Talk:Catechol

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Proposed move to catechol

Probably uncontroversial, but why not move this article to catechol? Please leave a note if you have concerns.--Smokefoot (talk) 17:21, 8 February 2009 (UTC)[reply]

You mean simply rename this article and run the redirect the other way, from pyrocatechol to catechol? Sure. Since 1,2 dihydroxybenzene is better known now as catechol than its historical name, and since a search on either will still recover the needed info, let's switch. SBHarris 23:31, 8 February 2009 (UTC)[reply]

Added a point on Catechin Jasoninkid (talk) 15:37, 23 February 2009 (UTC)[reply]

Cytotoxicity

Catechol was cytotoxic to neuroblastoma N2a cells in vitro. The minimal cytotoxic concentration after 72 h was 20 micromol/l. The concentration that killed 50 % of cells (EC50) was 38 micromol/l after 72 h. Catechol induced reduced glutathione (GSH) depletion after 24 h, prior to cell death by apoptosis.[1] —Preceding unsigned comment added by 200.128.60.24 (talk) 21:54, 3 August 2009 (UTC) [1] Lima, R. M. F.; Alvarez, L. D. G.; Costa, M. F. D.; Costa, S. L.; Clarêncio, J.; El-Bachá, R. S. Cytotoxic effects of catechol to neuroblastoma N2a cells. Gen. Physiol. Biophys. (2008), 27, 306-314. —Preceding unsigned comment added by 200.128.60.24 (talk) 21:33, 4 August 2009 (UTC)[reply]

Semi-empirical formula???

The opening phrase states that Catechol has a semi-empirical formula C6H4(OH)2. What exactly does this mean? This is also particularly confusing as this is its molecular formula. I have not come across this term in my degree. Is it in reference to hydrogen bonding networks this molecule participates in the solid state? I think this should be changed to just simply molecular formula, especially as in solution where most chemical reactions occur I would expect it to behave as discreet single units of 1,2-dihydroxybenzene (depending on solvent). Any comments/ideas? --DarkFission (talk) 20:26, 30 November 2009 (UTC)[reply]

Origin of name "Catechol"

I've been trying to discover the origin of the name "catechol".

When Hugo Reinsch discovered catechol in 1839, he called it Brenz-Katechusäure (burned catechu acid).[1]

In 1841, both Wackenroder and Zwenger independently rediscovered catechol. Wackenroder called it Brenzcatechusäure,[2] whereas Zwenger called it Brenzcatechin.[3]

In 1841, the English-language science journal, Philosophical Magazine, reported on Wackenroder and Zwenger's work, and rendered their names for catechol as pyrocatechin.[4]

Thereafter, catechol had many names, each name depending on the substance from which the catechol had been obtained. Some years were required before chemists realized that all of these substances were the same compound. — Preceding unsigned comment added by VexorAbVikipædia (talk • contribs) 14:56, 18 April 2015 (UTC)[reply]

By 1852, Erdmann realized that catechol was benzene with two oxygen atoms added to it, so he wanted to call it Oxyphensäure (oxyphenic / oxyphenyl acid).[5]

In 1856, Wagner argued that catechol was an isomer of hydroquinone (Hydrochinon).[6]

In 1866, Henry Watts listed catechol as oxyphenic acid.[7]

In 1867, August Kekulé called catechol bihydroxylbenzol (dihydroxybenzene).[8]

By 1868, catechol was being listed as pyrocatechol.[9]

By 1879, the Journal of the Chemical Society was recommending that catechol be called "catechol", and in the following year, it was listed as such.[10][11]

  1. ^ Hugo Reinsch (1839) "Einige Bemerkungen über Catechu" (Some observations about catechu), Repertorium für die Pharmacie, 68 : 49-58. Catechol is named Brenz-Katechusäure on p. 58.
  2. ^ H. Wackenroder (1841) "Eigenschaften der Catechusäure" (Properties of catechu acid), Annalen der Chemie und Pharmacie, 37 : 306-320. He names catechol on p. 309.
  3. ^ Constantin Zwenger (1841) "Ueber Catechin" (On catechin), Annalen der Chemie und Pharmacie, 37 : 320-336. He names catechol on p. 327.
  4. ^ (Anon.) (1841) "On catechin (catechinic acid) and pyrocatechin (pyrocatechinic acid)", Philosophical Magazine, 19 : 194-195.
  5. ^ Rudolf Wagner (1852) "Ueber die Farbstoffe des Gelbholzes (Morus tinctoria.)" (On the coloring matter of Dyer's mulberry (Morus tinctoria.)), Journal für praktische Chemie, 55 : 65-76. See p. 65.
  6. ^ Rudolf Wagner (1856) "Ueber die vermeintliche Identität der Oxyphensäure mit dem farblosen Hydrochinon" (On the putative identity of oxyphenyl acid and colorless hydroquinone), Journal für praktische Chemie, 67 : 490-491." See also the comment (Anmerkung) by editor Gustav Werther on p. 166: "W." (1856) "Die angebliche Pyrogallussäure im Holzessig" (The putative pyrogallic acid in pyroligneous acid), Journal für praktische Chemie, 67 : 164-167.
  7. ^ Henry Watts, ed. A Dictionary of Chemistry … (London, England: Longmans, Green, and Co., 1866), p. 315.
  8. ^ Note:
    • Here, Kekulé calls catechol bihydroxylbenzol: August Kekulé (1867) "Ueber die Sulfosäuren des Phenols" (On the sulfonates of phenol) Zeitschrift für Chemie, new series, 3 : 641-646 ; see p. 643.
    • However, here, Kekulé calls catechol bi-oxylbenzol: p. 254 of: August Kekulé, Chemie der Benzolderivate oder der aromatischen Substanzen (Chemistry of benzene derivates or of aromatic substances), vol. 1 (Erlangen, (Germany): Ferdinand Enke, 1867), section: "Hydroxylderivate des Benzols" (Hydroxyl derivatives of benzene), pp. 253 ff.
  9. ^ Joseph Alfred Naquet, with William Cortis, trans. and Thomas Stevenson, ed., Principles of Chemistry, founded on Modern Theories, (London, England: Henry Renshaw, 1868), p. 657. See also p. 720.
  10. ^ In 1879, the Publication Committee of the Journal of the Chemical Society issued instructions to its abstractors to "Distinguish all alcohols, i.e., hydroxyl-derivations of hydrocarbons, by names ending in ol, e.g., quinol, catechol, … " See: Alfred H. Allen (June 20, 1879) "Nomenclature of organic bodies," English Mechanic and World of Science, 29 (743) : 369.
  11. ^ William Allen Miller, ed., Elements of Chemistry: Theoretical and Practical, Part III: Chemistry of Carbon Compounds or Organic Chemistry, Section I … , 5th ed. (London, England: Longmans, Green and Co., 1880), p.524.

VexorAbVikipædia (talk) 14:30, 13 April 2015 (UTC)[reply]

Interesting insights. Such specialized historical research would be ideal for J. Chem. Ed. It is probably not, IMHO, suitable for Wikipedia per WP:NOTJOURNAL. --Smokefoot (talk) 14:28, 18 April 2015 (UTC)[reply]
Yes, I would agree that this subject is rather recondite. Typically, "John Smith" discovers compound XYZ and names it. However, in the case of catechol, the naming process was more convoluted: from pyrocatechin to pyrocatechol to catechol. Furthermore, the compound's names were (apparently) coined by anonymous editors. So in the article, I included only as many details as I thought necessary to explain the changes of name.VexorAbVikipædia (talk) 21:06, 18 April 2015 (UTC)[reply]
I, on the other hand, am in favor of cramming as much information as possible into Wikipedia, per WP:NOTPAPER. Such stuff is easy to skip over for those not interested, and quite invaluable as a time-saver for those who are. The separate question of what counts as WP:OR is a difficult and unresolved one, and IMHO, unresolvable. Generally a historical review of a subject drawn from many sources cannot avoid WP:SYNTH, nor should it, as the only type of WP:SYNTH that is really off limits is that which argues novelly toward some POV that is shockingly new and worthy of publication as some really amazing new historical synthesis of events that will interest scholars and overturn historical dogma (NOT a simple non-controversial chronological ordering as you give above). The kind of synthesis that results in ordinary WP:NPOV is still a kind of synthesis (a balanced kind) and if you read the policy on WP:SYNTH you will see that Wales and the early Wikipedists recognized this. However, later it became fashionable to deny this point, because it made heads explode to try to differentiate one type of SYNTH from the other, so it was just easier for some to boldly deny that any WP:SYNTH ever properly occurs, and pass on. Of course, that's nonsense. Wikipedia progresses in the WP:SYNTH department by the simple expedient of WP:IAR. In this case, one has no choice. Writing encyclopedia articles as a distillation from sources that contain very much more information IS a synthetic activity, if the word means anything at all. A non-judgmental computer with no sense of historical or pedagogical taste, could not possible do it. SBHarris 22:06, 18 April 2015 (UTC)[reply]
I could not agree more, we need more of this sort of content. Let us focus less on original research and more on original content! V8rik (talk) 22:41, 18 April 2015 (UTC)[reply]
Well, I guess I lost that argument! --Smokefoot (talk) 00:42, 19 April 2015 (UTC)[reply]

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C6H4(OH) listed at Redirects for discussion

An editor has asked for a discussion to address the redirect C6H4(OH). Please participate in the redirect discussion if you wish to do so. Ivanvector (Talk/Edits) 15:41, 9 July 2019 (UTC)[reply]

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