| Identification | More | [Name]
3-Hydroxy-2-methyl-4H-pyran-4-one | [CAS]
118-71-8 | [Synonyms]
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
LARIXINIC ACID
MALTENE
MALTOL
2-hydroxy-3-methyl-4H-pyran-4-one (maltol)
2-Methyl pyromeconic acid
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
3-hydroxy-2-methyl
3-hydroxy-2-methyl-4h-pyran-4-on | [EINECS(EC#)]
204-271-8 | [Molecular Formula]
C6H6O3 | [MDL Number]
MFCD00006578 | [Molecular Weight]
126.11 | [MOL File]
118-71-8.mol |
| Chemical Properties | Back Directory | [Appearance]
white crystalline powder | [Melting point ]
160-164 °C(lit.)
| [Boiling point ]
205 °C
| [density ]
1.046 g/mL at 25 °C
| [vapor pressure ]
0.15Pa at 24℃ | [FEMA ]
2656 | [refractive index ]
n20/D 1.541
| [Fp ]
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) | [JECFA Number]
1480 | [Merck ]
14,5713 | [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]
118-71-8(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R22:Harmful if swallowed.
R38:Irritating to the skin.
R36/37/38:Irritating to eyes, respiratory system and skin .
R41:Risk of serious damage to eyes. | [Safety Statements ]
S37:Wear suitable gloves .
S37/39:Wear suitable gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [RIDADR ]
UN 3334 | [WGK Germany ]
3
| [RTECS ]
UQ1050000
| [Autoignition Temperature]
1364 °F | [Hazard Note ]
Irritant | [TSCA ]
Yes | [HS Code ]
29329995 | [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. | [Hazardous Substances Data]
118-71-8(Hazardous Substances Data) |
| Hazard Information | Back Directory | [General Description]
White crystalline powder with a fragrant caramel-butterscotch odor. pH (5% aqueous solution) 5.3. | [Reactivity Profile]
MALTOL(118-71-8) is weakly acidic. Reacts with bases. May react with reducing agents. Volatile with steam. | [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. | [Fire Hazard]
Flash point data on this compound are not available; however, MALTOL is probably combustible. | [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]
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 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]
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. | [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. | [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). | [Flammability and Explosibility]
Notclassified | [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]
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. |
| Questions And Answer | Back Directory | [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 |
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