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ethyl maltol

Chemical Structure

General Material Information

Preferred name ethyl maltol
Trivial Name Ethyl maltol
Short Description 3-hydroxy-2-ethyl-4H-pyran-4-one
Formula C7 H8 O3
CAS Number 4940-11-8
FEMA Number 3487
ECHA Number 225-582-5
FDA UNII L6Q8K29L05
Nikkaji Number J35.389B
Beilstein Number 1618110
MDL MFCD00059795
COE Number 692
xLogP3-AA 0.80 (est)
Bio Activity Summary External link
NMR Predictor External link
JECFA Food Flavoring 1481 ethyl maltol
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 4940-11-8 ; ETHYL MALTOL
Synonyms
  • EM-1 crystal grain
  • EM-400 crystal grain
  • ethyl maltol FCC
  • ethyl maltol synthetic
  • ethyl maltol USP/NF
  • 2-ethyl pyromeconic acid
  • 2-ethyl-3-hydroxy-4-pyrone
  • 2-ethyl-3-hydroxy-4H-pyran-4-one
  • 2-ethyl-3-hydroxy-pyran-4-one
  • 2-ethyl-3-hydroxypyran-4-one
  • ethylmaltol
  • 3-hydroxy-2-ethyl-1,4-pyrone
  • 3-hydroxy-2-ethyl-4-pyrone
  • 3-hydroxy-2-ethyl-4H-pyran-4-one
  • 3-hydroxy-2-ethyl-gamma-pyrone
  • 4H- pyran-4-one, 2-ethyl-3-hydroxy-
  • 2-ethyl-3-hydroxypyran-4-one
  • 4H-Pyran-4-one, 2-ethyl-3-hydroxy-
  • 2-Ethyl-3-hydroxy-4H-pyran-4-one
  • 2-Ethylpyromeconic acid
  • 3-Hydroxy-2-ethyl-1,4-pyrone
  • 3-Hydroxy-2-ethyl-4-pyrone
  • 3-Hydroxy-2-ethyl-γ-pyrone
  • 2-Ethyl-3-hydroxy-4-pyrone
  • Veltol plus
  • NSC 638851
  • 2-Ethyl-3-hydroxy-pyran-4-one

US / EU / FDA / JECFA / FEMA / Scholar / Patents

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Literature & References

2-ethyl-3-hydroxypyran-4-one
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:4940-11-8
Pubchem (cid):21059
Pubchem (sid):134985580
Publications by Info
maltol and related substances
Publications by PubMed
Determination of flavor enhancers in milk powder by one-step sample preparation and two-dimensional liquid chromatography.
Simultaneous spectrophotometric kinetic determination of four flavor enhancers in foods with the aid of chemometrics.
Rapid sample screening method for authenticity controlling vanilla flavors using a CE microchip approach with electrochemical detection.
Evaluation of certain food additives and contaminants.
Sensitization of Escherichia coli to nisin by maltol and ethyl maltol.
Neonatal representation of odour objects: distinct memories of the whole and its parts.
Differential memory persistence of odor mixture and components in newborn rabbits: competition between the whole and its parts.
Determination of flavor enhancers in milk powder by one-step sample preparation and two-dimensional liquid chromatography.
Evaluation and comparison of zinc absorption level from 2-Alkyle 3-Hydroxy pyranon-zinc complexes and zinc sulfate in rat in vivo.
Electrosprayed core-shell polymer-lipid nanoparticles for active component delivery.
Solution equilibria of anticancer ruthenium(II)-(η(6)-p-cymene)-hydroxy(thio)pyr(id)one complexes: impact of sulfur vs. oxygen donor systems on the speciation and bioactivity.
The investigation of the binding behavior between ethyl maltol and human serum albumin by multi-spectroscopic methods and molecular docking.
Experience influences elemental and configural perception of certain binary odour mixtures in newborn rabbits.
Simultaneous spectrophotometric kinetic determination of four flavor enhancers in foods with the aid of chemometrics.
Perceptual blending in odor mixtures depends on the nature of odorants and human olfactory expertise.
Absorption, transport and insulin-mimetic properties of bis(maltolato)oxovanadium (IV) in streptozotocin-induced hyperglycemic rats by integrated mass spectrometric techniques.
Proportion of odorants impacts the configural versus elemental perception of a binary blending mixture in newborn rabbits.
Rapid sample screening method for authenticity controlling vanilla flavors using a CE microchip approach with electrochemical detection.
New lipophilic 3-hydroxy-4-pyridinonate iron(III) complexes: synthesis and EXAFS structural characterisation.
Tris(pyronato)- and tris(pyridonato)-ruthenium(III) complexes and solution NMR studies.
Vanadium complexes with mixed O,S anionic ligands derived from maltol: synthesis, characterization, and biological studies.
Group 13 and lanthanide complexes with mixed O,S anionic ligands derived from maltol.
Preparation and characterization of vanadyl complexes with bidentate maltol-type ligands; in vivo comparisons of anti-diabetic therapeutic potential.
Sensitization of Escherichia coli to nisin by maltol and ethyl maltol.
Platelet labelling with indium-hydroxypyridinone and indium-hydroxypyranone complexes.
Reversed-phase high-performance liquid chromatography of non-transferrin-bound iron and some hydroxypyridone and hydroxypyrone chelators.
Synthesis and iron(III) binding properties of 3-hydroxypyrid-4-ones derived from kojic acid.
Absorption of iron from ferric hydroxypyranone complexes.
Lead transport and binding by human erythrocytes in vitro.
Zinc improves the filterability of sickle erythrocytes at intermediate oxygen partial pressures.
Intracellular free zinc and zinc buffering in human red blood cells.
Facilitated uptake of zinc into human erythrocytes. Relevance to the treatment of sickle-cell anaemia.
Characteristics of iron(III) uptake by isolated fragments of rat small intestine in the presence of the hydroxypyrones, maltol and ethyl maltol.
Effects of the pyrones, maltol and ethyl maltol, on iron absorption from the rat small intestine.
Studies on passiflora incarnata dry extract. I. Isolation of maltol and pharmacological action of maltol and ethyl maltol.
The metabolism of ethyl maltol and maltol in the dog.
Toxicity studies with ethyl maltol.

Other Information

(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
FDA Substances Added to Food (formerly EAFUS):View
CHEMBL:View
KEGG (GenomeNet):C20362
HMDB (The Human Metabolome Database):HMDB31735
FooDB:FDB008403
Export Tariff Code:2932.99.9090
FDA Listing of Food Additive Status:View
ChemSpider:View
Wikipedia:View

Suppliers

ACS International Advanced Biotech
Anhui Haibei Anhui Jinghe
Aromiens International Associate Allied Chemicals
Astral Extracts Atlantic Chemicals
Augustus Oils Beijing Lys Chemicals
Berjé BOC Sciences
Charkit Chemical Citrus and Allied Essences
De Monchy Aromatics Diffusions Aromatiques
ECSA Chemicals Ernesto Ventós
Excellentia International Foodchem International
Frey + Lau Glentham Life Sciences
Global Essence Graham Chemical
Indenta Group Indukern F&F
John Kellys (London) K.L. Koh Enterprise
Lluch Essence M&U International
Moellhausen OQEMA
PCW France Pearlchem Corporation
Pell Wall Perfumes Penta International
Perfumer Supply House PerfumersWorld
Perfumery Laboratory Phoenix Aromas & Essential Oils
Primechem Prinova
Prodasynth Quimdis
R C Treatt & Co Ltd Reincke & Fichtner
Sigma-Aldrich Sinofi Food Ingredients
SRS Aromatics Sunaux International
Synerzine Taytonn ASCC
TCI AMERICA Tengzhou Xiang Yuan Aroma Chemicals
The Good Scents Company The John D. Walsh Company
The Lermond Company The Perfumers Apprentice
Tianjin Danjun International Tianjin Talent Chemical
Ungerer & Company United International
Universal Preserv-A-Chem Inc. Vigon International
Vistachem WEN International
WholeChem Zanos
ACS International GmbH Advanced Biotech. Inc.
Augustus Oils Ltd Beijing Lys Chemicals Co, LTD.
Berje Inc. Charkit Chemical Corporation
Glentham Life Sciences Ltd Global Essence Inc.
Indukern, S.A. F&F Ingredients Division Lluch Essence S.L.
M&U International LLC Moellhausen S.P.A.
Penta International Corporation PerfumersWorld Ltd.
Anhui Primechem Co., Ltd. SRS Aromatics Ltd
Synerzine, Inc. Taytonn ASCC Pte Ltd
The John D. Walsh Company, Inc Tianjin Danjun International Trade Co., LTD.
R C Treatt and Co Ltd Qingdao Free Trade Zone United International Co Ltd
Ernesto Ventós S.A. WholeChem, LLC
Zanos Ltd.

PhysChem Properties

Material listed in food chemical codex Yes
Molecular weight 140.13836669922
Melting Point 89 to 93°C @ 760 mm Hg
Boiling Point 289 to 290°C @ 760 mm Hg
Vapor Pressure 0.00022 mmHg @ 25 °C
Flash Point TCC Value 93.33 °C TCC
logP (o/w) 0.63
Shelf life 24 months (or longer if stored properly.)
Storage notes Store in cool, dry place in tightly sealed containers, protected from heat and light.
Solubility
alcohol, 12% Yes
benzyl alcohol, 10% Yes
phenethyl alcohol 5% Yes
propylene glycol, 5.5% Yes
water, 2.423e+004 mg/L @ 25 °C (est) Yes

Organoleptic Properties

Odor Type: Caramellic
sweet, caramellic, jammy, strawberry, cotton candy, berry, sugar
Odor strength high , recommend smelling in a 5.00 % solution or less
Substantivity 360 hour(s) at 20.00 % in benzyl alcohol
Luebke, William tgsc, (1996) At 5.00 % in benzyl alcohol. sweet caramel jam strawberry cotton candy
Mosciano, Gerard P&F 16, No. 1, 31, (1991) Sweet sugary, caramellic, jammy, strawberry-like
Flavor Type: Caramellic
sweet, sugar burnt sugar, cotton candy, jammy, strawberry
Mosciano, Gerard P&F 16, No. 1, 31, (1991) At 70.00 ppm. Sweet, burnt cotton sugar candy like, with jammy, strawberry notes
General comment Strawberry, caramel

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
Xn - Harmful.
R 22 - Harmful if swallowed.
S 02 - Keep out of the reach of children.
S 22 - Do not breath dust.
S 24/25 - Avoid contact with skin and eyes.
S 37/39 - Wear suitable gloves and eye/face protection.
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
Acute toxicity, Oral (Category 4), H302
GHS Label elements, including precautionary statements
Pictogramexclamation-mark.jpg
Signal word Warning
Hazard statement(s)
H302 - Harmful if swallowed
Precautionary statement(s)
P264 - Wash skin thouroughly after handling.
P270 - Do not eat, drink or smoke when using this product.
P301 + P312 - IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P330 - Rinse mouth.
P501 - Dispose of contents/ container to an approved waste disposal plant.
Human Experience:
10 % solution: no irritation or sensitization.
Oral/Parenteral Toxicity:
oral-rat LD50 1150 mg/kg
Toxicology and Applied Pharmacology. Vol. 15, Pg. 604, 1969.

oral-mouse LD50 780 mg/kg
Toxicology and Applied Pharmacology. Vol. 15, Pg. 604, 1969.

oral-chicken LD50 1270 mg/kg
Toxicology and Applied Pharmacology. Vol. 15, Pg. 604, 1969.

Dermal Toxicity:
skin-rabbit LD50 > 5000 mg/kg
Food and Cosmetics Toxicology. Vol. 13, Pg. 805, 1975.

subcutaneous-mouse LD50 910 mg/kg
Chemical and Pharmaceutical Bulletin. Vol. 22, Pg. 1008, 1974.

Inhalation Toxicity:
Not determined

Safety in use information

Category:
flavor enhancers, flavoring agents
RIFM Fragrance Material Safety Assessment: Search
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice
Recommendation for ethyl maltol usage levels up to:
4.0000 % in the fragrance concentrate.
Maximised Survey-derived Daily Intakes (MSDI-EU): 1580.00 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA): 6692.00 (μg/capita/day)
Structure Class: II
Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS).
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library
publication number: 10
Click here to view publication 10
average usual ppmaverage maximum ppm
baked goods: -152.00000
beverages(nonalcoholic): -12.40000
beverages(alcoholic): -18.60000
breakfast cereal: --
cheese: --
chewing gum: -83.00000
condiments / relishes: -15.00000
confectionery froastings: -139.00000
egg products: --
fats / oils: --
fish products: --
frozen dairy: -144.00000
fruit ices: -144.00000
gelatins / puddings: -119.00000
granulated sugar: --
gravies: -19.60000
hard candy: -27.90000
imitation dairy: --
instant coffee / tea: --
jams / jellies: -15.00000
meat products: -19.60000
milk products: --
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: --
snack foods: --
soft candy: --
soups: -19.60000
sugar substitutes: --
sweet sauces: --

Safety references

European Food Safety Athority(EFSA):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies...

European Food Safety Authority (EFSA) reference(s):

Flavouring Group Evaluation 213: alpha,beta-Unsaturated alicyclic ketones and precursors from chemical subgroup 2.7 of FGE.19
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 83, Revision 1 (FGE.83Rev1): Consideration of ethyl maltol and two 6-keto-1,4-dioxane derivatives substances evaluated by JECFA (65th meeting)
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 213, Revision 2 (FGE.213Rev2): Consideration of genotoxic potential for a,ß-unsaturated alicyclic ketones and precursors from chemical subgroup 2.7 of FGE.19
View page or View pdf

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):4940-11-8
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :21059
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
2-ethyl-3-hydroxypyran-4-one
Chemidplus:0004940118
RTECS:UQ0840000 for cas# 4940-11-8