FComEx: Indole (PC000102)

Record Information

Version

1.0

Creation date

2015-10-09 22:28:21 UTC

Update date

2017-01-19 02:36:12 UTC

FoodComEx ID

PC000102

FoodDB Record

FDB012008

Chemical Information

Name

Indole

Description

Constituent of several flower oils, especies of Jasminum and Citrus subspecies (Oleaceae) production of bacterial dec. of proteins. Flavouring ingredientand is also present in crispbread, Swiss cheese, Camembert cheese, wine, cocoa, black and green tea, rum, roasted filbert, rice bran, clary sage, raw shrimp and other foodstuffs Indole is a major constituent of coal-tar, and the 220-260 °C distillation fraction is the main industrial source of the material. Indole and its derivatives can also be synthesized by a variety of methods. The main industrial routes start from aniline.; Indole is a solid at room temperature. Indole can be produced by bacteria as a degradation product of the amino acid tryptophan. It occurs naturally in human feces and has an intense fecal odor. At very low concentrations, however, it has a flowery smell, and is a constituent of many flower scents (such as orange blossoms) and perfumes. It also occurs in coal tar.; Indole is an aromatic heterocyclic organic compound. It has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. Indole is a popular component of fragrances and the precursor to many pharmaceuticals. Compounds that contain an indole ring are called indoles. The most famous derivative is the amino acid tryptophan.; Indole is an aromatic heterocyclic organic compound. It has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. It can be produced by bacteria as a degradation product of the amino acid tryptophan. It occurs naturally in human feces and has an intense fecal smell. At very low concentrations, however, it has a flowery smell, and is a constituent of many flower scents (such as orange blossoms) and perfumes. Natural jasmine oil, used in the perfume industry, contains around 2.5% of indole. Indole also occurs in coal tar. The participation of the nitrogen lone electron pair in the aromatic ring means that indole is not a base, and it does not behave like a simple amine.; The Leimgruber-Batcho indole synthesis is an efficient method of sythesizing indole and substituted indoles. Originally disclosed in a patent in 1976, this method is high-yielding and can generate substituted indoles. This method is especially popular in the pharmaceutical industry, where many pharmaceutical drugs are made up of specifically substituted indoles.; The name indole is a portmanteau of the words indigo and oleum, since indole was first isolated by treatment of the indigo dye with oleum. Indole is found in many foods, some of which are flaxseed, agar, american pokeweed, and pear.

CAS Number

120-72-9

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
1-Azaindene	db_source
1-Benzazole	db_source
1-Benzo(b)pyrrole	biospider
1-H-indol	biospider
1H-Benzo[b]pyrrole	biospider
1H-Indole	biospider
1H-Indole (9CI)	biospider
2-Amino-3-hydroxy-3-phenylpropanoic acid	biospider
2, 3-Benzopyrrole	biospider
2,3-Benzopyrole	biospider
2,3-Benzopyrrole	db_source
Benzo[b]pyrrole	biospider
Benzopyrrole	biospider
DL-beta-phenylserine	biospider
FEMA 2593	db_source
IND	biospider
Indol	biospider
Indol(german)	biospider
Indole (8CI)	biospider
Indole benzo-pyrrole	biospider
Ketole	biospider
Ketole (obsol.)	db_source

Chemical Formula

C16H14N2

IUPAC name

1H-indole; 3H-indole

InChI Identifier

InChI=1S/2C8H7N/c2*1-2-4-8-7(3-1)5-6-9-8/h1-4,6H,5H2;1-6,9H

InChI Key

AYVVZVSBYJTFGL-UHFFFAOYSA-N

Isomeric SMILES

C1C=NC2=C1C=CC=C2.N1C=CC2=C1C=CC=C2

Average Molecular Weight

234.2958

Monoisotopic Molecular Weight

234.115698458

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

Indoles

Alternative Parents

Substituents

Indole
Benzenoid
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Imine
Aromatic heteropolycyclic compound

Molecular Framework

Not Available

External Descriptors

Not Available

Physico-Chemical Properties - Experimental

Property	Value	Reference
Experimental logP	2.14	HANSCH,C ET AL. (1995)
Experimental Water Solubility	3.56 mg/mL at 25 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Melting Point	Mp 52°	DFC

Foods of Origin