Hmdb loader
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:38:57 UTC
Update Date2023-02-21 17:19:41 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 a sweet, baked, and bread tasting compound. 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. 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. 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. Because it has the odor of cotton candy and caramel, maltol is used to impart a sweet aroma to fragrances.
Structure
Data?1676999981
Synonyms
ValueSource
e636ChEMBL, HMDB
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, MeSH
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
Physiological effect
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point161 - 162 °CNot Available
Boiling Point284.70 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility10.9 mg/mL at 15 °CNot Available
LogP0.09Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available117.742http://allccs.zhulab.cn/database/detail?ID=AllCCS00001121
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+123.60431661259
DarkChem[M-H]-121.58531661259
DeepCCS[M+H]+129.96730932474
DeepCCS[M-H]-127.66230932474
DeepCCS[M-2H]-163.78130932474
DeepCCS[M+Na]+138.64830932474
AllCCS[M+H]+124.232859911
AllCCS[M+H-H2O]+119.232859911
AllCCS[M+NH4]+128.832859911
AllCCS[M+Na]+130.132859911
AllCCS[M-H]-119.932859911
AllCCS[M+Na-2H]-121.932859911
AllCCS[M+HCOO]-124.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MaltolCC1=C(O)C(=O)C=CO11858.1Standard polar33892256
MaltolCC1=C(O)C(=O)C=CO11057.7Standard non polar33892256
MaltolCC1=C(O)C(=O)C=CO11055.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Maltol,1TMS,isomer #1CC1=C(O[Si](C)(C)C)C(=O)C=CO11273.8Semi standard non polar33892256
Maltol,1TBDMS,isomer #1CC1=C(O[Si](C)(C)C(C)(C)C)C(=O)C=CO11558.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Maltol GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-9500000000-9ab04dd29d36893ecd262016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Maltol GC-MS (1 TMS) - 70eV, Positivesplash10-05ir-7900000000-600ebd59fb30666527092017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Maltol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-004i-9400000000-e2ddaa7bab18abea72172015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Maltol Linear Ion Trap , negative-QTOFsplash10-0002-9000000000-c04cc7216a3bd4a235e72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Maltol 35V, Positive-QTOFsplash10-004i-4900000000-aa92125c58514d72564e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Maltol 40V, Positive-QTOFsplash10-0006-9000000000-683526173a1cb2e60e9a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Maltol 20V, Positive-QTOFsplash10-004i-4900000000-9cacfb0610f4c652bbfd2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Maltol 10V, Positive-QTOFsplash10-004i-0900000000-68373306ed89c51d3c8e2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Maltol 10V, Positive-QTOFsplash10-004i-0900000000-38440dc8d01235ec60302016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Maltol 20V, Positive-QTOFsplash10-004i-2900000000-d055c9796b264b599b6a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Maltol 40V, Positive-QTOFsplash10-014i-9000000000-d0af17e3cc2dd76131f32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Maltol 10V, Negative-QTOFsplash10-004i-0900000000-69feb02bb47c24872d732016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Maltol 20V, Negative-QTOFsplash10-016s-9300000000-76b24f4971833037af7b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Maltol 40V, Negative-QTOFsplash10-002g-9000000000-c6a03d90d227ae6c56532016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Maltol 10V, Negative-QTOFsplash10-004l-6900000000-962e671fbe15160f20042021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Maltol 20V, Negative-QTOFsplash10-0006-9100000000-46cfacfee845f86dc9592021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Maltol 40V, Negative-QTOFsplash10-0006-9000000000-6cab6127640d08dfd89f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Maltol 10V, Positive-QTOFsplash10-004i-3900000000-5b997e243689ece018722021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Maltol 20V, Positive-QTOFsplash10-0arv-9100000000-db550e8ed4a495f56e5c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Maltol 40V, Positive-QTOFsplash10-0006-9000000000-2ce65d95643025ecae242021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>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
MarkerDB IDNot Available
Good Scents IDrw1002341
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.. .