L-Tryptophan

• CAS: 73-22-3
• Catalog Number: ACM73223
• Category: Other Products
• Molecular Weight: 204.23
• Molecular Formula: C11H12N2O2
• Synonyms: L-Beta-3-indolylalanine
• IUPAC Name: (2S)-2-Amino-3-(1H-indol-3-yl)propanoic acid
• 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
• Boiling Point: 342.72 °C
• Melting Point: 289-290 °C(lit.)
• Density: 1.34 g/cm³
• 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.
• Storage: 2-8 °C
• Active Content: 95%
• Assay: 0.99
• Color/Form: Leaflets or plates from dilute alcohol;White to slightly yellowish-white ... crystals or crystalline powder
• Complexity: 245
• Covalently-Bonded Unit Count: 1
• Decomposition: When heated to decomposition it emits toxic fumes of /nitric oxide/.
• Defined Atom Stereocenter Count: 1
• EC Number: 200-795-6
• Exact Mass: 204.089877630
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Heavy Atom Count: 15
• Isomeric SMILES: C1=CC=C2C(=C1)C(=CN2)C[C@@H](C(=O)O)N
• MDL Number: MFCD00064340
• Monoisotopic Mass: 204.089877630
• NSC Number: 757373
• Octanol Water Partition Coefficient: -1.05 (LogP);log Kow = -1.06;-1.06
• Odor: Odorless
• 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)/
• Packaging: 1 kg
• 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
• Physical State: Solid
• pKa: 2.46(at 25 °C)
• Refractive Index: -32 ° (C=1, H₂O)
• Rotatable Bond Count: 3
• Solubility In Water: 11.4 g/L (25 ºC)
• Topological Polar Surface Area: 79.1 Ų
• UNII: 8DUH1N11BX
• Vapor Pressure: 2.1X10-9 mm Hg at 25 deg C (est)

Case Study

L-Tryptophan as A Kinetic Promoter of CO2 Hydrate Formation

Khandelwal, Himanshu, et al. Energy & Fuels, 2020, 35(1), 649-658.

Carbon dioxide (CO2) hydrates are a potential option for carbon dioxide capture and storage (CCS). L-tryptophan can be used as a kinetic accelerator for CO2 hydrate formation to increase the gas hydrate formation rate and process efficiency.
Performance evaluation of L-tryptophan accelerators
· The performance of the environmentally friendly accelerator L-tryptophan as a kinetic accelerator for CO2 hydrate formation was evaluated using a stirred tank reactor.
· The effect of L-tryptophan as a kinetic enhancer was studied using gas absorption measurements and front/top view visual observation.
· With the addition of only 300 ppm L-tryptophan, an average gas uptake of 114 v/v (78% water conversion to hydrate) was achieved at 273.65 K and 3.4 MPa, which is four times higher than without the accelerator.
· Experiments performed at 273.65 and 275.65 K showed shorter induction times and better gas absorption properties compared to 277.65 K.

Custom Q&A

What is the molecular formula of L-Tryptophan according to the reference?

The molecular formula of L-Tryptophan is C11H12N2O2.

What is the molecular weight of L-Tryptophan according to the reference?

The molecular weight of L-Tryptophan is 204.22 g/mol.

What are some synonyms for L-Tryptophan mentioned in the reference?

Some synonyms for L-Tryptophan are tryptophan, L-Tryptophane, and h-Trp-oh.

What role does L-Tryptophan have according to the reference?

L-Tryptophan has a role as an antidepressant, a nutraceutical, a plant metabolite, and a human metabolite.

What is the IUPAC name of L-Tryptophan?

The IUPAC name of L-Tryptophan is (2S)-2-amino-3-(1H-indol-3-yl)propanoic acid.

What is the InChIKey of L-Tryptophan?

The InChIKey of L-Tryptophan is QIVBCDIJIAJPQS-VIFPVBQESA-N.

What is the Canonical SMILES of L-Tryptophan?

The Canonical SMILES of L-Tryptophan is C1=CC=C2C(=C1)C(=CN2)CC(C(=O)O)N.

What is the EC Number of L-Tryptophan?

The European Community (EC) Number of L-Tryptophan is 200-795-6.

What is the UNII number of L-Tryptophan?

The UNII number of L-Tryptophan is 8DUH1N11BX.

What is the ChEMBL ID of L-Tryptophan?

The ChEMBL ID of L-Tryptophan is CHEMBL54976.

Synthetic Use

Upstream Synthesis Route 1

• 1218-34-4

• 73-22-3
• 2280-01-5

Reference: [1]Journal of the American Chemical Society,2011,vol. 133,p. 16970 - 16976
[2]Patent: CN111132962,2020,A .Location in patent: Paragraph 0192-0194
[3]Journal of Biological Chemistry,1932,vol. 96,p. 511,512, 514
[4]Bioscience, Biotechnology and Biochemistry,2014,vol. 78,p. 1129 - 1134
[5]MedChemComm,2017,vol. 8,p. 1640 - 1654

Upstream Synthesis Route 2

• 21753-16-2

• 73-22-3

Reference: [1]Journal of Biological Chemistry,1936,vol. 116,p. 429,430
[2]Patent: US4371536,1983,A

Downstream Synthesis Route 1

• 850232-59-6
• 73-22-3

• 57850-17-6

Reference: [1] Tetrahedron, 2009, vol. 65, # 25, p. 4923 - 4929
[2] Synthesis, 2006, # 3, p. 411 - 424

Downstream Synthesis Route 2

• 73-22-3

• 57850-17-6
• 52023-39-9

Reference: [1] Journal of the American Chemical Society, 1980, vol. 102, # 13, p. 4537 - 4538

Downstream Synthesis Route 3

• 73-22-3

• 57850-17-6

Reference: [1] Journal of Biological Chemistry, 1948, vol. 175, p. 39,46

Downstream Synthesis Route 4

• 73-22-3

• 6052-68-2

Reference: [1]Journal of Biological Chemistry,1932,vol. 96,p. 511,512, 514

* For details of the synthesis route, please refer to the original source to ensure accuracy.