Maltol

Maltol
Names
	Preferred IUPAC name 3-Hydroxy-2-methyl-4H-pyran-4-one
	Other names Larixinic acid; Palatone; Veltol
Identifiers
CAS Number	118-71-8 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL31422 ;
ChemSpider	8066 ;
ECHA InfoCard	100.003.884
PubChem CID	8369;
UNII	3A9RD92BS4 ;
CompTox Dashboard (EPA)	DTXSID0025523 ;
	InChI InChI=1S/C6H6O3/c1-4-6(8)5(7)2-3-9-4/h2-3,8H,1H3 Key: XPCTZQVDEJYUGT-UHFFFAOYSA-N ; 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	126.111 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). verify (what is ?) 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.

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] It is known in the European E number food additive series as E636.

References

^ 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.

[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.

[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.

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See also

References