Limunska kiselina

Limunska kiselina
	2-hydroxypropane-1,2,3-tricarboxylic acid
Drugi nazivi	3-karboksi-3-hidroksipentanedionska kiselina
Identifikacija
CAS registarski broj	77-92-9
PubChem	311
ChemSpider	305
UNII	XF417D3PSL
KEGG	D00037
ChEMBL	CHEMBL1261
Jmol-3D slike	Slika 1
SMILES
	C(C(=O)O)C(CC(=O)O)(C(=O)O)O
InChI
	InChI=1S/C6H8O7/c7-3(8)1-6(13,5(11)12)2-4(9)10/h13H,1-2H2,(H,7,8)(H,9,10)(H,11,12) ; Kod: KRKNYBCHXYNGOX-UHFFFAOYSA-N InChI=1/C6H8O7/c7-3(8)1-6(13,5(11)12)2-4(9)10/h13H,1-2H2,(H,7,8)(H,9,10)(H,11,12); Kod: KRKNYBCHXYNGOX-UHFFFAOYAM
Svojstva
Molekulska formula	C6H8O7
Molarna masa	192.124 g/mol (anhidrat); 210.14 g/mol (monohidrat)
Agregatno stanje	kristalna bela materija
Gustina	1.665 g/cm3
Tačka topljenja	153 °C, 426 K, 307 °F
Tačka ključanja	175 °C, 448 K, 347 °F (razlaže se)
Rastvorljivost u vodi	73 g/100 ml (20 °C)
Rastvorljivost u THF, etanol, metanol	ahidrat: THF 1.80 M, etanol 1.6 M, metanol 3.08 M; monohidrat: THF 1.52 M, etanol 1.78 M, metanol 2.27 M
pKa	pKa1 = 3.09; pKa2 = 4.75; pKa3 = 6.41
Opasnost
Opasnost u toku rada	iritant kože i očiju
Srodna jedinjenja
Srodna jedinjenja	natrijum citrat, kalcijum citrat
	(šta je ovo?) (verifikuj) ; Ukoliko nije drugačije napomenuto, podaci se odnose na standardno stanje (25 °C, 100 kPa) materijala
	Infobox references

Limunska kiselina, C₆H₈O₇, trobazna je organska kiselina^[9]^[10], prisutna u mnogim vrstama voća (u limunovom soku 5–6%).

Bela je kristalna supstanca kiselog ukusa, lako rastvorljiva u vodi. Industrijski se dobija iz limuna (u južnoj Italiji i Kaliforniji) ili iz šećera fermentacijom pomoću plesni Aspergillus niger. Upotrebljava se u proizvodnji bezalkoholnih napitaka i u medicini. Njene soli su citrati. Normalan je sastojak ljudske krvi i urina (mokraće). Koristi se u proizvodnji šumećih tableta i vitaminskih napitaka (npr. sastojak je Cedevite), voćnih sokova, smrznutog voća itd... Uzorci krvi i tkiva čuvaju se u rastvorima limunske kiseline.

Reference

↑ 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
↑ Joanne Wixon, Douglas Kell (2000). „Website Review: The Kyoto Encyclopedia of Genes and Genomes — KEGG”. Yeast 17 (1): 48–55. DOI:10.1002/(SICI)1097-0061(200004)17:1<48::AID-YEA2>3.0.CO;2-H.
↑ 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
↑ „Solubility of citric acid anhydrous in non-aqueous solvents”.
↑ „Solubility of citric acid monohydrate in non-aqueous solvents”.
↑ Dawson, R. M. C., et al., Data for Biochemical Research, Oxford, Clarendon Press, 1959.
↑ Clayden Jonathan, Nick Greeves, Stuart Warren, Peter Wothers (2001). Organic chemistry. Oxford, Oxfordshire: Oxford University Press. ISBN 0-19-850346-6.
↑ Thomas L. Lemke, David A. Williams, ur. (2007). Foye's Principles of Medicinal Chemistry (6 izd.). Baltimore: Lippincott Willams & Wilkins. ISBN 0-7817-6879-9.

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[1] 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

[2] 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.

[3] 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

[4] Joanne Wixon, Douglas Kell (2000). „Website Review: The Kyoto Encyclopedia of Genes and Genomes — KEGG”. Yeast 17 (1): 48–55. DOI:10.1002/(SICI)1097-0061(200004)17:1<48::AID-YEA2>3.0.CO;2-H.

[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] „Solubility of citric acid anhydrous in non-aqueous solvents”.

[7] „Solubility of citric acid monohydrate in non-aqueous solvents”.

[8] Dawson, R. M. C., et al., Data for Biochemical Research, Oxford, Clarendon Press, 1959.

[Clayden1st-9] Clayden Jonathan, Nick Greeves, Stuart Warren, Peter Wothers (2001). Organic chemistry. Oxford, Oxfordshire: Oxford University Press. ISBN 0-19-850346-6.

[Foye-10] Thomas L. Lemke, David A. Williams, ur. (2007). Foye's Principles of Medicinal Chemistry (6 izd.). Baltimore: Lippincott Willams & Wilkins. ISBN 0-7817-6879-9.

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