MALTOL

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 Search

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

Description
Sources: http://pubs.acs.org/doi/10.1021/ja01203a504 | http://www.inchem.org/documents/jecfa/jecmono/v44aje25.htm | http://www.foodchemadditives.com/side_effects_info/892 | https://www.ncbi.nlm.nih.gov/pubmed/12019523 | https://www.ncbi.nlm.nih.gov/pubmed/25352751

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

Targets

Primary Target	Pharmacology	Condition	Potency
NF-kappa B signaling pathway 77 Target ID: map04064 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25646062	Modulator 780

Conditions

Condition	Modality	Targets	Highest Phase	Product
Glaucoma 54 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25352751	Preventing		Basic research	Unknown Approved Use Unknown
Alcohol-induced liver injury 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25608939	Preventing		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Aroma compounds in sweet whey powder.	2004 Dec	15545366
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	15606180
Neuroprotective effect of maltol against oxidative stress in brain of mice challenged with kainic acid.	2004 Feb	15085556
New beginnings for matrix metalloproteinase inhibitors: identification of high-affinity zinc-binding groups.	2004 Jul 14	15237990
Cytotoxic activity of deferiprone, maltol and related hydroxyketones against human tumor cell lines.	2004 Mar-Apr	15161023
Comparison of anti-hyperglycemic effect amongst vanadium, molybdenum and other metal maltol complexes.	2004 May	15134913
Electrochemical determination of maltol in beverages with glassy carbon electrode and its silica sol-gel modified electrode.	2004 May 28	18969427
[Effect of acid hydrolysis of oak wood on its aroma-forming complex].	2004 Nov-Dec	15609864
A new insulin-mimetic bis(allixinato)zinc(II) complex: structure-activity relationship of zinc(II) complexes.	2004 Oct	15378407
Inhibitory effects of volatile antioxidants found in various beans on malonaldehyde formation in horse blood plasma.	2005 Apr	15721197
New insights into the interactions of serum proteins with bis(maltolato)oxovanadium(IV): transport and biotransformation of insulin-enhancing vanadium pharmaceuticals.	2005 Apr 13	15810845
Coordination chemistry and insulin-enhancing behavior of vanadium complexes with maltol C6H6O3 structural isomers.	2005 Apr 18	15819554
Vanadium complexes with mixed O,S anionic ligands derived from maltol: synthesis, characterization, and biological studies.	2005 Apr 18	15819553
Group 13 and lanthanide complexes with mixed O,S anionic ligands derived from maltol.	2005 Apr 18	15819552
[Studies on chemical constituents in Flos Sophorae Carbonisatus].	2005 Aug	16245902
Syntheses, crystal structure and cytotoxicity of diamine platinum(II) complexes containing maltol.	2005 Aug	16038978
[Studies on the chemical constituents in herb of Ludwigia octovalvis].	2005 Dec	16494025
Aroma composition of red wines by different extraction methods and Gas Chromatography-SIM/MASS spectrometry analysis.	2005 Jun	16136833
Tris(pyronato)- and tris(pyridonato)-ruthenium(III) complexes and solution NMR studies.	2005 Sep 19	16156610
Study on the nitric oxide scavenging effects of ginseng and its compounds.	2006 Apr 5	16569043
An in vitro study of interactions between insulin-mimetic zinc(II) complexes and selected plasma components.	2006 Dec	17034863
Maltol/iron-mediated apoptosis in HL60 cells: participation of reactive oxygen species.	2006 Feb 20	16143472
A novel heterocyclic atom exchange reaction with Lawesson's reagent: a one-pot synthesis of dithiomaltol.	2006 Jan 14	16372107
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	16799863
Metal complexes of maltol and close analogues in medicinal inorganic chemistry.	2006 Jun	16729148
New lipophilic 3-hydroxy-4-pyridinonate iron(III) complexes: synthesis and EXAFS structural characterisation.	2006 Mar 14	16505910
A new role for old ligands: discerning chelators for zinc metalloproteinases.	2006 Mar 15	16522091
Maltol inhibits apoptosis of human neuroblastoma cells induced by hydrogen peroxide.	2006 Mar 31	16584628
Evaluation of certain food additives and contaminants.	2007	18551832
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	17951174
The identification of antioxidants in dark soy sauce.	2007 Apr	17454130
Study on the hydroxyl radical scavenging activity changes of ginseng and ginsenoside-Rb2 by heat processing.	2007 Apr	17409510
A novel compound, maltolyl p-coumarate, attenuates cognitive deficits and shows neuroprotective effects in vitro and in vivo dementia models.	2007 Aug 15	17600377
Anticonvulsant effects of aerial parts of Passiflora incarnata extract in mice: involvement of benzodiazepine and opioid receptors.	2007 Aug 8	17686156
Mutagenicity of UV-irradiated maltol in Salmonella typhimurium.	2007 Jan	17169979
Flavonol tetraglycosides and other constituents from leaves of Styphnolobium japonicum (Leguminosae) and related taxa.	2007 May	17462679
Rapid sample screening method for authenticity controlling vanilla flavors using a CE microchip approach with electrochemical detection.	2007 Nov	17941116
Family meetings in palliative care: Multidisciplinary clinical practice guidelines.	2008 Aug 19	18710576
Speciation in the aqueous peroxovanadate-maltol and (peroxo)vanadate-uridine systems.	2008 Feb 28	18274691
Two new maltol glycosides and cyanogenic glycosides from Elsholtzia rugulosa Hemsl.	2008 Jan	18404347
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	18778067
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	18803731
Aqueous Ln(III) luminescence agents derived from a tasty precursor.	2008 Sep 15	18707093
Vanadium treatment of type 2 diabetes: a view to the future.	2009 Apr	19162329
Evaluation of the peroxynitrite scavenging activity of heat-processed ginseng.	2009 Feb	19298205
Antidiabetic Bis-Maltolato-OxoVanadium(IV): conversion of inactive trans- to bioactive cis-BMOV for possible binding to target PTP-1B.	2009 Feb 6	19920909
Synthesis of 4-pyridone-3-sulfate and an improved synthesis of 3-hydroxy-4-pyridone.	2009 Jan 9	19134189
Iron-binding characterization and polysaccharide production by Klebsiella oxytoca strain isolated from mine acid drainage.	2009 Oct	19508299
Vanadate complexes in serum: a speciation modeling study.	2010 Jan 7	20023952
A Maillard reaction product enhances eNOS activity in human endothelial cells.	2010 Jul	20112298

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

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 `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

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Name

Type

Language

MALTOL

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