| Record Information |
|---|
| Version |
3.5 |
| Creation Date |
2005-11-16 08:48:42 -0700 |
| Update Date |
2013-04-19 16:34:04 -0600 |
| HMDB ID |
HMDB00466 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
|---|
| Common Name |
3-Methylindole |
| Description |
3-Methylindole, or 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. 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. |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
|
| Synonyms |
- 3-Methyl-1H-indole
- 3-Methylindole
- 3-MI
- b-Methylindole
- beta-Methylindole
- Scatole
- Skatol
- Skatole
|
| Chemical Formula |
C9H9N |
| Average Molecular Weight |
131.1745 |
| Monoisotopic Molecular Weight |
131.073499293 |
| IUPAC Name |
3-methyl-1H-indole |
| Traditional IUPAC Name |
skatole |
| CAS Registry Number |
83-34-1 |
| SMILES |
CC1=CNC2=C1C=CC=C2 |
| 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 |
| Chemical Taxonomy |
|---|
| Kingdom |
Organic Compounds |
| Super Class |
Aromatic Heteropolycyclic Compounds |
| Class |
Indoles |
| Sub Class |
N/A |
| Other Descriptors |
- a small molecule(Cyc)
- methylindole(ChEBI)
|
| Substituents |
|
| Direct Parent |
Indoles |
| Ontology |
|---|
| Status |
Expected and Not Quantified |
| Origin |
|
| Biofunction |
Not Available |
| Application |
Not Available |
| Cellular locations |
- Membrane (predicted from logP)
|
| Physical Properties |
|---|
| State |
Solid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
97.5 °C |
Not Available |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
0.498 mg/mL |
Not Available |
| LogP |
2.60 |
HANSCH,C ET AL. (1995) |
|
| Predicted Properties |
|
| Spectra |
|---|
|
|
| Biological Properties |
|---|
| Cellular Locations |
- Membrane (predicted from logP)
|
| Biofluid Locations |
Not Available
|
| Tissue Location |
Not Available
|
| Pathways |
Not Available
|
| Normal Concentrations |
|---|
|
Not Available |
| Abnormal Concentrations |
|---|
|
Not Available |
| Associated Disorders and Diseases |
|---|
| Disease References |
None |
| Associated OMIM IDs |
None |
| External Links |
|---|
| DrugBank ID |
Not Available |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB010993 |
| KNApSAcK ID |
C00001430  |
| Chemspider ID |
6480 |
| KEGG Compound ID |
C08313 |
| BioCyc ID |
SKATOLE |
| BiGG ID |
Not Available |
| Wikipedia Link |
3-methylindole |
| NuGOwiki Link |
HMDB00466 |
| Metagene Link |
HMDB00466 |
| METLIN ID |
5453 |
| PubChem Compound |
6736 |
| PDB ID |
Not Available |
| ChEBI ID |
9171 |
| References |
|---|
| Synthesis Reference |
Xu, Jianguo; Xu, Lili; Shi, Hongxin. Synthesis of 3-methylindole and its new purification method. Huagong Shengchan Yu Jishu (2005), 12(4), 12-14. |
| Material Safety Data Sheet (MSDS) |
Download (PDF)
|
| General References |
- Karlin DA, Mastromarino AJ, Jones RD, Stroehlein JR, Lorentz O: Fecal skatole and indole and breath methane and hydrogen in patients with large bowel polyps or cancer. J Cancer Res Clin Oncol. 1985;109(2):135-41.
Pubmed: 3980562
- Moore JG, Jessop LD, Osborne DN: Gas-chromatographic and mass-spectrometric analysis of the odor of human feces. Gastroenterology. 1987 Dec;93(6):1321-9.
Pubmed: 3678751
- Cooke M, Leeves N, White C: Time profile of putrescine, cadaverine, indole and skatole in human saliva. Arch Oral Biol. 2003 Apr;48(4):323-7.
Pubmed: 12663078
- Zuccato E, Venturi M, Di Leo G, Colombo L, Bertolo C, Doldi SB, Mussini E: Role of bile acids and metabolic activity of colonic bacteria in increased risk of colon cancer after cholecystectomy. Dig Dis Sci. 1993 Mar;38(3):514-9.
Pubmed: 8444084
- Muller T, Thissen R, Braun S, Dott W, Fischer G: (M)VOC and composting facilities. Part 2: (M)VOC dispersal in the environment. Environ Sci Pollut Res Int. 2004;11(3):152-7.
Pubmed: 15259697
- Codipilly DP, Kaufman HW, Kleinberg I: Use of a novel group of oral malodor measurements to evaluate an anti-oral malodor mouthrinse (TriOralTM) in humans. J Clin Dent. 2004;15(4):98-104.
Pubmed: 15794454
|
