Talk:Skatole

message: http://www.newscientist.com/backpage.ns?id=mg18124397.000  —Preceding unsigned comment added by 66.238.211.199 (talk) 19:31, 11 September 2007 (UTC)
replies: text: I have removed the copied material.  Thanks for catching it.  --Ed (Edgar181) 19:52, 11 September 2007 (UTC)
thread_title:  I think sections of this were copied from the New Scientist: 

message: The statement It is also the smell that is used by skunks. if not entirely wrong, is at least misleading as it implies the the major scent of skunk spray is skatole rather than the various sulfur compounds that are mentioned in the article on skunks.
216.58.25.11 (talk) 04:01, 1 June 2011 (UTC)
replies: text: I agree.  A brief search of the primary literature didn't turn up any connection between skunk odor and skatole.  The claim is therefore dubious and unreferenced, so I have removed it.  -- Ed (Edgar181) 11:31, 1 June 2011 (UTC)
thread_title:  I suspect the reference to skunk scent is wrong 

message: I suspect that some people might be interested in how skatole was discovered; however, the details are frankly somewhat disgusting, so I don't know whether the editors want them to be posted.
Apparently, in the 1870s there was a controversy about how bacteria caused diseases.  Some people argued that bacteria produced poisons, and that it was these poisons that produced the disease symptoms; they cited ptomaine poisoning as a good example.  This led to studies of how food decayed; specifically, Ludwig Brieger tried to isolate the products of decay.
On pages 129 and 130 of his paper "Ueber die flüchtige Bestandtheile der menschlichen Excremente" (On the volitile components of human excrement), Journal für praktische Chemie, vol. 17, pages 124-138 (1878), Brieger detailed how he isolated skatole:
Original text:
Zur Gewinnung dieser Substanzen schlug ich nach vielen Vorversuchen in gläsernen Retorten folgendes Verfahren ein.
5-6 Kilo frischer Faeces wurden mit 8 Liter Wasser verrührt, mit 200-300 Ccm. Essigsäure angesäuert und in einer kupfernen Blase auf dem Sandbade destillirt, bis ungefähr 6 Liter in die Vorlage übergegangen.  Das filtrirte Destillat wurde mit Natronlauge neutralisirt, mit etwa einem Drittel Volumen Aether ausgeschüttelt, der Aether abdestillirt bis auf ein geringes Volumen, der letzte Rest des Aethers in einer kleinen Schaale verdunsten gelassen, wobei ein geringer öliger Rückstand zurückblieb, der dann meistentheils nach einiger Zeit krystallinisch erstarrte.  Wird derselbe mit wenig heissem Wasser im Reagensröhrchen gekocht, so löst er sich grösstentheils auf, und heiss filtrirt scheidet sich dann beim Erkalten das Skatol in krystallinschen Blättchen aus.  In Lösung bleiben Indol, Phenol, und ein gelbes Oel, auf das ich unten zurückkommen werde, und Spuren nicht näher definirbarer Substanzen.
Translation:
For the preparation of these substances, I adopted the following procedure after many preliminary tests in glass retorts.
5-6 kilograms of fresh feces were mixed with 8 liters of water, acidified with 200-300 ml. of acetic acid, and distilled in a copper still pot on a sand bath, until about 6 liters passed into the receiver.  The filtered distillate was neutralized with sodium hydroxide solution, shaken with about a 1/3 volume of ether, the ether distilled off until a small volume remained; the remaining ether [i.e., extract] was left to evaporate in a small bowl, where a slight oily residue was left, which then usually after some time solidified in crystalline form.  If this is simmered with a little hot water in a test tube, it largely dissolves, and after the hot solution is filtered, skatole separates upon cooling as crystalline flakes.  In the solution there remain indole, phenol, and a yellow oil, to which I will return below, as well as traces of not specifically definable substances.
Cwkmail (talk) 17:52, 3 January 2012 (UTC)
thread_title:  Discovery of skatole:  post? 

message: I came to this page looking for information on the physical chemistry of skatole (boiling point, etc.) If an expert in the subject could please include this information, it would be greatly appreciated.  — Preceding unsigned comment added by 70.54.129.23 (talk) 23:06, 22 August 2020 (UTC)
thread_title:  physical chemistry