Skatole

Skatole

Chembox new
Name = Skatole
ImageFile = Skatole.svg
ImageSize = 150px
ImageName = Skatole
IUPACName = 3-methylindole
OtherNames = 4-Methyl-2,3-benzopyrrole
Section1 = Chembox Identifiers
SMILES = C1=C2C(=CC=C1)C(=C [N] 2C)C
CASNo = 83-34-1
RTECS =
Section2 = Chembox Properties
Formula = C9H9N
MolarMass = 131.172 g/mol
Appearance = white crystalline solid
Density =
Solubility = insoluble
MeltingPt = 93-95 °C (366-369 K)
BoilingPt = 265 °C (583 K)
pKa =
pKb =
Viscosity =
Section3 = Chembox Structure
MolShape =
Coordination =
CrystalStruct =
Dipole =
Section7 = Chembox Hazards
MainHazards =
FlashPt =
RPhrases =
SPhrases =
Section8 = Chembox Related
OtherAnions =
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Function =
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OtherCpds =

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), 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 the Greek root "skato-" meaning "dung".

Chemical properties

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 π electrons. It can be synthesized through a Fischer indole synthesis which was developed by Emil Fischer.

Insect attractant

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. [cite journal | url=http://www.springerlink.com/content/kv52574k74438848/ |author=Schiestl, F.P. & Roubik, D.W. |year=2004 |title=Odor Compound Detection in Male Euglossine Bees | journal= Journal of Chemical Ecology |volume = 29 |pages=253–257]

3-Methylindole has been shown to be an attractant to gravid mosquitoes in both field and laboratory conditions. Because this compound is present in feces, it is found in combined sewage overflows (CSO) as steams and lakes containing CSO water have untreated human and industrial waste. Knowledge of this attractant makes CSO sites of particular interest when studying mosquito-borne diseases such as West Nile Virus. [cite journal|author = Beechler, J W., J G Miller, and M S Mulla | year=1994 |title=Field evaluation of synthetic compounds mediating oviposition in Culex mosquitoes (Diptera: Culicidae) |journal = J Chem Ecol]

afety

Skatole has been shown to cause pulmonary edema in goats, sheep, rats, and some strains of mice. It appears to selectively target Clara cells, which are the major site of cytochrome P450 enzymes in the lungs. These enzymes convert skatole to a reactive intermediate, 3-methyleneindolenine, which damages cells by forming protein adducts. [cite journal
last = Miller
first = M
coauthors = Kottler S, Ramos-Vara J, Johnson P, Ganjam V and Evans T
year = 2003
title = 3-Methylindole Induces Transient Olfactory Mucosal Injury in Ponies
journal = Veterinary Pathology
volume = 40
pages = 363–70
doi = 10.1354/vp.40-4-363
pmid = 12824507 ]

In a 1994 report released by five top cigarette companies, skatole was listed as one of the 599 additives to cigarettes. [cite web
url =http://quitsmoking.about.com/cs/nicotineinhaler/a/cigingredients.htm
title =What's in a cigarette?
accessdate =2006-05-31] It is added as a flavoring ingredient.

ee also

* Indole
* 1-Methylindole
* 2-Methylindole (methylketol)
* 5-Methylindole
* 7-Methylindole

References

External links

* [http://www.newscientist.com/backpage.ns?id=mg18124397.000 Whats that smell?]


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Look at other dictionaries:

  • skatole — [skat′ōl] n. [< Gr skōr (gen. skatos), dung (see SCATO ) + OL2] a foul smelling, colorless, crystalline compound, C9H9N, formed by the decomposition of proteins, as in the intestine …   English World dictionary

  • skatole — skatolas statusas T sritis chemija formulė NC₈H₆CH₃ atitikmenys: angl. skatole rus. скатол ryšiai: sinonimas – 3 metilindolas …   Chemijos terminų aiškinamasis žodynas

  • skatole — also skatol noun Etymology: International Scientific Vocabulary, from Greek skat , skōr excrement more at scatology Date: 1879 a foul smelling compound C9H9N found in the intestines and feces, in civet, and in several plants or made synthetically …   New Collegiate Dictionary

  • skatole — /skat ohl, awl/, n. a white, crystalline, watersoluble solid, C9H9N, having a strong, fecal odor: used chiefly as a fixative in the manufacture of perfume. [1875 80; < Gk skat (s. of skôr) dung + OLE2] * * * …   Universalium

  • skatole — noun A mildly toxic white crystalline organic compound of the indole family, occurring naturally in faeces and coal tar …   Wiktionary

  • skatole — 3 Methyl 1H indole, formed in the intestine by the bacterial decomposition of l tryptophan and found in fecal matter, to which it imparts its characteristic odor. * * * ska·tole skat .ōl, skāt also ska·tol .ȯl, .ōl n a foul smelling compound… …   Medical dictionary

  • skatole — n. white crystalline compound used in the manufacture of perfume (Chemistry) …   English contemporary dictionary

  • skatole — skat·ole …   English syllables

  • skatole — methyl indole; n. a derivative of the amino acid tryptophan, excreted in the urine and faeces …   The new mediacal dictionary

  • skatole — skat•ole [[t]ˈskæt oʊl, ɔl[/t]] n. chem. a white, crystalline, water soluble solid, C9H9N, having a strong, fecal odor: used chiefly as a fixative in perfume making • Etymology: 1875–80; < Gk skat (s. of skôr) dung + ole II …   From formal English to slang

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