Levulinska kiselina

Levulinska kiselina
	4-Oksopentanoinska kiselina
Drugi nazivi	β-Acetilpropionska kiselina, 3-Acetopropionska kiselina, β-acetilpropionska kiselina, γ-ketovalerinska kiselina, 4-oksopentanska kiselina
Identifikacija
CAS registarski broj	123-76-2
PubChem	11579
ChemSpider	11091
UNII	RYX5QG61EI
DrugBank	DB02239
ChEBI	45630
ChEMBL	CHEMBL1235931
Jmol-3D slike	Slika 1
SMILES
	CC(=O)CCC(=O)O
InChI
	InChI=1S/C5H8O3/c1-4(6)2-3-5(7)8/h2-3H2,1H3,(H,7,8) ; Kod: JOOXCMJARBKPKM-UHFFFAOYSA-N InChI=1/C5H8O3/c1-4(6)2-3-5(7)8/h2-3H2,1H3,(H,7,8); Kod: JOOXCMJARBKPKM-UHFFFAOYAR
Svojstva
Molekulska formula	C5H8O3
Molarna masa	116,11 g/mol
Gustina	1,1447 g/cm3
Tačka topljenja	33–35 °C
Tačka ključanja	245–246 °C
	(šta je ovo?) (verifikuj) ; Ukoliko nije drugačije napomenuto, podaci se odnose na standardno stanje (25 °C, 100 kPa) materijala
	Infobox references

Levulinska kiselina (4-oksopentanoinska kiselina) je organsko jedinjenje sa formulom CH₃C(O)CH₂CH₂CO₂H. Ona se klasifikuje kao ketokiselina. Ova bela kristalna materija je rastvorna u vodi, etanolu, i dietil etru. Ona se formira degradacijom celuloze i potencijalni je prekurzor biogoriva.^[6]

Sinteza i upotreba uredi

Poput njene originalne sinteze,^[7] levulinska kiselina se priprema u laboratoriji zagrevanjem saharoze sa koncentrovanom hlorovodoničnom kiselinom.^[8] Taj proces se odvija preko intermedijera glukoze, koja se izomerizuje do fruktoze i zatim hidroksimetilfurfurala. Drugi derivati šećera se mogu koristiti u ovom procesu uključujući levulozu (D-fruktozu), inulin i skrob kao i druge kiseline, kao što je sumporna.

Reference uredi

↑ Merck Index, 11th Edition, 5352
↑ 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
↑ Biorefineries – Industrial Processes and Products. Status Quo and Future Directions. Vol. 1, Edited by Birgit Kamm, Patrick R. Gruber, Michael Kamm. 2006, WILEY-VCH, Weinheim. ISBN: 3-527-31027-4
↑ A. Freiherrn, V. Grote, B. Tollens, "Untersuchungen über Kohlenhydrate. I. Ueber die bei Einwirkung von Schwefelsäure auf Zucker entstehende Säure (Levulinsäure)" Justus Liebigs Annalen der Chemie volume 175, pp. 181-204 (1875). DOI: 10.1002/jlac.18751750113
↑ B. F. McKenzie (1941), „Levulinic acid”, Organic Syntheses ; Coll. Vol. 1: 335

Spoljašnje veze uredi

Portal Hemija

[1] Merck Index, 11th Edition, 5352

[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

[6] Biorefineries – Industrial Processes and Products. Status Quo and Future Directions. Vol. 1, Edited by Birgit Kamm, Patrick R. Gruber, Michael Kamm. 2006, WILEY-VCH, Weinheim. ISBN: 3-527-31027-4

[7] A. Freiherrn, V. Grote, B. Tollens, "Untersuchungen über Kohlenhydrate. I. Ueber die bei Einwirkung von Schwefelsäure auf Zucker entstehende Säure (Levulinsäure)" Justus Liebigs Annalen der Chemie volume 175, pp. 181-204 (1875). DOI: 10.1002/jlac.18751750113

[8] B. F. McKenzie (1941), „Levulinic acid”, Organic Syntheses ; Coll. Vol. 1: 335

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