Structure via PubChem · Public domain (PubChem)
skatole
Sign in to saveAlso known as 3-Methylindole, Skatol, 3-methyl-4,5-benzopyrrole, beta-methylindole, 3-methyl-1H-indole, 3-MI, Scatole, b-Methylindole
Skatole (also spelled skatol) or 3-methylindole is an organic compound belonging to the indole family. It occurs naturally in the feces of mammals and birds and is the primary contributor to fecal odor. At high to moderate conentrations, its aroma is described as "animal, fecal, naphthyl, civet". 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 has also been identified in certain cannabis varieties.
Chemical data
- Formula
- C9H9N
- Molecular weight
- 131.17 g/mol
- IUPAC name
- 3-methyl-1H-indole
- SMILES
- CC1=CNC2=CC=CC=C12
- InChIKey
- ZFRKQXVRDFCRJG-UHFFFAOYSA-N
- XLogP
- 2.6
- Polar surface area
- 15.8 Ų
- H-bond donors
- 1
- H-bond acceptors
- 0
- Formal charge
- 0
via PubChem
Research
1,101 papers- Skatole: A thin red line between its benefits and toxicity.Biochimie · 2023
- Skatole-induced p38 and JNK activation coordinately upregulates, whereas AhR activation partially attenuates TNFα expression in intestinal epithelial cells.Bioscience, biotechnology, and biochemistry · 2023
- Decoding skatole: A comprehensive review on biosynthesis, metabolism, and mitigation in livestock production.Bioresource technology · 2026
- Skatole regulates intestinal epithelial cellular functions through activating aryl hydrocarbon receptors and p38.Biochemical and biophysical research communications · 2019
- Unraveling the skatole biodegradation process in an enrichment consortium using integrated omics and culture-dependent strategies.Journal of environmental sciences (China) · 2023
via PubMed
Wikidata facts
- Mass
- 131.073
Show 5 more facts
- chemical formula
- C₉H₉N
- canonical SMILES
- CC1=CNC2=CC=CC=C12
- boiling point
- 265
- melting point
- 96
- Commons category
- Skatole
Sources (6)
via Wikidata · CC0
~4 min read
Article
6 sectionsContents
- Biosynthesis, chemical synthesis, and reactions
- Insect studies
- Animal studies
- Applications
- See also
- References
Skatole (also spelled skatol) or 3-methylindole is an organic compound belonging to the indole family. It occurs naturally in the feces of mammals and birds and is the primary contributor to fecal odor. At high to moderate conentrations, its aroma is described as "animal, fecal, naphthyl, civet". 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 has also been identified in certain cannabis varieties.
It is used as a fragrance and fixative in many perfumes and as an aroma compound. It is also used in low concentrations in some ice cream as a flavor enhancer. Its name derives from the Greek root skato-, meaning feces. Skatole was discovered in 1877 by the German physician Ludwig Brieger (1849–1919).