Indole-3-carboxaldehyde

Names

[ CAS No. ]:
487-89-8

[ Name ]:
Indole-3-carboxaldehyde

[Synonym ]:
3-Indolecarboxaldehyde
INDOLE-3-ALDEHYDE
1H-Indole-3-carboxaldehyde
indole-3-carbaldehyde
1H-Indole-3-carbaldehyde
I3CA
indol-3-carboxaldehyde
INDOL-3-ALDEHYDE
3-Formylindol
3-Indolealdehyde
3-Indolecarbaldehyde
3-Indoledehyde
Indole-3-carboxyaldehyde
EINECS 207-665-8
Indole-3-carboxaldehyde
AURORA KA-4265
MFCD00005622
3-Formylindole
Indole-3-methand

Biological Activity

[Description]:

Indole-3-carboxaldehyde (3-Formylindole), a cabbage extract, is the product of the oxidative degradation of indole-3-acetic acid (IAA) by crude enzyme preparations from etiolated pea seedlings. Indole-3-carboxaldehyde (3-Formylindole) is a biochemical used to prepare analogs of the indole phytoalexin cyclobrassinin[1].

[Related Catalog]:

Research Areas >> Others

Signaling Pathways >> Others >> Others

[References]

[1]. Robert E. Stutz, et al. Enzymatic Formation of Indole-3-Carboxaldehyde from Indole-3-Acetic Acid. Plant Physiol. 1958 May; 33(3): 207–212.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
339.1±15.0 °C at 760 mmHg

[ Melting Point ]:
193-198 °C(lit.)

[ Molecular Formula ]:
C₉H₇NO

[ Molecular Weight ]:
145.158

[ Flash Point ]:
166.8±27.8 °C

[ Exact Mass ]:
145.052765

[ PSA ]:
32.86000

[ LogP ]:
1.68

[ Vapour Pressure ]:
0.0±0.7 mmHg at 25°C

[ Index of Refraction ]:
1.729

[ Storage condition ]:
Keep Cold

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: NL5993600

CHEMICAL NAME :: Indole-3-carboxaldehyde

CAS REGISTRY NUMBER :: 487-89-8

BEILSTEIN REFERENCE NO. :: 0114117

LAST UPDATED :: 199701

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C9-H7-N-O

MOLECULAR WEIGHT :: 145.17

WISWESSER LINE NOTATION :: T56 BMJ DVH

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 600 mg/kg

TOXIC EFFECTS :: Autonomic Nervous System - smooth muscle relaxant (mechanism undefined, spasmolytic) Behavioral - anticonvulsant Behavioral - changes in motor activity (specific assay)

REFERENCE :: PCJOAU Pharmaceutical Chemistry Journal (English Translation). Translation of KHFZAN. (Plenum Pub. Corp., 233 Spring St., New York, NY 10013) No.1- 1967- Volume(issue)/page/year: 6,33,1972

Safety Information

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

[ Hazard Codes ]:
Xi: Irritant;

[ Safety Phrases ]:
S22-S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
NL5993600

[ HS Code ]:
2942000000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2942000000

Articles

A chemical screening approach reveals that indole fluorescence is quenched by pre-fibrillar but not fibrillar amyloid-beta.

Bioorg. Med. Chem. Lett. 19 , 4952-7, (2009)

Aggregated amyloid-beta (Abeta) peptide is implicated in the pathology of Alzheimer's disease. In vitro and in vivo, these aggregates are found in a variety of morphologies, including globular oligome...

Antioxidative properties of ascorbigen in using multiple antioxidant assays.

Biosci. Biotechnol. Biochem. 78(10) , 1723-30, (2014)

The antioxidative properties of ascorbigen, one of the major indole-derived compounds of Brassica vegetables, were systematically evaluated using multiple assay systems with comparison to the well-kno...

Rational design of novel CYP2A6 inhibitors.

Bioorg. Med. Chem. 22(23) , 6655-64, (2015)

Inhibition of CYP2A6-mediated nicotine metabolism can reduce cigarette smoking. We sought potent and selective CYP2A6 inhibitors to be used as leads for drugs useful in smoking reduction therapy, by e...