Acetosirćetna kiselina

Acetosirćetna kiselina
	3-oksobutanoiska kiselina
Identifikacija
CAS registarski broj	541-50-4
PubChem	96
ChemSpider	94
DrugBank	DB01762
KEGG	C00164
ChEBI	15344
ChEMBL	CHEMBL1230762
Jmol-3D slike	Slika 1
SMILES
	O=C(C)CC(=O)O
InChI
	InChI=1S/C4H6O3/c1-3(5)2-4(6)7/h2H2,1H3,(H,6,7) ; Kod: WDJHALXBUFZDSR-UHFFFAOYSA-N InChI=1/C4H6O3/c1-3(5)2-4(6)7/h2H2,1H3,(H,6,7); Kod: WDJHALXBUFZDSR-UHFFFAOYAH
Svojstva
Molekulska formula	C4H6O3
Molarna masa	102,09 g/mol
Tačka topljenja	36.5 °C
Tačka ključanja	Razlaže se
pKa	3.58
	(šta je ovo?) (verifikuj) ; Ukoliko nije drugačije napomenuto, podaci se odnose na standardno stanje (25 °C, 100 kPa) materijala
	Infobox references

Acetosirćetna kiselina (diacilna kiselina) je organsko jedinjenje sa formulom CH₃C(O)CH₂CO₂H. Ona je najjednostavnija beta-ketokiselina, i poput drugih članova ove klase je nestabilna.

Sinteza i osobine

Acetosirćetna kiselina je slaba kiselina (slično većini drugih alkil karboksilnih kiseline) sa pK_a vrednošću od 3.77. Ona se može pripremiti hidrolizom etil acetoacetata čemu sledi acidifikacija anjona.^[7]

Acetosirćetna kiselina se formira na 0 °C i koristi in situ.^[8] Ona se razlaže sa umerenom brzinom reakcije do acetona i ugljen-dioksida:

CH₃C(O)CH₂CO₂H → CH₃C(O)CH₃ + CO₂

Kisela forma ima poluživot od 140 minuta na 37 °C u vodi, dok bazni oblik (anjon) ima poluživot od 130 sata. Drugim rečima, on reaguje oko 50 puta sporije.^[9]

Literatura

↑ 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
↑ Dawson, R. M. C., et al., Data for Biochemical Research, Oxford, Clarendon Press, 1959.
↑ Krueger, Robert C. (1952). „Crystalline Acetoacetic Acid”. Journal of the American Chemical Society 74 (21): 5536–5536. DOI:10.1021/ja01141a521.
↑ George A. Reynolds and J. A. VanAllan "Methylglyoxal-ω-Phenylhydrazone" Organic Syntheses, Collected Volume 4, p.633 (1963).
↑ Hay, R. W.; Bond, M. A. (1967). „Kinetics of decarboxilation of acetoacetic acid”. Aust. J. Chem. 20 (9): 1823–8. DOI:10.1071/CH9671823.

Povezano

3-hidroksibutirat dehidrogenaza

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

[7] Krueger, Robert C. (1952). „Crystalline Acetoacetic Acid”. Journal of the American Chemical Society 74 (21): 5536–5536. DOI:10.1021/ja01141a521.

[8] George A. Reynolds and J. A. VanAllan "Methylglyoxal-ω-Phenylhydrazone" Organic Syntheses, Collected Volume 4, p.633 (1963).

[9] Hay, R. W.; Bond, M. A. (1967). „Kinetics of decarboxilation of acetoacetic acid”. Aust. J. Chem. 20 (9): 1823–8. DOI:10.1071/CH9671823.

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