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3-Methyl-1H-indole (FDB010993)

Record Information
Version1.0
Creation date2010-04-08 22:09:25 UTC
Update date2019-08-01 18:42:32 UTC
Primary IDFDB010993
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name3-Methyl-1H-indole
DescriptionA 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 Number83-34-1
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted PropertiesNot Available
Chemical FormulaC9H9N
IUPAC name
InChI IdentifierInChI=1S/C9H9N/c1-7-6-10-9-5-3-2-4-8(7)9/h2-6,10H,1H3
InChI KeyZFRKQXVRDFCRJG-UHFFFAOYSA-N
Isomeric SMILESCC1=CNC2=C1C=CC=C2
Average Molecular Weight131.1745
Monoisotopic Molecular Weight131.073499293
Classification
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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndoles
Direct Parent3-methylindoles
Alternative Parents
Substituents
  • 3-methylindole
  • Benzenoid
  • Substituted pyrrole
  • Heteroaromatic compound
  • Pyrrole
  • Azacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 82.41%; H 6.92%; N 10.68%DFC
Melting PointMp 95°DFC
Boiling PointBp755 265-266°DFC
Experimental Water Solubility0.498 mg/mL at 25 oCPEARLMAN,RS et al. (1984)
Experimental logP2.60HANSCH,C ET AL. (1995)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MSNot Available
NMRNot Available
ChemSpider ID6480
ChEMBL IDCHEMBL1329793
KEGG Compound IDC08313
Pubchem Compound ID6736
Pubchem Substance IDNot Available
ChEBI ID9171
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00466
CRC / DFC (Dictionary of Food Compounds) IDFXX35-E:FXX35-E
EAFUS ID3401
Dr. Duke IDSKATOLE
BIGG IDNot Available
KNApSAcK IDC00001430
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID83-34-1
GoodScent IDrw1006331
SuperScent ID6736
Wikipedia ID3-methylindole
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
mothball
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
fecal
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
animal
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
very strong
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
indole
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
civet
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).