Maltol

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

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)

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

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.

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