830-96-6 Usage
Description
3-Indolepropionic acid, also known as Indole-3-propionic acid, is a bacterial metabolite derived from the deamination of Tryptophan. It possesses antioxidant and neuroprotective properties, making it a promising candidate for various applications in the pharmaceutical and chemical industries. Its ability to protect neurons and inhibit the aggregation of misfolded β-amyloid protein (Abeta) highlights its potential in the development of therapeutic agents for neurodegenerative diseases.
Uses
Used in Pharmaceutical Industry:
3-Indolepropionic acid is used as a reactant for the preparation of various pharmaceutical agents, including:
Fluorescent analogues of strigolactones for plant growth regulation
Anti-tumor agents for the treatment of cancer
Melanocortin receptor ligands for the regulation of pigmentation and energy homeostasis
Immunosuppressive agents for the suppression of immune responses
Inhibitors of hepatitis C virus for the treatment of viral infections
Histamine H4 receptor agonists for the modulation of immune and inflammatory responses
NR2B/NMDA receptor antagonists for the treatment of neurological disorders
CB1 antagonists for the treatment of obesity
Antibacterial agents for the treatment of bacterial infections
Inhibitor of TGF-β receptor binding for the regulation of cell growth and differentiation
Used in Chemical Industry:
3-Indolepropionic acid is used as a reactant for the synthesis of oxindole-3-propionic acid, which can be achieved through a three-component one-pot procedure. This synthesis involves the reaction with N-bromosuccinimide in acetic acid followed by treatment with H2/Pd catalyst.
Used in Neuroprotection:
3-Indolepropionic acid is used as a neuroprotective agent for the protection of the hippocampus from ischemic damage and oxidative stress. Its potent antioxidative effects contribute to the protection of neurons, particularly in the context of neurodegenerative diseases.
Used in Thyroid Protection:
3-Indolepropionic acid is hypothesized to have protective effects on the thyroid gland, although further research is needed to elucidate the specific mechanisms and applications in this area.
Synthesis Reference(s)
Tetrahedron Letters, 25, p. 3159, 1984 DOI: 10.1016/S0040-4039(01)90997-9
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.).