Maltol

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Not to be confused with Maltitol.
Maltol
Maltol.svg
Names
Preferred IUPAC name
3-Hydroxy-2-methyl-4H-pyran-4-one
Other names
Larixinic acid; Palatone; Veltol
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.003.884 Edit this at Wikidata
UNII
  • InChI=1S/C6H6O3/c1-4-6(8)5(7)2-3-9-4/h2-3,8H,1H3 checkY
    Key: XPCTZQVDEJYUGT-UHFFFAOYSA-N checkY
  • InChI=1/C6H6O3/c1-4-6(8)5(7)2-3-9-4/h2-3,8H,1H3
    Key: XPCTZQVDEJYUGT-UHFFFAOYAH
  • O=C1C=COC(C)=C1O
Properties
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).
checkY  (what is checkY☒N ?)
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.

Derivatives[]

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.[5][6]

See also[]

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.
  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.
  5. ^ Amatori, G.Ambrosi; Fanelli, M.Formica; Fusi, L.Giorgi; Macedi, M.Micheloni; Paoli, R.Pontellini (2012). "Synthesis, basicity, structural characterization, and biochemical properties of two [(3-hydroxy-4-pyron-2-yl)methyl]amine derivatives showing antineoplastic features". J. Org. Chem. 77 (5): 2207–18. doi:10.1021/jo202270j. PMID 22296279.
  6. ^ Amatori, I.Bagaloni; Macedi, M.Formica; Giorgi, V.Fusi (2010). "Malten, a new synthetic molecule showing in vitro antiproliferative activity against tumour cells and induction of complex DNA structural alterations". Br. J. Cancer. 103 (2): 239–48. doi:10.1038/sj.bjc.6605745. PMC 2906739. PMID 20571494.
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