Oleinska kiselina — разлика између измена
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м ispravke; козметичке измене |
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| verifiedrevid = 416953907 |
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| Name = Oleinska kiselina |
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| ImageFile = Oleic-acid-based-on-xtal-1997-2D-skeletal.png |
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| ImageSize = 250px |
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| ImageFile2 = Oleic-acid-3D-vdW.png |
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| ImageSize2 = 250px |
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| ImageName = Oleic acid |
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| IUPACName = (9''Z'')-Octadec-9-enoic acid |
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| OtherNames = (-{9''Z''}-)-Oktadecenoinska kiselina<br />(''Z'')-Oktadec-9-enoinska kiselina<br />''cis''-9-Octadecenoinska kiselina<br />''cis''-Δ<sup>9</sup>-Oktadecenoinska kiselina<br />18:1 cis-9 |
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| Section1 = {{Chembox Identifiers-lat |
| Section1 = {{Chembox Identifiers-lat |
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| Section2 = {{Chembox Properties-lat |
| Section2 = {{Chembox Properties-lat |
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| Formula = C<sub>18</sub>H<sub>34</sub>O<sub>2</sub> |
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| MolarMass = 282.4614 -{g/mol}- |
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| Appearance = Bledo žuta ili smeđo žuta uljasta tečnost |
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| Density = 0.895 -{g/mL}- |
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| Solubility = Nerastvorna |
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| SolubleOther = rastvorna |
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| Solvent = [[metanol]] |
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| MeltingPt = 13-14 °-{C}- (286 -{K}-) |
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| BoilingPt = 360 °-{C}- (633 -{K}-) (760-{mm Hg}-)<ref>[http://membership.acs.org/c/ccs/pubs/CLIPS/JCE20020024.pdf -{Oleic acid}-], -{Chemical Laboratory Information Profile, American Chemical Society}-</ref> |
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| Section3 = {{Chembox Structure-lat |
| Section3 = {{Chembox Structure-lat |
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'''Oleinska kiselina''' je [[mononezasićena]] [[omega-9 masna kiselina|omega-9]] [[masna kiselina]] nađena u raznim životinjskim i biljnim mastima. Njena formula je -{CH<sub>3</sub>(CH<sub>2</sub>)<sub>7</sub>CH=CH(CH<sub>2</sub>)<sub>7</sub>COOH.}-<ref name=Ullmann>{{cite encyclopedia|author=Alfred Thomas |title=Fats and Fatty Oils|encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry|publisher=Wiley-VCH|place=Weinheim|year=2002|doi=10.1002/14356007.a10_173}}</ref> Ona je ulje be boje i mirisa, mada komercijalni uzorci mogu da budu žuti. [[cis-trans izomerizam|''Trans'' izomer]] oleinske kiseline je [[elaidinska kiselina]] (stoga se [[elaidinizacija|elaidinizacijom]] naziva reakcija kojom se menjaju ''cis'' izomeri u ''trans'' izomere). Termin "oleinski" znači srodan sa, ili izveden iz, [[ulje|ulja]] ili [[maslina|masline]]. |
'''Oleinska kiselina''' je [[mononezasićena]] [[omega-9 masna kiselina|omega-9]] [[masna kiselina]] nađena u raznim životinjskim i biljnim mastima. Njena formula je -{CH<sub>3</sub>(CH<sub>2</sub>)<sub>7</sub>CH=CH(CH<sub>2</sub>)<sub>7</sub>COOH.}-<ref name=Ullmann>{{cite encyclopedia|author=Alfred Thomas |title=Fats and Fatty Oils|encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry|publisher=Wiley-VCH|place=Weinheim|year=2002|doi=10.1002/14356007.a10_173}}</ref> Ona je ulje be boje i mirisa, mada komercijalni uzorci mogu da budu žuti. [[cis-trans izomerizam|''Trans'' izomer]] oleinske kiseline je [[elaidinska kiselina]] (stoga se [[elaidinizacija|elaidinizacijom]] naziva reakcija kojom se menjaju ''cis'' izomeri u ''trans'' izomere). Termin "oleinski" znači srodan sa, ili izveden iz, [[ulje|ulja]] ili [[maslina|masline]]. |
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==Zastupljenost== |
== Zastupljenost == |
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Trigliceridni esteri oleinske kiseline sačinjavaju najveći deo [[maslinovo ulje|maslinovog ulja]], mada ima manje od 2,0% slobodne kiseline. Veće koncentracije čine maslinovo ulja nejestivim. Oleinska kiselina takođe sačinjava do 59-75% orahovog ulja,<ref>{{cite journal| author = Villarreal, J.E., L. Lombardini, and L. Cisneros-Zevallos| title = Phytochemical constituents and antioxidant capacity of different pecan [Carya illinoinensis (Wangenh.) K. Koch] cultivars| journal = Food Chemistry| volume = 102| issue = 4| pages = 1241–1249| year = 2007| doi = 10.1016/j.foodchem.2006.07.024| url = http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6T6R-4M1DB79-2&_user=952835&_coverDate=12%2F31%2F2007&_rdoc=1&_fmt=high&_orig=search&_sort=d&_docanchor=&view=c&_searchStrId=1412335994&_rerunOrigin=google&_acct=C000049198&_version=1&_urlVersion=0&_userid=952835&md5=589de1e394ce2412a09767a3b5f542be}}</ref> 36-67% ulja kikirikija,<ref>{{cite web |url=http://jhered.oxfordjournals.org/cgi/pdf_extract/80/3/252 |title=The inheritance of high oleic acid in peanut}}</ref> 15-20% ulje semenki grožđa, ulja morske pasjakovine, i susamovog ulja,<ref name=Ullmann /> i 14% ulja maka.<ref name="pmid17093176">{{cite journal | author = Untoro J, Schultink W, West CE, Gross R, Hautvast JG | title = Efficacy of oral iodized peanut oil is greater than that of iodized poppy seed oil among Indonesian schoolchildren | journal = The American Journal of Clinical Nutrition | volume = 84 | issue = 5 | pages = 1208–14 | year = 2006 | month = November | pmid = 17093176 | doi = | url = | issn = }}</ref> Ona je u izobilju prisutna u mnogim životinjskim mastima. Ona sačinjava 37 do 56% pileće i ćureće masnoće,<ref>{{cite journal |url=http://www.springerlink.com/content/0837289583682243/ |journal=Chemistry and Materials Science |volume=20 |issue=11 |pages=231-234 |doi=10.1007/BF02630880 |title=The chemical composition of depot fats in chickens and turkeys |author=Mary K. Nutter, Ernest E. Lockhart and Robert S. Harris}}</ref> i 44 do 47% sala, etc. |
Trigliceridni esteri oleinske kiseline sačinjavaju najveći deo [[maslinovo ulje|maslinovog ulja]], mada ima manje od 2,0% slobodne kiseline. Veće koncentracije čine maslinovo ulja nejestivim. Oleinska kiselina takođe sačinjava do 59-75% orahovog ulja,<ref>{{cite journal| author = Villarreal, J.E., L. Lombardini, and L. Cisneros-Zevallos| title = Phytochemical constituents and antioxidant capacity of different pecan [Carya illinoinensis (Wangenh.) K. Koch] cultivars| journal = Food Chemistry| volume = 102| issue = 4| pages = 1241–1249| year = 2007| doi = 10.1016/j.foodchem.2006.07.024| url = http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6T6R-4M1DB79-2&_user=952835&_coverDate=12%2F31%2F2007&_rdoc=1&_fmt=high&_orig=search&_sort=d&_docanchor=&view=c&_searchStrId=1412335994&_rerunOrigin=google&_acct=C000049198&_version=1&_urlVersion=0&_userid=952835&md5=589de1e394ce2412a09767a3b5f542be}}</ref> 36-67% ulja kikirikija,<ref>{{cite web |url=http://jhered.oxfordjournals.org/cgi/pdf_extract/80/3/252 |title=The inheritance of high oleic acid in peanut}}</ref> 15-20% ulje semenki grožđa, ulja morske pasjakovine, i susamovog ulja,<ref name=Ullmann /> i 14% ulja maka.<ref name="pmid17093176">{{cite journal | author = Untoro J, Schultink W, West CE, Gross R, Hautvast JG | title = Efficacy of oral iodized peanut oil is greater than that of iodized poppy seed oil among Indonesian schoolchildren | journal = The American Journal of Clinical Nutrition | volume = 84 | issue = 5 | pages = 1208–14 | year = 2006 | month = November | pmid = 17093176 | doi = | url = | issn = }}</ref> Ona je u izobilju prisutna u mnogim životinjskim mastima. Ona sačinjava 37 do 56% pileće i ćureće masnoće,<ref>{{cite journal |url=http://www.springerlink.com/content/0837289583682243/ |journal=Chemistry and Materials Science |volume=20 |issue=11 |pages=231-234 |doi=10.1007/BF02630880 |title=The chemical composition of depot fats in chickens and turkeys |author=Mary K. Nutter, Ernest E. Lockhart and Robert S. Harris}}</ref> i 44 do 47% sala, etc. |
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Oleinska kiselina je najrasprostanjenija masna kiselina u ljudskom [[masno tkivo|masnom tkivu]].<ref>{{cite journal |journal=American Journal of Clinical Nutrition |title=Fatty acid composition of human adipose tissue from two anatomical sites in a biracial community |author=MG Kokatnur, MC Oalmann, WD Johnson, GT Malcom and JP Strong |volume=32 |pages=2198–2205 |url=http://www.ajcn.org/cgi/content/abstract/32/11/2198 |pmid=495536 |issue=11 |pages=2198–205 |date= November 1, 1979 }}</ref> |
Oleinska kiselina je najrasprostanjenija masna kiselina u ljudskom [[masno tkivo|masnom tkivu]].<ref>{{cite journal |journal=American Journal of Clinical Nutrition |title=Fatty acid composition of human adipose tissue from two anatomical sites in a biracial community |author=MG Kokatnur, MC Oalmann, WD Johnson, GT Malcom and JP Strong |volume=32 |pages=2198–2205 |url=http://www.ajcn.org/cgi/content/abstract/32/11/2198 |pmid=495536 |issue=11 |pages=2198–205 |date= November 1, 1979 }}</ref> |
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===Kao insektni feromon=== |
=== Kao insektni feromon === |
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Oleinsku kiselinu emituju raspadajući leševi brojnih insekata, kao što su [[pčela|pčele]] i -{''[[Pogonomyrmex]]''}- [[mrav]]i, i ona podstiče instikte živih radnika da uklone mrtvo telo iz [[košnica|košnice]]. Ako su živa pčela<ref name=Anies2005>{{cite journal |
Oleinsku kiselinu emituju raspadajući leševi brojnih insekata, kao što su [[pčela|pčele]] i -{''[[Pogonomyrmex]]''}- [[mrav]]i, i ona podstiče instikte živih radnika da uklone mrtvo telo iz [[košnica|košnice]]. Ako su živa pčela<ref name=Anies2005>{{cite journal |
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| author = Anies Hannawati Purnamadjaja, R. Andrew Russell |
| author = Anies Hannawati Purnamadjaja, R. Andrew Russell |
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Ред 72: | Ред 72: | ||
}}</ref> ili mrav<ref name="BroodProt">{{cite book |last=Ayasse |first=M. |last2=Paxton |first2=R. |year=2002 |chapter=Brood protection in social insects |editor1-last=Hilker |editor1-first=M. |editor2-last=Meiners |editor2-first=T. |title=Chemoecology of Insect Eggs and Egg Deposition |publisher=Blackwell |location=Berlin |pages=117–148 |isbn=1405106948 }}</ref><ref name="imdead">{{cite web |last=Krulwich |first=Robert |year=2009 |title=Hey I'm Dead! The Story Of The Very Lively Ant |url=http://www.npr.org/templates/story/story.php?storyId=102601823 |work=National Public Radio}}</ref> namazani oleinskom kiselinom, oni bivaju odvučeni na otpad kao da su mrtvi. Miris oleinske kiseline isto tako može da indicira opasnost za žive insekte, navodeći ih da se izbegavaju druge koji su podlegli bolesti ili mesta gde vrebaju predatori.<ref>{{Cite web | last = Walker | first = Matt | date = 9. 9. 2009. | title = Ancient 'smell of death' revealed | work = BBC - Earth News | accessdate = 13. 9. 2009. | url = http://news.bbc.co.uk/earth/hi/earth_news/newsid_8232000/8232607.stm }}</ref> |
}}</ref> ili mrav<ref name="BroodProt">{{cite book |last=Ayasse |first=M. |last2=Paxton |first2=R. |year=2002 |chapter=Brood protection in social insects |editor1-last=Hilker |editor1-first=M. |editor2-last=Meiners |editor2-first=T. |title=Chemoecology of Insect Eggs and Egg Deposition |publisher=Blackwell |location=Berlin |pages=117–148 |isbn=1405106948 }}</ref><ref name="imdead">{{cite web |last=Krulwich |first=Robert |year=2009 |title=Hey I'm Dead! The Story Of The Very Lively Ant |url=http://www.npr.org/templates/story/story.php?storyId=102601823 |work=National Public Radio}}</ref> namazani oleinskom kiselinom, oni bivaju odvučeni na otpad kao da su mrtvi. Miris oleinske kiseline isto tako može da indicira opasnost za žive insekte, navodeći ih da se izbegavaju druge koji su podlegli bolesti ili mesta gde vrebaju predatori.<ref>{{Cite web | last = Walker | first = Matt | date = 9. 9. 2009. | title = Ancient 'smell of death' revealed | work = BBC - Earth News | accessdate = 13. 9. 2009. | url = http://news.bbc.co.uk/earth/hi/earth_news/newsid_8232000/8232607.stm }}</ref> |
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==Literatura== |
== Literatura == |
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{{reflist|2}} |
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==Spoljašnje veze== |
== Spoljašnje veze == |
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*[http://webbook.nist.gov/cgi/cbook.cgi?ID=C2027476&Units=SI NIST hemijska veb knjiga] |
* [http://webbook.nist.gov/cgi/cbook.cgi?ID=C2027476&Units=SI NIST hemijska veb knjiga] |
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{{Masne kiseline-lat}} |
{{Masne kiseline-lat}} |
Верзија на датум 15. октобар 2013. у 15:38
Nazivi | |
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IUPAC naziv
(9Z)-Octadec-9-enoic acid
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Drugi nazivi
(9Z)-Oktadecenoinska kiselina
(Z)-Oktadec-9-enoinska kiselina cis-9-Octadecenoinska kiselina cis-Δ9-Oktadecenoinska kiselina 18:1 cis-9 | |
Identifikacija | |
3D model (Jmol)
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ECHA InfoCard | 100.003.643 |
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Svojstva | |
C18H34O2 | |
Molarna masa | 282,4614 g/mol |
Agregatno stanje | Bledo žuta ili smeđo žuta uljasta tečnost |
Gustina | 0,895 g/mL |
Tačka topljenja | 13-14 °C (286 K) |
Tačka ključanja | 360 °C (633 K) (760mm Hg)[1] |
Nerastvorna | |
Rastvorljivost u metanol | rastvorna |
Ukoliko nije drugačije napomenuto, podaci se odnose na standardno stanje materijala (na 25 °C [77 °F], 100 kPa). | |
verifikuj (šta je ?) | |
Reference infokutije | |
Oleinska kiselina je mononezasićena omega-9 masna kiselina nađena u raznim životinjskim i biljnim mastima. Njena formula je CH3(CH2)7CH=CH(CH2)7COOH.[2] Ona je ulje be boje i mirisa, mada komercijalni uzorci mogu da budu žuti. Trans izomer oleinske kiseline je elaidinska kiselina (stoga se elaidinizacijom naziva reakcija kojom se menjaju cis izomeri u trans izomere). Termin "oleinski" znači srodan sa, ili izveden iz, ulja ili masline.
Zastupljenost
Trigliceridni esteri oleinske kiseline sačinjavaju najveći deo maslinovog ulja, mada ima manje od 2,0% slobodne kiseline. Veće koncentracije čine maslinovo ulja nejestivim. Oleinska kiselina takođe sačinjava do 59-75% orahovog ulja,[3] 36-67% ulja kikirikija,[4] 15-20% ulje semenki grožđa, ulja morske pasjakovine, i susamovog ulja,[2] i 14% ulja maka.[5] Ona je u izobilju prisutna u mnogim životinjskim mastima. Ona sačinjava 37 do 56% pileće i ćureće masnoće,[6] i 44 do 47% sala, etc.
Oleinska kiselina je najrasprostanjenija masna kiselina u ljudskom masnom tkivu.[7]
Kao insektni feromon
Oleinsku kiselinu emituju raspadajući leševi brojnih insekata, kao što su pčele i Pogonomyrmex mravi, i ona podstiče instikte živih radnika da uklone mrtvo telo iz košnice. Ako su živa pčela[8] ili mrav[9][10] namazani oleinskom kiselinom, oni bivaju odvučeni na otpad kao da su mrtvi. Miris oleinske kiseline isto tako može da indicira opasnost za žive insekte, navodeći ih da se izbegavaju druge koji su podlegli bolesti ili mesta gde vrebaju predatori.[11]
Literatura
- ^ Oleic acid, Chemical Laboratory Information Profile, American Chemical Society
- ^ а б Alfred Thomas (2002). „Fats and Fatty Oils”. Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a10_173.
- ^ Villarreal, J.E., L. Lombardini, and L. Cisneros-Zevallos (2007). „Phytochemical constituents and antioxidant capacity of different pecan [Carya illinoinensis (Wangenh.) K. Koch] cultivars”. Food Chemistry. 102 (4): 1241—1249. doi:10.1016/j.foodchem.2006.07.024.
- ^ „The inheritance of high oleic acid in peanut”.
- ^ Untoro J, Schultink W, West CE, Gross R, Hautvast JG (2006). „Efficacy of oral iodized peanut oil is greater than that of iodized poppy seed oil among Indonesian schoolchildren”. The American Journal of Clinical Nutrition. 84 (5): 1208—14. PMID 17093176. Непознати параметар
|month=
игнорисан (помоћ) - ^ Mary K. Nutter, Ernest E. Lockhart and Robert S. Harris. „The chemical composition of depot fats in chickens and turkeys”. Chemistry and Materials Science. 20 (11): 231—234. doi:10.1007/BF02630880.
- ^ MG Kokatnur, MC Oalmann, WD Johnson, GT Malcom and JP Strong (1. 11. 1979). „Fatty acid composition of human adipose tissue from two anatomical sites in a biracial community”. American Journal of Clinical Nutrition. 32 (11): 2198—205. PMID 495536.
- ^ Anies Hannawati Purnamadjaja, R. Andrew Russell (2005). „Pheromone communication in a robot swarm: necrophoric bee behaviour and its replication”. Robotica. 23 (6): 731—742. doi:10.1017/S0263574704001225.
- ^ Ayasse, M.; Paxton, R. (2002). „Brood protection in social insects”. Ур.: Hilker, M.; Meiners, T. Chemoecology of Insect Eggs and Egg Deposition. Berlin: Blackwell. стр. 117—148. ISBN 1405106948.
- ^ Krulwich, Robert (2009). „Hey I'm Dead! The Story Of The Very Lively Ant”. National Public Radio.
- ^ Walker, Matt (9. 9. 2009). „Ancient 'smell of death' revealed”. BBC - Earth News. Приступљено 13. 9. 2009.