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Details

Stereochemistry ACHIRAL
Molecular Formula C6H6O3
Molecular Weight 126.11
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MALTOL

SMILES

CC1=C(O)C(=O)C=CO1

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 126.11
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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.

Originator

Approval Year

1977
76
Targets

Targets

Primary TargetPharmacologyConditionPotency
Modulator
846
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Basic research
Unknown

Approved Use

Unknown
Preventing
Preclinical
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
The kinetics and mechanisms of the reactions of aluminium(III) with gallic acid, gallic acid methyl ester and adrenaline.
2001 Mar
Insulinomimetic bis(maltolato)zinc(II) complex: blood glucose normalizing effect in KK-A(y) mice with type 2 diabetes mellitus.
2001 Mar
Syntheses, structure, and reactivity of chiral titanium compounds: procatalysts for olefin polymerization.
2001 Mar 2
Gas chromatography/mass spectrometric characterisation of pyrolysis/silylation products of glucose and cellulose.
2002
Different complexation properties of some hydroxy keto heterocycles toward beryllium(II) in aqueous solutions: experimental and theoretical studies.
2002 Jul 29
Simultaneous quantitative analysis of maillard reaction precursors and products by high-performance anion exchange chromatography.
2003 Dec 3
Examination of novel zinc-binding groups for use in matrix metalloproteinase inhibitors.
2003 Jun 2
Metal complexes of the trans-influencing ligand thiomaltol.
2003 Nov 17
Aroma compounds in sweet whey powder.
2004 Dec
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
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
Maltol inhibits apoptosis of human neuroblastoma cells induced by hydrogen peroxide.
2006 Mar 31
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
Subthreshold olfactory stimulation can enhance sweetness.
2007 Mar
Vanadium treatment of type 2 diabetes: a view to the future.
2009 Apr
Speciation in aqueous vanadate-ligand and peroxovanadate-ligand systems.
2009 Apr
Biospeciation of various antidiabetic V(IV)O compounds in serum.
2009 Apr 7
Evaluation of the peroxynitrite scavenging activity of heat-processed ginseng.
2009 Feb
Synthesis of 4-pyridone-3-sulfate and an improved synthesis of 3-hydroxy-4-pyridone.
2009 Jan 9
Synthesis, antimicrobial evaluation and QSAR study of some 3-hydroxypyridine-4-one and 3-hydroxypyran-4-one derivatives.
2009 May
A Maillard reaction product enhances eNOS activity in human endothelial cells.
2010 Jul
Patents

Patents

05104865
1
JPH00977615A
1
JPH01211468A
1
JPH02247116A
1
JPH0680907A
1
JPH10146156A
1
JPS5588675A
1
JPS5664764A
1
JPS57115162A
2
JPS5927898A
1
JPS62143668A
1

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
In Vitro Use Guide
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 Mon Mar 31 17:48:02 GMT 2025
Edited
by admin
on Mon Mar 31 17:48:02 GMT 2025
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
NSC-2829
Preferred 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
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
Classification Tree Code System Code
CFR 21 CFR 172.515
Created by admin on Mon Mar 31 17:48:02 GMT 2025 , Edited by admin on Mon Mar 31 17:48:02 GMT 2025
CODEX ALIMENTARIUS (GSFA) INS-636
Created by admin on Mon Mar 31 17:48:02 GMT 2025 , Edited by admin on Mon Mar 31 17:48:02 GMT 2025
JECFA EVALUATION INS-636
Created by admin on Mon Mar 31 17:48:02 GMT 2025 , Edited by admin on Mon Mar 31 17:48:02 GMT 2025
JECFA EVALUATION MALTOL
Created by admin on Mon Mar 31 17:48:02 GMT 2025 , Edited by admin on Mon Mar 31 17:48:02 GMT 2025
Code System Code Type Description
EPA CompTox
DTXSID0025523
Created by admin on Mon Mar 31 17:48:02 GMT 2025 , Edited by admin on Mon Mar 31 17:48:02 GMT 2025
PRIMARY
HSDB
8320
Created by admin on Mon Mar 31 17:48:02 GMT 2025 , Edited by admin on Mon Mar 31 17:48:02 GMT 2025
PRIMARY
EVMPD
SUB34393
Created by admin on Mon Mar 31 17:48:02 GMT 2025 , Edited by admin on Mon Mar 31 17:48:02 GMT 2025
PRIMARY
RS_ITEM_NUM
1375003
Created by admin on Mon Mar 31 17:48:02 GMT 2025 , Edited by admin on Mon Mar 31 17:48:02 GMT 2025
PRIMARY
WIKIPEDIA
MALTOL
Created by admin on Mon Mar 31 17:48:02 GMT 2025 , Edited by admin on Mon Mar 31 17:48:02 GMT 2025
PRIMARY
RXCUI
1362894
Created by admin on Mon Mar 31 17:48:02 GMT 2025 , Edited by admin on Mon Mar 31 17:48:02 GMT 2025
PRIMARY RxNorm
DAILYMED
3A9RD92BS4
Created by admin on Mon Mar 31 17:48:02 GMT 2025 , Edited by admin on Mon Mar 31 17:48:02 GMT 2025
PRIMARY
FDA UNII
3A9RD92BS4
Created by admin on Mon Mar 31 17:48:02 GMT 2025 , Edited by admin on Mon Mar 31 17:48:02 GMT 2025
PRIMARY
ChEMBL
CHEMBL31422
Created by admin on Mon Mar 31 17:48:02 GMT 2025 , Edited by admin on Mon Mar 31 17:48:02 GMT 2025
PRIMARY
PUBCHEM
8369
Created by admin on Mon Mar 31 17:48:02 GMT 2025 , Edited by admin on Mon Mar 31 17:48:02 GMT 2025
PRIMARY
NSC
2829
Created by admin on Mon Mar 31 17:48:02 GMT 2025 , Edited by admin on Mon Mar 31 17:48:02 GMT 2025
PRIMARY
SMS_ID
100000127991
Created by admin on Mon Mar 31 17:48:02 GMT 2025 , Edited by admin on Mon Mar 31 17:48:02 GMT 2025
PRIMARY
MESH
C008316
Created by admin on Mon Mar 31 17:48:02 GMT 2025 , Edited by admin on Mon Mar 31 17:48:02 GMT 2025
PRIMARY
NCI_THESAURUS
C76894
Created by admin on Mon Mar 31 17:48:02 GMT 2025 , Edited by admin on Mon Mar 31 17:48:02 GMT 2025
PRIMARY
ECHA (EC/EINECS)
204-271-8
Created by admin on Mon Mar 31 17:48:02 GMT 2025 , Edited by admin on Mon Mar 31 17:48:02 GMT 2025
PRIMARY
NSC
404458
Created by admin on Mon Mar 31 17:48:02 GMT 2025 , Edited by admin on Mon Mar 31 17:48:02 GMT 2025
PRIMARY
CAS
118-71-8
Created by admin on Mon Mar 31 17:48:02 GMT 2025 , Edited by admin on Mon Mar 31 17:48:02 GMT 2025
PRIMARY
JECFA MONOGRAPH
1471
Created by admin on Mon Mar 31 17:48:02 GMT 2025 , Edited by admin on Mon Mar 31 17:48:02 GMT 2025
PRIMARY
MERCK INDEX
m7047
Created by admin on Mon Mar 31 17:48:02 GMT 2025 , Edited by admin on Mon Mar 31 17:48:02 GMT 2025
PRIMARY Merck Index
Related Record Type Details
Structure of GALLIUM MALTOLATE
SALT/SOLVATE -> PARENT
Structure of FERRIC MALTOL
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of DEFERIPRONE
PARENT -> IMPURITY
Related Record Type Details
Structure of MALTOL
ACTIVE MOIETY
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