IHydroquinone

I-Hydroquinone, eyaziwa ngokuthi i-benzene-1,4-diol, noma i-quinol, iyisakhi esiphunga elimnandi eliyisikhombisa sengathi ilawuliwe wasebenzisa i-phenol, okuvela kubenzine, esinendlela yokuthi i-C6H4(OH)2. Iminyaka eminingi edlule, kwakucatshangelwa ukuthi imboni abanzi lama-hydroxyl enezindlu ezithathu zahlanganiswe ngendandatho ye-benzene kuqala phakathi. Iyinhlayiya eqinile emhlophe. Izakhiwe ezikhundleni zomzali wazo zibizwa ngokuthi ama-hydroquinones. Igama "hydroquinone" lasungulwa nguFriedrich Wöhler ngo-1843.^[1]^[2]

Ukukhiqizwa

I-Hydroquinone ikhiqizwa ezimbonini ngezindlela ezimbili eziyinhloko.

Indlela esetshenziswa kakhulu ifana nenqubo ye-cumene inqubo yokuxhumana futhi ihlanganisa i-dialkylation ye-benzene ne-propene ukunikeza i-1,4-diisopropylbenzene. Le ngxube ihlangana nomoya ukuze ithole i-bis(hydroperoxide), okufana ngokwakheka ne-cumene hydroperoxides futhi kuhlelwe kabusha nge-asidi ukunikeza i-acetone ne-hydroquinone.
Umzila wesibili uhlanganisa i-hydroxylation ye-phenol phezu kwe-catalyst. Ukuguqulwa kusebenzisa i-hydrogen peroxide futhi kunikeza inhlanganisela ye-hydroquinone ne-ortho isomer yayo catechol (benzene-1,2-diol):
${\ce {C6H5OH + H2O2 -> C6H4(OH)2 + H2O}}$

Ezinye izindlela ezingavamile zihlanganisa:

Ukuhlanganiswa kwe-hydroquinone okuphawulekayo kusuka ku-acetylene ne-iron pentacarbonyl kuhlongozwa ukuthi i-iron pentacarbonyl isebenza njenge-catalyst, kunokuba ibe yi-reactant. Lapho kukhona igesi ye-carbon monoxide ekhululekile.^[3] I-rodium noma i-ruthenium ingathatha indawo yensimbi njenge-catalyst enokukhiqizwa kwamakhemikhali okuhle kodwa ngokuvamile ayisetshenziswa ngenxa yezindleko zayo zokubuyiselwa engxenyeni yokuxhumana.^[3]
I-hydroquinone kanye nemikhiqizo yayo nayo ingalungiswa ngokuxutshwa kwama-phenols ahlukahlukene. Izibonelo zihlanganisa i-Elbs persulfate oxidation kanye ne-Dakin oxidation.
I-Hydroquinone yatholakala okokuqala ngo-1820 ngamakhemikhali aseFrance uPelletier noCaventou ngokusebenzisa ukuhlunga okomile kwe-quinic acid.^[4]^[5]^[6]^[7]

Ukusabela

Ukusabela kwamaqembu e-hydroquinone e-hydroidxyl kufana nokwezinye ama-phenols, njengoba kunesibindzi esiphansi. Isisekelo esiwumphumela esihlanganisiwe sibhekana ne-O-alkylation elula ukunikeza i-mono- ne-diethers. Ngokufanayo, i-hydroquinone ithinteka kakhulu ekushayweni kwendandatho yizinqubo ze-FriedelʹCrafts ezifana ne-alkylation. Le nqubo isetshenziswa endleleni ye-antioxidants ethandwayo njenge-2-tert-butyl-4-methoxyphenol (BHA). Udayi oyisibonakaliso we-quinizarin ukhiqizwa nge-diacylation ye-hydroquinone nge-phthalic anhydride.

I-Redox

I-hydroquinone ihlangana ne-oxidation ngaphansi kwezimo ezincane ukuze inikeze i-benzoquinone. Le nqubo ingashintshwa. Ezinye izinhlobo ze-hydroquinone ezivela ngokwemvelo zibonisa lolu hlobo lokusabela, esinye isibonelo yi-coenzyme Q. Ezimbonini le nqubo isetshenziswa kokubili nge-hydrochinone uqobo kodwa kaningi ngezakhi zayo lapho i-OH eyodwa ithathelwe indawo yi-amine.

Lapho i-hydroquinone engenambala ne-benzoquinone, okuqinile okuphuzi okukhanyayo, kuhlanganiswa ngesilinganiso se-1:1, kwakheka i-dark-green crystalline charge-transfer complex (indawo yokuncibilikisa i-171 °C) ebizwa ngokuthi i-quinhydrone (C6H6O2·C6H4O2). Le nkimbinkimbi incibilika emanzini ashisayo, lapho ama-molecule amabili ehlukana khona ngenhlanganisela.

Ukuvuselelwa

Ukusabela okubalulekile ukuguqulwa kwe-hydroquinone ibe yi-mono- ne-diamine derivatives. I-Methylaminophenol, esetshenziswa ekuthwebuleni izithombe, ikhiqizwa ngale ndlela:

{\ce {C6H4(OH)2 + {\overset {methylamine}{CH3NH2}}-> HOC6H4NHCH3 + H2O}}

Ama-diamines, awusizo embonini yenjoloba njenge-antiozone agents, akhiqizwa ngokufanayo nge-aniline:

{\ce {C6H4(OH)2 + {\overset {aniline}{2 C6H5NH2}}-> C6H4(N(H)C6H5)2 + 2 H2O}}

Ukusetshenziswa

I-Hydroquinone inokusetshenziswa okuhlukahlukene okuhlobene ngokuyinhloko nokusebenza kwayo njengento yokunciphisa encibilikayo encibilekayo emanzini. Kuyingxenye eyinhloko kubathuthukisi abaningi bezithombe ezimnyama nezimhlophe zefilimu nephepha lapho, nge-metol eyingxube, inciphisa ama-halides esiliva abe yi-elemental silver.

Kuneminye imisebenzi ehlukahlukene ehlobene namandla ayo anciphisa. Njenge-inhibitor ye-polymerization, esebenzisa izakhiwo zayo ze-antioxidant, i-hydroquinone ivimbela i-polymerisation ye-acrylic acid, i-methyl methacrylate, i-cyanoacrylate, namanye ama-monomers athinteka kalula ku-radical-initiated polymerization. Ngokusebenza njenge-free radical scavenger, i-hydroquinone isebenza ukwelula isikhathi sokulondoloza inhlaka ezwela ukukhanya njenge-preceramic polymers.^[8]

I-Hydroquinone ingalahlekelwa yi-hydrogen cation kuwo womabili amaqembu e-hydroxyl ukuze yakhe i-diphenolate ion. Usawoti we-disodium diphenolate we-hydroquinone usetshenziswa njenge-comonomer unit eshintshanayo ekukhiqizeni i-polymer PEEK.

Ukukhishwa kwesikhumba

I-Hydroquinone isetshenziswa njengendlela yokwenziwa kwesikhumba sibe mhlophe ukuze kuncishiswe umbala wesikhumba. Ayinawo amathuba afanayo okubangela i-dermatitis njenge-metol. Lesi yisithako esivela emithethweni yokwelapha kuphela kwamanye amazwe, kufaka phakathi amazwe angamalungu e-European Union ngaphansi kwe-Directives 76/768/EEC:1976.

Ngo-2006, i-United States Food and Drug Administration yahoxisa ukuvunyelwa kwayo kwangaphambili kwe-hydroquinone futhi yahlongoza ukuvinjelwa kwazo zonke izindlela zokulungiselela ezisemakethe. I-FDA yavimbela ngokusemthethweni i-hydroquinone ngo-2020 njengengxenye yenguquko enkulu yenqubo yokubuyekezwa kwemithi ngaphandle kwe-counter. I-FDA yathi i-hydroquinone ayikwazi ukukhipha njengento engase ibangele umdlavuza. Lesi siphetho safinyelelwa ngokusekelwe ezingeni lokumunca kubantu kanye nokwenzeka kwe-neoplasms emagundeni ocwaningweni oluningana lapho amagundane amadala atholakala khona enezinga eliphakeme lezimila, kufaka phakathi i-thyroid follicular cell hyperplasias, i-anisokaryosis (ukuguquguquka kobukhulu be-nucleus), i-mononuclear cell leukemia, i-hepatocellular adenomas kanye ne-renal tubule cell adenomas. Umkhankaso Wezimonyo Ezingaphephile nawo ugcizelele ukukhathazeka.

Ucwaningo oluningi luveze ukuthi i-hydroquinone, uma ithathwa ngomlomo, ingabangela i-exogenous ochronosis, isifo esiphazamisa lapho umbala oluhlaza okwesibhakabhaka-omnyama ufakwa esikhunjeni. Nokho, amalungiselelo esikhumba aqukethe isithako anikezwa endaweni. I-FDA yahlukanisa i-hydroquinone ngo-1982 njengomkhiqizo ophephile - ngokuvamile owaziwa njengophephile futhi osebenzayo (i-GRASE). Ngokubhekisela kwezinqumo ze-National Toxicology Program (i-NTP), ucwaningo olwengeziwe ngaphansi kwalo lwaphakanyiswa ukuze kutholakale ukuthi ngabe kunengozi kubantu ngokusetshenziswa kwe-hydroquinone.^[9] Ukuhlolwa kwe-NTP kwabonisa ubufakazi obuthile bemiphumela yesikhathi eside ye-carcinogenic ne-genotoxic

Ngenkathi i-hydroquinone isala inikezwa kabanzi ukwelashwa kwe-hyperpigmentation, imibuzo ephakamwe mayelana nesimo sayo sokuphepha ngama-ejensi alawulayo e-EU, eJapane, nase-USA ikhuthaza ukufunwa kwamanye ama-agent anokusebenza okufana.^[10] Amaningana anjalo asevele etholakala noma acwaningwe, kufaka phakathi i-azelaic acid, i-kojic acid, i'retinoids, i-cysteamine, i-topical steroids, i'glycolic acid, nezinye izinto.^[11]^[12]^[13] Enye yalezi, i-4-butylresorcinol, kuboniswe ukuthi isebenza kangcono ekwelapheni izifo zesikhumba ezihlobene ne-melanin ngamanani amakhulu, kanye nokuphephile ngokwanele ukuba itholakale phezu kwe-counter.

Izenzakalo ezingokwemvelo

Ama-hydroquinones angenye ye-reactants emibili eyinhloko ezindlaleni zokuzivikela zamabhungane ama-bombardier, kanye ne-hydrogen peroxide (futhi mhlawumbe nezinye izakhi, kuye ngezinhlobo), eziqoqa emthonjeni. I-tank ivula nge-valve elawulwa imisipha iye egunjini lokusabela elinezindonga eziwugqinsi. Leli gumbi ligcwele amangqamuzana akhipha ama-catalases nama-peroxidases. Lapho okuqukethwe kuleli thange kuphoqelelwa ukuba kungene egunjini lokuhlangana, ama-catalases nama-peroxidases ngokushesha abulala i-hydrogen peroxide futhi akhuthaze i-oxidation yama-hydroquinones abe ama-p-quinones. Lezi zinguquko zikhipha umoya-mpilo okhululekile futhi zikhiqize ukushisa okwanele ukuletha ingxube endaweni yokubila. Bese ihwamuka cishe ingxenye yesihlanu yayo, ikhiqize ukufafaza okushisayo esiswini sebhungane.

I-Hydroquinone kucatshangwa ukuthi iyisihlungu esinamandla kumakhowe e-Agaricus hondensis.^[14]

I-Hydroquinone iboniswe ukuthi ingenye yezakhi zamakhemikhali zomkhiqizo wemvelo we-propolis.^[15]

Futhi ingenye yezakhi zamakhemikhali ezitholakala ku-castoreum. Lesi sakhiwo siqoqwa ezikhwameni ze-beaver.^[16]

Izikhombo

↑ F. Wöhler (1844) "Untersuchungen über das Chinon" (Investigations of quinone), Annalen der Chemie und Pharmacie, 51 : 145-163.
↑ Additive manufacturing of ceramics from preceramic polymers Additive manufacturing 2019 vol. 27. pp 80-90
↑ ^3.0 ^3.1 Reppe, Walter; Kutepow, N (1969). Cyclization of Acetylenic Compounds. p. 727–733.
↑ See:
↑ Template:CELEX
↑ "Clear N Smooth Skin Toning Cream recalled". 2011-10-04. Kulandwe ngomhlaka 4 April 2018.
↑ Research, Center for Drug Evaluation and. "About the Center for Drug Evaluation and Research - Hydroquinone Studies Under The National Toxicology Program (NTP)". www.fda.gov (in i-English). Archived from the original on 2017-01-22. Kulandwe ngomhlaka 2017-02-12. Unknown parameter |url-status= ignored (help)
↑ Additive manufacturing of ceramics from preceramic polymers Additive manufacturing 2019 vol. 27. pp 80-90
↑ Olumide, YM. Complications of chronic use of skin lightening cosmetics. p. 344–53.
↑ Draelos (2007-09-01). Skin lightening preparations and the hydroquinone controversy. p. 308–313.
↑ Bandyopadhyay (2009-01-01). Topical treatment of melasma. p. 303–309.
↑ Mazurek (2016-09-01). Comparison of efficacy of products containing azelaic acid in melasma treatment. p. 269–282.
↑ Mansouri (2015-07-01). Evaluation of the efficacy of cysteamine 5% cream in the treatment of epidermal melasma: a randomized double-blind placebo-controlled trial. p. 209–217.
↑ Joval, E; Kroeger, P; N (April 1996). "Hydroquinone: the toxic compound of Agaricus hondensis". Planta Medica 62 (2): 185. doi:10.1055/s-2006-957852. PMID 17252436.
↑ Burdock. Review of the biological properties and toxicity of bee propolis (propolis). p. 347–363.
↑ The Beaver: Its Life and Impact.

Izixhumanisi zangaphandle

[1] F. Wöhler (1844) "Untersuchungen über das Chinon" (Investigations of quinone), Annalen der Chemie und Pharmacie, 51 : 145-163.

[2] Additive manufacturing of ceramics from preceramic polymers Additive manufacturing 2019 vol. 27. pp 80-90

[Cyclization-3] 3.0 ^3.1 Reppe, Walter; Kutepow, N (1969). Cyclization of Acetylenic Compounds. p. 727–733.

[4] See:

[5] Template:CELEX

[6] "Clear N Smooth Skin Toning Cream recalled". 2011-10-04. Kulandwe ngomhlaka 4 April 2018.

[:0-7] Research, Center for Drug Evaluation and. "About the Center for Drug Evaluation and Research - Hydroquinone Studies Under The National Toxicology Program (NTP)". www.fda.gov (in i-English). Archived from the original on 2017-01-22. Kulandwe ngomhlaka 2017-02-12. Unknown parameter |url-status= ignored (help)

[8] Additive manufacturing of ceramics from preceramic polymers Additive manufacturing 2019 vol. 27. pp 80-90

[9] Olumide, YM. Complications of chronic use of skin lightening cosmetics. p. 344–53.

[10] Draelos (2007-09-01). Skin lightening preparations and the hydroquinone controversy. p. 308–313.

[11] Bandyopadhyay (2009-01-01). Topical treatment of melasma. p. 303–309.

[12] Mazurek (2016-09-01). Comparison of efficacy of products containing azelaic acid in melasma treatment. p. 269–282.

[13] Mansouri (2015-07-01). Evaluation of the efficacy of cysteamine 5% cream in the treatment of epidermal melasma: a randomized double-blind placebo-controlled trial. p. 209–217.

[14] Joval, E; Kroeger, P; N (April 1996). "Hydroquinone: the toxic compound of Agaricus hondensis". Planta Medica 62 (2): 185. doi:10.1055/s-2006-957852. PMID 17252436.

[Propolis-15] Burdock. Review of the biological properties and toxicity of bee propolis (propolis). p. 347–363.

[16] The Beaver: Its Life and Impact.

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