3-Indolepropionic acid

Base Information

• Chemical Name: 3-Indolepropionic acid
• CAS No.: 830-96-6
• Molecular Formula: C11H11NO2
• Molecular Weight: 189.214
• Hs Code.: Oral rat LD50: 100 mg/kg
• European Community (EC) Number: 212-600-1
• NSC Number: 47831,3252
• UNII: JF49U1Q7KN
• DSSTox Substance ID: DTXSID7061192
• Nikkaji Number: J7.131E
• Wikipedia: 3-indolepropionic acid
• Wikidata: Q21098993
• Pharos Ligand ID: T1TAGV6DSU7W
• Metabolomics Workbench ID: 38116
• ChEMBL ID: CHEMBL207225
• Mol file: 830-96-6.mol

Synonyms:indole propionate;indole-3-propanoic acid;indolepropionic acid

Chemical Property of 3-Indolepropionic acid

Chemical Property:

• Appearance/Colour: pale yellow to yellow crystalline powder
• Vapor Pressure: 33 mm Hg ( 20 °C)
• Melting Point: 134-135 °C(lit.)
• Refractive Index: n20/D 1.377(lit.)
• Boiling Point: 417.6 °C at 760 mmHg
• PKA: 4.77±0.10(Predicted)
• Flash Point: 206.4 °C
• PSA: 53.09000
• Density: 1.297 g/cm³
• LogP: 2.18510
• Storage Temp.: −20°C
• Solubility.: ethanol: soluble50mg/mL, clear, yellow to orange
• Water Solubility.: slightly soluble
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 189.078978594
• Heavy Atom Count: 14
• Complexity: 217

Purity/Quality:

99% ^*data from raw suppliers

3-Indolepropionic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 11-36-67-36/37/38-22-10
• Safety Statements: 7-16-24/25-26-36/37-37/39-22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=CN2)CCC(=O)O
• Recent ClinicalTrials: Safety and Pharmacology Study of VP 20629 in Adults With Friedreich's Ataxia
• Description: Indole-3-propionic acid is a bacterial metabolite that has antioxidant and neuroprotective activities. It scavenges ABTS radicals in a cell-free assay when used at concentrations ranging from 50 to 150 μM and decreases hydrogen peroxide-induced malondialdehyde (MDA) levels in rat striatal membranes (IC50 = 180 μM). Indole-3-propionic acid also decreases increases in MDA levels induced by amyloid β (1-42) in PC12 cells. It decreases ischemia-induced increases in cell death of pyramidal neurons and levels of 4-hydroxy nonenal (HNE; ) and glial fibrillary acidic protein (GFAP) in the hippocampal CA1 region in gerbils when administered at a dose of 10 mg/kg per day.
• Uses: 3-Indolepropionic acid is a deamination product of Tryptophan (T947200) that protects the hippocampus (studied in gerbils) from ischemic damage and oxidative stress. It’s ability to protect the neurons in this way is attributed to its potent antioxidative effects. 3-Indolepropionic acid is also hypothesized to have protective effects on the thyroid gland. Reactant for preparation of:Fluorescent analogues of strigolactonesAnti-tumor agentsMelanocortin receptors ligandsImmunosuppressive agentsIinhibitors of hepatitis C virusHistamine H4 receptor agonistsNR2B/NMDA receptor antagonistsCB1 antagonist for the treatment of obesityAntibacterial agentsInhibitor of TGF-β receptor bindingIndole-3-propionic acid may be used in the synthesis of oxindole-3-propionic acid via reaction with N-bromosuccinimide in acetic acid followed by treatment with H2/Pd catalyst.

Technology Process of 3-Indolepropionic acid

There total 32 articles about 3-Indolepropionic 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: 95.0%

indobinine (109897-76-9) → Indole-3-propionic acid (830-96-6)

Guidance literature:

With sodium hydroxide; for 0.25h; Heating;

Reference yield: 95.0%

benzyl 3-indole propionate (85612-35-7) → Indole-3-propionic acid (830-96-6)

Guidance literature:

With sodium hydroxide; water; for 0.25h; Heating;

Reference yield: 89.0%

indole (120-72-9) + acrylic acid (79-10-7) → Indole-3-propionic acid (830-96-6)

Guidance literature:

With tetraacetyl diborate; In acetonitrile; at 20 ℃; Reagent/catalyst; Solvent;

upstream raw materials:

1H-indole-3-propiononitrile

indole

β-Propiolactone

indol-3-ylmethyl-malonic acid

Downstream raw materials:

ethyl 3-(indol-3-yl)propanoate

1,4-dihydrocyclopenta[b]indol-3(2H)-one

3-(3-indolyl)-propanamide

3-(1-benzoyl-indolin-3-yl)-propionic acid