57400
Indole-3-propionic acid
≥99.0% (T)
Synonym(s):
3-(3-Indolyl)propanoic acid, 3-(3-Indolyl)propionic acid, IPA, NSC 3252, NSC 47831
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About This Item
Empirical Formula (Hill Notation):
C11H11NO2
CAS Number:
Molecular Weight:
189.21
Beilstein:
147733
EC Number:
MDL number:
UNSPSC Code:
12352106
PubChem Substance ID:
NACRES:
NA.77
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Quality Level
Assay
≥99.0% (T)
form
solid
ign. residue
≤0.1%
mp
~133 °C
SMILES string
OC(=O)CCc1c[nH]c2ccccc12
InChI
1S/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)
InChI key
GOLXRNDWAUTYKT-UHFFFAOYSA-N
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Application
- Elucidating the Interaction of Indole-3-Propionic Acid and Calf Thymus DNA: Multispectroscopic and Computational Modeling Approaches.: This study investigates the binding interaction between indole-3-propionic acid and calf thymus DNA, employing multispectroscopic techniques and computational modeling. The insights gained could lead to a deeper understanding of the molecular mechanisms underpinning the protective effects of this compound on DNA integrity, critical for developing novel therapeutic strategies in biochemistry (Wei Y et al., 2024).
- The Tryptophan Metabolite Indole-3-Propionic Acid Raises Kynurenic Acid Levels in the Rat Brain In Vivo.: This research demonstrates how indole-3-propionic acid, a metabolite of tryptophan, can increase levels of kynurenic acid in the brain, offering potential benefits in neuroprotective strategies and the study of psychiatric disorders. Such findings highlight significant implications for mental health research and therapeutic applications (Sathyasaikumar KV et al., 2024).
- Serum-Derived Bovine Immunoglobulin Promotes Barrier Integrity and Lowers Inflammation for 24 Human Adults Ex Vivo.: This study explores how indole-3-propionic acid impacts inflammatory responses and gut barrier integrity, providing valuable data for nutritional science and clinical applications aimed at reducing gastrointestinal disorders and enhancing overall gut health (Van den Abbeele P et al., 2024).
- The Effect of Type 2 Resistant Starch and Indole-3-Propionic Acid on Ameliorating High-Fat-Diet-Induced Hepatic Steatosis and Gut Dysbiosis.: This publication discusses the beneficial effects of indole-3-propionic acid in conjunction with type 2 resistant starch on reducing hepatic steatosis and correcting gut dysbiosis caused by high-fat diets, pointing to potential dietary interventions for managing obesity and associated metabolic disorders (Yang M et al., 2024).
- Gut microbiome and cardiometabolic comorbidities in people living with HIV.: This review highlights the role of indole-3-propionic acid in modulating the gut microbiome and its potential effects on cardiometabolic health in HIV-positive individuals. The findings suggest a promising avenue for improving the quality of life and health outcomes in this population through microbiome-based interventions (Trøseid M et al., 2024).
Biochem/physiol Actions
Studied as an adjunct to improve perfusion after liver transplant.
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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Zhongqi Cheng et al.
Environmental science & technology, 39(19), 7662-7666 (2005-10-26)
Field and laboratory experiments were conducted to study the potential use of Fe filings to remove monomethyl arsenate (MMA) and dimethyl arsenate (DMA) from contaminated waters. Batch experiments show that the affinity of MMAfor Fe filings is comparable to that
Shardulendra P Sherchand et al.
Proceedings of the National Academy of Sciences of the United States of America, 116(25), 12468-12477 (2019-05-18)
A striking difference between genital and ocular clinical isolates of Chlamydia trachomatis is that only the former express a functional tryptophan synthase and therefore can synthesize tryptophan by indole salvage. Ocular isolates uniformly cannot use indole due to inactivating mutations
Andrew W Woodward et al.
Plant physiology, 144(2), 976-987 (2007-04-24)
The ubiquitin-like protein RELATED TO UBIQUITIN (RUB) is conjugated to CULLIN (CUL) proteins to modulate the activity of Skp1-Cullin-F-box (SCF) ubiquitylation complexes. RUB conjugation to specific target proteins is necessary for the development of many organisms, including Arabidopsis (Arabidopsis thaliana).
B Poeggeler et al.
Brain research, 815(2), 382-388 (1999-01-08)
The hydroxyl radical scavenging activity of indole-3-propionate was evaluated by kinetic competition studies with the hydroxyl radical trapping reagent 2,2'-azino-bis-(3-ethyl-benz-thiazoline-6-sulfonic acid) (ABTS) and by measuring hydroxyl radical-initiated lipid peroxidation in the rat striatum. Using ABTS, the indole was shown to
K L Borden et al.
European journal of biochemistry, 202(2), 459-470 (1991-12-05)
The antirepressor indole 3-propanoate has been shown by X-ray crystallography to bind in a different orientation compared with the natural corepressor for the tryp repressor, L-tryptophan (Lawson, C.L. & Sigler, P. B. (1988) Nature 333, 869-871). This suggests a simple
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