FComEx: 3-Methyl-1H-indole (PC000066)

Record Information

Version

1.0

Creation date

2015-10-09 22:27:52 UTC

Update date

2017-01-19 02:36:11 UTC

FoodComEx ID

PC000066

FoodDB Record

Not Available

Chemical Information

Name

3-Methyl-1H-indole

Description

A major contributor to boar taint in meat products from uncastrated male pigs. Flavouring ingredient It is one of many compounds that is attractive to males of various species of orchid bees, who apparently gather the chemical to synthesize pheromones; it is commonly used as bait to attract and collect these bees for study.; Skatole can be found as a white crystalline or fine powder solid, and it browns upon aging. It is nitrogenous and one of the rings is a pyrrole. It is soluble in alcohol and benzene and it gives a violet color in potassium ferrocyanide (K4Fe(CN)6·3H2O) and sulfuric acid (H2SO4). Skatole has a double ring system which displays aromaticity. It is continuous (all atoms in the ring are sp² hybridized), planar, and follows the 4n+2 rule because it has 10 ? electrons. It can be synthesized through a Fischer indole synthesis which was developed by Emil Fischer.; Skatole can be found as a white crystalline or fine powder solid, and it browns upon aging. It is nitrogenous and one of the rings is a pyrrole. This is probably the reason it's so foul smelling. It is soluble in alcohol and benzene and it gives violet color in potassium ferrocyanide (K4Fe(CN)6.3H2O) and sulfuric acid (H2SO4). Skatole has a double ring system which displays aromaticity that comes from the lone pair electrons on the nitrogen. It is continuous (all atoms in the ring are sp2 hybridized), planar, and follows the 4n+2 rule because it has 10 pi electrons. It can be synthesized through a Fischer indole synthesis which was developed by Emil Fischer.In a 1994 report released by five top cigarette companies, skatole was listed as one of the 599 additives to cigarettes. It is a flavoring ingredient. Skatole or 3-methylindole is a mildly toxic white crystalline organic compound with chemical formula C9H9N and CAS number 83-34-1. The compound belongs to the indole family and has a methyl substituent in position 3 of the indole ring. It occurs naturally in feces (it is produced from tryptophan in the mammalian digestive tract), beets, and coal tar, and has a strong fecal odor. In low concentrations it has a flowery smell and is found in several flowers and essential oils, including those of orange blossoms, jasmine, and Ziziphus mauritiana. It is used as a fragrance and fixative in many perfumes and as an aroma compound. Its name is derived from skato, the Greek word for dung.; Skatole or 3-methylindole is a mildly toxic white crystalline organic compound belonging to the indole family. It occurs naturally in feces (it is produced from tryptophan in the mammalian digestive tract), and coal tar, and has a strong fecal odor. In low concentrations it has a flowery smell and is found in several flowers and essential oils, including those of orange blossoms, jasmine, and Ziziphus mauritiana. It is used as a fragrance and fixative in many perfumes and as an aroma compound. Its name is derived from the Greek root skato- meaning "dung".

CAS Number

83-34-1

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
β-methylindole	biospider
1H-Indole, 3-methyl-	biospider
3 Methylindole	biospider
3-methyl-2,3-dihydro-1H-indole	biospider
3-methyl-4,5-benzopyrrole	biospider
3-methylindole	biospider
3-Methylindole (skatol)	biospider
3-Methylindole (skatole)	biospider
3-methylindoline	biospider
3-MI	HMDB
b-Methylindole	db_source
Beta-methylindole	biospider
FEMA 3019	db_source
Indole, 3-methyl-	biospider
Indole, 3-methyl- (skatole)	biospider
methyl-3-indole	biospider
Scatole	db_source
Skatol	biospider
Skatole	db_source
β-methylindole	Generator

Chemical Formula

Not Available

IUPAC name

Not Available

InChI Identifier

InChI=1S/C9H9N/c1-7-6-10-9-5-3-2-4-8(7)9/h2-6,10H,1H3

InChI Key

ZFRKQXVRDFCRJG-UHFFFAOYSA-N

Isomeric SMILES

CC1=CNC2=C1C=CC=C2

Average Molecular Weight

131.1745

Monoisotopic Molecular Weight

131.073499293

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-methylindoles. These are aromatic heterocyclic compounds that contain an indole moiety substituted at the 3-position with a methyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

3-methylindoles

Alternative Parents