MALTOL

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 Search

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
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 84 Target ID: map04064 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25646062	Modulator 828

Conditions

Condition	Modality	Targets	Highest Phase	Product
Glaucoma 57 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
Electrochemical determination of maltol in beverages with glassy carbon electrode and its silica sol-gel modified electrode.	2004 May 28	18969427
[Studies on chemical constituents in Flos Sophorae Carbonisatus].	2005 Aug	16245902
[Studies on the chemical constituents in herb of Ludwigia octovalvis].	2005 Dec	16494025
Tris(pyronato)- and tris(pyridonato)-ruthenium(III) complexes and solution NMR studies.	2005 Sep 19	16156610
Increase in the free radical scavenging activity of ginseng by heat-processing.	2006 Apr	16595912
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
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
Induction of cytochrome P450 1a1 by the food flavoring agent, maltol.	2007 Jun	17317091
Subthreshold olfactory stimulation can enhance sweetness.	2007 Mar	17079696
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
Lanthanide containing compounds for therapeutic care in bone resorption disorders.	2007 Nov 21	17992287
Role of maltol in advanced glycation end products and free radicals: in-vitro and in-vivo studies.	2008 Apr	18380916
The influence of citrate, maltolate and fluoride on the gastrointestinal absorption of aluminum at a drinking water-relevant concentration: A 26Al and 14C study.	2008 Apr	18207247
Unexpected C-H activation of Ru(II)-dithiomaltol complexes upon oxidation.	2008 Apr 7	18257546
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
Singlet oxygen scavenging activity and cytotoxicity of essential oils from rutaceae.	2008 Jul	18648659
Interactions of insulin-mimetic zinc(II) complexes with cell constituents: glutathione and ATP.	2008 Jul	18282604
Determination of volatile organic compounds generated from fresh, white and red Panax ginseng (C. A. Meyer) using a direct sample injection technique.	2008 May	18205137
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
Speciation in aqueous vanadate-ligand and peroxovanadate-ligand systems.	2009 Apr	19162328
Biospeciation of various antidiabetic V(IV)O compounds in serum.	2009 Apr 7	19290378
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
Synthesis, antimicrobial evaluation and QSAR study of some 3-hydroxypyridine-4-one and 3-hydroxypyran-4-one derivatives.	2009 May	19056147
Identification of dihydromaltol (2,3-dihydro-5-hydroxy-6-methyl-4H-pyran-4-one) in Ryazhenka Kefir and comparative sensory impact assessment of related cycloenolones.	2009 Nov 11	19817423
Maltol-derived ruthenium-cymene complexes with tumor inhibiting properties: the impact of ligand-metal bond stability on anticancer activity in vitro.	2009 Nov 16	19821465
Iron-binding characterization and polysaccharide production by Klebsiella oxytoca strain isolated from mine acid drainage.	2009 Oct	19508299
Mixed-ligand copper(II) maltolate complexes: synthesis, characterization, DNA binding and cleavage, and cytotoxicity.	2009 Oct 5	19780613
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 `Fri Dec 15 15:08:47 UTC 2023` Edited by `admin` on `Fri Dec 15 15:08:47 UTC 2023`
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