Skatole

Actually, skatole is an important molecule, and crops up in some surprising places. 

It is used in very small amounts as a flavoring material in ice cream. The skatole put in ice cream is man-made. No, let me rephrase that... The skatole put in ice cream is synthetic it has no human connections. 

The odor of skatole depends on its concentration. At low concentrations, skatole actually has a rather nice, sweet smell it crops up in orange blossom and jasmine in small amounts. It s also used by Zantedeschia aethiopica. 

It s an Arum lily which makes skatole to attract pollinating insects. It has flowers on the central part (the spadix) in male and female zones. The faint scent attracts crawling insects and bees which pollinate the flowers. 

Other Arum plants use it, including Arum creticum 

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Sizing material Sizing tests Sjogren s syndrome Skane M-8 Skatole [83-34-1]... 

Most ring syntheses of this type are of modern origin. The cobalt or rhodium carbonyl catalyzed hydrocarboxylation of unsaturated alcohols, amines or amides provides access to tetrahydrofuranones, pyrrolidones or succinimides, although appreciable amounts of the corresponding six-membered heterocycle may also be formed (Scheme 55a) (73JOM(47)28l). Hydrocarboxylation of 4-pentyn-2-ol with nickel carbonyl yields 3-methylenetetrahy-drofuranone (Scheme 55b). Carbonylation of Schiff bases yields 2-arylphthalimidines (Scheme 55c). The hydroformylation of o-nitrostyrene, subsequent reduction of the nitro group and cyclization leads to the formation of skatole (Scheme 55d) (81CC82). 

Present-day nomenclature is partly the result of the conflict and interplay of two functions the need to communicate in speech and on the printed page on the one hand, and the need for archival storage of information and its efficient, reliable retrieval. The former function came first, and laid the basis for the nomenclature most commonly used even today, and gave birth to a wealth of trivial names (i.e. names that give little or no information on structure). These were often coined on the basis of the origin of the substance, as in the case of collidine, obtained from distillation of bones in glue factories, or were derived from a special characteristic, as in the case of skatole, which has a fecal odor. Such names are short and generally euphonious, but they must be memorized they cannot be deduced from the structure. 

Methylindole (skatole) [83-34-1] M 131.2, m 95 , pK -4.55 (C-3-protonation, aq H2SO4). Crystd from benzene. Purified by zone melting. 

Methylindole has also been prepared by lithium aluminum hydride reduction of 1-methylindoxyl. Compounds giving rise to NH absorption in the infrared (indole, skatole) can be completely removed by refluxing the crude 1-methylindole over sodium for 2 days and then distilling the unreacted 1-methylindole from the sodio derivatives and tarry decomposition products. 

Oddo reported that the organomagnesium derivatives of p3Trole, indole, skatole, and carbazole could be prepared in a single operation by mixing the parent heterocyclic compound with an alkyl halide and magnesium in anhydrous ether.The product formed was reported to be the same as that obtained by the more conventional procedure. However, this approach to the synthesis of the indole Grignard reagents does not seem to have been exploited in subsequent work. 

Acetyl-3-methyIindoIe (117) was obtained when the. skatole Grignard reagent was treated with acetyl chloride at 100° in the absence of Solvent, but l-acetyl-3-methylindole (118) was obtained when the... 

Mingoia reported that 2-chloroacetyl-3-methylindole (139) was obtained by the action of chloroacetyl chloride on the skatole Grignard reagent. ... 

Carboxyphenyl-(2-methyl-3-indoleninjdidene)methanol (303) was said to be formed by the action of phthalic anhydride on 2-methyl-indole magnesium bromide. Skatole magnesium bromide, on the other hand, apparently gave 2-carboxyphenyl-(3-methyl-2-indole-ninylidene)methanol (304) and 3-hydroxy-3-(3-methyl-l-indolyl)-phthalide (305) on treatment with 1 mole of phthalic anhydride. The derivative 305 was easily hydrolyzed in alkali, giving skatole and phthalic acid, and was thus formulated as a 1-skatolyl derivative. ... 

In 1912 Oddo reported the results of an investigation of the products obtained on carbonation of both the 2- and 3-methylindole Grignard reagents. In the former case the relatively unstable l-carboxy-2-methylindole (377) was the main product obtained when the reaction was carried out at temperatures up to 35° however, at 110° the isomeric 3-carboxy-2-methylindole (378) was the major product formed. According to Oddo l-carboxy-3-methylindole (379) is more stable than the corresponding 2-methyl compound (i.e., 377) and can be obtained by carbonation of the skatole Grignard reagent at 100°. ... 

Ingraffia studied the oxidation of the Grignard reagents derived from indole, skatole, and 2-methylindole with hydrogen peroxide and... 

Skatole (3-methylindole) readily forms a dimer hydrochloride with HCl in ether or with 15% aqueous HCl, as docs 1,3-dimethyl-indole. 3-n-Propylindole is also readily dimerized in dry ether/HCl/ ... 

Methylindole is, however, incorporated into mixed dimers and trimers. It thus reacts with indole and with skatole to form mixed dimers, and 2 moles react with 1 mole of indole for form a mixed trimcr. Likewise indole forms a dimer with 1,2-dimethylindole, 2-phenylindole, and even with 2,5-dimethylpyrrole, ... 

Again based on the failure of 2-methylindole to form a dimer, Schmitz-DuMont proposed structure (29) for skatole dimer. Structure (30) was, however, shown to be the correct one independently in three... 

The structure (39) proposed for this compound by analogy with indole and skatole dimers was confirmed by an analysis of the NMR spectrum. ... 

The dimerization of skatole proceeds in an entirely analogous manner, cation (44) now being the electrophilic reagent. This is sufficiently reactive to effect substitution at the a-position of a neutral skatole molecule. Attack by the less hindered side of cation (44) will be favored, leading to the stereochemistry shown in structure (30). The failure of 2-methylindole to dimerize is paralleled by the failure of 2-methylpyrrole dimer to react with a further molecule of 2-methylpyrrole. The main reason is almost certainly again the reduction in the electrophilic character of the immonium carbon by... 

Sack has recently isolated a ketone from natural civet. The civet was boiled for some hours with alcoholic potash, the alcohol evaporated and the residue extracted, with ether. The residue left on evaporating the ether was distilled with steam to remove skatole, again extracted with ether, the ether evaporated and the residue dissolved in alcohol. The alcohol was evaporated, and the residual ketone purified by conversion into its semi-carbazone, from which it was regenerated. It has the formula CjjHggO, and its characters are as follows —... 

It is found in civet and in the wood of Celtis reticulosa. It forms crystals melting at 95° and boiling at 265° to 266°. It yields a hydrochloride, 2(C9HgN). HCl, melting at 167° 10 168°, and a picric acid compound melting at 172° to 173°. Skatol yields a blue colour with a solution of dimethyl-aminobenzaldehyde. 

Skatol is a foul-smelling compound, but when used in very minute amount is useful in the manufacture of flower blossom perfumes. 

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