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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 17:38:57 UTC

Update Date

2023-02-21 17:19:41 UTC

HMDB ID

HMDB0030776

Secondary Accession Numbers

HMDB30776

Metabolite Identification

Common Name

Maltol

Description

Maltol, 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
e636	ChEMBL, HMDB
2-Hydroxy-3-methyl-4H-pyran-4-one	HMDB
2-Methyl pyromeconic acid	HMDB
2-Methyl-3-hydroxy-4-pyranone	HMDB
2-Methyl-3-hydroxy-4-pyrone	HMDB
2-Methyl-3-hydroxypyrone	HMDB
2-Methyl-3-oxy-gamma-pyrone	HMDB
3-Hydroxy-2-methyl-1,4-pyrone	HMDB
3-Hydroxy-2-methyl-4-pyranone	HMDB
3-Hydroxy-2-methyl-4-pyrone	HMDB, MeSH
3-Hydroxy-2-methyl-4H-pyran-4-one	HMDB
3-Hydroxy-2-methyl-g-pyrone	HMDB
3-Hydroxy-2-methyl-gamma-pyrone	HMDB
3-Hydroxy-2-methylpyrone	HMDB
3-Hydroxy-2-pyran-4-one	HMDB
5-Hydroxy-6-methyl-4H-pyran-4-one	HMDB
FEMA 2656	HMDB
Laricinic acid	HMDB
Larixic acid	HMDB
Larixinic acid	HMDB
Palatone	HMDB
Talmon	HMDB
Veltol	HMDB
Vetol	HMDB

Chemical Formula

C₆H₆O₃

Average Molecular Weight

126.11

Monoisotopic Molecular Weight

126.031694058

IUPAC Name

3-hydroxy-2-methyl-4H-pyran-4-one

Traditional Name

talmon

CAS Registry Number

118-71-8

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 Key

XPCTZQVDEJYUGT-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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrans

Sub Class

Pyranones and derivatives

Direct Parent

Pyranones and derivatives

Alternative Parents

Substituents

Pyranone
Heteroaromatic compound
Cyclic ketone
Oxacycle
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

pyranone (CHEBI:69438 )
Monocyclic gamma-pyrones (C11918 )

Ontology

Sweet

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0030776)
Cytoplasm (HMDB: HMDB0030776)

Excreta

Biofluid or Excreta

Feces (PMID: 25037050)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030776)

Source

Endogenous

Endogenous (HMDB: HMDB0030776)

Plant

Animal

Animal (HMDB: HMDB0030776)

Exogenous

Food

Food (HMDB: HMDB0030776)

Beverage

Fermented beverage

Beer (FooDB: FOOD00268)

Pulse

Bean

Mung bean (FooDB: FOOD00200)

Pulses (FooDB: FOOD00867)

Soy

Soy bean (FooDB: FOOD00085)

Red raspberry (FooDB: FOOD00162)

Snack

Tortilla chip (FooDB: FOOD00721)

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Coffee and coffee products (FooDB: FOOD00861)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Cocoa and cocoa products (FooDB: FOOD00860)

Nut

Nuts (FooDB: FOOD00869)

Milk and milk product

Milk and milk products (FooDB: FOOD00863)

Process

Not Available

Role

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	161 - 162 °C	Not Available
Boiling Point	284.70 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	10.9 mg/mL at 15 °C	Not Available
LogP	0.09	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	117.742	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001121

Predicted Molecular Properties

Property	Value	Source
Water Solubility	134 g/L	ALOGPS
logP	-0.24	ALOGPS
logP	0.55	ChemAxon
logS	0.03	ALOGPS
pKa (Strongest Acidic)	9.45	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	33.72 m³·mol⁻¹	ChemAxon
Polarizability	11.6 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	123.604	31661259
DarkChem	[M-H]-	121.585	31661259
DeepCCS	[M+H]+	129.967	30932474
DeepCCS	[M-H]-	127.662	30932474
DeepCCS	[M-2H]-	163.781	30932474
DeepCCS	[M+Na]+	138.648	30932474
AllCCS	[M+H]+	124.2	32859911
AllCCS	[M+H-H2O]+	119.2	32859911
AllCCS	[M+NH4]+	128.8	32859911
AllCCS	[M+Na]+	130.1	32859911
AllCCS	[M-H]-	119.9	32859911
AllCCS	[M+Na-2H]-	121.9	32859911
AllCCS	[M+HCOO]-	124.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Maltol	CC1=C(O)C(=O)C=CO1	1858.1	Standard polar	33892256
Maltol	CC1=C(O)C(=O)C=CO1	1057.7	Standard non polar	33892256
Maltol	CC1=C(O)C(=O)C=CO1	1055.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Maltol,1TMS,isomer #1	CC1=C(O[Si](C)(C)C)C(=O)C=CO1	1273.8	Semi standard non polar	33892256
Maltol,1TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)C(=O)C=CO1	1558.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Maltol GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-9500000000-9ab04dd29d36893ecd26	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Maltol GC-MS (1 TMS) - 70eV, Positive	splash10-05ir-7900000000-600ebd59fb3066652709	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Maltol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-004i-9400000000-e2ddaa7bab18abea7217	2015-03-01	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Maltol Linear Ion Trap , negative-QTOF	splash10-0002-9000000000-c04cc7216a3bd4a235e7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Maltol 35V, Positive-QTOF	splash10-004i-4900000000-aa92125c58514d72564e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Maltol 40V, Positive-QTOF	splash10-0006-9000000000-683526173a1cb2e60e9a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Maltol 20V, Positive-QTOF	splash10-004i-4900000000-9cacfb0610f4c652bbfd	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Maltol 10V, Positive-QTOF	splash10-004i-0900000000-68373306ed89c51d3c8e	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Maltol 10V, Positive-QTOF	splash10-004i-0900000000-38440dc8d01235ec6030	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Maltol 20V, Positive-QTOF	splash10-004i-2900000000-d055c9796b264b599b6a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Maltol 40V, Positive-QTOF	splash10-014i-9000000000-d0af17e3cc2dd76131f3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Maltol 10V, Negative-QTOF	splash10-004i-0900000000-69feb02bb47c24872d73	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Maltol 20V, Negative-QTOF	splash10-016s-9300000000-76b24f4971833037af7b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Maltol 40V, Negative-QTOF	splash10-002g-9000000000-c6a03d90d227ae6c5653	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Maltol 10V, Negative-QTOF	splash10-004l-6900000000-962e671fbe15160f2004	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Maltol 20V, Negative-QTOF	splash10-0006-9100000000-46cfacfee845f86dc959	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Maltol 40V, Negative-QTOF	splash10-0006-9000000000-6cab6127640d08dfd89f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Maltol 10V, Positive-QTOF	splash10-004i-3900000000-5b997e243689ece01872	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Maltol 20V, Positive-QTOF	splash10-0arv-9100000000-db550e8ed4a495f56e5c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Maltol 40V, Positive-QTOF	splash10-0006-9000000000-2ce65d95643025ecae24	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Feces

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
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