Alfa-linoleinska kiselina

α-Linoleinska kiselina
Drugi nazivi	ALA; Linoleinska kiselina; cis,cis,cis-9,12,15-Oktadekatrienska kiselina; (9Z,12Z,15Z)-9,12,15-Oktadekatrienoiska kiselina; (9Z,12Z,15Z)-oktadeka-9,12,15-trienoiska kiselina; Industren 120
Identifikacija
CAS registarski broj	463-40-1
PubChem	5280934
ChemSpider	4444437
UNII	0RBV727H71
DrugBank	DB00132
ChEBI	27432
ChEMBL	CHEMBL8739
Jmol-3D slike	Slika 1; Slika 2
SMILES
	O=C(O)CCCCCCC\C=C/C\C=C/C\C=C/CC CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)O
InChI
	InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h3-4,6-7,9-10H,2,5,8,11-17H2,1H3,(H,19,20)/b4-3-,7-6-,10-9- ; Kod: DTOSIQBPPRVQHS-PDBXOOCHSA-N InChI=1/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h3-4,6-7,9-10H,2,5,8,11-17H2,1H3,(H,19,20)/b4-3-,7-6-,10-9-; Kod: DTOSIQBPPRVQHS-PDBXOOCHBH
Svojstva
Molekulska formula	C18H30O2
Molarna masa	278.43 g mol−1
	(šta je ovo?) (verifikuj) ; Ukoliko nije drugačije napomenuto, podaci se odnose na standardno stanje (25 °C, 100 kPa) materijala
	Infobox references

α-Linoleinska kiselina je ogransko jedinjenje nađeno u mnogim biljnim uljima. Njena struktura se naziva sve-cis-9,12,15-oktadekatrienoinska kiselina.^[6] U fiziološkoj literaturi, ona je poznata kao 18:3 (n−3).

α-Linoleinska kiselina je karboksilna kiselina sa 18-ugljenika dugim lancom i tri cis dvostruke veze. Prva dvostruka veza je locirana na trećem ugljeniku sa metilnog kraja lanca masne kiseline, poznatom kao n kraj. α-linoleinska kiseline je polinezasićena n−3 (omega-3) masna kiselina. Ona je izomer gama-linoleinske kiseline, polinezasićene n−6 (omega-6) masne kiseline.

Istorija uredi

Alfa-linoleinsku kiselinu je privi izolovao Rolet.^[7]^[8]^[9] Prvi put je bila veštaćki sintetisana 1995.^[10]

Reference uredi

↑ Loreau O, Maret A, Poullain D, Chardigny JM, Sébédio JL, Beaufrère B, Noël JP (2000). „Large-scale preparation of (9Z,12E)-1-(13)C-octadeca-9,12-dienoic acid, (9Z,12Z,15E)-1-(13)C-octadeca-9,12,15-trienoic acid and their 1-(13)C all-cis isomers”. Chemistry and physics of lipids 106 (1): 65–78. PMID 10878236.
↑ Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. edit
↑ Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1.
↑ Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846. edit
↑ Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP. (2012). „ChEMBL: a large-scale bioactivity database for drug discovery”. Nucleic Acids Res 40 (Database issue): D1100-7. DOI:10.1093/nar/gkr777. PMID 21948594. edit
↑ Beare-Rogers (2001). „IUPAC Lexicon of Lipid Nutrition” (pdf). Pristupljeno 22. 2. 2006.
↑ Rollett, A. (1909). Z. Physiol. Chem.. 62. pp. 422.
↑ J. W. McCutcheon (1955), „Linolenic Acid”, Organic Syntheses ; Coll. Vol. 3: 351
↑ Green, TG; Hilditch, TP (1935). „The identification of linoleic and linolenic acids”. Biochem. J. 29 (7): 1552–63. PMC 1266662. PMID 16745822.
↑ Sandri, J.; Viala, J. (1995). „Direct preparation of (Z,Z)-1,4-dienic units with a new C6 homologating agent: synthesis of alpha-linolenic acid”. Synthesis 3: 271–275.

Spoljašnje veze uredi

Portal Hemija

[1] Loreau O, Maret A, Poullain D, Chardigny JM, Sébédio JL, Beaufrère B, Noël JP (2000). „Large-scale preparation of (9Z,12E)-1-(13)C-octadeca-9,12-dienoic acid, (9Z,12Z,15E)-1-(13)C-octadeca-9,12,15-trienoic acid and their 1-(13)C all-cis isomers”. Chemistry and physics of lipids 106 (1): 65–78. PMID 10878236.

[2] Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. edit

[3] Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1.

[4] Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846. edit

[5] Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP. (2012). „ChEMBL: a large-scale bioactivity database for drug discovery”. Nucleic Acids Res 40 (Database issue): D1100-7. DOI:10.1093/nar/gkr777. PMID 21948594. edit

[Beare-6] Beare-Rogers (2001). „IUPAC Lexicon of Lipid Nutrition” (pdf). Pristupljeno 22. 2. 2006.

[7] Rollett, A. (1909). Z. Physiol. Chem.. 62. pp. 422.

[8] J. W. McCutcheon (1955), „Linolenic Acid”, Organic Syntheses ; Coll. Vol. 3: 351

[9] Green, TG; Hilditch, TP (1935). „The identification of linoleic and linolenic acids”. Biochem. J. 29 (7): 1552–63. PMC 1266662. PMID 16745822.

[10] Sandri, J.; Viala, J. (1995). „Direct preparation of (Z,Z)-1,4-dienic units with a new C6 homologating agent: synthesis of alpha-linolenic acid”. Synthesis 3: 271–275.

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