3-Indolepropionic acid

Names

[ CAS No. ]:
830-96-6

[ Name ]:
3-Indolepropionic acid

[Synonym ]:
3-Indolepropionic acid
MFCD00005660
1H-Indole-3-propanoic acid
3-(1H-Indol-3-yl)propanoic acid
b-(3-Indolyl)propionic acid
Indole-3-propionic acid
EINECS 212-600-1
3-(1H-Indol-3-yl)propionic acid
IPA

Biological Activity

[Description]:

3-Indolepropionic acid is shown to be a powerful antioxidant and has potential in the treatment for Alzheimer’s disease.

[Related Catalog]:

Natural Products >> Saccharides and Glycosides

Research Areas >> Metabolic Disease

Research Areas >> Neurological Disease

[Target]

Human Endogenous Metabolite

[In Vitro]

3-Indolepropionic acid is shown to be a powerful antioxidant and has potential in the treatment for Alzheimer’s disease[1]. 3-Indolepropionic acid is a more potent scavenger of hydroxyl radicals than melatonin. Similar to melatonin but unlike other antioxidants, 3-Indolepropionic acid scavenges radicals without subsequently generating reactive and pro-oxidant intermediate compounds[2]. It is also suggested that indolepropionic acid, a gut microbiota-produced metabolite, is a potential biomarker for the development of type 2 diabetes (T2D) that may mediate its protective effect by preservation of β-cell function[3].

[References]

[1]. Wikoff WR, et al. 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]. Reiter RJ, et al. Reactive oxygen intermediates, molecular damage, and aging. Relation to melatonin. Ann N Y Acad Sci. 1998 Nov 20;854:410-24.

[3]. de Mello VDet al. 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.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
417.6±20.0 °C at 760 mmHg

[ Melting Point ]:
134-135 °C(lit.)

[ Molecular Formula ]:
C₁₁H₁₁NO₂

[ Molecular Weight ]:
189.210

[ Flash Point ]:
206.4±21.8 °C

[ Exact Mass ]:
189.078979

[ PSA ]:
53.09000

[ LogP ]:
1.76

[ Vapour density ]:
2.1 (vs air)

[ Vapour Pressure ]:
0.0±1.0 mmHg at 25°C

[ Index of Refraction ]:
1.667

[ Storage condition ]:
−20°C

[ Water Solubility ]:
slightly soluble

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: NM1329000

CHEMICAL NAME :: 1H-Indole-3-propionic acid

CAS REGISTRY NUMBER :: 830-96-6

BEILSTEIN REFERENCE NO. :: 0147733

LAST UPDATED :: 199701

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C11-H11-N-O2

MOLECULAR WEIGHT :: 189.23

WISWESSER LINE NOTATION :: T56 BMJ D2VQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 100 mg/kg

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - chronic pulmonary edema Lungs, Thorax, or Respiration - dyspnea

REFERENCE :: PSEBAA Proceedings of the Society for Experimental Biology and Medicine. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1903/04- Volume(issue)/page/year: 34,138,1936

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xi:Irritant;

[ Risk Phrases ]:
R22;R36/37/38

[ Safety Phrases ]:
S7-S16-S24/25-S26-S36/37-S37/39-S22

[ RIDADR ]:
UN 1987 3/PG 3

[ WGK Germany ]:
3

[ RTECS ]:
NT8050000

[ HS Code ]:
29339990

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Metabolomics Approach Reveals Integrated Metabolic Network Associated with Serotonin Deficiency.

Sci. Rep. 5 , 11864, (2015)

Serotonin is an important neurotransmitter that broadly participates in various biological processes. While serotonin deficiency has been associated with multiple pathological conditions such as depre...

QSAR study on permeability of hydrophobic compounds with artificial membranes.

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We previously reported a classical quantitative structure-activity relationship (QSAR) equation for permeability coefficients (P(app-pampa)) by parallel artificial membrane permeation assay (PAMPA) of...

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Human kynurenine aminotransferase I (hKAT I) catalyzes the formation of kynurenic acid, a neuroactive compound. Here, we report three high-resolution crystal structures (1.50-1.55 A) of hKAT I that ar...