Skatole

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Skatole
Skatole structure.svg Skatole 3d structure.png
Identifiers
CAS number 83-34-1 YesY
PubChem 6736
ChemSpider 6480 YesY
UNII 9W945B5H7R YesY
ChEBI CHEBI:9171 YesY
Jmol-3D images Image 1
Properties
Molecular formula C9H9N
Molar mass 131.17 g mol−1
Appearance White crystalline solid
Melting point 93 to 95 °C (199 to 203 °F; 366 to 368 K)
Boiling point 265 °C (509 °F; 538 K)
Solubility in water Insoluble
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

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". Skatole was discovered in 1877 by the German physician Ludwig Brieger (1849-1919).[1] Skatole is also used by U.S. military in its non-lethal weaponry; specifically, malodorants.[2]

Chemical properties[edit]

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 that 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.[3]

Insect attractant[edit]

Skatole 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.[4]

Skatole 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 streams 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.[5]

Safety[edit]

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 (see fog fever).[6]

See also[edit]

References[edit]

  1. ^ Brieger, Ludwig (1877) "Ueber die flüchtigen Bestandtheile der menschlichen Excremente" (On the volitile components of human excrement), Berichte der deutschen chemischen Gesellschaft, vol. 10, pages 1027-1032; reprinted in: "Ueber die flüchtigen Bestandtheile der menschlichen Excremente", Journal für Praktische Chemie, vol. 17, pages 124-138 (1878). See also: Brieger, Ludwig (1879) "Ueber Skatol" (On skatole), Berichte der deutschen chemischen Gesellschaft, vol. 12, pages 1985-1988.
    Brieger named skatole in Brieger (1877), page 1028:

    Original : Ich habe mich zuerst mit der Untersuchung der flüchtigen Bestandtheile der Excremente aus sauerer Lösung beschäftigt. Es wurden dabei die flüchtigen Fettsäuren: Essigsäure, normale und Isobuttersäure, sowie die aromatischen Substanzen: Phenol, Indol und eine neue dem Indol verwandte Substanz, die ich Skatol nennen werde, erhalten.

    Translation : I was occupied initially with the investigation of the volitile components of excrement in acidic solution. One obtained thereby volitile fatty acids; acetic acid; normal and isobutyric acid; as well as the aromatic substances: phenol, indole and a new substance which is related to indole and which I will name "skatole".

    ; Brieger (1877), page 1030: Das Skatol ... (von το σχατος = faeces) ... (Skatole ... (from το σχατος = feces) ....)
  2. ^ U.S. Patent 6,386,113
  3. ^ Emil Fischer (1886) "Indole aus Phenylhydrazin" (Indole from phenylhydrazine), Annalen der Chemie, vol. 236, pages 126-151; for Fischer's synthesis of skatole, see page 137. (It should be noted that Fischer was not the first to prepare skatole. It was prepared, via other methods, in 1880 by von Baeyer, and in 1883 by Otto Fischer and German and by Fileti.)
  4. ^ Schiestl, F.P. & Roubik, D.W. (2004). "Odor Compound Detection in Male Euglossine Bees". Journal of Chemical Ecology 29 (1): 253–257. doi:10.1023/A:1021932131526. PMID 12647866. 
  5. ^ Beechler, J W., J G Miller, and M S Mulla (1994). "Field evaluation of synthetic compounds mediating oviposition in Culex mosquitoes (Diptera: Culicidae)". J Chem Ecol 20 (2): 281–291. doi:10.1007/BF02064436. 
  6. ^ Miller, M; Kottler S, Ramos-Vara J, Johnson P, Ganjam V and Evans T (2003). "3-Methylindole Induces Transient Olfactory Mucosal Injury in Ponies". Veterinary Pathology 40 (4): 363–70. doi:10.1354/vp.40-4-363. PMID 12824507. 

External links[edit]