118-71-8 Usage
Uses
1. Analytical Reference Standard:
3-Hydroxy-2-methyl-4H-pyran-4-one is 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 and in food and beverage matrices using FIA-direct chemiluminescence procedure.
2. Flavor Enhancer in Food Production:
3-Hydroxy-2-methyl-4H-pyran-4-one is used as a flavor enhancer to improve mouthfeel and enhance the flavor of candy and baked foods in the food production industry.
3. Flavoring Agent in Beverage Industry:
3-Hydroxy-2-methyl-4H-pyran-4-one is used as a flavoring agent to impart a "freshly baked" odor and flavor to bread and cakes, as well as to enhance the flavor of soft drinks in the beverage industry.
4. Intermediate in Pharmaceutical Industry:
3-Hydroxy-2-methyl-4H-pyran-4-one is used as an intermediate in the pharmaceutical industry for medicine manufacturing.
5. Flavoring Agent in Cosmetic and Personal Care Industries:
3-Hydroxy-2-methyl-4H-pyran-4-one is used as a flavoring agent in cosmetic and personal care industries to enhance flavor.
6. Animal Feed Additive:
According to the FEEDAP Panel, 3-Hydroxy-2-methyl-4H-pyran-4-one is safe to be added to feed for all animal species at the normal use level of 5 mg/kg feed.
Used in Analytical Chemistry:
3-Hydroxy-2-methyl-4H-pyran-4-one is used as an analytical reference standard for the quantification of analytes in various samples, improving the accuracy and reliability of analytical results.
Used in Flavor and Fragrance Industry:
3-Hydroxy-2-methyl-4H-pyran-4-one is used as a fragrance molecule in flavor enhancers and fragrances, providing a pleasant and desirable sensory experience.
Used in Food and Beverage Industry:
3-Hydroxy-2-methyl-4H-pyran-4-one is used as a flavor enhancer and flavoring agent in the food and beverage industry, imparting a "freshly baked" odor and flavor to various products.
Used in Pharmaceutical Industry:
3-Hydroxy-2-methyl-4H-pyran-4-one is used as an intermediate in the pharmaceutical industry, contributing to the development and manufacturing of various medicines.
Used in Cosmetic and Personal Care Industries:
3-Hydroxy-2-methyl-4H-pyran-4-one is used as a flavoring agent in cosmetic and personal care industries, enhancing the sensory appeal of products.
Used in Animal Feed Industry:
3-Hydroxy-2-methyl-4H-pyran-4-one is used as an additive in the animal feed industry, ensuring the safety and effectiveness of feed for various animal species.
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
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.
Synthesis Reference(s)
The Journal of Organic Chemistry, 45, p. 1109, 1980 DOI: 10.1021/jo01294a037Tetrahedron 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).
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
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 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.
Check Digit Verification of cas no
The CAS Registry Mumber 118-71-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,1 and 8 respectively; the second part has 2 digits, 7 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 118-71:
(5*1)+(4*1)+(3*8)+(2*7)+(1*1)=48
48 % 10 = 8
So 118-71-8 is a valid CAS Registry Number.
InChI:InChI=1/C7H8O3/c1-2-6-7(9)5(8)3-4-10-6/h3-4,9H,2H2,1H3
118-71-8Relevant articles and documents
Preparation method of natural maltol
-
, (2019/01/08)
The invention provides a preparation method of natural maltol. The preparation method has the characteristics that methyl metal halide is not prepared and used, 2-furan ethanol is directly prepared through the reduction of natural 2-acetylfuran, and the like. The method is simple in process and easy and convenient to operate, few devices are adopted, the pollution and occupational hazard caused bymethyl halide to air and operators are avoided, and the method is suitable for industrial production.
Formation of Reactive Intermediates, Color, and Antioxidant Activity in the Maillard Reaction of Maltose in Comparison to d -Glucose
Kanzler, Clemens,Schestkowa, Helena,Haase, Paul T.,Kroh, Lothar W.
, p. 8957 - 8965 (2017/10/17)
In this study, the Maillard reaction of maltose and d-glucose in the presence of l-alanine was investigated in aqueous solution at 130 °C and pH 5. The reactivity of both carbohydrates was compared in regards of their degradation, browning, and antioxidant activity. In order to identify relevant differences in the reaction pathways, the concentrations of selected intermediates such as 1,2-dicarbonyl compounds, furans, furanones, and pyranones were determined. It was found, that the degradation of maltose predominantly yields 1,2-dicarbonyls that still carry a glucosyl moiety and thus subsequent reactions to HMF, furfural, and 2-acetylfuran are favored due to the elimination of d-glucose, which is an excellent leaving group in aqueous solution. Consequently, higher amounts of these heterocycles are formed from maltose. 3-deoxyglucosone and 3-deoxygalactosone represent the only relevant C6-1,2-dicarbonyls in maltose incubations and are produced in nearly equimolar amounts during the first 60 min of heating as byproducts of the HMF formation.
Maltol and homolog preparation method by means of molecular oxygen oxidation
-
Paragraph 0028-0032; 0058-0062, (2017/09/26)
The invention provides a maltol and homolog preparation method by means of molecular oxygen oxidation. The method comprises the following steps of charging, a first-stage oxidation reaction, a second-stage oxidation reaction and hydrolysis. According to the first-stage oxidation reaction, alpha-furyl alcohol is used as a raw material, gas with an oxygen content of 15%-85% is used as an oxidizing agent, a heteroatom molecular sieve and basic resin are used as a composite catalyst in a solvent, and an oxidizing ring opening rearrangement reaction is conducted at the temperature of 50-160 DEG C; according to the second-stage oxidation reaction, the temperature drops to 10-40 DEG C, gas with an oxygen content of 90% or above is pumped in, an epoxidation reaction is conducted, and the temperature of the reaction is kept for 0.5-3 h. According to the method, the production yield reaches 50% or above, and the production yield reaches 67% or above in the condition of optimization; the oxidation reaction conducted by using molecular oxygen has the advantages of energy conservation, low cost and environmental protection, and recycling and application of the catalysts are easier to achieve by means of the composite catalyst made from the heteroatom molecular sieve and the basic resin.
A process for the separation of methyl maltol
-
Paragraph 0042; 0043, (2016/10/20)
The invention provides a methyl maltol separating method. Methyl maltol in a methyl maltol crude product and barium hydroxide or barium oxide perform selective reaction to generate barium methyl maltol; after water washing and centrifugal filtration, the barium methyl maltol reacts with sodium sulfate to generate barium sulfate precipitate and sodium methyl maltol; centrifugal filtration is performed again, and a sodium methyl maltol solution and barium sulfate are obtained; the sodium methyl maltol solution is subjected to acidification, crystallization and centrifugal filtration to obtain a methyl maltol solid and a sodium sulfate water solution; and the methyl maltol solid is recrystallized and dried to obtain a finished product, and the sodium sulfate solution is circularly used. According to the method, carbonization and decomposition of methyl maltol due to high-temperature sublimation with a conventional separating method are avoided, and the yield of methyl maltol is increased to be higher than 95% from 85%-88%.
Investigation of self-immolative linkers in the design of hydrogen peroxide activated metalloprotein inhibitors
Jourden, Jody L. Major,Daniel, Kevin B.,Cohen, Seth M.
supporting information; experimental part, p. 7968 - 7970 (2011/08/07)
A series of self-immolative boronic ester protected methyl salicylates and metal-binding groups with various linking strategies have been investigated for their use in the design of matrix metalloproteinase proinhibitors.
STIMULUS-TRIGGERED PRODRUGS
-
Page/Page column 54-56, (2012/01/13)
Set forth herein, inter alia, are compositions and methods for treating diseases with prodrugs. Provided herein are prodrug compositions for inhibiting the function of proteins, compositions and methods for treating diseases associated with oxidative compounds, oxidatively-sensitive prodrugs of inhibitors of metalloproteases. and methods of inhibiting metalloproteases using oxidatively-sensitive prodrugs.
Enzymatic activation of a matrix metalloproteinase inhibitor
Major Jourden, Jody L.,Cohen, Seth M.
experimental part, p. 1241 - 1243 (2010/06/15)
Matrix metalloproteinase inhibitors (MMPi) possessing a glucose protecting group on the zinc-binding group (ZBG) show a dramatic increase in inhibitory activity upon cleavage by β-glucosidase.
Hydrogen peroxide activated matrix metalloproteinase inhibitors: A prodrug approach
Major Jourden, Jody L.,Cohen, Seth M.
supporting information; experimental part, p. 6795 - 6797 (2010/12/19)
(Figure Presented) Doing double duty: A metalloproteinase inhibitor that can be activated by reactive oxygen species (ROS) has been designed to protect the blood-brain barrier (BBB) in ischemic reperfusion injury. By both neu-tralizing damaging ROS and inhibiting degradative metalloproteinases, a single compound can eliminate both threats to the BBB upon activation.
Practical, environment-benign and atom economic KOAc-catalysed deprotection of aryl TIPS ethers under mild fluoride-free conditions
Wang, Bing,Sun, Hui-Xia,Chen, Bo,Sun, Zhi-Hua
supporting information; experimental part, p. 1112 - 1114 (2010/04/23)
A KOAc-catalysed, fluoride-free protocol not only effects chemoselective deprotection of phenolic TIPS ethers without affecting acetal, ketal, carbamate, O-acetyl and aliphatic silyl ethers, but also improves its atom economy by recycling the silanol byproduct.
