3-Methylindole
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 its so foli smelling. It is soluble in alcohol and benzene and it gives violet color in potassium ferrocyanide (K4Fe(CN)6.3H2O) and slifuric 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 rlie 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 formlia 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 for HMDB00466 (3-Methylindole)
C9H9N
131.1745
131.073499293
3-methyl-1H-indole
scatole
83-34-1
ZFRKQXVRDFCRJG-UHFFFAOYSA-N
Not classified
Detected but not Quantified
Not Available
Not Available
Solid
LC-MS/MS Spectrum – Quattro_QQQ 10V, Positive (Annotated)splash10-001i-0900000000-a7cd474bc90f9a0227e5View in MoNA
LC-MS/MS Spectrum – Quattro_QQQ 25V, Positive (Annotated)splash10-014i-2900000000-cb7f6d8c4ad7b0a1523bView in MoNA
LC-MS/MS Spectrum – Quattro_QQQ 40V, Positive (Annotated)splash10-000l-9200000000-e9a200fb7b8fc93ced48View in MoNA
LC-MS/MS Spectrum – EI-B (HITACHI M-80) , Positivesplash10-0ufr-9200000000-7120fbb6f78f440ff725View in MoNA
LC-MS/MS Spectrum – Linear Ion Trap , negativesplash10-002b-9800000000-a8de490dffcbc2cb0c24View in MoNA
Predicted LC-MS/MS Spectrum – 10V, Positivesplash10-001i-0900000000-355610a12cde08bb25c8View in MoNA
Predicted LC-MS/MS Spectrum – 20V, Positivesplash10-001i-0900000000-36a1bcb0093fec9dd5c5View in MoNA
Predicted LC-MS/MS Spectrum – 40V, Positivesplash10-0zfr-3900000000-d8aebbf9a6779cddc735View in MoNA
Predicted LC-MS/MS Spectrum – 10V, Negativesplash10-001i-0900000000-ed646ab44a1fcc84725bView in MoNA
Predicted LC-MS/MS Spectrum – 20V, Negativesplash10-001i-0900000000-ed6f0939d3598782a893View in MoNA
Predicted LC-MS/MS Spectrum – 40V, Negativesplash10-0f89-2900000000-a801a40b2fcba369d3d4View in MoNA
Mass Spectrum (Electron Ionization)splash10-001i-2900000000-dba6ed7df0e1ee94cafeView in MoNA
1H NMR SpectrumNot Available
1H NMR SpectrumNot Available
13C NMR SpectrumNot Available
[1H,13C] 2D NMR SpectrumNot Available
Not Available
Not Available
Normal
Normal
Normal
Normal
Normal
Nonalcoholic fatty liver disease (NAFLD)
Campylobacter jejuni infection
Clostridium difficile infection
Ulcerative Colitis
None
None
Not Available
Not Available
Not Available
Not Available
FDB010993
C00001430
6480
C08313
SKATOLE
Not Available
3-methylindole
HMDB00466
HMDB00466
5453
6736
Not Available
9171
- 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 ]
Enzymes
- General function:
- Secondary metabolites biosynthesis, transport and catabolism
- Specific function:
- May be involved in the metabolism of various pneumotoxicants including naphthalene. Is able to dealkylate ethoxycoumarin, propoxycoumarin, and pentoxyresorufin but possesses no activity toward ethoxyresorufin and only trace dearylation activity toward benzyloxyresorufin. Bioactivates 3-methylindole (3MI) by dehydrogenation to the putative electrophile 3-methylene-indolenine.
- Gene Name:
- CYP2F1
- Uniprot ID:
- P24903
- Molecular weight:
- 55500.64