(2R)-2-hydroxy-3-(1H-indol-3-yl)propanoic acid

Base Information

• Chemical Name: (2R)-2-hydroxy-3-(1H-indol-3-yl)propanoic acid
• CAS No.: 101312-07-6
• Molecular Formula: C11H11 N O3
• Molecular Weight: 205.213
• UNII: ET6F387NGD
• Nikkaji Number: J931.598E
• Wikidata: Q27124345
• Metabolomics Workbench ID: 58888
• Mol file: 101312-07-6.mol

Synonyms:(R)-indole-3-lactic acid;(2R)-2-hydroxy-3-(1H-indol-3-yl)propanoic acid;D-Indole-3-lactic acid;Indole-3-lactic acid, D-;ET6F387NGD;D-3-(3-indolyl)lactic acid;Indole-3-lactic acid, (R)-;(R)-2-Hydroxy-3-(1H-indol-3-yl)propanoic acid;101312-07-6;4Z9;UNII-ET6F387NGD;(R)-(Indol-3-yl)lactate;SCHEMBL891879;CHEBI:55528;C22006;(alphaR)-alpha-Hydroxy-1H-indole-3-propanoic acid;A4D2DECF-89F8-4BCF-A207-A11FA1E72999;Q27124345;1H-Indole-3-propanoic acid, alpha-hydroxy-, (alphaR)-;(.ALPHA.R)-.ALPHA.-HYDROXY-1H-INDOLE-3-PROPANOIC ACID;1H-INDOLE-3-PROPANOIC ACID, .ALPHA.-HYDROXY-, (.ALPHA.R)-

Chemical Property of (2R)-2-hydroxy-3-(1H-indol-3-yl)propanoic acid

Chemical Property:

• Melting Point: 100-103℃
• Boiling Point: 477.3±30.0 °C(Predicted)
• PKA: 3.86±0.11(Predicted)
• PSA: 73.32000
• Density: 1.428±0.06 g/cm3(Predicted)
• LogP: 1.15590
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 205.07389321
• Heavy Atom Count: 15
• Complexity: 244

Purity/Quality:

98%Min ^*data from raw suppliers

(S)-2-HYDROXY-3-(3-INDOLYL)PROPIONIC ACID 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=CN2)CC(C(=O)O)O
• Isomeric SMILES: C1=CC=C2C(=C1)C(=CN2)C[C@H](C(=O)O)O

Technology Process of (2R)-2-hydroxy-3-(1H-indol-3-yl)propanoic acid

There total 3 articles about (2R)-2-hydroxy-3-(1H-indol-3-yl)propanoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 83.0%

L-Tryptophan (73-22-3,27732-43-0,80206-30-0,27813-82-7) → Indole-3-pyruvic acid (392-12-1) + (R)-2-hydroxy-3-(1H-indol-3-yl)propanoic acid (101312-07-6,1821-52-9)

Guidance literature:

With formate dehydrogenase; oxygen; ammonium formate; NADH; In aq. phosphate buffer; at 21 ℃; for 7h; under 750.075 Torr; pH=7; stereoselective reaction; Enzymatic reaction;

DOI:10.1002/chem.201403195

Reference yield: 27.0%

D-tryptophan (153-94-6,27732-43-0,80206-30-0,27813-82-7) → (R)-2-hydroxy-3-(1H-indol-3-yl)propanoic acid (101312-07-6,1821-52-9)

Guidance literature:

Chromobacterium violaceum;

Reference yield:

indole (120-72-9) + methyl (2R)-glycidate (4538-50-5,85485-00-3,118712-39-3,111058-32-3) → (R)-2-hydroxy-3-(1H-indol-3-yl)propanoic acid (101312-07-6,1821-52-9)

Guidance literature:

indole; methyl (2R)-glycidate; With tin(IV) chloride; In tetrachloromethane;

With sodium hydroxide; In tetrahydrofuran; Further stages.;

DOI:10.1016/j.tetlet.2004.05.076

upstream raw materials:

D-tryptophan

indole

methyl (2R)-glycidate

L-Tryptophan

Refernces

• 1、 Yamaji, Nahoko,Horikawa, Manabu,Corzo, Gerardo,Naoki, Hideo,Haupt, Joachim,Nakajima, Terumi,Iwashita, Takashi. "Structure and enantioselective synthesis of polyamine toxin MG30 from the venom of the spider Macrothele gigas". . p. 5371 - 5373. Retrieved 2007/10/03.