Maltol
| Maltol | |
|---|---|
 | |
| IUPAC name 3-Hydroxy-2-methyl-4H-pyran-4-one | |
| Other names Larixinic acid; Palatone; Veltol | |
| Identifiers | |
| CAS number | 118-71-8  |
| PubChem | 8369 |
| ChemSpider | 8066 |
| UNII | 3A9RD92BS4 |
| ChEMBL | CHEMBL31422 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C6H6O3 |
| Molar mass | 126.11 g mol−1 |
| Density | 1.348 g/cm3 |
| Melting point | 161 to 162 °C; 322 to 324 °F; 434 to 435 K |
(verify) (what is: / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | |
| Infobox references | |
Maltol is a naturally occurring organic compound that is used primarily as a flavor enhancer. It is found in the bark of larch tree, in pine needles, and in roasted malt (from which it gets its name). It is a white crystalline powder that is soluble in hot water, chloroform, and other polar solvents. Because it has the odor of cotton candy and caramel, maltol is used to impart a sweet aroma to fragrances. Maltol's sweetness adds to the odor of freshly baked bread, and is used as a flavor enhancer (INS Number 636) in breads and cakes. It is not registered as a food additive in the EU and thus has no E-number.[1] Instead, maltol is registered as a flavor component in the EU.[2]
Maltol, like related 3-hydroxy-4-pyrones such as kojic acid, binds to hard metal centers such as Fe3+, Ga3+, Al3+, and VO2+.[3] Related to this property, maltol has been reported to greatly increase aluminum uptake in the body[4] and to increase the oral bioavailability of gallium[5] and iron.[6]
Derivatives of maltol
Some synthetic derivatives of maltol, developed at the University of Urbino, have got antiproliferative activity towards cancer cells, that induce apoptosis mechanisms against these cells[7][8]
See also
References
- ↑ Official Journal of the European Union, Volume 54, November 12, 2011
- ↑ Official Journal of the European Union, Volume 55, October 2, 2012
- ↑ B. D. Liboiron, K. H. Thompson, G. R. Hanson, E. Lam, N. Aebischer, C. Orvig (2005). "New Insights into the Interactions of Serum Proteins with Bis(maltolato)oxovanadium(IV): Transport and Biotransformation of Insulin-Enhancing Vanadium Pharmaceuticals". J. Am. Chem. Soc. 127 (14): 5104–5115. doi:10.1021/ja043944n. PMID 15810845.
- ↑ N. Kaneko, H. Yasui, J. Takada, K. Suzuki, H. Sakurai (2004). "Orally administrated aluminum-maltolate complex enhances oxidative stress in the organs of mice". J. Inorg. Biochem. 98 (12): 2022–2031. doi:10.1016/j.jinorgbio.2004.09.008. PMID 15541491.
- ↑ L. R. Bernstein, T. Tanner, C. Godfrey, B. Noll (2000). "Chemistry and pharmacokinetics of gallium maltolate, a compound with high oral gallium bioavailability". Metal Based Drugs 7 (1): 33–48. doi:10.1155/MBD.2000.33. PMC 2365198. PMID 18475921.
- ↑ D.M. Reffitt, T.J. Burden, P.T. Seed, J. Wood J, R.P. Thompson, J.J. Powell (2000). "Assessment of iron absorption from ferric trimaltol". Ann. Clin. Biochem. 37 (4): 457–66. doi:10.1258/0004563001899645. PMID 10902861.
- ↑ S.Amatori, G.Ambrosi, M.Fanelli, M.Formica, V.Fusi, L.Giorgi, E.Macedi, M.Micheloni, P.Paoli, R.Pontellini, P.Rossi, Synthesis, basicity, structural characterization, and biochemical properties of two [(3-hydroxy-4-pyron-2-yl)methyl]amine derivatives showing antineoplastic features, J. Org. Chem., 2 marzo 2012; 77(5):2207-18. DOI: 10.1021/jo202270j. Epub 22 febbraio 2012.
- ↑ S.Amatori, I.Bagaloni, E.Macedi, M.Formica, L.Giorgi, V.Fusi, M.Fanelli,Malten, a new synthetic molecule showing in vitro antiproliferative activity against tumour cells and induction of complex DNA structural alterations, Br. J. Cancer., 13 luglio 2010; 103(2):239-48. DOI: 10.1038/sj.bjc.6605745. Epub 22 giugno 2010.