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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

ZINC Benzyl chloride Uraldehyde naptho[1’,8a’,8’:bc]-bicyclo[3.1.0]hex-2-ene Soy bean Isoflavone Isoflavone 10-40% Manganese dioxide Cyclohexane Diethyl oxalate Pyromeconic acid Oxygen Chloroform Sodium ethoxide Tetrahydrofuran Kojic acid Furfuryl alcohol Aza Benzyl ether Furfural Methyl bromide Magnesium CREOSOTE

Preparation Products

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

HEBEI SHENGSUAN CHEMICAL INDUSTRY CO.,LTD
Product
3-Hydroxy-2-methyl-4H-pyran-4-one 118-71-8
Price
US $99.00-66.00/kg
Min. Order
0.0010000000474974513kg
Purity
99%
Supply Ability
5000
Release date
2024-08-19
Hebei Zhuanglai Chemical Trading Co.,Ltd
Product
Maltol 118-71-8
Price
US $120.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20ton
Release date
2024-05-15
WUHAN FORTUNA CHEMICAL CO., LTD
Product
3-Hydroxy-2-methyl-4H-pyran-4-one 118-71-8
Price
US $0.00/KG
Min. Order
1KG
Purity
98%min
Supply Ability
30tons/month
Release date
2023-02-07

118-71-8, 3-Hydroxy-2-methyl-4H-pyran-4-oneRelated Search:

Ethanol Xylitol Ammonium bicarbonate Potassium sorbate Maltol acetate 3-Hydroxy-2-methyl-4H-pyran-4-one Maltol propionate Maltol isobutyrate Ethyl maltol 3-(BENZYLOXY)-2-METHYL-4H-PYRAN-4-ONE MALTOL BUTYRATE 3-ACETYL-4-HYDROXY-6-METHYL-2H-PYRAN-2-ONE 4-HYDROXY-6-METHYL-2H-PYRAN-2-ONE 4H-PYRAN-4-ONE aspalatone ALUMINUM 3-HYDROXY-2-METHYL-4-PYRONATE 3-HYDROXY-2,6-BIS(HYDROXYMETHYL)-4-PYRONE 5,6-DIHYDRO-4-HYDROXY-6-METHYL-2H-PYRAN-2-ONE

  • LARIXINIC ACID
  • 3-HYDROXY-2-METHYL-1,4-PYRONE
  • 3-HYDROXY-2-METHYL-4H-PYRAN-4-ONE
  • 3-HYDROXY-2-METHYL-4-PYRANONE
  • 3-HYDROXY-2-METHYL-4-PYRONE
  • 3-HYDROXY-2-METHYL-PYRAN-4-ONE
  • FEMA 2656
  • Maltol (4 g)
  • Maltol ,98%
  • NSC 2829
  • NSC 404458
  • 2-Methyl-3-hydroxy-4H-pyran-4-one
  • 3-HYDROXY-2-METHYL-4-PYRANONE FOR SYNTHE
  • 2-hydroxy-3-Methyl-4H-pyran-4-one
  • 3-Hydroxy-2-Methyl-4-pyrone, 99% 5GR
  • 2-hydroxy-3-methyl-4H-pyran-4-one (maltol)
  • 2-Methyl pyromeconic acid
  • 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