3-羟基-2-乙基-4-吡喃酮
ethylmaltol
CAS: 4940-11-8
Molecular Formula: C7H8O3
3-羟基-2-乙基-4-吡喃酮 - Names and Identifiers
| Name | ethylmaltol |
| Synonyms | ethylmaltol Ethyl Maltol ETHYLMALTOL FCCIV 2-Ethyl-3-hydroxy-4-pyrone 3-HYDROXY-2-ETHYL-4-PYRONE 2-Ethyl-3-hydroxy-4H-pyran-4-one Ethylmaltol (Subject To Patent Free) 3-Hydroxy-2-ethyl-4-pyrone,ethyl maltol 6-ETHYL-3-HYDROXY-2-METHYL-4H-PYRAN-4-ONE PYRAN-4-ONE,3-HYDROXY-2-METHYL-,2-ETHYLESTER 2-Ethyl-3-hydroxy-4H-pyran-4-one, Ethyl maltol |
| CAS | 4940-11-8 |
| EINECS | 225-582-5 |
| InChI | InChI=1/C7H8O3/c1-2-6-7(9)5(8)3-4-10-6/h3-4,9H,2H2,1H3 |
3-羟基-2-乙基-4-吡喃酮 - Physico-chemical Properties
| Molecular Formula | C7H8O3 |
| Molar Mass | 140.14 |
| Density | 1.1624 (rough estimate) |
| Melting Point | 85-95 °C (lit.) |
| Boling Point | 196.62°C (rough estimate) |
| JECFA Number | 1481 |
| Water Solubility | 9.345g/L at 24℃ |
| Solubility | Soluble in hot water, ethanol and other organic solvents, slightly soluble in water. |
| Vapor Presure | 0.2Pa at 24℃ |
| Appearance | White or yellowish needle crystal or crystalline powder |
| Color | White to Pale Yellow |
| Merck | 14,3824 |
| pKa | 8.38±0.10(Predicted) |
| Storage Condition | 2-8°C |
| Refractive Index | 1.4850 (estimate) |
| MDL | MFCD00059795 |
| Physical and Chemical Properties | Melting point 85-95°C |
| Use | It is used in food, tobacco, cosmetics and other industries, and has the effect of flavoring, fixing and sweetening. |
3-羟基-2-乙基-4-吡喃酮 - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | 22 - Harmful if swallowed |
| Safety Description | 36 - Wear suitable protective clothing. |
| WGK Germany | 3 |
| RTECS | UQ0840000 |
| HS Code | 29329990 |
| Toxicity | LD50 orally in male mice, male rats, female rats, chicks (mg/kg): 780, 1150, 1200, 1270 (Gralla) |
3-羟基-2-乙基-4-吡喃酮 - Nature
Open Data Verified Data
white or yellowish needle-like crystals or crystalline powder with a sweet caramel aroma.
Last Update：2024-01-02 23:10:35
3-羟基-2-乙基-4-吡喃酮 - Preparation Method
Open Data Verified Data
with starch as raw material, it is obtained by fermentation, etherification, oxidation, debenzylation, decarboxylation, condensation and reduction. Also can be furfuryl alcohol chlorination, hydrolysis, and then condensation, reduction system. Or from furfural and ethyl magnesium bromide reaction, oxidation, hydrolysis.
Last Update：2022-01-01 10:07:25
3-羟基-2-乙基-4-吡喃酮 - Use
Open Data Verified Data
is a broad-spectrum, high-efficiency flavoring and sweetening agent, and is also a flavor improver and fixative. With acid suppression, suppression, in addition to stimulation, anti-corrosion and other effects. The flavor is 4~6 times stronger than that of maltol, which has a significant effect on the aroma. Widely used in spices, baked goods and used in the preparation of sweets, cakes, chocolate and tobacco and alcohol flavor. Generally in the candy and chewing gum 5~10 mg/kg; Ice cream, seasoning, jelly 5~15mg/kg; Soft drinks 1- 5~6 mg/kg.
Last Update：2022-01-01 10:07:25
3-羟基-2-乙基-4-吡喃酮 - Reference Information
| FEMA | 3487 | ETHYL MALTOL |
| LogP | 2.9 at 25℃ |
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| introduction | ethyl maltol is a derivative of γ-pyrone. it is a broad-spectrum and efficient fragrance enhancer. it can also be used as a sweetener, aroma synthesis agent, fragrance improver and fixer. it has the effects of inhibiting acid, bitterness, fishness and irritation. These have the same characteristics as maltol, except that maltol can be obtained from nature (barley, soybean, etc.), while ethyl maltol can be synthesized artificially. Appearance white powder, needle or granular crystal. The aroma has a fruit-like scorched sweet aroma, no miscellaneous gas. |
| application | ethyl maltol is divided into pure flavor type, burnt flavor type and special alcohol type according to its characteristics. Mainly used for food fragrance enhancement, daily fragrance, photosensitive materials, anti-corrosion and skin care products. |
| use | ethyl maltol is an ideal fragrance synergist with safety, non-toxicity, wide application, good effect and low dosage. it has significant effect on improving and enhancing the fragrance of food, plays a sweetening role on sweets, and can prolong the storage period of food. Widely used in tobacco, food, beverages, flavors, fruit wine, daily cosmetics and other products. It has a significant effect on improving and enhancing the flavor of food, and has a sweetening effect on sweets, and has antibacterial and antiseptic properties, which can extend the storage period of food. Its coding as a perfume additive: GBA 3005;INS 637;FEMA 3487,(GBA-the People's Republic of China National Standard Artificial Flavor Number; INS-International Coding System; FEMA-American Association of Flavor and Extract Manufacturers). Ethyl maltol is a edible spice allowed to be used in our country. Its fragrance is 4-6 times stronger than maltol, and it has a significant fragrance enhancement effect. It is mainly used to prepare the essence of candy, pastry, chocolate, tobacco and wine. The dosage is 5~50 mg/kg in candy and chewing gum according to normal production requirements. 5~15 mg/kg in ice cream, seasoning and jelly; 1.5~6 mg/kg in soft drinks. used in food, tobacco, cosmetics and other industries, with fragrance enhancement, fragrance enhancement and sweetening effects GB 2760-96 stipulates that edible spices are allowed to be used. Mainly used to prepare strawberries, grapes, pineapples, herbs and other flavors. China's GB2760-86 regulations are allowed to use food and spices. Mainly used to prepare strawberries, grapes, pineapples, herbs and other flavors. Ethyl maltol is a flavor synergist, widely used in food, cigarette drugs, beverages, toothpaste and cosmetics, is a safe and non-toxic, with a flavor, sweetening, fragrance and cover up the role of food additives. And maltol belong to pyranone derivatives, ethyl maltol flavoring effect is about 6 times of maltol. Mice were orally administered LD5050-1200mg/kg. |
| identification test | preparation of standard solution accurately weigh 50mg of standard ethyl maltol, dissolve in 0.1mol/L hydrochloric acid, fix the volume to 250.0ml, and mix. Take 5.0ml of this solution and transfer it into a 100ml volumetric flask, dilute it to scale with 0.1mol/L hydrochloric acid, and mix well. The content is 10 μg/ml. Preparation of sample solution Accurately weigh the sample about 50mg, dissolve it with 0.1mol/L hydrochloric acid, fix the volume to 250.0ml, and mix it. Take 5.0ml of this solution and transfer it into a 100 ml volumetric flask, then use 0.1mol/L hydrochloric acid to fix the volume to 100 ml, and mix it. Operate with an appropriate spectrophotometer, each solution was separately loaded into an lcm colorimetric cell, and the absorbance was measured at a maximum absorption wavelength of about 276nm. 0.1mol/L hydrochloric acid was used for blank determination. The content (mg) of ethyl maltol (C7H8O3) in the sample is obtained by the following formula: concentration of c-ethyl maltol standard solution in 5c(Au/As) formula, μg/ml;A μ-absorbance of sample solution; As-absorbance of standard solution. |
| toxicity | ADI 0~2(FAO/WHO,1994). LD50 150mg/kg (rat, oral). Chronic toxicology test rats were fed at a dose of 200mg/kg/d for two years, and their growth, weight and blood tests were normal. |
| usage limit | FEMA(mg/kg): soft drink 12.4; Cold drink 144; Soft candy 139; Baked food 152; Pudding, jam, jelly products 119; Gum candy 83; Meat products, soup 19.6; Hard candy 27.9; Wine 18.6. It is mostly used in chocolate, sweets and wine in the United States. Moderate is limited (FDA § 172.515.2000). 100mg/L(BATF-27CFR § 240.1051). |
| production methods | mainly include fermentation, sugar alcohol chlorination and sugar aldehyde. 1. The fermentation method is to obtain kojic acid from starch fermentation, and then through etherification, oxidation, debenzylation, decarboxylation, hydroxylation, and reduction to obtain ethyl maltol. 2. Sugar alcohol chlorination method Sugar alcohol is oxidized with chlorine (or oxidized with sodium hypochlorite), heated and decomposed to obtain caramel acid, and then reacted with acetaldehyde to reduce to obtain ethyl maltol. 3. Furfural is used as raw material to react with ethyl Grignard reagent to prepare furfuryl acetone, and then oxidized with chlorine, and then hydrolyzed to prepare ethyl maltol. It is made from starch fermentation into kojic acid, and then synthesized. It is synthesized from furfural or furfuryl alcohol. Furfuryl alcohol is chlorinated in methanol aqueous solution by chlorination of human chlorine to generate 4-chloro-6-hydroxy-2 [H]-pyran-3 [6H]-one, and then heated to hydrolyze to obtain pyroaconic acid; under alkaline conditions, pyroaconic acid is condensed with acetaldehyde to obtain hydroxyethyl pyroaconic acid, which is reduced to ethyl maltol with zinc powder in hydrochloric acid. Furfural method furfural reacts with ethyl magnesium bromide to obtain ethyl furfuryl alcohol, which is then oxidized by chlorine at 0°C in methanol aqueous solution, and then heated to 100°C to hydrolyze to obtain ethyl maltol. This method has a wide source of raw materials, short route, mild process conditions, simple equipment, less three wastes, and has a good development prospect. The semi-synthesis method uses starch as the raw material and is fermented by Plough Mould to obtain kojic acid; kojic acid and benzyl chloride are etherified in sodium hydroxide-methanol solution to form benzyl kojic acid ether; then manganese dioxide is oxidized to benzyl codelic acid ether, and debenzyl in the presence of hydrochloric acid to form codelic acid; then decarboxylated to become pyroconic acid, and finally condensed with acetaldehyde, and reduced to maltol with zinc powder. |
Last Update：2024-04-09 19:05:12
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View History
3-羟基-2-乙基-4-吡喃酮
BIS(TETRAMETHYLENE)FLUOROFORMAMIDINIUM HEXAFLUOROPHOSPHATE
(2R,4R)-1-[(2S)-5-[[亚氨基(硝基氨基)甲基]氨基]-2-[[(3-甲基-8-喹啉基)磺酰基]氨基]-1-氧代戊基]-4-甲基-2-哌啶甲酸
(3-氨基吡啶-2-基)甲醇
2-[(4-乙氧苯基)氨基]-4-硝基-苯甲酸
2-甲基-4-氯-5-氟嘧啶
肝细胞胞液/肝细胞浆 LIVER CYTOSOL
2-氨基-3-环己基丙酸
(Z)-7-[(2S)-2-氨基-3-羟基-3-氧代丙基]硫-2-[[(1S)-2,2-二甲基环丙甲酰]氨基]庚-2-烯酸
SODIUM TRIMETAPHOSPHATE
BIS(TETRAMETHYLENE)FLUOROFORMAMIDINIUM HEXAFLUOROPHOSPHATE
(2R,4R)-1-[(2S)-5-[[亚氨基(硝基氨基)甲基]氨基]-2-[[(3-甲基-8-喹啉基)磺酰基]氨基]-1-氧代戊基]-4-甲基-2-哌啶甲酸
(3-氨基吡啶-2-基)甲醇
2-[(4-乙氧苯基)氨基]-4-硝基-苯甲酸
2-甲基-4-氯-5-氟嘧啶
肝细胞胞液/肝细胞浆 LIVER CYTOSOL
2-氨基-3-环己基丙酸
(Z)-7-[(2S)-2-氨基-3-羟基-3-氧代丙基]硫-2-[[(1S)-2,2-二甲基环丙甲酰]氨基]庚-2-烯酸
SODIUM TRIMETAPHOSPHATE