Maltol

Maltol
Names

IUPAC name 3-Hydroxy-2-methyl-4H-pyran-4-one
Other names Larixinic acid; Palatone; Veltol
Identifiers
CAS Number	118-71-8^Y
3D model (Jmol)	Interactive image
ChEMBL	ChEMBL31422^Y
ChemSpider	8066^Y
ECHA InfoCard	100.003.884
PubChem	8369
UNII	3A9RD92BS4^Y
InChI InChI=1S/C6H6O3/c1-4-6(8)5(7)2-3-9-4/h2-3,8H,1H3^Y Key: XPCTZQVDEJYUGT-UHFFFAOYSA-N^Y InChI=1/C6H6O3/c1-4-6(8)5(7)2-3-9-4/h2-3,8H,1H3 Key: XPCTZQVDEJYUGT-UHFFFAOYAH
SMILES O=C1C=COC(C)=C1O
Properties
Chemical 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)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y (what is ^YN ?)
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. Instead, maltol is registered as a flavor component in the EU.

Maltol, like related 3-hydroxy-4-pyrones such as kojic acid, binds to hard metal centers such as Fe³⁺, Ga³⁺, Al³⁺, and VO²⁺. Related to this property, maltol has been reported to greatly increase aluminum uptake in the body and to increase the oral bioavailability of gallium and iron.

Some synthetic derivatives of maltol, developed at the University of Urbino, showed limited in vitro antiproliferative activity towards cancer cells lines, perhaps inducing apoptosis in these cells