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DL-Tryptophan

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Name

DL-Tryptophan

EINECS 200-194-9
CAS No. 54-12-6 Density 1.363 g/cm3
PSA 79.11000 LogP 1.82260
Solubility Water: 10 g/L (20 °C) Melting Point 289-290 °C
Formula C11H12N2O2 Boiling Point 447.908 °C at 760 mmHg
Molecular Weight 204.228 Flash Point 224.687 °C
Transport Information N/A Appearance Wite or off-white powder or crystal
Safety 24/25-36/37/39-36-26 Risk Codes 22-36/37/38-37/38-41
Molecular Structure Molecular Structure of 54-12-6 (DL-Tryptophan) Hazard Symbols IrritantXi
Synonyms

Tryptophan, DL-(8CI);Racemic tryptophan;1H-Indole-3-alanine;DL-Tryptophane;DL-a-Amino-3-indolepropionic acid;NSC 13118;CCRIS 719;UNII-X9U7434L7A;AI3-24395;DL-alpha-Amino-3-indolepropionic acid;(+-)-Tryptophan;

Article Data 62

DL-Tryptophan Synthetic route

70380-01-7

DL-γ-glutamaldehydic acid dimethyl acetal

59-88-1

phenylhydrazine hydrochloride

Conditions
ConditionsYield
With sulfuric acid In water for 1h; Heating;85%
104331-05-7

rac-3-(1H-indol-3-yl)-2-(benzoylamino)propionic acid methyl ester

Conditions
ConditionsYield
In potassium hydroxide hydrolysis;70%
60438-65-5

α-(hydroxyimino)-β-(indol-3-yl)propionic acid

Conditions
ConditionsYield
With ethanol; nickel Hydrogenation;
With ammonia; water at 60℃;
117490-34-3

5-(3-indolylmethylene)hydantoin

Conditions
ConditionsYield
With diammonium sulfide at 100℃;
With diammonium sulfide at 150℃;
860375-04-8

formylamino-indol-3-ylmethyl-malonic acid

Conditions
ConditionsYield
With sodium hydroxide; water
4354-88-5

acetylamino-indol-3-ylmethyl-malonic acid

Conditions
ConditionsYield
With sulfuric acid; water
Multi-step reaction with 2 steps
1: H2O
2: NaOH; water
View Scheme
64258-95-3

ethyl 2-formamido-3-(3-indolyl)-2-carbethoxypropionate

Conditions
ConditionsYield
With sodium hydroxide; water at 120℃; anschl. mit Essigsaeure;
Multi-step reaction with 2 steps
1: aq.-ethanolic NaOH
2: H2O; NaOH
View Scheme
854885-91-9

Nα-ethoxycarbonyl-DL-tryptophan-nitrile

Conditions
ConditionsYield
With hydrogenchloride; water; acetic acid

indol-3-ylmethyl-phthalimido-malonic acid diethyl ester

Conditions
ConditionsYield
With sodium hydroxide; water
149828-46-6

Nα-ethoxycarbonyl-DL-tryptophan-ethyl ester

Conditions
ConditionsYield
With sodium hydroxide; ethanol; water

DL-Tryptophan Consensus Reports

Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

DL-Tryptophan Specification

The DL-Tryptophan with CAS registry number of 54-12-6 is also known as Tryptophan. The IUPAC name is 2-Amino-3-(1H-indol-3-yl)propanoic acid. It belongs to product categories of Amino Acids Derivatives; Tryptophan [Trp, W]; alpha-Amino Acids; Amino Acids; Biochemistry; Indoles; Tryptophans; Alphabetical Listings; Stable Isotopes. Its EINECS registry number is 200-194-9. In addition, the formula is C11H12N2O2 and the molecular weight is 204.23. This chemical is a white or off-white powder or crystal and should be stored in sealed containers away from light.

Physical properties about DL-Tryptophan are: (1)ACD/LogP: 0.70; (2)ACD/BCF (pH 5.5): 1; (3)ACD/BCF (pH 7.4): 1; (4)ACD/KOC (pH 5.5): 1; (5)ACD/KOC (pH 7.4): 1; (6)#H bond acceptors: 4; (7)#H bond donors: 4; (8)#Freely Rotating Bonds: 4; (9)Index of Refraction: 1.698; (10)Molar Refractivity: 57.769 cm3; (11)Molar Volume: 149.875 cm3; (12)Surface Tension: 71.162 dyne/cm; (13)Density: 1.363 g/cm3; (14)Flash Point: 224.687 °C; (15)Enthalpy of Vaporization: 74.437 kJ/mol; (16)Boiling Point: 447.908 °C at 760 mmHg.

Preparation of DL-Tryptophan: it is prepared by reaction of indole with α-acetyl amino acid. Firstly, the reaction occurs with media of glacial acetic acid and acetic anhydride. After the reaction, the mixture solution is adjusted to alkaline by NaOH and extracted by ether. Secondly, the reaction mixture is extracted by dilute sodium hydroxide for three times. The sodium hydroxide solution is combined and a few grains of sodium bisulfite is added to the solution. Acetyl-DL-tryptophan is generated by cooling and adding concentrated hydrochloric acid. At last, acetyl-DL-tryptophan is refluxed with 10% sodium hydroxide solution to obtain the product.

Uses of DL-Tryptophan: it is not only used for biochemical research but also used as nutritional supplement and antioxidant. it is used to produce 2-indol-3-yl-ethylamine. The reaction occurs with solvent diphenyl ether and other condition of heating for 10 hours. The yield is about 63%.

DL-Tryptophan is used to produce 2-indol-3-yl-ethylamine.

When you are using this chemical, please be cautious about it. As a chemical, it is irritating to eyes, respiratory system and skin. What's more, it is harmful if swallowed and has risk of serious damage to eyes. During using it, wear suitable protective clothing, gloves and eye/face protection. Avoid contact with skin and eyes. If contact with eyes accidently, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
1. Canonical SMILES: C1=CC=C2C(=C1)C(=CN2)CC(C(=O)O)N
2. InChI: InChI=1S/C11H12N2O2/c12-9(11(14)15)5-7-6-13-10-4-2-1-3-8(7)10/h1-4,6,9,13H,5,12H2,(H,14,15)
3. InChIKey: QIVBCDIJIAJPQS-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal > 1gm/kg (1000mg/kg)   Biochemical Pharmacology. Vol. 15, Pg. 2134, 1966.

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