Category
Heterocyclic Organic Compound
Synonyms
L-Beta-3-indolylalanine
IUPAC Name
(2S)-2-Amino-3-(1H-indol-3-yl)propanoic acid
Molecular Formula
C11H12N2O2
Canonical SMILES
C1=CC=C2C(=C1)C(=CN2)CC(C(=O)O)N
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)/t9-/m0/s1
InChI Key
QIVBCDIJIAJPQS-VIFPVBQESA-N
Melting Point
289-290 °C(lit.)
Solubility
Slightly soluble in acetic acid, ethanol, insoluble in ethyl ether
Appearance
White to yellow-white powder
Application
Amino acids-type drug:
It can be used in amino acid infusion, being often combined with iron and vitamins. Its co-administration with VB6 can improve depression and prevention/treatment of skin disease; as a sleep sedative, it can be combined with L-dopa for the treatment of Parkinson's disease. It is carcinogenic to experimental animals; it may cause adverse reactions including nausea, anorexia and asthmas. Avoid combination with monoamine oxidase inhibitors.
Nutritional supplements:
Tryptophan contained in egg white protein, fish meat, corn meal and other amino acids are limited; content in cereals such as rice is also low. It can be combined with lysine, methionine and threonine for enhanced amino acids. It can be supplemented to corn product at the content of 0.02% tryptophan and 0.1% lysine, being capable of significantly improving the protein potency.tryptophan is one of the 21 amino acids comprising a protein. Tryptophan is a component of the skin's natural moisturizing factors.
Color/Form
Leaflets or plates from dilute alcohol;White to slightly yellowish-white ... crystals or crystalline powder;
Covalently-Bonded Unit Count
1
Decomposition
When heated to decomposition it emits toxic fumes of /nitric oxide/.;
Defined Atom Stereocenter Count
1
Isomeric SMILES
C1=CC=C2C(=C1)C(=CN2)C[C@@H](C(=O)O)N
Monoisotopic Mass
204.089877630
Octanol Water Partition Coefficient
-1.05 (LogP);log Kow = -1.06;-1.06;
Other Experimental
Decomposes at 289 deg C (rapid heating);Needles from methanol, decomposes at 251 deg C /Tryptophan hydrochloride/;IR: 8612 (Sadtler Research Laboratories IR Grating Collection) /Tryptophan (DL)/;UV: 3453 (Sadtler Research Laboratories Spectral Collection) /Tryptophan (DL)/;1H NMR: 582 (Sadtler Research Laboratories Spectral Collection) /Tryptophan (DL)/;MASS: 1229 (National Bureau of Standards EPA-NIH Mass Spectra Data Base, NSRDS-NBS-63) /Tryptophan (DL)/;1H NMR: 582 (Sadtler Research Laboratories Spectral Collection) /Tryptophan (D)/;MASS: 1229 (National Bureau of Standards EPA-NIH Mass Spectra Data Base, NSRDS-NBS-63) /Tryptophan (D)/;
pH
5.5-7.0 (10g/l, H₂O, 20°C)
Physical Description
L-TRYPTOPHAN is a white powder with a flat taste. An essential amino acid; occurs in isomeric forms. (NTP, 1992);Solid;
Refractive Index
-32 ° (C=1, H₂O)
Topological Polar Surface Area
79.1 Ų
Vapor Pressure
2.1X10-9 mm Hg at 25 deg C (est);
Download
Khandelwal, Himanshu, et al. Energy & Fuels, 2020, 35(1), 649-658.
