Maltol

Maltol
IUPAC name 3-hydroxy-2-methyl-4H-pyran-4-one
Identifiers
CAS number	118-71-8 Y
UNII	3A9RD92BS4 Y
Jmol-3D images	Image 1
SMILES O=C1C=COC(C)=C1O
Properties
Molecular formula	C6H6O3
Molar mass	126.11 g/mol
Density	1.348 g/cm3
Melting point	161-162 °C
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 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 (E number E636) in breads and cakes.

Maltol, like related 3-hydroxy-4-pyrones such as kojic acid, binds to hard metal centers such as Fe³⁺, Ga³⁺, Al³⁺, and VO²⁺.^[1] Related to this property, maltol has been reported to greatly increase aluminum uptake in the body ^[2] and to increase the oral bioavailability of gallium ^[3] and iron. ^[4]

See also

• Ethyl maltol
• Gallium maltolate
• 5-hydroxymaltol
• Isomaltol

References

1. ^ 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. 
2. ^ 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. 
3. ^ 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. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2365198. 
4. ^ 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.