830-96-6 Usage
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
Different sources of media describe the Uses of 830-96-6 differently. You can refer to the following data:
1. 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.
2. 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.
Definition
ChEBI: An indol-3-yl carboxylic acid that is propionic acid substituted by a 1H-indol-3-yl group at position 3.
Synthesis Reference(s)
Tetrahedron Letters, 25, p. 3159, 1984 DOI: 10.1016/S0040-4039(01)90997-9
General Description
3-Indolepropionic acid is an effective inhibitor of aggregation of misfolded β-amyloid protein (Abeta). Three-component one-pot procedure has been reported to assemble 3-indolepropionic acids.
Biochem/physiol Actions
Studied as an adjunct to improve perfusion after liver transplant.
Purification Methods
Recrystallise it from EtOH/water [James & Ware J Phys Chem 89 5450 1985]. The picrate has m 143-144o, and the methyl ester crystallises from *C6H6 or MeOH with m 81-83o. [Beilstein 22 III/IV 1113, 22/3 V 114.]
Check Digit Verification of cas no
The CAS Registry Mumber 830-96-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 8,3 and 0 respectively; the second part has 2 digits, 9 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 830-96:
(5*8)+(4*3)+(3*0)+(2*9)+(1*6)=76
76 % 10 = 6
So 830-96-6 is a valid CAS Registry Number.
InChI:InChI=1/C11H11NO2/c13-11(14)6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5-6H2,(H,13,14)/p-1
830-96-6Relevant articles and documents
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Johnson,Crosby
, p. 569,570 (1960)
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BORON-BASED CYCLOADDITION CATALYSTS AND METHODS FOR THE PRODUCTION OF BIO-BASED TEREPHTHALIC ACID, ISOPHTHALIC ACID AND POLY (ETHYLENE TEREPHTHALATE)
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Paragraph 00224-00227, (2017/04/11)
Methods for producing cycloaddition products comprising: reacting a diene with a dienophile in the presence of one or more boron-based catalysts of Formula I or Formula II are provided. In particular, the methods can be used to prepare 4-methyl-3-cyclohexene- 1-carboxylic acid and 3-methyl-3-cyclohexene-l-carboxylic acid, including bio-based versions thereof. The cycloaddition products can be advantageously used in the production of terephthalic acid and isophthalic acid, and ultimately, poly(ethylene terephthalate), and bio-based versions thereof. Formula I Formula II
Sodium Iodide/Hydrogen Peroxide-Mediated Oxidation/Lactonization for the Construction of Spirocyclic Oxindole-Lactones
Li, Guofeng,Huang, Liwu,Xu, Jiecheng,Sun, Wangsheng,Xie, Junqiu,Hong, Liang,Wang, Rui
supporting information, p. 2873 - 2877 (2016/09/16)
The sodium iodide/hydrogen peroxide-mediated oxidation/lactonization of indolepropionic acids was achieved, affording the corresponding spirocyclic oxindole-lactones in moderate to high yields. This metal-free procedure features mild reaction conditions, non-toxicity and easy handling, with hydrogen peroxide (H2O2) as a clean oxidant. (Figure presented.).
