3-Hydroxy-2-methyl-4H-pyran-4-one

ChemicalBook > CAS DataBase List > 3-Hydroxy-2-methyl-4H-pyran-4-one

3-Hydroxy-2-methyl-4H-pyran-4-one

Description References

Product Name: 3-Hydroxy-2-methyl-4H-pyran-4-one
CAS No.: 118-71-8
Chemical Name: 3-Hydroxy-2-methyl-4H-pyran-4-one
Synonyms: MALTOL;3-HYDROXY-2-METHYL-4-PYRONE;LARIXINIC ACID;3-HYDROXY-2-METHYL-4-PYRANONE;4H-Pyran-4-one, 3-hydroxy-2-methyl-;Veltol;Maltol (4 g);Vetol;Maltol ,98%;Methyl maltol
CBNumber: CB5768714
Molecular Formula: C6H6O3
Formula Weight: 126.11
MOL File: 118-71-8.mol

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3-Hydroxy-2-methyl-4H-pyran-4-one Property

Melting point:: 160-164 °C(lit.)
Boiling point:: 205 °C
Density: 1.046 g/mL at 25 °C
vapor pressure: 0.15Pa at 24℃
refractive index: n20/D 1.541
FEMA: 2656 | MALTOL
Flash point:: 198 °F
storage temp.: 2-8°C
solubility: methanol: 50 mg/mL, clear
form: Liquid
pka: 8.41±0.10(Predicted)
color: Clear colorless
Odor: at 5.00 % in benzyl alcohol. sweet caramel cotton candy jam fruity baked bread
PH: 5.3 (0.5g/l, H2O)
explosive limit: 25%
Odor Type: caramellic
Water Solubility: 1.2 g/100 mL (25 ºC)
Merck: 14,5713
JECFA Number: 1480
BRN: 112169
InChIKey: XPCTZQVDEJYUGT-UHFFFAOYSA-N
LogP: 2.3 at 25℃
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)

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Safety

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
Hazardous Substances Data: 118-71-8(Hazardous Substances Data)

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: W265624
Product name: Maltol
Purity: natural, FG
Packaging: 1kg
Price: $185
Updated: 2024/03/01

Sigma-Aldrich

Product number: W265608
Product name: Maltol
Purity: ≥99.0%, FCC, FG
Packaging: 250g
Price: $76.5
Updated: 2024/03/01

Sigma-Aldrich

Product number: W265624
Product name: Maltol
Purity: natural, FG
Packaging: 5kg
Price: $760
Updated: 2024/03/01

Sigma-Aldrich

Product number: W265608
Product name: Maltol
Purity: ≥99.0%, FCC, FG
Packaging: 1kg
Price: $110
Updated: 2024/03/01

Sigma-Aldrich

Product number: W265608
Product name: Maltol
Purity: ≥99.0%, FCC, FG
Packaging: 5kg
Price: $371
Updated: 2024/03/01

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3-Hydroxy-2-methyl-4H-pyran-4-one Chemical Properties,Usage,Production

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 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.

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 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.

Occurrence

Reported found in the bark of young larch trees (Pinus larix), pine needles (Abies alba), chicory, wood tars and oils, and roasted malt. Also reported found in wheat and rye bread, milk, butter, smoked pork, beer, cocoa, coffee, roasted barley, filberts, peanuts, soybean, beans, tamarind, licorice, sake, malt, dried bonito, clam and cocoa liquor.

Uses

Maltol may be used as an analytical reference standard for the quantification of the analyte in:

Synthetic and commercial food samples using UV–Vis spectrophotometry with chemometrics methods.
Food and beverage matrices using FIA-direct chemiluminescence procedure.

Uses

Flavoring agent, to impart "freshly baked" odor and flavor to bread and cakes.

Uses

A fragrance molecule used in flavor enhancers and fragrances.

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.

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).

Aroma threshold values

Detection: 29 ppb

Taste threshold values

Taste characteristics at 100 ppm: sweet, caramellic, cotton candy, with jamy fruity and berry notes.

Synthesis Reference(s)

The Journal of Organic Chemistry, 45, p. 1109, 1980 DOI: 10.1021/jo01294a037
Tetrahedron Letters, 17, p. 1363, 1976 DOI: 10.1016/S0040-4039(00)78065-8

Toxicity evaluation

The acute oral LD₅₀ in rats was reported to be 2.33 g/kg (1.57-3.09 g/kg) (Moreno, 1974). The acute oral 7-day LD₅₀s in mice, rats and chicks were reported to be 848, 1440 and 3720 mg/kg, respectively (Gralla, Stebbins, Coleman & Delahunt, 1969). Acute oral LD₅₀ values were found to be 550 mg/kg in mice, 1620 mg/kg in rabbits and 1410 mg/kg in guinea-pigs (Dow Chemical Company, 1967). The acute sc LD₅₀ in mice was found to be 820 mg/kg. Sc injection of 400 mg/kg resulted in decreased spontaneous activity, bradycardia, hypothermia, skeletal-muscle relaxation and diminution of pinna, corneal, and ipsilateral flexor reflexes (Aoyagi, Kimura & Murata, 1974). Because of a lack of sample, 5 g/kg could only be applied to one rabbit in the dermal LD₅₀ study, but this dosage was not lethal in the one rabbit (Moreno, 1974).

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.

Flammability and Explosibility

Not classified

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.

Pharmacology

In mice, spontaneous motor activity was depressed by sc injection oi relatively low doses of maltol (75 mg/kg), hexobarbitone sleeping time was prolonged by sc or oral administration of 300 mg/kg, and convulsions induced by pentylenetetrazole or strychnine were inhibited by sc injection of toxic doses (500 mg/kg), but 1 mM concentrations of maltol had no effect on oxygen uptake by slices of the brain cortex of the rat (Aoyagi et al. 1974).

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.

Safety

Maltol is generally regarded as an essentially nontoxic and nonirritant material. In animal feeding studies, it has been shown to be well tolerated with no adverse toxic, reproductive, or embryogenic effects observed in rats and dogs fed daily intakes of up to 200mg/kg body-weight of maltol, for 2 years.The WHO has set an acceptable daily intake for maltol at up to 1mg/kg body-weight.A case of allergic contact dermatitis, attributed to the use of maltol in a lip ointment, has been reported.
LD₅₀ (chicken, oral): 3.72 g/kg
LD₅₀ (guinea pig, oral): 1.41 g/kg
LD₅₀ (mouse, oral): 0.85 g/kg
LD₅₀ (mouse, SC): 0.82 g/kg
LD₅₀ (rabbit, oral): 1.62 g/kg
LD₅₀ (rat, oral): 1.41 g/kg

Synthesis

By alkaline hydrolysis of streptomycin salts; also from piperdine to pyromeconic acid and subsequent methylation at the 2 position.

Metabolism

Maltol is rapidly and extensively metabolized in the dog and excreted by the conjugation pathway common to phenolic compounds. Rennhard (1971) reported that 57% of an iv dose was recovered in 24 hr, 88% of the total excretion occurring in the first 6 hr and 65-70% of the dose administered being recovered as sulphate and glucuronide conjugates

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.

3-Hydroxy-2-methyl-4H-pyran-4-one Preparation Products And Raw materials

Raw materials

Preparation Products

Tobacco essence

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View Lastest Price from 3-Hydroxy-2-methyl-4H-pyran-4-one manufacturers

Shaanxi TNJONE Pharmaceutical Co., Ltd

Product: Maltol 118-71-8
Price: US $0.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 20tons
Release date: 2024-03-26

Henan Fengda Chemical Co., Ltd

Product: Maltol 118-71-8
Price: US $5.00-0.50/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: g-kg-tons, free sample is available
Release date: 2024-01-13

Hebei Yanxi Chemical Co., Ltd.

Product: 3-Hydroxy-2-methyl-4H-pyran-4-one 118-71-8
Price: US $0.00/kg
Min. Order: 25kg
Purity: 99%
Supply Ability: 20 tons
Release date: 2024-01-19

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3-hydroxy-2-methyl

3-hydroxy-2-methyl-4h-pyran-4-on

3-Hydroxy-2-methyl-4H-pyran-4-one (maltol)

3-hydroxy-2-methyl-4-pyrone (maltol)

3-Hydroxy-2-methyl-gamma-pyrone

3-Hydroxy-2-methylpyrone

3-Hydroxy-2-methyl-pyrone

4H-Pyran-4-one, 3-hydroxy-2-methyl-

Corps praline

corpspraline

Laricin

Laricinicacid

Larixic acid

larixicacid

Palatone

Talmon

Veltol

Vetol

3-Hydroxy-2-methyl-4-oxo-4H-pyran, 3-Hydroxy-2-methyl-4-pyrone

Maltol, 99%,FCC,FG

3-Hydroxy-2-methyl-4-pyranone for synthesis

Maltol FCC4

5-(difluoromethoxy)-N1-((3,4-dimethoxypyridin-2-yl)methyl)benzene-1,2-diamine

Pantoprazole Impurity 39

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

2-Methylpromeconicacid

2-methylpyromeconicacid

MALTENE

MALTOL

Methyl maltol

MALTOL FCC

3-Hydroxy-4-Pyranone

MALTOL 99+% FCC

MALTOL 1 WT. % SOLUTION IN BENZYL ALCO&

MALTOL 99+%

maltol,hydromethylpyrone,3-hydroxyl-2-methyl-4H-pyran-4-one