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|Section2= |Section3= |Section7= |Section8= }} 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).〔See: * Brieger, Ludwig (1877) ("Ueber die flüchtigen Bestandtheile der menschlichen Excremente" ) (On the volitile components of human excrement), ''Berichte der deutschen chemischen Gesellschaft'', 10 : 1027-1032. * Reprinted in: Brieger, Ludwig (1878) ("Ueber die flüchtigen Bestandtheile der menschlichen Excremente" ), ''Journal für Praktische Chemie'', 17 : 124-138. * See also: Brieger, Ludwig (1879) ("Ueber Skatol" ) (On skatole), ''Berichte der deutschen chemischen Gesellschaft'', 12 : 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) ....)〕 Skatole is also used by U.S. military in its non-lethal weaponry; specifically, malodorants.〔(U.S. Patent 6,386,113 )〕 ==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 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.〔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.)〕 抄文引用元・出典: フリー百科事典『 ウィキペディア（Wikipedia）』 ■ウィキペディアで「skatole」の詳細全文を読む スポンサード リンク
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