all modes of transport
WGK Germany	3
RTECS	AY7535000
HS Code	29224995

Customs

HS Code	29224995

Articles233

Assessment of protein modifications in liver of rats under chronic treatment with paracetamol (acetaminophen) using two complementary mass spectrometry-based metabolomic approaches.

J. Proteomics 120 , 194-203, (2015)

Liver protein can be altered under paracetamol (APAP) treatment. APAP-protein adducts and other protein modifications (oxidation/nitration, expression) play a role in hepatotoxicity induced by acute o...

Enhanced Indirect Photochemical Transformation of Histidine and Histamine through Association with Chromophoric Dissolved Organic Matter.

Environ. Sci. Technol. 49 , 5511-9, (2015)

Photochemical transformations greatly affect the stability and fate of amino acids (AAs) in sunlit aquatic ecosystems. Whereas the direct phototransformation of dissolved AAs is well investigated, the...

Use of Commercial Dry Yeast Products Rich in Mannoproteins for White and Rosé Sparkling Wine Elaboration.

J. Agric. Food Chem. 63 , 5670-81, (2015)

In sparkling wines, mannoproteins released during yeast autolysis largely affect their final quality. This process is very slow and may take several months. The aim of this work was to study the effec...

Synonyms

Benzenepropanethioic acid,S-phenyl ester

(S)-phenylalanine

L-Phenylalanine

EINECS 200-568-1

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

L-PHENYLALININE

α-Amino-β-phenylpropionic acid, L-

H-Phe-OH

Alanine, 3-phenyl-

L-phenylalanine zwitterion

S-phenylalanine

(S)-(-)-Phenylalanine

Thiohydrozimtsaeurephenylester

(S)-a-Amino-b-phenylpropionic Acid

Alanine, phenyl-, L-

L-2-Amino-3-phenylpropionic acid

(S)-2-Amino-3-phenylpropionic acid

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

C6H5CH2CH(NH2)COOH

(S)-a-Aminohydrocinnamic Acid

Phenylalanine

α-Aminohydrocinnamic acid, L-

(L)-Phenylalanine

Phenylalanine (VAN)

Phenylalanine, L-

Benzenepropanoic acid, α-amino-, (S)-

l-Phe

PhE

phenyl 4-phenylthiobutanoate

S-Phenyl-3-phenylpropanthioat

β-phenyl-L-alanine

(-)-Phenylalanine

(S)-α-Aminobenzenepropanoic acid

MFCD00064227

3-Phenylpropionyl-phenyl-thioether

α-Amino-β-phenylpropionic acid

3-Phenylthiopropionic acid,S-phenyl ester

(S)-A-Aminobenzenepropanoic Acid

Acetylcysteine Impurity 3

Recommended......