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

Description References
3-Hydroxy-2-methyl-4H-pyran-4-one
3-Hydroxy-2-methyl-4H-pyran-4-one structure
CAS No.
118-71-8
Chemical Name:
3-Hydroxy-2-methyl-4H-pyran-4-one
Synonyms
Vetol;MALTOL;Talmon;Veltol;MALTENE;Laricin;Palatone;NSC 2829;FEMA 2656;MALTOL FCC
CBNumber:
CB5768714
Molecular Formula:
C6H6O3
Formula Weight:
126.11
MOL File:
118-71-8.mol

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

Melting point:
160-164 °C(lit.)
Boiling point:
205 °C
Density 
1.046 g/mL at 25 °C
refractive index 
n20/D 1.541
FEMA 
2656 | MALTOL
Flash point:
198 °F
storage temp. 
Store below +30°C.
solubility 
methanol: 50 mg/mL, clear
form 
Liquid
color 
Clear colorless
PH
5.3 (0.5g/l, H2O)
explosive limit
25%
Water Solubility 
1.2 g/100 mL (25 ºC)
Merck 
14,5713
JECFA Number
1480
BRN 
112169
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
4H-Pyran-4-one, 3-hydroxy-2-methyl-(118-71-8)
SAFETY
  • Risk and Safety Statements
  • Hazard and Precautionary Statements (GHS)
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
Symbol(GHS):
Signal word: Warning
Hazard statements:
Code Hazard statements Hazard class Category Signal word Pictogram P-Codes
H301 Toxic if swalloed Acute toxicity,oral Category 3 Danger P264, P270, P301+P310, P321, P330,P405, P501
H302 Harmful if swallowed Acute toxicity,oral Category 4 Warning P264, P270, P301+P312, P330, P501
H315 Causes skin irritation Skin corrosion/irritation Category 2 Warning P264, P280, P302+P352, P321,P332+P313, P362
H319 Causes serious eye irritation Serious eye damage/eye irritation Category 2A Warning P264, P280, P305+P351+P338,P337+P313P
H332 Harmful if inhaled Acute toxicity,inhalation Category 4 Warning P261, P271, P304+P340, P312
H335 May cause respiratory irritation Specific target organ toxicity, single exposure;Respiratory tract irritation Category 3 Warning
Precautionary statements:
P261 Avoid breathing dust/fume/gas/mist/vapours/spray.
P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P405 Store locked up.

3-Hydroxy-2-methyl-4H-pyran-4-one price More Price(19)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 18299 Maltol analytical standard 118-71-8 100mg $50.5 2018-11-13 Buy
Sigma-Aldrich 1375003 Maltol United States Pharmacopeia (USP) Reference Standard 118-71-8 4g $341 2018-11-13 Buy
TCI Chemical M0673 3-Hydroxy-2-methyl-4-pyrone >99.0%(HPLC)(T) 118-71-8 25g $40 2018-11-22 Buy
TCI Chemical M0673 3-Hydroxy-2-methyl-4-pyrone >99.0%(HPLC)(T) 118-71-8 100g $105 2018-11-22 Buy
Alfa Aesar A10735 3-Hydroxy-2-methyl-4-pyrone, 99% 118-71-8 100g $95.5 2018-11-13 Buy

3-Hydroxy-2-methyl-4H-pyran-4-one Chemical Properties,Uses,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 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.

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

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.

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

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.

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

Raw materials

Preparation Products


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

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Henan DaKen Chemical CO.,LTD.
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Mainchem Co., Ltd.
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View Lastest Price from 3-Hydroxy-2-methyl-4H-pyran-4-one manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2018-07-23 3-Hydroxy-2-methyl-4H-pyran-4-one
118-71-8
US $1025.00 / KG 1KG 99% 10tons career henan chemical co

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