ChemFOnt: Showing chemical card for Maltol (CFc000011982)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:59:54 UTC

Chemfont ID

CFc000011982

Molecule Identification

Common Name

Maltol

Definition

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 SDF PDB SMILES InChI

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 )

Functional Ontology

Sweet

Feces (PMID: 25037050)

Cellular substructure

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

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)

Exogenous (HMDB: HMDB0030776)

Process

Not Available

Role

Physical Properties

Predicted 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