Array ( [0] => 16549244 [id] => 16549244 [1] => cswiki [site] => cswiki [2] => Omega-hydroxykyseliny [uri] => Omega-hydroxykyseliny [3] => [img] => [4] => [day_avg] => [5] => [day_diff] => [6] => [day_last] => [7] => [day_prev_last] => [8] => [oai] => [9] => [is_good] => [10] => [object_type] => [11] => 0 [has_content] => 0 [12] => [oai_cs_optimisticky] => ) Array ( [0] => '''Omega-hydroxykyseliny''' (též '''ω-hydroxykyseliny''' nebo '''ω-hydroxykarboxylové kyseliny''') jsou skupina přirozeně se vyskytujících [[alifatická sloučenina|alifatických]] [[hydroxykyseliny|hydroxykyselin]], jejichž [[hydroxyl]]ové skupiny se nacházejí na koncových pozicích ''n'', kde ''n'' > 3. Kyselina [[kyselina palmitová|16-hydroxypalmitová]] a [[kyselina stearová|18-hydroxystearová]] jsou hlavními složkami [[kutin]]u v [[kutikula|kutikulách]] rostlin.{{Citace periodika [1] => | autor1 = P. E. Kolattukudy [2] => | autor2 = T. J. Walton [3] => | titul = Structure and biosynthesis of the hydroxy fatty acids of cutin in ''Vicia faba'' leaves [4] => | periodikum = [[Biochemistry]] [5] => | rok vydání = 1972 [6] => | strany = 1897–1907 [7] => | doi = 10.1021/bi00760a026 [8] => | pmid = 5025632 [9] => }}{{Citace periodika [10] => | autor1 = C. L. Soliday [11] => | autor2 = P. E. Kolattukudy [12] => | titul = Biosynthesis of Cutin ω-hydroxylation of fatty acids by a microsomal preparation from germinating ''Vicia faba'' [13] => | periodikum = [[Plant Physiology]] [14] => | rok vydání = 1977 [15] => | strany = 1116–1121 [16] => | doi = 10.1104/pp.59.6.1116 [17] => | pmid = 16660004 [18] => }} [19] => [20] => Kutinový [[polymer]] se vytváří [[esterifikace|interesterifikacemi]] omega-hydroxykyselin a jejich derivátů substituovaných uvnitř řetězců, jako je kyselina 10,16-dihydroxypalmitová.T. J. Walton and P. E. Kolattukudy (1972) Enzymatic conversion of 16-hydroxypalmitic acid into 10,16-dihydroxypalmitic acid in ''Vicia faba'' epidermal extracts. Biochem Biophys Res Communications 46, (1), 16–21P. J. Holloway (1982) The chemical constitution of plant cutins. p45-85 The Plant Cuticle. ed. by D. F. Cutler, K. L. Alvin and C. E. Price. Academic Press, London {{ISBN|0-12-199920-3}} Kutin vyrábějí pouze buňky v pokožce rostlin.Kolattukudy, P. E. (1996) Biosynthetic pathways of cutin and waxes, and their sensitivity to environmental stresses. Plant Cuticles. Ed. by G. Kerstiens, BIOS Scientific publishers, Oxford, pp 83-108 [21] => [22] => Omega-hydroxykyseliny byly nalezeny i u živočichů. Omega-hydroxylázy [[mikrozom]]u [[cytochrom P450|cytochromu P450]] (CYP450), například [[CYP4A11]], [[CYP4A22]], [[CYP4F2]] a [[CYP4F3]] u lidí, Cyp4a10 a Cyp4a12 u myší, a Cyp4a1, Cyp4a2, Cyp4a3 a Cyp4a8 u krys přeměňují [[kyselina arachidonová|kyselinu arachidonovou]] a mnohé její metabolity na příslušné omega-hydroxylované sloučeniny.{{Citace periodika [23] => | autor1 = S. L. Hoopes [24] => | autor2 = V. Garcia [25] => | autor3 = M. L. Edin [26] => | autor4 = M. L. Schwartzman [27] => | autor5 = D. C. Zeldin [28] => | titul = Vascular actions of 20-HETE [29] => | periodikum = Prostaglandins & Other Lipid Mediators [30] => | rok vydání = 2015 [31] => | strany = 9–16 [32] => | doi = 10.1016/j.prostaglandins.2015.03.002 [33] => | pmid = 25813407 [34] => }} [35] => [36] => Tímto metabolismem kyseliny arachidonové vzniká [[kyselina 20-hydroxyikosatetraenová]] (20-HETE), látka, jež je součástí řady fyziologických a patologických dějů;Annu Rev Pharmacol Toxicol. 2005;45:413-38 obdobně z několika bioaktivních derivátů kyseliny arachidonové, jako jsou [[leukotrien B4]] a [[kyselina 5-hydroxyikosatetraenová]], vznikají 20-hydroxylované produkty, které jsou 100- až 1000krát slabší než jejich prekurzory, a způsobují tak jejich deaktivaci.{{Citace periodika [37] => | autor1 = L. Du [38] => | autor2 = H. Yin [39] => | autor3 = J. D. Morrow [40] => | autor4 = H. W. Strobel [41] => | autor5 = D. S. Keeney [42] => | titul = 20-Hydroxylation is the CYP-dependent and retinoid-inducible leukotriene B4 inactivation pathway in human and mouse skin cells [43] => | periodikum = [[Archives of Biochemistry and Biophysics]] [44] => | rok vydání = 2009 [45] => | strany = 80–86 [46] => | doi = 10.1016/j.abb.2009.01.012 [47] => | pmid = 19467632 [48] => }}J Immunol. 1986 Nov 15;137(10):3277-3283 [49] => [50] => {{Citace periodika [51] => | autor1 = W. S. Powell [52] => | autor2 = J. Rokach [53] => | titul = Biosynthesis, biological effects, and receptors of hydroxyeicosatetraenoic acids (HETEs) and oxoeicosatetraenoic acids (oxo-ETEs) derived from arachidonic acid [54] => | periodikum = [[Biochimica et Biophysica Acta]] [55] => | rok vydání = 2015 [56] => | strany = 340–355 [57] => | doi = 10.1016/j.bbalip.2014.10.008 [58] => | pmid = 25449650 [59] => }} [60] => [61] => == Příklady == [62] => Aby byla sloučenina řazena mezi omega-hydroxykyseliny, tak musí obsahovat alespoň tři atomy [[uhlík]]u. V tabulce jsou uvedena i nižší čísla odpovídající vzorci C''n''H2''n''O3. [63] => [64] => {|class="wikitable" [65] => !Počet uhlíků [66] => !systematický název [67] => !triviální název [68] => !teplota tání [69] => [70] => °C [71] => !sumární vzorec [72] => ![[SMILES]] [73] => ![[Registrační číslo CAS|číslo CAS]] [74] => ![[PubChem]] [75] => ![[ChemSpider]] [76] => !UNII [77] => ![[ChEBI]] [78] => !výskyt [79] => !poznámky [80] => |- [81] => |1 [82] => | [83] => |[[kyselina uhličitá]] [84] => | [85] => |CH2O3 [86] => |OC(=O)O [87] => |463-79-6 [88] => |767 [89] => |747 [90] => |142M471B3J [91] => |28976 [92] => | [93] => | [94] => |- [95] => |2 [96] => |kyselina 2-hydroxyoctová [97] => |[[kyselina glykolová]] [98] => |75 [99] => |C2H4O3 [100] => |OCC(=O)O [101] => |79-14-1 [102] => |757 [103] => |737 [104] => |0WT12SX38S [105] => |17497 [106] => |rostliny [107] => | [108] => |- [109] => |3 [110] => |[[kyselina 3-hydroxypropanová]] [111] => |kyselina β-mléčná [112] => |139-140 [113] => |C3H6O3 [114] => |OCCC(=O)O [115] => |503-66-2 [116] => |68152 [117] => |61460 [118] => | [119] => | [120] => |většina organismů [121] => | [122] => |- [123] => |4 [124] => | kyselina 4-hydroxybutanová [125] => | [[Γ-Hydroxymáselná kyselina|kyselina ''gama''-hydroxymáselná]] [126] => |? [127] => |C4H8O3 [128] => |OCCCC(=O)O [129] => |591-81-1 [130] => |10413 [131] => |9984 [132] => |30IW36W5B2 [133] => |30830 [134] => |[[neurotransmiter]] u člověka [135] => | [136] => |- [137] => |5 [138] => |[[kyselina 5-hydroxypentanová]] [139] => |kyselina 5-hydroxyvalerová [140] => | [141] => |C5H10O3 [142] => |OCCCCC(=O)O [143] => |13392-69-3 [144] => |25945 [145] => |24171 [146] => |H5EVV4LP59 [147] => |45564 [148] => | [149] => | [150] => |- [151] => |6 [152] => |kyselina 6-hydroxyhexanová [153] => |kyselina 6-hydroxykapronová [154] => | [155] => |C6H12O3 [156] => |OCCCCCC(=O)O [157] => |1191-25-9 [158] => |14490 [159] => |13835 [160] => |3Y3OX37NM8 [161] => |17869 [162] => | [163] => | [164] => |- [165] => |7 [166] => |kyselina 7-hydroxyheptanová [167] => |kyselina 7-hydroxyenanthová [168] => | [169] => |C7H14O3 [170] => |OCCCCCCC(=O)O [171] => |3710-42-7 [172] => |138016 [173] => |121660 [174] => | [175] => |79112 [176] => | [177] => | [178] => |- [179] => |8 [180] => |kyselina 8-hydroxyoktanová [181] => |kyselina omega-hydroxykaprylová [182] => | [183] => |C8H16O3 [184] => |OCCCCCCCC(=O)O [185] => |764-89-6 [186] => |69820 [187] => |63018 [188] => | [189] => |79162 [190] => | [191] => | [192] => |- [193] => |9 [194] => |kyselina 9-hydroxynonanová [195] => |kyselina 9-hydroxypelargonová [196] => | [197] => |C9H18O3 [198] => |OCCCCCCCCC(=O)O [199] => |3788-56-5 [200] => |138052 [201] => |121694 [202] => |HV672SU12G [203] => |79121 [204] => | [205] => | [206] => |- [207] => |10 [208] => |kyselina 10-hydroxydekanová [209] => |kyselina 10-hydroxykaprinová [210] => | [211] => |C10H20O3 [212] => |OCCCCCCCCCC(=O)O [213] => |1679-53-4 [214] => |74300 [215] => |66903 [216] => |NP03XO416B [217] => |17409 [218] => | [219] => | [220] => |- [221] => |11 [222] => |kyselina 11-hydroxyundekanová [223] => | [224] => | [225] => |C11H22O3 [226] => |OCCCCCCCCCCC(=O)O [227] => |3669-80-5 [228] => |77237 [229] => |69664 [230] => |SD6J9LX2XK [231] => |79126 [232] => | [233] => | [234] => |- [235] => |12 [236] => |kyselina 12-hydroxydodekanová [237] => |[[kyselina sabinová]] [238] => | [239] => |C12H24O3 [240] => |OCCCCCCCCCCCC(=O)O [241] => |505-95-3 [242] => |79034 [243] => |71366 [244] => |SUH3LR2K9D [245] => |39567 [246] => | [247] => |{{Cite journal |last1=Lycan |first1=W. H. |last2=Adams |first2=Roger |title=Omega-Hydroxy Aliphatic Acids. Synthesis of Sabinic Acid |date=February 1929 |url=https://pubs.acs.org/doi/abs/10.1021/ja01377a042 |journal=Journal of the American Chemical Society |volume=51 |issue=2 |pages=625–629 |doi=10.1021/ja01377a042 |issn=0002-7863}} [248] => |- [249] => |13 [250] => |kyselina 13-hydroxytridecanoic acid [251] => | [252] => | [253] => |C13H26O3 [254] => |OCCCCCCCCCCCCC(=O)O [255] => |7735-38-8 [256] => |139065 [257] => |122656 [258] => | [259] => |79166 [260] => | [261] => | [262] => |- [263] => |14 [264] => |kyselina 14-hydroxytetradekanová [265] => |kyselina ω-hydroxy myristová [266] => | [267] => |C14H28O3 [268] => |OCCCCCCCCCCCCCC(=O)O [269] => |17278-74-9 [270] => |084276 [271] => |2341369 [272] => | [273] => |77168 [274] => | [275] => | [276] => |- [277] => |15 [278] => |kyselina 15-hydroxypentadekanová [279] => | [280] => | [281] => |C15H30O3 [282] => |OCCCCCCCCCCCCCCC(=O)O [283] => |4617-33-8 [284] => |78360 [285] => |70730 [286] => |FU65P3692T [287] => |79169 [288] => |[[andělika lékařská]] [289] => | [290] => |- [291] => |16 [292] => |[[kyselina 16-hydroxyhexadekanová]] [293] => | [294] => | [295] => |C16H32O3 [296] => |OCCCCCCCCCCCCCCCC(=O)O [297] => |506-13-8 [298] => |10466 [299] => |10034 [300] => | [301] => |55328 [302] => |kutikuly rostlin [303] => |{{Cite journal |last=Spring |first=F. S. |date=March 1945 |title=Naturally Occurring Polyesters |url=https://www.nature.com/articles/155272b0 |journal=Nature |volume=155 |issue=3931 |pages=272 |doi=10.1038/155272b0 |bibcode=1945Natur.155..272S |s2cid=4108900 |issn=0028-0836}} [304] => |- [305] => |17 [306] => |kyselina 17-hydroxyheptadekanová [307] => | [308] => | [309] => |C17H34O3 [310] => |OCCCCCCCCCCCCCCCCC(=O)O [311] => |13099-34-8 [312] => |4308451 [313] => |3513977 [314] => | [315] => |79177 [316] => |[[Borovice montereyská]] [317] => | [318] => |- [319] => |18 [320] => |kyselina 18-hydroxyoktadekanová [321] => |kyselina ω-hydroxystearová [322] => | [323] => |C18H36O3 [324] => |OCCCCCCCCCCCCCCCCCC(=O)O [325] => |3155-42-8 [326] => |5282915 [327] => |4446042 [328] => |CCR5P6ICT2 [329] => |79182 [330] => |kutin [331] => | [332] => |- [333] => |19 [334] => |kyselina 19-hydroxynonadekanová [335] => | [336] => | [337] => |C19H38O3 [338] => |OCCCCCCCCCCCCCCCCCCC(=O)O [339] => | [340] => |5282917 [341] => |4446044 [342] => | [343] => |79179 [344] => | [345] => | [346] => |- [347] => |20 [348] => |kyselina 20-hydroxyikosanová [349] => |kyselina ω-hydroxyarachidová [350] => | [351] => |C20H40O3 [352] => |OCCCCCCCCCCCCCCCCCCCC(=O)O [353] => |62643-46-3 [354] => |5282919 [355] => |4446046 [356] => | [357] => |79190 [358] => |kutin v kmenech a semenech [359] => | [360] => |- [361] => |21 [362] => |kyselina 21-hydroxyhenikosanová [363] => | [364] => | [365] => |C21H42O3 [366] => |OCCCCCCCCCCCCCCCCCCCCC(=O)O [367] => | [368] => |5282920 [369] => |4446047 [370] => | [371] => |79195 [372] => | [373] => | [374] => |- [375] => |22 [376] => |kyselina 22-hydroxydokosanová [377] => |kyselina 22-hydroxybehenová [378] => | [379] => |C22H44O3 [380] => |OCCCCCCCCCCCCCCCCCCCCCC(=O)O [381] => |506-45-6 [382] => |5282922 [383] => |4446049 [384] => | [385] => |76322 [386] => | [387] => | [388] => |- [389] => |23 [390] => |kyselina 23-hydroxytrikosanová [391] => | [392] => | [393] => |C23H46O3 [394] => |OCCCCCCCCCCCCCCCCCCCCCCC(=O)O [395] => |61658-18-2 [396] => |11760442 [397] => |9935141 [398] => | [399] => | [400] => |kutin [401] => | [402] => |- [403] => |24 [404] => |kyselina 24-hydroxytetrakosanová [405] => | [406] => | [407] => |C24H48O3 [408] => |OCCCCCCCCCCCCCCCCCCCCCCCC(=O)O [409] => |75912-18-4 [410] => |5312780 [411] => |4472205 [412] => | [413] => | [414] => | [415] => | [416] => |- [417] => |25 [418] => |kyselina 25-hydroxypentakosanová [419] => | [420] => | [421] => |C25H50O3 [422] => |OCCCCCCCCCCCCCCCCCCCCCCCCC(=O)O [423] => |82612-07-5 [424] => |14325176 [425] => |57507583 [426] => | [427] => | [428] => | [429] => | [430] => |- [431] => |26 [432] => |kyselina 26-hydroxyhexakosanová [433] => |kyselina ω-hydroxycerotová [434] => | [435] => |C26H52O3 [436] => |OCCCCCCCCCCCCCCCCCCCCCCCCCC(=O)O [437] => |506-47-8 [438] => |5312785 [439] => |4472210 [440] => | [441] => |76325 [442] => | [443] => | [444] => |- [445] => |27 [446] => |kyselina 27-hydroxyheptakosanová [447] => | [448] => | [449] => |C27H54O3 [450] => |OCCCCCCCCCCCCCCCCCCCCCCCCCCC(=O)O [451] => | [452] => |14325177 [453] => |13739624 [454] => | [455] => |84861 [456] => | [457] => | [458] => |- [459] => |28 [460] => |kyselina 28-hydroxyoktakosanová [461] => | [462] => | [463] => |C28H56O3 [464] => |OCCCCCCCCCCCCCCCCCCCCCCCCCCCC(=O)O [465] => |52900-17-1 [466] => |5312786 [467] => |4472211 [468] => | [469] => |84863 [470] => | [471] => | [472] => |- [473] => |29 [474] => |kyselina 29-hydroxynonakosanová [475] => | [476] => | [477] => |C29H58O3 [478] => |OCCCCCCCCCCCCCCCCCCCCCCCCCCCCC(=O)O [479] => | [480] => |14325178 [481] => |34449103 [482] => | [483] => |84865 [484] => | [485] => | [486] => |- [487] => |30 [488] => |kyselina 30-hydroxytriakontanová [489] => | [490] => | [491] => |C30H60O3 [492] => |OCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC(=O)O [493] => |52900-18-2 [494] => |5312787 [495] => |4472212 [496] => | [497] => |76220 [498] => | [499] => | [500] => |} [501] => [502] => == Odkazy == [503] => [504] => === Reference === [505] => {{Překlad | jazyk = en | článek = Omega hydroxy acid | revize = 1129579006}} [506] => [507] => === Související články === [508] => * [[Alfa-hydroxykyseliny]] [509] => * [[Beta hydroxykyseliny]] [510] => {{Autoritní data}} [511] => [512] => {{Portály|Chemie}} [513] => [514] => [[Kategorie:Hydroxykyseliny]] [515] => [[Kategorie:Fyziologie rostlin]] [] => )
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Omega-hydroxykyseliny

Omega-hydroxykyseliny (též ω-hydroxykyseliny nebo ω-hydroxykarboxylové kyseliny) jsou skupina přirozeně se vyskytujících alifatických hydroxykyselin, jejichž hydroxylové skupiny se nacházejí na koncových pozicích n, kde n > 3. Kyselina 16-hydroxypalmitová a 18-hydroxystearová jsou hlavními složkami kutinu v kutikulách rostlin.

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,'alifatická sloučenina','esterifikace','Registrační číslo CAS','Kategorie:Fyziologie rostlin','Beta hydroxykyseliny','leukotrien B4','uhlík','CYP4F3','CYP4F2','CYP4A22','kyselina arachidonová','CYP4A11'

Esterifikace

Uhlík

Uhlík je chemický prvek s atomovým číslem 6 a chemickým symbolem C, který je základním stavebním prvkem veškerého živého materiálu na Zemi.