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DL-Phenylalanine

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Name

DL-Phenylalanine

EINECS 205-756-7
CAS No. 150-30-1 Density 1.202 g/cm3
PSA 63.32000 LogP 1.34130
Solubility 14.11 g/L (25 °C) in water Melting Point 266-267 °C
Formula C9H11NO2 Boiling Point 307.5 °C at 760 mmHg
Molecular Weight 165.192 Flash Point 139.771 °C
Transport Information N/A Appearance white crystalline powder
Safety 37/39-24/25-45-36/37/39-27-26 Risk Codes 36/37/38-34
Molecular Structure Molecular Structure of 150-30-1 (DL-3-Phenylalanine) Hazard Symbols IrritantXi,CorrosiveC
Synonyms

alpha-Aminohydrocinnamic acid, dl-;H-DL-Phe-OH;2-Amino-3-phenylpropionic acid, dl-;Phenylalanine DL-form;Alanine, phenyl-, DL- (8CI);DL-alpha-Amino-beta-phenylpropionic acid;(2R)-2-azaniumyl-3-phenyl-propanoate;

Article Data 164

DL-Phenylalanine Synthetic route

3235-26-5

2-(N-acetylamino)-2-benzylpropanedioic diethyl ester

150-30-1

Phenylalanine

Conditions
ConditionsYield
With hydrogenchloride; water at 90℃; for 0.166667h; Microwave irradiation;98%
With water; hydrogen cation Heating;82%
With hydrogen bromide anschliessend Erwaermen mit wss. Schwefelsaeure;
With sodium hydroxide anschliessend Erwaermen mit wss. Schwefelsaeure;
With hydrogenchloride In water at 110℃; Microwave irradiation;
63-91-2

L-phenylalanine

150-30-1

Phenylalanine

Conditions
ConditionsYield
salicylaldehyde In acetic acid at 100℃; for 1h;94%
With barium dihydroxide; water at 155 - 160℃;
With hydrogenchloride; ethanethiol at 110℃; Rate constant; various times;
100-39-0

benzyl bromide

C21H15N3O3(2-)*Ni(2+)

150-30-1

Phenylalanine

Conditions
ConditionsYield
With potassium hydroxide; C-7 In dichloromethane at 20℃;90%
126181-40-6

2-(Benzhydryl-amino)-3-phenyl-propionic acid tert-butyl ester

150-30-1

Phenylalanine

Conditions
ConditionsYield
palladium on activated charcoal In acetic acid Heating;89%
Multi-step reaction with 2 steps
1: 60 percent / formic acid / 10percent Pd/C / methanol
2: trifluoroacetic acid
View Scheme

2-Benzyl-2-benzyloxycarbonylamino-malonic acid dimethyl ester

150-30-1

Phenylalanine

Conditions
ConditionsYield
With water; hydrogen cation Heating;88%

2-[2-Benzoylamino-1-methoxy-eth-(Z)-ylideneamino]-3-phenyl-propionic acid

A

150-30-1

Phenylalanine

B

1205-08-9

methyl hippurate

Conditions
ConditionsYield
With hydrogenchloride In diethyl ether Yields of byproduct given;A n/a
B 69%

2-[2-Benzoylamino-1-ethoxy-eth-(Z)-ylideneamino]-3-phenyl-propionic acid

A

150-30-1

Phenylalanine

B

1499-53-2

ethyl hippurate

Conditions
ConditionsYield
With hydrogenchloride In diethyl etherA n/a
B 63%
154279-16-0

(±)-N-Boc-2-amino-2-benzylacetonitrile

150-30-1

Phenylalanine

Conditions
ConditionsYield
With hydrogenchloride In methanol for 6h; Heating;50%
81477-94-3

N-(diphenylmethylene)glycine tert-butyl ester

100-39-0

benzyl bromide

150-30-1

Phenylalanine

Conditions
ConditionsYield
Stage #1: N-(diphenylmethylene)glycine tert-butyl ester; benzyl bromide With sodium hydroxide; (R)-2-amino-2'-hydroxy-1,1'-binaphthyl In dichloromethane at 20℃; for 1h;
Stage #2: With hydrogenchloride In methanol; water Heating;
50%
140-10-3

(E)-3-phenylacrylic acid

150-30-1

Phenylalanine

Conditions
ConditionsYield
With ammonium bicarbonate Ambient temperature; detonation; also with (NH4)2CO3;45%
With ammonium bicarbonate Ambient temperature; detonation; also with (NH4)2CO3;45%
With ammonium hydroxide; Anabaena variabilis phenylalanine ammonia lyase at 30℃; pH=9.5; Kinetics; Enzymatic reaction;
With ammonium hydroxide; phenylalanine ammonia-lyase from Anabaena variabilis N347A mutant In aq. buffer at 35℃; for 12h;
With phenylalanine ammonia lyase from Anabaena variabilis; ammonium carbamate at 30℃; for 22h; pH=9.9; Catalytic behavior; pH-value; Enzymatic reaction;99 %Chromat.

DL-Phenylalanine History

In 1961,J. Heinrich Matthaei and Marshall W. Nirenberg discovered the genetic codon for phenylalanine was firstly . They pointed out that by using m-RNA to insert multiple uracil repeats into the bacterium E. coli, the bacterium produced a new protein consisting solely of repeated phenylalanine amino acids. This discovery caused the determination of the relationship between RNA and amino acids, which was fundamental to the understanding of the Genetic Code.

DL-Phenylalanine Consensus Reports

Dl-phenylalanine is reported in EPA TSCA Inventory.

DL-Phenylalanine Specification

The IUPAC name of DL-Phenylalanine is 2-amino-3-phenylpropanoic acid. With the CAS registry number 150-30-1, it is also named as Phenylalanine DL-form. The product's categories are Food & Feed Additives; Amino Acids Series; Amino Acids; Chiral; Organic Acids; Phenylalanine [Phe, F]; alpha-Amino Acids; Biochemistry; Amino Acids; Phenlalnine; Amino Acid; Food Additive; Pharmaceutical Intermediate. Besides, it is white crystalline powder, which should be sealed in a cool, dry place. It is stable, and incompatible with strong oxidizing agents. In addition, its molecular formula is C9H11NO2 and molecular weight is 165.19.

The other characteristics of this product can be summarized as: (1)EINECS: 205-756-7; (2)ACD/LogP: 0.24; (3)# of Rule of 5 Violations: 0; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 1; (7)ACD/KOC (pH 7.4): 1; (8)#H bond acceptors: 3; (9)#H bond donors: 3; (10)#Freely Rotating Bonds: 4; (11)Index of Refraction: 1.576; (12)Molar Refractivity: 45.493 cm3; (13)Molar Volume: 137.437 cm3; (14)Surface Tension: 53.597 dyne/cm; (15)Density: 1.202 g/cm3; (16)Flash Point: 139.771 °C; (17)Melting point: 266-267 °C; (18)Water solubility: 14.11 g/L (25 °C); (19)Enthalpy of Vaporization: 57.873 kJ/mol; (20)Boiling Point: 307.5 °C at 760 mmHg; (21)Vapour Pressure: 0 mmHg at 25 °C.

Preparation of DL-Phenylalanine: this chemical can be prepared by the reaction of Acetyl-L-phenylalanine with HCl. Furthermore, it is produced by acetylamino-benzyl-malonic acid diethyl ester.



This reaction needs H+, water by heating. The yield is 82 %.

Uses of DL-Phenylalanine: this chemical is used as a dietary supplement and as a nutritional supplement for its supposed analgesic and antidepressant activities. Additionally, it can react with acetic acid anhydride to get N-(1-benzyl-2-oxo-propyl)-acetamide.



This reaction needs pyridine by heating. The yield is 76 %.

When you are using this chemical, please be cautious about it as the following: it may cause burns. It is also irritating to eyes, respiratory system and skin. In case of contact with eyes, please rinse immediately with plenty of water and seek medical advice. And you should wear suitable protective clothing, gloves and eye/face protection to avoid contact with skin and eyes. Moreover, please take off immediately all contaminated clothing. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)

People can use the following data to convert to the molecule structure.
(1)Canonical SMILES: C1=CC=C(C=C1)CC(C(=O)O)N
(2)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)
(3)InChIKey: COLNVLDHVKWLRT-UHFFFAOYSA-N

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