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Maltol Basic information

Description References

Product Name:	Maltol
Synonyms:	Pantoprazole Sodium Impurity X;2-Methyl-3-hydroxy-.gamma.-pyranone;2-Methyl-3-hydroxy-4-pyrone;2-Methyl-3-hydroxy-gamma.-pyranone;2-Methyl-3-hydroxypyrone;2-Methyl-3-oxy-gamma-pyrone;Pantoprazole Impurity 39;2-Methylpromeconicacid
CAS:	118-71-8
MF:	C6H6O3
MW:	126.11
EINECS:	204-271-8
Product Categories:	Food and Feed Additive;Food & Feed ADDITIVES;Aromatics;Miscellaneous Reagents;Heterocycles;Food & Flavor Additives;C3 to C6;Cichorium intybus (Chicory);Building Blocks;Carbonyl Compounds;Chemical Synthesis;Ketones;Nutrition Research;Organic Building Blocks;Phytochemicals by Plant (Food/Spice/Herb);Flavor
Mol File:	118-71-8.mol

Maltol Chemical Properties

Melting point	160-164 °C(lit.)
Boiling point	205 °C
density	1.046 g/mL at 25 °C
FEMA	2656 \| MALTOL
refractive index	n20/D 1.541
Fp	198 °F
storage temp.	Store below +30°C.
solubility	methanol: 50 mg/mL, clear
form	Liquid
pka	8.41±0.10(Predicted)
color	Clear colorless
PH	5.3 (0.5g/l, H2O)
explosive limit	25%
Water Solubility	1.2 g/100 mL (25 ºC)
JECFA Number	1480
Merck	14,5713
BRN	112169
InChIKey	XPCTZQVDEJYUGT-UHFFFAOYSA-N
CAS DataBase Reference	118-71-8(CAS DataBase Reference)
NIST Chemistry Reference	3-Hydroxy-2-methyl-4h-pyran-4-one(118-71-8)
EPA Substance Registry System	Maltol (118-71-8)

Maltol Safety Information

Hazard Codes	Xn,Xi
Risk Statements	22-38-36/37/38-41-20/22
Safety Statements	37-37/39-26-36-36/37/39-36/37
RIDADR	UN 3334
WGK Germany	3
RTECS	UQ1050000
Autoignition Temperature	1364 °F
Hazard Note	Irritant
TSCA	Yes
HS Code	29329995

Maltol Usage And Synthesis

Description	3-hydroxy-2-methyl-4h-pyran-4-one (also named as Maltol, Larixinic acid, Palatone and Veltol) is a natural compound. Maltol is found in chicory, roasted malt, breads, milk, heated butter, uncured smoked pork, cocoa, coffee, roasted barley, roasted peanuts, roasted filbert, soybean, in the bark of larch tree, in pine needles, and in roasted malt (from which it gets its name) etc. It has the odor of cotton candy and caramel. Maltol is widely used as flavor enhancer to improve mouthfeel and to enhance flavor of candy and baked foods in food production and of soft drinks in beverage industry. It is used as intermediate in pharmaceutical for medicine manufacturing. It is used as flavoring agent in cosmetic and personal care industries to enhance flavor. According to FEEDAP Panel, maltol is safe to be added to feed for all animal species at the normal use level of 5 mg/kg feed.
References	[1] https://en.wikipedia.org/wiki/Maltol [2] http://onlinelibrary.wiley.com/doi/10.2903/j.efsa.2016.4619/full [3] http://www.foodchemadditives.com/applications-uses/1694
Description	Maltol has a warm, sweet, fruity odor and a jam-like odor in solution. It may be prepared by alkaline hydrolysis of streptomycin salts; also from piperidine to pyromeconic acid and subsequent methylation at the 2 position.
Chemical Properties	Maltol has a caramel–butterscotch odor and in solution it has a jam-like odor. This compound is also reported to have a suggestive of fruity, strawberry aroma in dilute solution.
Chemical Properties	White, crystalline powder; characteristic caramel-butterscotch odor and suggestive of a fruity-strawberry aroma in dilute solution. Melting range 160–164C. Slightly soluble in water; more soluble in alcohol and propylene glycol.
Chemical Properties	White crystalline solid with a characteristic, caramel-like odor and taste. In dilute solution it possesses a sweet, strawberry-like or pineapple-like flavor and odor.
Chemical Properties	Maltol occurs in pine needles and the bark of young larch trees. It is produced when cellulose or starch is heated and is a constituent of wood tar oils. It forms crystals (mp 162–164°C) with a caramel-like odor, reminiscent of freshly baked cakes.
Uses	A fragrance molecule used in flavor enhancers and fragrances.
Uses	Flavoring agent, to impart "freshly baked" odor and flavor to bread and cakes.
Definition	ChEBI: A natural product found in Cordyceps sinensis.
Preparation	Maltol may be produced synthetically starting from kojic acid . Alternatively, it can be isolated from beechwood tar or from extracts of needles from the genus Abies. Commercially available extracts fromAbies balsamea needles, which are also used as flavor and fragrance materials, usually contain 3–8% maltol. It is used in aroma compositions with a caramel note and as a taste intensifier in, for example, fruit flavors (particularly in strawberry flavor compositions).
Production Methods	Maltol is mainly isolated from naturally occurring sources such as beechwood and other wood tars; pine needles; chicory; and the bark of young larch trees. It may also be synthesized by the alkaline hydrolysis of streptomycin salts or by a number of other synthetic methods.
Aroma threshold values	Detection: 29 ppb
Taste threshold values	Taste characteristics at 100 ppm: sweet, caramellic, cotton candy, with jamy fruity and berry notes.
General Description	White crystalline powder with a fragrant caramel-butterscotch odor. pH (5% aqueous solution) 5.3.
Air & Water Reactions	May be sensitive to prolonged exposure to light and air. Somewhat soluble in water at room temperature. Freely soluble in hot water [Merck]. Slightly soluble in cold water.
Reactivity Profile	3-Hydroxy-2-methyl-4H-pyran-4-one is weakly acidic. Reacts with bases. May react with reducing agents. Volatile with steam.
Fire Hazard	Flash point data on 3-Hydroxy-2-methyl-4H-pyran-4-one are not available; however, 3-Hydroxy-2-methyl-4H-pyran-4-one is probably combustible.
Pharmaceutical Applications	Maltol is used in pharmaceutical formulations and food products as a flavoring agent or flavor enhancer. In foods, it is used at concentrations up to 30 ppm, particularly with fruit flavorings, although it is also used to impart a freshly baked odor and flavor to bread and cakes. When used at concentrations of 5–75 ppm, maltol potentiates the sweetness of a food product, permitting a reduction in sugar content of up to 15% while maintaining the same level of sweetness. Maltol is also used at low levels in perfumery.
Safety Profile	Moderately toxic by ingestion, intraperitoneal, and subcutaneous routes. A skin irritant. Human mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.
Chemical Synthesis	By alkaline hydrolysis of streptomycin salts; also from piperdine to pyromeconic acid and subsequent methylation at the 2 position.
storage	Maltol solutions may be stored in glass or plastic containers. The bulk material should be stored in a well-closed container, protected from light, in a cool, dry place.
Purification Methods	It crystallises from CHCl3, toluene, aqueous 50% EtOH or H2O, and is volatile in steam. It can be readily sublimed in a vacuum. It forms a Cu2+ complex. [Beilstein 17 III/IV 5916, 18/1 V 114.]
Incompatibilities	Concentrated solutions in metal containers, including some grades of stainless steel, may discolor on storage.
Regulatory Status	GRAS listed. Included in the FDA Inactive Ingredients Database (oral solutions and syrups). Included in the Canadian List of Acceptable Non-medicinal Ingredients.

Maltol Preparation Products And Raw materials

Raw materials	Tetrahydrofuran-->Chloroform-->Magnesium-->Diethyl oxalate-->ZINC-->Benzyl chloride-->Sodium ethoxide-->Manganese dioxide-->Oxygen-->Cyclohexane-->Furfural-->Methyl bromide-->Furfuryl alcohol-->Soy bean Isoflavone Isoflavone 10-40%-->CREOSOTE-->Benzyl ether-->Kojic acid-->Pyromeconic acid
Preparation Products	Tobacco essence