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W265608

Sigma-Aldrich

Maltol

≥99.0%, FCC, FG

Synonym(s):

3-Hydroxy-2-methyl-4-pyrone, 3-Hydroxy-2-methyl-4H-pyran-4-one, Larixinic acid, Maltol

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About This Item

Empirical Formula (Hill Notation):
C6H6O3
CAS Number:
118-71-8
Molecular Weight:
126.11
FEMA Number:
2656
Beilstein:
112169
EC Number:
204-271-8
Council of Europe no.:
148
MDL number:
MFCD00006578
UNSPSC Code:
12164502
PubChem Substance ID:
24901222
Flavis number:
7.014
NACRES:
NA.21

biological source

synthetic

Quality Level

400

grade

FG
Fragrance grade
Halal
Kosher

Agency

follows IFRA guidelines

reg. compliance

EU Regulation 1223/2009
EU Regulation 1334/2008 & 178/2002
FCC
FDA 21 CFR 117
FDA 21 CFR 172.515

Assay

≥99.0%

autoignition temp.

1364 °F

expl. lim.

25 %

mp

160-164 °C (lit.)

application(s)

flavors and fragrances

Documentation

see Safety & Documentation for available documents

food allergen

no known allergens

fragrance allergen

no known allergens

Organoleptic

caramel; jam; fruity; sweet

SMILES string

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

InChI

1S/C6H6O3/c1-4-6(8)5(7)2-3-9-4/h2-3,8H,1H3

InChI key

XPCTZQVDEJYUGT-UHFFFAOYSA-N

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Application


  • Maltol prevents the progression of osteoarthritis by targeting PI3K/Akt/NF-κB pathway: In vitro and in vivo studies.: This article details the mechanisms through which maltol mitigates osteoarthritis, focusing on its effects on key signaling pathways which could be beneficial for therapeutic applications (Lu et al., 2021).

  • The Liver Protection Effects of Maltol, a Flavoring Agent, on Carbon Tetrachloride-Induced Acute Liver Injury in Mice via Inhibiting Apoptosis and Inflammatory Response.: This study explores maltol′s hepatoprotective properties, demonstrating its potential to inhibit apoptosis and inflammation in models of acute liver injury (Liu et al., 2018).

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SHBP1703
SHBN6956
STBK2946
SHBN2766
STBK0993

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Xiao-Jie Mi et al.
Journal of agricultural and food chemistry, 67(5), 1392-1401 (2019-01-16)
Our previous study has confirmed that maltol can attenuate alcohol-induced acute hepatic damage and prevent oxidative stress in mice. Therefore, maltol might have the capacity to improve thioacetamide (TAA)-induced liver fibrosis. The purpose of this work was to explore the
Anwar Anwar-Mohamed et al.
Toxicology in vitro : an international journal published in association with BIBRA, 21(4), 685-690 (2007-02-24)
Maltol is used extensively as a flavor-enhancing agent, food preservative, antioxidant, and also in cosmetic and pharmaceutical formulations. However, a number of studies have shown that maltol may induce carcinogenicity and toxicity but the mechanisms involved remain unknown. Therefore, we
Tamás Jakusch et al.
Dalton transactions (Cambridge, England : 2003), (13)(13), 2428-2437 (2009-03-18)
The interactions of various insulin mimetic oxovanadium(IV) compounds with serum proteins were studied in model systems and in ex vivo samples. For the modeling study, an earlier in situ method was extended and applied to the formation of ternary complexes
Sílvia Chaves et al.
Journal of inorganic biochemistry, 114, 38-46 (2012-06-13)
The O,S-donor analogues of maltol and deferiprone (DMHP), respectively, thiomaltol and DMHTP, have been investigated in solution for their iron-complexation ability, as well as their electrochemical behaviors, in the presence and absence of iron, aimed at the rationalization of their
Stefano Amatori et al.
The Journal of organic chemistry, 77(5), 2207-2218 (2012-02-03)
The N,N'-bis[(3-hydroxy-4-pyron-2-yl)methyl]-N,N'-dimethylethylendiamine (malten) and 4,10-bis[(3-hydroxy-4-pyron-2-yl)methyl]-1,7-dimethyl-1,4,7,10-tetraazacyclododecane (maltonis) were synthesized and characterized. The acid-base behavior, structural characterizations, and biochemical studies in aqueous solution were reported. Each compound contains two 3-hydroxy-2-methyl-4-pyrone units (maltol) symmetrically spaced by a polyamine fragment, the 1,4-dimethylethylendiamine (malten), or
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