DL-Tryptophan
DL-Tryptophan
CAS: 54-12-6
Molecular Formula: C11H12N2O2
DL-Tryptophan - Names and Identifiers
| Name | DL-Tryptophan |
| Synonyms | H-DL-Trp-OH DL-Trytophan DL-Tryptohan DL-Trytophane DL-Tryptophan DL-Tryptophane DL-Tryptoplaan (rs)-tryptophan DL-Trytophan (1.08375) DL-TRYPTOPHAN extrapure CHR α-amino-β-indolepropinic acid 2-Amino-3,3'-IndolylpropanoicAcid (±)-α-Amino-3-indolepropionic acid, (±)-2-Amino-3-(3-indolyl)propionic acid, DL-3β-Indolylalanine |
| CAS | 54-12-6 |
| EINECS | 200-194-9 |
| 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) |
| InChIKey | QIVBCDIJIAJPQS-UHFFFAOYSA-N |
DL-Tryptophan - Physico-chemical Properties
| Molecular Formula | C11H12N2O2 |
| Molar Mass | 204.23 |
| Density | 1.1754 (rough estimate) |
| Melting Point | 289-290°C (dec.)(lit.) |
| Boling Point | 342.72°C (rough estimate) |
| Specific Rotation(α) | [α]D20 -1～1°(c=1, dil. HCl) |
| Water Solubility | 10 g/L (20 ºC) |
| Solubility | Soluble in alkali solution, slightly soluble in water and ethanol, insoluble in chloroform and ether |
| Appearance | White flake crystal |
| Color | White to light beige or light yellow |
| Odor | Odorless |
| BRN | 86196 |
| pKa | 2.30±0.10(Predicted) |
| Storage Condition | Keep in dark place,Inert atmosphere,Room temperature |
| Stability | Stable. Incompatible with strong oxidizing agents, strong acids. |
| Sensitive | Sensitive to light |
| Refractive Index | 1.5200 (estimate) |
| MDL | MFCD00064339 |
| Physical and Chemical Properties | White Flake Crystal, sweet; Soluble in alkali solution, slightly soluble in water and ethanol, insoluble in chloroform and ether, the aqueous solution is weakly acidic, when strong acid decomposition; mp is 275-282 ℃. |
DL-Tryptophan - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | R22 - Harmful if swallowed R36/37/38 - Irritating to eyes, respiratory system and skin. R37/38 - Irritating to respiratory system and skin. R41 - Risk of serious damage to eyes |
| 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 | 1 |
| RTECS | YN6129200 |
| FLUKA BRAND F CODES | 8 |
| TSCA | Yes |
| HS Code | 29339990 |
DL-Tryptophan - Reference
| Reference Show more | 1. Li Lili, Li Yue, Lu Heng, Wang Xiao. Metabolomics analysis of Flos lonicerae at different flowering stages based on liquid chromatography-mass spectrometry [J]. Chinese Journal of analysis and testing, 2020,39(12):1501-1507. 2. [IF = 4.759] Jingtang Li et al."Synthesis and application of ionic liquid functionalized β-cyclodextrin, mono-6-deoxy-6-(4-amino-1,2,4-triazolium)-β-cyclodextrin chloride, as chonal selector in caillary ionization." J Chromatogr A. 2018 Jul;1559:178 3. [IF = 4.556] Dandan Zhao et al."Physico-chemical properties and free amino acids profiles of six wolfberry cultivars in Zhongning." J Food Compos Anal. 2020 May;88:103460 4. [IF = 4.379] Feng Lin et al."Chemical profile changes during pile fermentation of Qingzhuan tea affect inhibition of α-amylase and lipase."Sci Rep-Uk. 2020 Feb;10(1):1-10 5. [IF=4.35] Xiaomei Dai et al."1-Methylcyclopropene Preserves the Quality of Chive (Allium schoenoprasum L.) by Enhancing Its Antioxidant Capacities and Organosulfur Profile during Storage."Foods. 2021 Aug;10(8):1792 6. [IF=4.142] Li Cong et al."A fluorescence strategy for monitoring α-glucosidase activity and screening its inhibitors from Chinese herbal medicines based on Cu nanoclusters with aggregation-induced emission."Anal Bioanal Chem. 2021 Apr;413(9):2553-2563 7. [IF=2.863] Qiang Wang et al."Effects of turmeric on reducing heterocyclic aromatic amines in Chinese tradition braised meat products and the underlying mechanism."Food Sci Nutr. 2021 Oct;9(10):5575-5582 |
DL-Tryptophan - Nature
Open Data Verified Data
white to light yellow crystals or powder, odorless, sweet. Melting point 295 °c (decomposition). Slightly soluble in water and ethanol, soluble in dilute acid and alkali, insoluble in chloroform and ether. The pH of the 0. 2% aqueous solution was 5.5-7.0.
Last Update：2024-01-02 23:10:35
DL-Tryptophan - Preparation Method
Open Data Verified Data
with Indole as raw material, under the catalysis of enzyme, in the high concentration of pyruvate and ammonia atmosphere to prepare tryptophan. Alternatively prepared from indole and acetamido malonate.
Last Update：2022-01-01 10:10:36
DL-Tryptophan - Introduction
The taste is slightly sweet. Sensitive to light. It is stable in lye and decomposes in strong acid. Soluble in alkaline hydroxide solution, soluble in hot ethanol, insoluble in chloroform, soluble in dilute hydrochloric acid.
Last Update：2022-10-16 17:26:02
DL-Tryptophan - Use
Open Data Verified Data
as a feed Nutrition Fortifier, it can significantly increase the body antibody of animal fetus and promote the lactation of lactating cows and sows. When animals lack tryptophan, growth is arrested, body weight is reduced, and fat accumulation is reduced. Mainly used for artificial milk of piglets, a small amount of sows and laying hens, the general dosage of 0.02% ~ 0.05%.
Last Update：2022-01-01 10:10:37
DL-Tryptophan - Safety
Open Data Verified Data
light shielding, closed storage.
Last Update：2022-01-01 11:10:29
DL-Tryptophan - Reference Information
| update date: | 2022/11/14 8:43:08 |
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| tryptophan | tryptophan, one of the essential amino acids for human body. The chemical name is α-amino-β-indole alanine. It is abbreviated as Try (or Trp) or W. Non-polar amino acids, isoelectric point of 5.98, low solubility in water, bitter taste, and maximum light absorption at a wavelength of 280nm. It is the first essential amino acid to be confirmed. In humans and animals, in addition to being a component of protein and maintaining the balance of nitrogen in the body, its metabolite-serotonin not only has a contractile effect on peripheral blood vessels, but also can control the nervous system; metabolism Another product is vitamin B5. In plants, through deamination and decarboxylation reactions, plant growth hormone-indole acetic acid can be formed. Tryptophan is an aromatic amino acid. It is an amino acid with the least but widespread amino acid content in various proteins. Tryptophan can be converted into niacin in the body, so when niacin is lacking in the feed, the requirement for tryptophan increases accordingly. Tryptophan is produced by chemical synthesis, fermentation and natural protein hydrolysis. The synthetic product is DL mixed tryptophan. For pigs, its bioavailability is 80% of L tryptophan. The appearance of DL tryptophan is white to light yellow powder, odorless or slightly peculiar smell, difficult to dissolve in water. Tryptophan can improve the disease resistance and stress resistance of newborn piglets, thus improving the survival rate of piglets. It is generally used in artificial milk of piglets with an addition amount of 0.02% ~ 0.05%. Due to its high price, tryptophan additive is generally not used in growing and finishing pigs and breeding pigs. |
| content analysis | accurately weigh about 300mg of the sample pre-dried at 105 ℃ for 3h, dissolve in 3ml of formic acid and 50ml of glacial acetic acid, add 2 drops of crystal violet test solution (TS-74), titrate with 0.1mol/L perchloric acid to the green end point or until the blue color completely disappears. Perchloric acid is equivalent to DL-tryptophan (C11H12N2O2)20.42mg per Ml0.1mol/L. |
| toxicity | L-type: LD508mmol/kg (rat, intraperitoneal injection);D-type LD5021mmol/kg (rat, intraperitoneal injection). |
| use | for biochemical research. DL-tryptophan is a feed nutrition fortifier, which can significantly increase the internal antibody of animal fetus and promote the lactation of dairy cows and sows during lactation. When animals lack tryptophan, growth arrest, weight loss, and fat accumulation are reduced. Mainly used in artificial milk of piglets, a small amount of sows and laying hens, the general dosage is 0.02%-0.05%. nutritional supplement. Antioxidants can be added to foods with low tryptophan content such as gelatin and corn. Requirement (Japan): 30 mg/kg for young children? D, 160mg/d or 320mg/d for adults. Combined with lysine, methionine, threonine for beef, rice, corn, etc. to get the best results. Adding 0.05% ~ 0.5% to salted fish can reduce barbituric acid value and prevent flavor deterioration. Nutritional supplements and antioxidants can be added to foods with low tryptophan content such as gelatin and corn. Combined with lysine, methionine and threonine for beef, rice, corn, etc., the best results can be obtained. L-tryptophan is prepared by optical rotation of L-tryptophan, which is amino acid infusion and comprehensive amino acid preparation and important ingredient, and can treat niacin deficiency. As a feed additive, it participates in the renewal of plasma protein in animals, promotes the role of riboflavin, contributes to the synthesis of niacin and heme, can significantly increase antibodies in pregnant animal fetuses, and can promote lactating cows and sows during lactation. The role of milk. When livestock and poultry lack tryptophan, growth arrest, weight loss, decreased fat accumulation, male livestock testicular atrophy. Highly toxic psychedelic drugs. |
| Production method | Indole is condensed to form jaramine (3-dimethylaminomethylindole), and further condensed to form α-ethyl carboxylate-β (3-indole)-N-acetyl-α-alanine ethyl ester, which is hydrolyzed, decarboxylated, and rehydrolyzed to form DL-tryptophan. by indophenol derivatives through the synthesis of refurbine derivatives. It is synthesized from acrolein. 1. Fermentation and enzymatic methods (1) Dongya Chemical Company uses indole as raw material and synthesizes tryptophan in high concentration pyruvate and ammonia under enzyme catalysis. 10mg/L pyridoxal phosphate and 0 were added to indole 80% at 34 ℃ and PH = 8.8. 1% sodium sulfite, and a small amount of inosine (can reduce the solubility of tryptophan). The conversion rate of indole was 72%, the product concentration was 91g/L, and the yield was 96%. (2) Japanese Mitsubishi Petrochemical Company uses indole and serine as raw materials to cultivate tryptophan with recombinant Escherichia coli. (3) Japan's Shari Electric Company uses corn starch as the main raw material and uses Bacillus to ferment and cultivate tryptophan. The product contains 85% L-tryptophan and 15% L-tyrosine and L-phenylalanine. 2. Chemical synthesis method (1) Indole and acetaminomalonic acid ethylene ester as raw materials. The mixture of 0.05mol dimethylamine (40%-50% aqueous solution), 7g glacial acetic acid and 0.05mol formaldehyde aqueous solution is heated in 0.049mol indole after ice-cold, and then placed at room temperature for several hours, then added dilute sodium hydroxide solution for alkalization, and the dimethylindole is precipitated, namely, ketamine using indole and α-acetoaminoacrylic acid as raw materials, after the reaction is complete in glacial acetic acid-acetic anhydride medium, naOH is adjusted to alkaline, ether is extracted, and then diluted sodium hydroxide is used for extraction 3 times, sodium hydroxide solution is combined, a few grains of sodium bisulfite are added, cooled to 5 ℃, adjusted to neutral with concentrated hydrochloric acid, and acetyl-DL-tryptophan is precipitated, refluxed in 10% sodium hydroxide solution, concentrated and crystallized to obtain DL-tryptophan. |
Last Update：2024-04-09 21:54:55
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