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
Antioxidative activity of volatile chemicals extracted from beer.	2001 Aug	11513716
The kinetics and mechanisms of the reactions of aluminium(III) with gallic acid, gallic acid methyl ester and adrenaline.	2001 Mar	11330467
Analysis of Furaneol in tomato using dynamic headspace sampling with sodium sulfate.	2001 Sep	11559136
Different complexation properties of some hydroxy keto heterocycles toward beryllium(II) in aqueous solutions: experimental and theoretical studies.	2002 Jul 29	12132927
Effects of the administration routes and chemical forms of aluminum on aluminum accumulation in rat brain.	2002 Jun	12019523
Identification and quantification of aroma-active components that contribute to the distinct malty flavor of buckwheat honey.	2002 Mar 27	11902950
Characterization of the aroma of a meatlike process flavoring from soybean-based enzyme-hydrolyzed vegetable protein.	2002 May 8	11982417
Chronic low-Ca/Mg high-Al diet induces neuronal loss.	2002 Sep	12416556
Monitoring chemical and physical changes during thermal flavor generation.	2002 Sep 11	12207483
Volatile compounds in a spanish red wine aged in barrels made of Spanish, French, and American oak wood.	2003 Dec 17	14664527
The effects of Al(III) speciation on the activity of trypsin.	2003 Sep 15	14507467
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
Maltol glucosides from the tuber of Smilax bockii.	2004 Feb	14759545
New beginnings for matrix metalloproteinase inhibitors: identification of high-affinity zinc-binding groups.	2004 Jul 14	15237990
Electrochemical determination of maltol in beverages with glassy carbon electrode and its silica sol-gel modified electrode.	2004 May 28	18969427
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
[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
Maltol inhibits apoptosis of human neuroblastoma cells induced by hydrogen peroxide.	2006 Mar 31	16584628
Evaluation of certain food additives and contaminants.	2007	18551832
The identification of antioxidants in dark soy sauce.	2007 Apr	17454130
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
Flavonol tetraglycosides and other constituents from leaves of Styphnolobium japonicum (Leguminosae) and related taxa.	2007 May	17462679
Role of maltol in advanced glycation end products and free radicals: in-vitro and in-vivo studies.	2008 Apr	18380916
Two new maltol glycosides and cyanogenic glycosides from Elsholtzia rugulosa Hemsl.	2008 Jan	18404347
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
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
Synthesis of 4-pyridone-3-sulfate and an improved synthesis of 3-hydroxy-4-pyridone.	2009 Jan 9	19134189
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
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 GMT 2023` Edited by `admin` on `Fri Dec 15 15:08:47 GMT 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