Gentizinska kiselina

Gentizinska kiselina
	2,5-dihidroksibenzojeva kiselina
Drugi nazivi	DHB; 2,5-dihidroksibenzojeva kiselina; 5-Hidroksisalicilna kiselina; Gentijanska kiselina; Karboksihidrohinon; 2,5-Dioksibenzojeva kiselina; Hidrohinonkarboksilna kiselina
Identifikacija
CAS registarski broj	490-79-9
PubChem	3469
ChemSpider	3350
UNII	VP36V95O3T
KEGG	C00628
ChEBI	17189
ChEMBL	CHEMBL1461
Jmol-3D slike	Slika 1
SMILES
	O=C(O)c1cc(O)ccc1O
InChI
	InChI=1S/C7H6O4/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,8-9H,(H,10,11) ; Kod: WXTMDXOMEHJXQO-UHFFFAOYSA-N InChI=1/C7H6O4/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,8-9H,(H,10,11); Kod: WXTMDXOMEHJXQO-UHFFFAOYAO
Svojstva
Molekulska formula	C7H6O4
Molarna masa	154.12 g/mol
Agregatno stanje	belo-žuti prah
Tačka topljenja	200 - 205 C (sublimira)
	(šta je ovo?) (verifikuj) ; Ukoliko nije drugačije napomenuto, podaci se odnose na standardno stanje (25 °C, 100 kPa) materijala
	Infobox references

Gentisinska kiselina je dihidroksibenzojeva kiselina. Ona je derivat benzojeve kiseline, i manje zastupljeni (1%) proizvod metaboličkog raspada aspirina. Izlučuje se iz organizma putem bubrega.^[7]

Proizvodnja

Gentisinska kiselina se proizvodi karboksilacijom hidrohinona.^[8]

C₆H₄(OH)₂ + CO₂ → C₆H₃(CO₂H)(OH)₂

Ova konverzija je primer Kolbe–Šmitove reakcije.

Primena

Kao hidrohinon, gentisinska kiselina se lako oksiduje i koristi se kao antioksidans i ekscipijent u nekim farmaceutskim preparatima.

U laboratorijskim uslovima ona se koristi kao jednostavni matriks u MALDI masenoj spektrometriji.^[9] Poznato je da je ona podesna za detekciju peptida koji sadrže boronsku kiselinu putem MALDI-a.^[10]

Reference

↑ Gentisic acid - Compound Summary, PubChem.
↑ 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
↑ Levy, G; Tsuchiya, T (1972-09-30). „Salicylate accumulation kinetics in man”. New England Journal of Medicine 287 (9): 430–2. DOI:10.1056/NEJM197208312870903. PMID 5044917.
↑ Ullmann’s Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. 2005.
↑ Strupat K, Karas M, Hillenkamp F (1991). „2,5-Dihidroxybenzoic acid: a new matrix for laser desorption-ionization mass spectrometry”. Int. J. Mass Spectrom. Ion Processes 72 (111): 89–102. Bibcode 1991IJMSI.111...89S. DOI:10.1016/0168-1176(91)85050-V.
↑ Crumpton, J.; Zhang, W.; Santos, W. L. (2011). „Facile Analysis and Sequencing of Linear and Branched Peptide Boronic Acids by MALDI Mass Spectrometry”. Analytical Chemistry 83 (9): 3548–3554. DOI:10.1021/ac2002565. PMC 3090651. PMID 21449540.

Vanjske veze

Portal Hemija

[1] Gentisic acid - Compound Summary, PubChem.

[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] 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.

[6] 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

[7] Levy, G; Tsuchiya, T (1972-09-30). „Salicylate accumulation kinetics in man”. New England Journal of Medicine 287 (9): 430–2. DOI:10.1056/NEJM197208312870903. PMID 5044917.

[Ullmann-8] Ullmann’s Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. 2005.

[9] Strupat K, Karas M, Hillenkamp F (1991). „2,5-Dihidroxybenzoic acid: a new matrix for laser desorption-ionization mass spectrometry”. Int. J. Mass Spectrom. Ion Processes 72 (111): 89–102. Bibcode 1991IJMSI.111...89S. DOI:10.1016/0168-1176(91)85050-V.

[10] Crumpton, J.; Zhang, W.; Santos, W. L. (2011). „Facile Analysis and Sequencing of Linear and Branched Peptide Boronic Acids by MALDI Mass Spectrometry”. Analytical Chemistry 83 (9): 3548–3554. DOI:10.1021/ac2002565. PMC 3090651. PMID 21449540.

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