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Details

Stereochemistry ACHIRAL
Molecular Formula C6H6O3
Molecular Weight 126.1103
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MALTOL

SMILES

Cc1c(c(=O)cco1)O

InChI

InChIKey=XPCTZQVDEJYUGT-UHFFFAOYSA-N
InChI=1S/C6H6O3/c1-4-6(8)5(7)2-3-9-4/h2-3,8H,1H3

HIDE SMILES / InChI

Molecular Formula C6H6O3
Molecular Weight 126.1103
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Maltol is a naturally occurring organic compound isolated from pine needles, larch bark, the destructive distillates of various organic materials and the alkaline hydrolysis products of streptomycin. Because of caramel-butterscotch odor, and suggestive of fruity-strawberry aroma in dilute solutions, maltol is used as a food additive mainly in confectionary and bakery products. Maltol is considered safe by FDA according to existing data and granted GRAS status. Maltol chelates metal ions such as Fe3+, Al3+, and is reported to increase uptake of aluminum and iron in the body. Maltol was reported to have a neuroprotective effect on retinal ganglion cells under oxidative stress, and hepatoprotective effect on alcohol-induced liver oxidative injury.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Unknown

Approved Use

Unknown
Preventing
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Aroma compounds in sweet whey powder.
2004 Dec
Synthesis, structure, and solution dynamics of UO22+-hydroxy ketone compounds [UO2(ma)2(H2O)] and [UO2(dpp)(Hdpp)2(H2O)]ClO4 [ma = 3-hydroxy-2-methyl-4-pyrone, Hdpp = 3-hydroxy-1,2-dimethyl-4(1H)-pyridone].
2004 Dec 27
Neuroprotective effect of maltol against oxidative stress in brain of mice challenged with kainic acid.
2004 Feb
New beginnings for matrix metalloproteinase inhibitors: identification of high-affinity zinc-binding groups.
2004 Jul 14
Cytotoxic activity of deferiprone, maltol and related hydroxyketones against human tumor cell lines.
2004 Mar-Apr
Comparison of anti-hyperglycemic effect amongst vanadium, molybdenum and other metal maltol complexes.
2004 May
Electrochemical determination of maltol in beverages with glassy carbon electrode and its silica sol-gel modified electrode.
2004 May 28
[Effect of acid hydrolysis of oak wood on its aroma-forming complex].
2004 Nov-Dec
A new insulin-mimetic bis(allixinato)zinc(II) complex: structure-activity relationship of zinc(II) complexes.
2004 Oct
Inhibitory effects of volatile antioxidants found in various beans on malonaldehyde formation in horse blood plasma.
2005 Apr
New insights into the interactions of serum proteins with bis(maltolato)oxovanadium(IV): transport and biotransformation of insulin-enhancing vanadium pharmaceuticals.
2005 Apr 13
Coordination chemistry and insulin-enhancing behavior of vanadium complexes with maltol C6H6O3 structural isomers.
2005 Apr 18
Vanadium complexes with mixed O,S anionic ligands derived from maltol: synthesis, characterization, and biological studies.
2005 Apr 18
Group 13 and lanthanide complexes with mixed O,S anionic ligands derived from maltol.
2005 Apr 18
[Studies on chemical constituents in Flos Sophorae Carbonisatus].
2005 Aug
Syntheses, crystal structure and cytotoxicity of diamine platinum(II) complexes containing maltol.
2005 Aug
[Studies on the chemical constituents in herb of Ludwigia octovalvis].
2005 Dec
Aroma composition of red wines by different extraction methods and Gas Chromatography-SIM/MASS spectrometry analysis.
2005 Jun
Tris(pyronato)- and tris(pyridonato)-ruthenium(III) complexes and solution NMR studies.
2005 Sep 19
Study on the nitric oxide scavenging effects of ginseng and its compounds.
2006 Apr 5
An in vitro study of interactions between insulin-mimetic zinc(II) complexes and selected plasma components.
2006 Dec
Maltol/iron-mediated apoptosis in HL60 cells: participation of reactive oxygen species.
2006 Feb 20
A novel heterocyclic atom exchange reaction with Lawesson's reagent: a one-pot synthesis of dithiomaltol.
2006 Jan 14
Prooxidant action of maltol: role of transition metals in the generation of reactive oxygen species and enhanced formation of 8-hydroxy-2'-deoxyguanosine formation in DNA.
2006 Jun
Metal complexes of maltol and close analogues in medicinal inorganic chemistry.
2006 Jun
New lipophilic 3-hydroxy-4-pyridinonate iron(III) complexes: synthesis and EXAFS structural characterisation.
2006 Mar 14
A new role for old ligands: discerning chelators for zinc metalloproteinases.
2006 Mar 15
Maltol inhibits apoptosis of human neuroblastoma cells induced by hydrogen peroxide.
2006 Mar 31
Evaluation of certain food additives and contaminants.
2007
Comparison of bipyridyl, maltol and kojic acid action as organic vanadium ligands on activity of galactosyltransferase (EC 2.4.1.38), some physiological parameters and ultrastructure of Golgi complexes in rat hepatocytes.
2007
The identification of antioxidants in dark soy sauce.
2007 Apr
Study on the hydroxyl radical scavenging activity changes of ginseng and ginsenoside-Rb2 by heat processing.
2007 Apr
A novel compound, maltolyl p-coumarate, attenuates cognitive deficits and shows neuroprotective effects in vitro and in vivo dementia models.
2007 Aug 15
Anticonvulsant effects of aerial parts of Passiflora incarnata extract in mice: involvement of benzodiazepine and opioid receptors.
2007 Aug 8
Mutagenicity of UV-irradiated maltol in Salmonella typhimurium.
2007 Jan
Flavonol tetraglycosides and other constituents from leaves of Styphnolobium japonicum (Leguminosae) and related taxa.
2007 May
Rapid sample screening method for authenticity controlling vanilla flavors using a CE microchip approach with electrochemical detection.
2007 Nov
Family meetings in palliative care: Multidisciplinary clinical practice guidelines.
2008 Aug 19
Speciation in the aqueous peroxovanadate-maltol and (peroxo)vanadate-uridine systems.
2008 Feb 28
Two new maltol glycosides and cyanogenic glycosides from Elsholtzia rugulosa Hemsl.
2008 Jan
Volatile compounds and sensorial characterization of wines from four Spanish denominations of origin, aged in Spanish Rebollo (Quercus pyrenaica Willd.) oak wood barrels.
2008 Oct 8
Effect of grain type and toasting conditions of barrels on the concentration of the volatile substances released by the wood and on the sensory characteristics of Montepulciano d'Abruzzo.
2008 Sep
Aqueous Ln(III) luminescence agents derived from a tasty precursor.
2008 Sep 15
Vanadium treatment of type 2 diabetes: a view to the future.
2009 Apr
Evaluation of the peroxynitrite scavenging activity of heat-processed ginseng.
2009 Feb
Antidiabetic Bis-Maltolato-OxoVanadium(IV): conversion of inactive trans- to bioactive cis-BMOV for possible binding to target PTP-1B.
2009 Feb 6
Synthesis of 4-pyridone-3-sulfate and an improved synthesis of 3-hydroxy-4-pyridone.
2009 Jan 9
Iron-binding characterization and polysaccharide production by Klebsiella oxytoca strain isolated from mine acid drainage.
2009 Oct
Vanadate complexes in serum: a speciation modeling study.
2010 Jan 7
A Maillard reaction product enhances eNOS activity in human endothelial cells.
2010 Jul
Patents

Sample Use Guides

In Vivo Use Guide
Maltol is used in many products, mainly confectionary and bakery products. The acceptable daily intake is up to 1 mg/kg bodyweight.
Route of Administration: Oral
When the retinal ganglion cells were exposed to 20 μM of H2O2 for 16 h, their viability dropped to 40.3±3.4%. However, the maltol treatment restored the cells in a dose-dependent manner. The viability recovered to 73.9±5.1% with 10 μM of maltol and even reached 175.1±11.3% with 2 mM of maltol, as measured by ATP assay.
Substance Class Chemical
Created
by admin
on Sat Jun 26 00:02:07 UTC 2021
Edited
by admin
on Sat Jun 26 00:02:07 UTC 2021
Record UNII
3A9RD92BS4
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MALTOL
FCC   FHFI   II   INCI   MART.   MI   USP-RS  
INCI  
Official Name English
2-METHYLPYROMECONIC ACID
Common Name English
4H-PYRAN-4-ONE, 3-HYDROXY-2-METHYL-
Systematic Name English
E-636
Common Name English
MALTOL [MART.]
Common Name English
INS-636
Common Name English
PALATONE
Common Name English
INS NO.636
Common Name English
MALTOL [MI]
Common Name English
MALTOL [II]
Common Name English
3-HYDROXY-2-METHYL-4H-PYRAN-4-ONE
Systematic Name English
VELTOL
Common Name English
MALTOL [INCI]
Common Name English
3-HYDROXY-2-METHYL-4-PYRONE
Systematic Name English
MALTOL [FCC]
Common Name English
FEMA NO. 2656
Code English
LARIXIC ACID
Common Name English
MALTOL [FHFI]
Common Name English
NSC-404458
Code English
MALTOL [USP-RS]
Common Name English
NSC-2829
Code English
Classification Tree Code System Code
CFR 21 CFR 172.515
Created by admin on Sat Jun 26 00:02:07 UTC 2021 , Edited by admin on Sat Jun 26 00:02:07 UTC 2021
CODEX ALIMENTARIUS (GSFA) INS-636
Created by admin on Sat Jun 26 00:02:07 UTC 2021 , Edited by admin on Sat Jun 26 00:02:07 UTC 2021
JECFA EVALUATION INS-636
Created by admin on Sat Jun 26 00:02:07 UTC 2021 , Edited by admin on Sat Jun 26 00:02:07 UTC 2021
JECFA EVALUATION MALTOL
Created by admin on Sat Jun 26 00:02:07 UTC 2021 , Edited by admin on Sat Jun 26 00:02:07 UTC 2021
Code System Code Type Description
EPA CompTox
118-71-8
Created by admin on Sat Jun 26 00:02:07 UTC 2021 , Edited by admin on Sat Jun 26 00:02:07 UTC 2021
PRIMARY
HSDB
8320
Created by admin on Sat Jun 26 00:02:07 UTC 2021 , Edited by admin on Sat Jun 26 00:02:07 UTC 2021
PRIMARY
EVMPD
SUB34393
Created by admin on Sat Jun 26 00:02:07 UTC 2021 , Edited by admin on Sat Jun 26 00:02:07 UTC 2021
PRIMARY
WIKIPEDIA
MALTOL
Created by admin on Sat Jun 26 00:02:07 UTC 2021 , Edited by admin on Sat Jun 26 00:02:07 UTC 2021
PRIMARY
RXCUI
1362894
Created by admin on Sat Jun 26 00:02:07 UTC 2021 , Edited by admin on Sat Jun 26 00:02:07 UTC 2021
PRIMARY RxNorm
FDA UNII
3A9RD92BS4
Created by admin on Sat Jun 26 00:02:07 UTC 2021 , Edited by admin on Sat Jun 26 00:02:07 UTC 2021
PRIMARY
ChEMBL
CHEMBL31422
Created by admin on Sat Jun 26 00:02:07 UTC 2021 , Edited by admin on Sat Jun 26 00:02:07 UTC 2021
PRIMARY
PUBCHEM
8369
Created by admin on Sat Jun 26 00:02:07 UTC 2021 , Edited by admin on Sat Jun 26 00:02:07 UTC 2021
PRIMARY
MESH
C008316
Created by admin on Sat Jun 26 00:02:07 UTC 2021 , Edited by admin on Sat Jun 26 00:02:07 UTC 2021
PRIMARY
NCI_THESAURUS
C76894
Created by admin on Sat Jun 26 00:02:07 UTC 2021 , Edited by admin on Sat Jun 26 00:02:07 UTC 2021
PRIMARY
JECFA MONOGRAPH
INS-636
Created by admin on Sat Jun 26 00:02:07 UTC 2021 , Edited by admin on Sat Jun 26 00:02:07 UTC 2021
PRIMARY
ECHA (EC/EINECS)
204-271-8
Created by admin on Sat Jun 26 00:02:07 UTC 2021 , Edited by admin on Sat Jun 26 00:02:07 UTC 2021
PRIMARY
CAS
118-71-8
Created by admin on Sat Jun 26 00:02:07 UTC 2021 , Edited by admin on Sat Jun 26 00:02:07 UTC 2021
PRIMARY
USP_CATALOG
1375003
Created by admin on Sat Jun 26 00:02:07 UTC 2021 , Edited by admin on Sat Jun 26 00:02:07 UTC 2021
PRIMARY USP-RS
MERCK INDEX
M7047
Created by admin on Sat Jun 26 00:02:07 UTC 2021 , Edited by admin on Sat Jun 26 00:02:07 UTC 2021
PRIMARY Merck Index
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
PARENT -> IMPURITY
Related Record Type Details
ACTIVE MOIETY