Survey with prize
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:38:57 UTC
Update Date2019-07-23 06:07:16 UTC
HMDB IDHMDB0030776
Secondary Accession Numbers
  • HMDB30776
Metabolite Identification
Common NameMaltol
DescriptionMaltol, also known as E636 or fema 2656, belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone. 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. Maltol is an extremely weak basic (essentially neutral) compound (based on its pKa). Maltol is a sweet, baked, and bread tasting compound. Outside of the human body, Maltol has been detected, but not quantified in, several different foods, such as milk and milk products, nuts, soy beans, pepper (c. annuum), and coffee and coffee products. This could make maltol a potential biomarker for the consumption of these foods. 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. 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. Maltol is a naturally occurring organic compound that is used primarily as a flavor enhancer. It is a white crystalline powder that is soluble in hot water, chloroform, and other polar solvents. 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+. It is known in the European E number food additive series as E636. It is not registered as a food additive in the EU and thus has no E-number. Because it has the odor of cotton candy and caramel, maltol is used to impart a sweet aroma to fragrances.
Structure
Data?1563862036
Synonyms
ValueSource
e636HMDB
2-Hydroxy-3-methyl-4H-pyran-4-oneHMDB
2-Methyl pyromeconic acidHMDB
2-Methyl-3-hydroxy-4-pyranoneHMDB
2-Methyl-3-hydroxy-4-pyroneHMDB
2-Methyl-3-hydroxypyroneHMDB
2-Methyl-3-oxy-gamma-pyroneHMDB
3-Hydroxy-2-methyl-1,4-pyroneHMDB
3-Hydroxy-2-methyl-4-pyranoneHMDB
3-Hydroxy-2-methyl-4-pyroneHMDB
3-Hydroxy-2-methyl-4H-pyran-4-oneHMDB
3-Hydroxy-2-methyl-g-pyroneHMDB
3-Hydroxy-2-methyl-gamma-pyroneHMDB
3-Hydroxy-2-methylpyroneHMDB
3-Hydroxy-2-pyran-4-oneHMDB
5-Hydroxy-6-methyl-4H-pyran-4-oneHMDB
FEMA 2656HMDB
Laricinic acidHMDB
Larixic acidHMDB
Larixinic acidHMDB
PalatoneHMDB
TalmonHMDB
VeltolHMDB
VetolHMDB
Chemical FormulaC6H6O3
Average Molecular Weight126.11
Monoisotopic Molecular Weight126.031694058
IUPAC Name3-hydroxy-2-methyl-4H-pyran-4-one
Traditional Nametalmon
CAS Registry Number118-71-8
SMILES
CC1=C(O)C(=O)C=CO1
InChI Identifier
InChI=1S/C6H6O3/c1-4-6(8)5(7)2-3-9-4/h2-3,8H,1H3
InChI KeyXPCTZQVDEJYUGT-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrans
Sub ClassPyranones and derivatives
Direct ParentPyranones and derivatives
Alternative Parents
Substituents
  • Pyranone
  • Heteroaromatic compound
  • Cyclic ketone
  • Oxacycle
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point161 - 162 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility10.9 mg/mL at 15 °CNot Available
LogP0.09Not Available
Predicted Properties
PropertyValueSource
Water Solubility134 g/LALOGPS
logP-0.24ALOGPS
logP0.55ChemAxon
logS0.03ALOGPS
pKa (Strongest Acidic)9.45ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity33.72 m³·mol⁻¹ChemAxon
Polarizability11.6 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-9500000000-9ab04dd29d36893ecd26Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05ir-7900000000-600ebd59fb3066652709Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0002-9000000000-c04cc7216a3bd4a235e7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-38440dc8d01235ec6030Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-2900000000-d055c9796b264b599b6aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9000000000-d0af17e3cc2dd76131f3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-69feb02bb47c24872d73Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-016s-9300000000-76b24f4971833037af7bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002g-9000000000-c6a03d90d227ae6c5653Spectrum
MSMass Spectrum (Electron Ionization)splash10-004i-9400000000-e2ddaa7bab18abea7217Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB002712
KNApSAcK IDC00037471
Chemspider ID8066
KEGG Compound IDC11918
BioCyc IDCPD-15508
BiGG IDNot Available
Wikipedia LinkMaltol
METLIN IDNot Available
PubChem Compound8369
PDB IDNot Available
ChEBI ID142577
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .