Indole-2-carboxylic acid

Names

[ Name ]:
Indole-2-carboxylic acid

[Synonym ]:
1H-Indole-2-carboxylic acid
T56 BMJ CVQ
Indole-2-carboxylic acid
2-Carboxyindole
2-Indolecarboxylic acid
MFCD00005611
EINECS 216-030-4

Biological Activity

[Description]:

Indole-2-carboxylic acid is a strong inhibitor of lipid peroxidation. Indole-2-carboxylic acid (I2CA) specifically and competitively inhibits the potentiation by glycine of NMDA-gated current[1][2].

[Related Catalog]:

Signaling Pathways >> Neuronal Signaling >> iGluR

Research Areas >> Neurological Disease

Signaling Pathways >> Membrane Transporter/Ion Channel >> iGluR

[Target]

Human Endogenous Metabolite

[References]

[1]. 2-Indolecarboxylic acid.

[2]. J E Huettner, et al. Indole-2-carboxylic Acid: A Competitive Antagonist of Potentiation by Glycine at the NMDA Receptor. Science. 1989 Mar 24;243(4898):1611-3.

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
419.6±18.0 °C at 760 mmHg

[ Melting Point ]:
202-206 °C(lit.)

[ Molecular Formula ]:
C₉H₇NO₂

[ Molecular Weight ]:
161.157

[ Flash Point ]:
207.6±21.2 °C

[ Exact Mass ]:
161.047684

[ PSA ]:
53.09000

[ LogP ]:
2.31

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

[ Index of Refraction ]:
1.726

MSDS

Click to get detail MSDS

Safety Information

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

[ Hazard Codes ]:
Xi: Irritant;Xn: Harmful;

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S22-S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
NK7882812

[ 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

Molecular modifications on carboxylic acid derivatives as potent histone deacetylase inhibitors: Activity and docking studies.

Bioorg. Med. Chem. 17 , 5219-28, (2009)

In the light of known HDAC inhibitors, 33 carboxylic acid derivatives were tested to understand the structural requirements for HDAC inhibition activity. Several modifications were applied to develop ...

In vitro and in vivo assessment of the antioxidant activity of melatonin and related indole derivatives.

Gen. Physiol. Biophys. 21(2) , 153-62, (2002)

Effects of melatonin and some structurally related indole compounds were studied by in vitro methods such as (i) an inhibition of the hyaluronic acid degradation and (ii) a standard lipid peroxidation...

Protonated carbonic acid and reactive intermediates in the acidic decarboxylation of indolecarboxylic acids.

J. Org. Chem. 77(15) , 6505-9, (2012)

Elucidation of the mechanism for decarboxylation of indolecarboxylic acids over a wide range of solution acidity reveals the importance of protonated carbonic acid (PCA) as a reaction intermediate. In...