2-Amino-3-(1H-indol-3-yl)propanoic acid

2-Amino-3-(1H-indol-3-yl)propanoic acid - Names and Identifiers

Name	L-Tryptophan
Synonyms	TRP H-Trp-OH L-Trp-OH Tryptophan L-Tryptohan L-Tryptophan L-Tryptophane L-Tryptophan, Trp Indole-3-alanine L-Tryptophan(pharm grade) L-Tryptophan, Animal-Free L-TRYPTOPHAN (13C11,D8,15N2) Trytophan (W) Solution, 100ppm VWR SURFACE SAMPLING SPONGE WITH NE L-alphs-Amino-3-indolepropionic acid (S)-2-Amino-3-(3-indolyl)propionic acid 2-Amino-3-(1H-indol-3-yl)propanoic acid (S)-2-Amino-3-(1H-indol-3-yl)propanoic acid
CAS	73-22-3 80206-30-0
EINECS	200-795-6
InChI	InChI=1/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
InChIKey	QIVBCDIJIAJPQS-VIFPVBQESA-N

2-Amino-3-(1H-indol-3-yl)propanoic acid - Physico-chemical Properties

Molecular Formula	C11H12N2O2
Molar Mass	204.23
Density	1.34
Melting Point	289-290°C (dec.)(lit.)
Boling Point	342.72°C (rough estimate)
Specific Rotation(α)	-31.1 º (c=1, H20)
Flash Point	224.7°C
Water Solubility	11.4 g/L (25 ºC)
Solubility	Slightly soluble in water (1.14%, 25°C), hardly soluble in ethanol. Soluble in dilute acid or base.
Vapor Presure	8.3E-09mmHg at 25°C
Appearance	Crystalline powder
Color	White to yellow-white
Merck	14,9797
BRN	86197
pKa	2.46(at 25℃)
PH	5.5-7.0 (10g/l, H2O, 20℃)
Storage Condition	2-8°C
Stability	Stable. Incompatible with strong acids, strong oxidizing agents.
Sensitive	Sensitive to light
Refractive Index	-32 ° (C=1, H2O)
MDL	MFCD00064340
Physical and Chemical Properties	density 1.34 melting point 280-285°C specific optical rotation -31.1 ° (c = 1, H20) water-soluble 11.4g/L (25°C)
Use	Improve nutrition, enhance physical fitness.

2-Amino-3-(1H-indol-3-yl)propanoic acid - Risk and Safety

Hazard Symbols	Xi - Irritant
Risk Codes	R33 - Danger of cumulative effects R40 - Limited evidence of a carcinogenic effect R62 - Possible risk of impaired fertility R41 - Risk of serious damage to eyes R37/38 - Irritating to respiratory system and skin. R36/37/38 - Irritating to eyes, respiratory system and skin. R22 - Harmful if swallowed
Safety Description	S24/25 - Avoid contact with skin and eyes. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S36 - Wear suitable protective clothing. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
WGK Germany	2
RTECS	YN6130000
FLUKA BRAND F CODES	8
TSCA	Yes
HS Code	29339990
Toxicity	LD508mmol / kg (rat, intraperitoneal injection). It is safe when used in food (FDA, §172.320, 2000).

2-Amino-3-(1H-indol-3-yl)propanoic acid - Nature

Open Data Verified Data

This product is white or off-white crystalline powder. Odorless or slightly malodorous, slightly bitter. Melting point 289 °c (decomposition). Slightly soluble in water (1.14%,25 ° C), very slightly soluble in ethanol; Dissolved in dilute acid or dilute alkali. Long time light is colored. A small amount of indole is produced by co-heating with water, and a large amount of indole is produced by heating in the presence of sodium hydroxide, copper sulfate. And acid in the dark heating more stable. With other amino acids, sugars, aldehydes coexist easily decomposed. If there is no coexistence of hydrocarbons, it is still stable when heated to 125 ℃ with 5mol sodium hydroxide. When the protein is decomposed by acid, tryptophan is completely decomposed to form a rot black substance.
tryptophan is a heterocyclic amino acid and is an essential amino acid. In the body can be converted into 5 serotonin, nicotinic acid, melanin Nervousness, pineal hormone and yellow uric acid and other physiological active substances. When the human body lacks tryptophan, it will not only cause general hypoproteinemia, but also produce skin diseases, cataracts, vitreous degeneration and myocardial fibrosis and other special diseases. It also enhances the body's resistance to radiation. The minimum daily requirement of human body is 0. 2G.

Last Update：2024-01-02 23:10:35

2-Amino-3-(1H-indol-3-yl)propanoic acid - Preparation Method

Open Data Verified Data

chemical synthesis method.
fermentation method with addition of precursor.
direct fermentation method.

Last Update：2022-01-01 11:10:27

2-Amino-3-(1H-indol-3-yl)propanoic acid - Use

Open Data Verified Data

amino acid drugs. For amino acid infusion. Often combined with iron, vitamins and so on. Combined with vitamin B6 for the improvement of depression, prevention and treatment of pellagra; As a Sleep Initiation and Maintenance Disorders sedative with L-dopa for the treatment of Parkinson's disease; Also for vitamin B6 deficiency test.
usage and dose of oral, daily 0. 25~0. lg, fractional administration. Tryptophan may also be used in nutrition-fortified foods. Used as the third feeding amino acid.

Last Update：2022-01-01 11:10:28

2-Amino-3-(1H-indol-3-yl)propanoic acid - Safety

Open Data Verified Data

adult oral tolerance dose is 20~50mg/kg, the experimental animals have carcinogenicity; Nausea, anorexia, sleepiness and other adverse reactions. Avoid co-use with monoamine oxidase inhibitors.
protected from light and sealed.

Last Update：2022-01-01 11:10:28

2-Amino-3-(1H-indol-3-yl)propanoic acid - Reference Information

NIST chemical information	information provided by: webbook.nist.gov (external link)
EPA chemical substance information	information provided by: ofmpeb.epa.gov (external link)
Introduction	L-tryptophan is a neutral aromatic amino acid containing an indole group, for white or yellowish leaf-like crystals or powder, solubility in water 1. 14G (25°C ), soluble in dilute acid or dilute alkali, more stable in alkali, strong acid decomposition. Slightly soluble in ethanol, insoluble in chloroform, ether.
trait	White Crystal or crystalline powder
identification test	take about 1g of sample, dissolve in 20% ml of hydrochloric acid solution, add 1ml of 5% sodium sulfite solution,
content analysis	accurately weigh about 300mg of sample, dissolve in 3ml of formic acid and 50ml of glacial acetic acid, two drops of crystal violet test solution (TS-250) were added and titrated with 0.1mol/L perchloric acid to the green end point or to the blue color completely disappeared. Per Mi,0.1 mol/L perchloric acid corresponds to 20.42mg of L-tryptophan (C11H12N2O2).
toxicity	LD508mmol/kg (rat, intraperitoneal injection). Safe for use in food (FDA,§ 172.320,2000).
usage limit	accounts for 1.6% by weight of the total protein in the food product (FDA,§ 172.320,2000).
Use	amino acid drugs. For amino acid infusion. Often combined with iron, vitamins, etc., combined with VB6 to improve depression, prevention and treatment of coarse skin disease; As a Sleep Initiation and Maintenance Disorders sedative with L-dopa for the treatment of Parkinson's disease. Carcinogenicity of experimental animals; Nausea, anorexia, sleep and other adverse reactions. Combination with monoamine oxidase inhibitor. nutritional supplements. Egg white protein, fish, corn flour, etc. contain tryptophan as a limiting amino acid, rice and other grains in less content. Lysine, methionine, threonine can be used to strengthen amino acids. By 0.02% of tryptophan and 0.1% of lysine added to corn products, can significantly improve the protein titer. An important component of amino acid infusion and comprehensive amino acid preparation. Niacin deficiency can be treated. used in biochemical studies and medically as a sedative. The substitution of tryptophan in Sephadex? And Sepharose? A precursor of serotonin and melatonin for improved cellulase chromatographic separation; As a spacer in isotachophoresis of serum proteins, to meet the growth requirements of various microorganisms L-tryptophan can improve nutrition, enhance physical fitness, for nutrition and biochemical research, preparation of tissue culture medium.
production method	DL-tryptophan is used as the raw material, and chloroacetic anhydride is added to react under cooling, after acidification with sulfuric acid, it is ground in ice water, recrystallized in water after filtration, finally treated with pancreatic carboxypeptidase to remove D-form, and purified by acidification with acetic acid and recrystallization with ethanol. synthesis method DL-tryptophan is obtained by a synthetic method, and then by an optical rotation disassembly method. It is obtained from the decomposition of casein by Pancreatin. The preparation of L-tryptophan can be produced by adding precursor, using glucose as carbon source and energy source, adding precursor anthranilic acid or indole for culture, converting precursor into L-amino acid; the second can be produced by enzymatic method; The third can use chemical synthesis method; The fourth can use protein hydrolysis method and so on. The production of L-tryptophan by the protease hydrolysis method is described in detail below. Process fibrin [protease, toluene, chloroform] →[45 ℃, enzymatic hydrolysis] hydrolysis filtrate [porous H-type resin] → adsorption [0.3mol/L ammonia] → [elution] eluent [concentration, crystallization] → [in refrigerator, 24h]L-tryptophan crude product [65% ethanol recrystallization] → L-tryptophan product enzymatic hydrolysis first 25kg fibrin, add 37.5 distilled water. It is denatured by heating, dried and dispersed, then put into the hydrolysis tank, add 40-45l of distilled water, stir, heat to 45 ℃, and then add a certain amount of protease or a specified substance sequentially, keeping the temperature at 45 ℃, controlling the pH value of the solution and the hydrolysis time, the protein was completely hydrolyzed and the yield of amino acid was increased. 25g of 3942 neutral protease and 1398G of 7.0 neutral protease, 2590ml of toluene and chloroform were added, stirred for 10min at half an hour intervals, and the pH value of the solution was adjusted to 7.2-with Ca(OH)2 suspension, after 48h, add 166g of enzyme preparation, hydrolyze for 8H, and add kidney homogenate (40g of manganese chloride), Control pH 7.5-8.0, maintain 40H. Then add NaHSO3 110g, with 12mol/L H2SO4 to adjust the pH value of 5.0, keeping the temperature at 80 ℃ for 20min, and finally filtering, the filter residue is washed with water twice, the washing liquid is combined with the filtrate to obtain the hydrolysis liquid. Adsorption and elution the hydrolysate was placed in a refrigerator, kept at 0 ℃, and allowed to stand for 24h. The sediment was removed by filtration, and the filtrate was diluted with equal volume of water and passed through a column equipped with porous cation exchange resin, the amino acid in the hydrolysis solution is adsorbed, check the effluent to stop the column when there is tryptophan reaction, first wash the column with water, then wash with 0.3mol/L ammonia water, collect the eluate, the elution was stopped until the pH of the eluent was 12 or no tryptophan was checked. Concentration and crystallization when the eluate is concentrated under reduced pressure until crystals are precipitated, cool to 0 ℃ and stand for 24h. The crystals are filtered and washed with 65% and 95% ethanol, crude tryptophan was obtained. The mother liquor was adjusted to pH 6.0, and crystals were precipitated, which were allowed to stand for 24h. The crystals were removed by filtration and eluted with the above method, The crude tryptophan was dried under vacuum at 60 °c. Recrystallization purification the above crude product was recrystallized twice from 65% ethanol solution, washed once with 95% ethanol solution, and vacuum dried for 8H to obtain L-tryptophan finished product.
toxic substance data	information provided by: pubchem.ncbi.nlm.nih.gov (external link)