Menadion

Menadion
	2-Metilnaftalen-1,4-dion
Drugi nazivi	Menafton; Vitamin K3; β-Metil-1,4-naftohinon; 2-Metil-1,4-naftodion; 2-Metil-1,4-naftohinon
Identifikacija
CAS registarski broj	58-27-5
PubChem	4055
ChemSpider	3915
UNII	723JX6CXY5
DrugBank	DB00170
KEGG	D02335
ChEBI	28869
ChEMBL	CHEMBL590
ATC code	B02BA02
Jmol-3D slike	Slika 1
SMILES
	O=C\2c1c(cccc1)C(=O)/C(=C/2)C
InChI
	InChI=1S/C11H8O2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6H,1H3 ; Kod: MJVAVZPDRWSRRC-UHFFFAOYSA-N InChI=1/C11H8O2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6H,1H3; Kod: MJVAVZPDRWSRRC-UHFFFAOYAY
Svojstva
Molekulska formula	C11H8O2
Molarna masa	172.18 g mol−1
Agregatno stanje	Svetlo žuti kristali
Gustina	1,225 g/cm3
Tačka topljenja	105–107 °C
Tačka ključanja	304.5 °C @ 760mmHg
Rastvorljivost u vodi	Nerastvoran je
Opasnost
Tačka paljenja	113,8 °C
LD50	0,5 g/kg (oralno, miš)
	(šta je ovo?) (verifikuj) ; Ukoliko nije drugačije napomenuto, podaci se odnose na standardno stanje (25 °C, 100 kPa) materijala
	Infobox references

Menadion je sintetičko hemijsko jedinjenje koje se ponekad koristi kao nutricioni suplement zbog njegove aktivnosti poput vitamina K. On je analog 1,4-naftohinona sa metil grupom u 2-poziciji.^[7]

Terminologija

On se ponekad naziva vitaminom K₃,^[8] mada derivati naftohinona bez bočnog lanca u 3-poziciji ne mogu da vrše sve funkcije vitamina K. Menadion je vitaminski prekurzor K₂, iz koga se alkilacijom formiraju menahinoni (MK-n, n=1-13; K₂ provitamini), i stoga je podesnije da se klasifikuje kao provitamin.

On je takođe poznat kao "menafton".^[9]

Reference

↑ The Merck Index, 11th Edition, 5714
↑ 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 21948863. edit
↑ Castro FA, Mariani D, Panek AD, Eleutherio EC, Pereira MD (2008). Fox, Debbie. ur. „Cytotoxicity Mechanism of Two Naphthoquinones (Menadione and Plumbagin) in Saccharomyces cerevisiae”. PLoS ONE 3 (12): e3999. DOI:10.1371/journal.pone.0003999. PMC 2600608. PMID 19098979.
↑ Scott GK, Atsriku C, Kaminker P, et al (September 2005). „Vitamin K3 (menadione)-induced oncosis associated with keratin 8 phosphorylation and histone H3 arylation”. Mol. Pharmacol. 68 (3): 606–15. DOI:10.1124/mol.105.013474. PMID 15939799. Arhivirano iz originala na datum 2019-12-14. Pristupljeno 2014-04-11.
↑ „Vitamin K”. Pristupljeno 18. 3. 2009.

Spoljašnje veze

Portal Hemija

[1] The Merck Index, 11th Edition, 5714

[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 21948863. edit

[pmid19098979-7] Castro FA, Mariani D, Panek AD, Eleutherio EC, Pereira MD (2008). Fox, Debbie. ur. „Cytotoxicity Mechanism of Two Naphthoquinones (Menadione and Plumbagin) in Saccharomyces cerevisiae”. PLoS ONE 3 (12): e3999. DOI:10.1371/journal.pone.0003999. PMC 2600608. PMID 19098979.

[pmid15939799-8] Scott GK, Atsriku C, Kaminker P, et al (September 2005). „Vitamin K3 (menadione)-induced oncosis associated with keratin 8 phosphorylation and histone H3 arylation”. Mol. Pharmacol. 68 (3): 606–15. DOI:10.1124/mol.105.013474. PMID 15939799. Arhivirano iz originala na datum 2019-12-14. Pristupljeno 2014-04-11.

[urlVitamin_K-9] „Vitamin K”. Pristupljeno 18. 3. 2009.

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