Indole-3-lactic acid

Base Information

• Chemical Name: Indole-3-lactic acid
• CAS No.: 1821-52-9
• Molecular Formula: C₁₁H₁₁NO₃
• Molecular Weight: 205.213
• European Community (EC) Number: 217-347-0
• UNII: 5SW11R7M7M
• DSSTox Substance ID: DTXSID70862758
• Nikkaji Number: J101.661J
• Wikidata: Q27109857
• Metabolomics Workbench ID: 78524
• ChEMBL ID: CHEMBL485011
• Mol file: 1821-52-9.mol

Synonyms:5-hydroxyindolepropionic acid;5-iHIPA;indole-3-lactate;indole-3-lactic acid;indole-3-lactic acid, (+-)-isomer

Chemical Property of Indole-3-lactic acid

Chemical Property:

• Melting Point: 145-146 °C(lit.)
• Boiling Point: 477.3 °C at 760 mmHg
• PKA: 3.86±0.11(Predicted)
• Flash Point: 242.4 °C
• PSA: 73.32000
• Density: 1.428 g/cm³
• LogP: 1.15590
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• 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%,99%, ^*data from raw suppliers

DL-Indole-3-lactic Acid ^*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
• Uses: DL-Indole-3-lactic Acid is used as a reagent in the synthesis of 2-hydroxy-1-(1H-indol-3-yl)-4-methylpentan-3-one which has weak antibacterial activity against 16 bacterial strains, including Escherichia coli, Bacillus subtilis and Staphylococcus aureus. DL-Indole-3-lactic Acid is also used in the preparation of Monatin, a natural sweet peptidomimetic.

Technology Process of Indole-3-lactic acid

There total 20 articles about Indole-3-lactic 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: 92.0%

methyl 2-hydroxy-3-(1H-indol-3-yl)propanoate (18372-16-2) → indole-3-lactic acid (832-97-3,1821-52-9)

Guidance literature:

With sodium hydroxide; In methanol; water; at 55 - 60 ℃; for 0.5h;

DOI:10.1002/jlac.198319830207

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) + (S)-2-hydroxy-3-(1H-indol-3-yl)-propionic acid (7417-65-4,1821-52-9)

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: 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

upstream raw materials:

Indole-3-pyruvic acid

3-(indol-3-yl)pyruvic acid methyl ester

indol-3-yl-pyruvic acid ethyl ester

hydroxy-indol-3-ylmethyl-malonic acid

Downstream raw materials:

(S)-2-hydroxy-3-(1H-indol-3-yl)-propionic acid

3-indol-3-yl-propane-1,2-diol

methyl 2-tosyloxy-3-(3-indolyl)propionate

Toluene-4-sulfonate1-[2-(1H-indol-3-yl)-2-methoxycarbonyl-ethyl]-4-methyl-pyridinium;

Refernces

• 1、 Shimada, Naoyuki,Takahashi, Naoya,Ohse, Naoki,Koshizuka, Masayoshi,Makino, Kazuishi. "Synthesis of Weinreb amides using diboronic acid anhydride-catalyzed dehydrative amidation of carboxylic acids". supporting information. p. 13145 - 13148. Retrieved 2020/11/09.
• 2、 Busto, Eduardo,Grischek, Barbara,Kroutil, Wolfgang,Richter, Nina. "Biocontrolled formal inversion or retention of L -α-amino acids to enantiopure (R)- or (S)-hydroxyacids". supporting information. p. 11225 - 11228,4. Retrieved 2015/01/07.