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Indole-3-propionic acid

Alias: IPA; Indole 3 propionic acid; 3-Indolepropionic acid; 830-96-6; Indole-3-propionic acid; 3-(1H-Indol-3-yl)propanoic acid; 1H-Indole-3-propanoic acid; Indolepropionic acid; 3-(3-Indolyl)propionic acid; Indolylpropionic Acid; Indole-3-propionic acid
Cat No.:V22550 Purity: =99.92%
3-Indolepropionic acid is a potent antioxidant with potential in Alzheimer's disease (AD) research.
Indole-3-propionic acid
Indole-3-propionic acid Chemical Structure CAS No.: 830-96-6
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
1g
Other Sizes

Other Forms of Indole-3-propionic acid:

  • 3-Indolepropionic acid-d2
Official Supplier of:
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Top Publications Citing lnvivochem Products
Purity & Quality Control Documentation

Purity: =99.92%

Product Description
3-Indolepropionic acid is a potent antioxidant with potential in Alzheimer's disease (AD) research.
Biological Activity I Assay Protocols (From Reference)
Targets
Endogenous Metabolite; Microbial Metabolite
ln Vitro
3-Indolepropionic acid has been demonstrated to be an effective antioxidant that may be used to treat Alzheimer's [1]. 3. Compared to melatonin, indolepropionic acid is a more effective hydroxyl radical scavenger. 3-indolepropionic acid scavenges free radicals without causing the subsequent generation of reactive and pro-oxidant intermediate molecules, which is similar to melatonin but different from other antioxidants [2]. Research has additionally demonstrated that the metabolite indolepropionic acid, which is generated by gut microorganisms, may serve as a preventive factor against type 2 diabetes (T2D) by maintaining β-cell activity and acting as a possible biomarker for the disease's onset [3].
ln Vivo
Wide-scale profiling technologies including metabolomics broaden the possibility of novel discoveries related to the pathogenesis of type 2 diabetes (T2D). By applying non-targeted metabolomics approach, we investigated here whether serum metabolite profile predicts T2D in a well-characterized study population with impaired glucose tolerance by examining two groups of individuals who took part in the Finnish Diabetes Prevention Study (DPS); those who either early developed T2D (n = 96) or did not convert to T2D within the 15-year follow-up (n = 104). Several novel metabolites were associated with lower likelihood of developing T2D, including indole and lipid related metabolites. Higher indolepropionic acid was associated with reduced likelihood of T2D in the DPS. Interestingly, in those who remained free of T2D, indolepropionic acid and various lipid species were associated with better insulin secretion and sensitivity, respectively. Furthermore, these metabolites were negatively correlated with low-grade inflammation. We replicated the association between indolepropionic acid and T2D risk in one Finnish and one Swedish population. We suggest that indolepropionic acid, a gut microbiota-produced metabolite, is a potential biomarker for the development of T2D that may mediate its protective effect by preservation of β-cell function. Novel lipid metabolites associated with T2D may exert their effects partly through enhancing insulin sensitivity.[3]
Enzyme Assay
Although it has long been recognized that the enteric community of bacteria that inhabit the human distal intestinal track broadly impacts human health, the biochemical details that underlie these effects remain largely undefined. Here, we report a broad MS-based metabolomics study that demonstrates a surprisingly large effect of the gut "microbiome" on mammalian blood metabolites. Plasma extracts from germ-free mice were compared with samples from conventional (conv) animals by using various MS-based methods. Hundreds of features were detected in only 1 sample set, with the majority of these being unique to the conv animals, whereas approximately 10% of all features observed in both sample sets showed significant changes in their relative signal intensity. Amino acid metabolites were particularly affected. For example, the bacterial-mediated production of bioactive indole-containing metabolites derived from tryptophan such as indoxyl sulfate and the antioxidant indole-3-propionic acid (IPA) was impacted. Production of IPA was shown to be completely dependent on the presence of gut microflora and could be established by colonization with the bacterium Clostridium sporogenes. Multiple organic acids containing phenyl groups were also greatly increased in the presence of gut microbes. A broad, drug-like phase II metabolic response of the host to metabolites generated by the microbiome was observed, suggesting that the gut microflora has a direct impact on the drug metabolism capacity of the host. Together, these results suggest a significant interplay between bacterial and mammalian metabolism.[1]
Toxicity/Toxicokinetics
mouse LDLo intraperitoneal 100 mg/kg
References

[1]. Metabolomics analysis reveals large effects of gut microflora on mammalian blood metabolites. Proc Natl Acad Sci U S A. 2009 Mar 10;106(10):3698-703.

[2]. Reactive oxygen intermediates, molecular damage, and aging. Relation to melatonin. Ann N Y Acad Sci. 1998 Nov 20;854:410-24.

[3]. Indolepropionic acid and novel lipid metabolites are associated with a lower risk of type 2 diabetes in the Finnish Diabetes Prevention Study. Sci Rep. 2017 Apr 11;7:46337. doi: 10.1038/srep46337.

Additional Infomation
3-(1H-indol-3-yl)propanoic acid is an indol-3-yl carboxylic acid that is propionic acid substituted by a 1H-indol-3-yl group at position 3. It has a role as an auxin, a human metabolite and a plant metabolite. It is functionally related to a propionic acid. It is a conjugate acid of a 3-(1H-indol-3-yl)propanoate.
3-Indolepropionic acid has been reported in Scheffersomyces spartinae, Tetrastigma hemsleyanum, and other organisms with data available.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C11H11NO2
Molecular Weight
189.214
Exact Mass
189.078
Elemental Analysis
C, 69.83; H, 5.86; N, 7.40; O, 16.91
CAS #
830-96-6
Related CAS #
3-Indolepropionic acid-d2;2469257-98-3
PubChem CID
3744
Appearance
Off-white to yellow solid powder
Density
1.3±0.1 g/cm3
Boiling Point
417.6±20.0 °C at 760 mmHg
Melting Point
134-135 °C(lit.)
Flash Point
206.4±21.8 °C
Vapour Pressure
0.0±1.0 mmHg at 25°C
Index of Refraction
1.667
LogP
1.76
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
3
Heavy Atom Count
14
Complexity
217
Defined Atom Stereocenter Count
0
InChi Key
GOLXRNDWAUTYKT-UHFFFAOYSA-N
InChi Code
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)
Chemical Name
3-(1H-indol-3-yl)propanoic acid
Synonyms
IPA; Indole 3 propionic acid; 3-Indolepropionic acid; 830-96-6; Indole-3-propionic acid; 3-(1H-Indol-3-yl)propanoic acid; 1H-Indole-3-propanoic acid; Indolepropionic acid; 3-(3-Indolyl)propionic acid; Indolylpropionic Acid; Indole-3-propionic acid
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ≥ 100 mg/mL (~528.51 mM)
H2O : ~1 mg/mL (~5.29 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (13.21 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (13.21 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 5.2851 mL 26.4257 mL 52.8513 mL
5 mM 1.0570 mL 5.2851 mL 10.5703 mL
10 mM 0.5285 mL 2.6426 mL 5.2851 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
  • To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.
Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

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  • The answer appears in the Volume (to add to vial) box
In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

Clinical Trial Information
Safety and Pharmacology Study of VP 20629 in Adults With Friedreich's Ataxia
CTID: NCT01898884
Phase: Phase 1
Status: Completed
Date: 2021-06-02
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