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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 | Hazard Symbols | Xi | |
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 |
Conditions | Yield |
---|---|
With sulfuric acid In water for 1h; Heating; | 85% |
rac-3-(1H-indol-3-yl)-2-(benzoylamino)propionic acid methyl ester
Trp
Conditions | Yield |
---|---|
In potassium hydroxide hydrolysis; | 70% |
α-(hydroxyimino)-β-(indol-3-yl)propionic acid
Trp
Conditions | Yield |
---|---|
With ethanol; nickel Hydrogenation; | |
With ammonia; water at 60℃; |
5-(3-indolylmethylene)hydantoin
Trp
Conditions | Yield |
---|---|
With diammonium sulfide at 100℃; | |
With diammonium sulfide at 150℃; |
formylamino-indol-3-ylmethyl-malonic acid
Trp
Conditions | Yield |
---|---|
With sodium hydroxide; water |
Conditions | Yield |
---|---|
With sulfuric acid; water | |
Multi-step reaction with 2 steps 1: H2O 2: NaOH; water View Scheme |
ethyl 2-formamido-3-(3-indolyl)-2-carbethoxypropionate
Trp
Conditions | Yield |
---|---|
With sodium hydroxide; water at 120℃; anschl. mit Essigsaeure; | |
Multi-step reaction with 2 steps 1: aq.-ethanolic NaOH 2: H2O; NaOH View Scheme |
Nα-ethoxycarbonyl-DL-tryptophan-nitrile
Trp
Conditions | Yield |
---|---|
With hydrogenchloride; water; acetic acid |
Trp
Conditions | Yield |
---|---|
With sodium hydroxide; water |
Nα-ethoxycarbonyl-DL-tryptophan-ethyl ester
Trp
Conditions | Yield |
---|---|
With sodium hydroxide; ethanol; water |
Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.
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%.
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. |