Ethyl protal
3-Ethoxy-4-hydroxybenzaldehyde
CAS: 121-32-4
Molecular Formula: C9H10O3
Ethyl protal - Names and Identifiers
| Name | 3-Ethoxy-4-hydroxybenzaldehyde |
| Synonyms | Ethavan Bourbonal 3-ethoxy- Ethyl protal ethvlvanillin Ethyl vanillin 3-Ethoxy-4-hydroxybenzaldehyd 3-ethoxy-4-hydroxy-benzaldehyd 3-Ethoxy-4-hydroxybenzaldehyde 4-Hydroxy-3-ethoxybenzaldehyde 3-Ethoxy-4-hydroxy-benzaldehyde protocatechualdehyde ethyl ether Benzaldehyde,3-ethoxy-4-hydroxy- Benzaldehyde, 3-ethoxy-4-hydroxy- Ethyl protocatechualdehyde 3-ethyl ether |
| CAS | 121-32-4 |
| EINECS | 204-464-7 |
| InChI | InChI=1/C9H10O3/c1-2-12-9-5-7(6-10)3-4-8(9)11/h3-6,11H,2H2,1H3 |
Ethyl protal - Physico-chemical Properties
| Molecular Formula | C9H10O3 |
| Molar Mass | 166.17 |
| Density | 1.1097 (rough estimate) |
| Melting Point | 74-77 °C (lit.) |
| Boling Point | 285°C |
| Flash Point | 127°C |
| JECFA Number | 893 |
| Water Solubility | slightly soluble |
| Solubility | Soluble in alcohol, ether, chloroform, and also soluble in sodium hydroxide solution |
| Vapor Presure | <0.01 mm Hg ( 25 °C) |
| Appearance | White to white-like fine crystals |
| Color | White to off-white |
| Merck | 14,3859 |
| BRN | 1073761 |
| pKa | 7.91±0.18(Predicted) |
| Storage Condition | Store below +30°C. |
| Stability | Hygroscopic |
| Sensitive | Light Sensitive |
| Refractive Index | 1.4500 (estimate) |
| MDL | MFCD00006944 |
| Physical and Chemical Properties | Melting point 76-79°C boiling point 285°C water-soluble easily soluble |
| Use | Widely used in food, chocolate, ice cream, beverage and daily cosmetics to play the role of flavoring and fixing flavor |
Ethyl protal - Risk and Safety
| Risk Codes | R22 - Harmful if swallowed R36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. |
| WGK Germany | 1 |
| RTECS | CU6125000 |
| TSCA | Yes |
| HS Code | 29124200 |
| Hazard Note | Harmful/Irritant/Light Sensitive |
| Toxicity | LD50 orally in rats: >2000 mg/kg, P. M. Jenner et al., Food Cosmet. Toxicol. 2, 327 (1964) |
Ethyl protal - Upstream Downstream Industry
| Raw Materials | xylidine mixture of isomers |
Ethyl protal - Nature
Open Data Verified Data
white to yellowish needle-like crystals or crystalline powder with strong vanilla bean aroma. Soluble in ethanol, ether, glycerol, propylene glycol, chloroform and alkali, water-soluble (50 ° C 1.3%).
Last Update：2024-01-02 23:10:35
Ethyl protal - Hair-making
Open Data Verified Data
from O-ethoxyphenol, p-nitrosodimethylaniline hydrochloride and urotropine condensation, extraction, distillation, refined. Alternatively, it can be obtained from the condensation of O-ethoxyphenol and glyoxylic acid by heating and oxidation. It can also be obtained from the condensation of O-ethoxyphenol with trichloroacetaldehyde by hydrolysis and chlorination. It can also be prepared by the reaction of catechuic aldehyde with sodium ethyl sulfate through distillation, extraction and fractionation.
Last Update：2022-01-01 10:07:42
Ethyl protal - Introduction
Slightly soluble in water, soluble in alcohol, ether, chloroform, glycerin and propylene glycol, 1g of the product is soluble in about 2ml of 95% ethanol.
Last Update：2022-10-16 17:12:44
Ethyl protal - Use
Open Data Verified Data
ethyl vanillin is a broad-spectrum fragrance and one of the most important synthetic fragrances in the world today. Its aroma is methyl vanillin 3~4 times, with strong vanilla bean aroma, and long-lasting. It is widely used in food, chocolate, ice cream, beverage and cosmetics for daily use. In chocolate, the usage amount is 250mg/kg; In gum 110mg/kg; In alcoholic beverages 100mg/kg; In pudding 74mg/kg; In candy 65mg/kg; 63 mg/kg in baked food/47 mg/kg in cold drinks; 20 mg/kg in soft drinks. Also
Can be used as feed additives; Brightener electroplating industry; Pharmaceutical industry intermediates.
Last Update：2022-01-01 10:07:43
Ethyl protal - Reference Information
| FEMA | 2464 | ETHYL VANILLIN |
| LogP | 1.58 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 vanillin is a broad-spectrum spice, is one of the most important synthetic spices in the world today, and is an indispensable and important raw material in the food additive industry. its aroma is 3-4 times that of vanillin, with strong vanilla bean aroma and lasting fragrance. Widely used in food, chocolate, ice cream, beverages and daily cosmetics to enhance and fix fragrance. In addition, ethyl vanillin can also be used as a feed additive, a brightener in the electroplating industry, and an intermediate in the pharmaceutical industry. |
| use | ethyl vanillin is a broad-spectrum perfume, is one of the most important synthetic spices in the world today, and is an indispensable and important raw material in the food additive industry. its aroma is 3-4 times that of vanillin, and its fragrance is lasting. Because the aroma is strong and the amount of addition is small, it can effectively reduce the bitter taste in food, is an alternative product of vanillin, and can reduce costs. It is widely used in food, chocolate, ice cream, beverages and daily cosmetics to enhance and fix fragrance. In addition, ethyl vanillin can also be used as a feed additive; an intermediate in the pharmaceutical industry. Ethyl vanillin is a food spice allowed to be used in my country's "Hygienic Standards for the Use of Food Additives". The aroma intensity is 3 to 4 times that of vanillin. It is mainly used to prepare vanilla edible essence, soda, ice cream, chocolate, tobacco and alcohol. The amount used in chocolate is 250mg/kg; 110mg/kg in gum sugar; 100mg/kg in alcoholic beverages; 74 mg/kg in pudding; 65 mg/kg in candy; 63 mg/kg in baked food; 47 mg/kg in cold drinks; 20 mg/kg in soft drinks. It is widely used in food, chocolate, ice cream, beverages and daily cosmetics to enhance and fix fragrance It is basically the same as vanillin. It can be used as a sweetener and fixer. It can be used for sweet floral fragrance, fruit lipstick fragrance, and also used as a fixer for formulas that require sweet milk fragrance. It has the performance of causing discoloration, so avoid white cream and soap. It is used in large quantities in vanilla bean and chocolate edible flavors. It is also used as a sweetener and fixer in the fragrance of cream, fruity, cigarette sugar, caramel, nuts, and rum. GB 2760-96 stipulates that it is temporarily allowed to use edible spices. Mainly used to prepare vanilla, chocolate and soda, ice cream and other flavors. According to FAO/WHO(1 983), it can be used for canned food for infants and processed cereal products for infants, with a maximum allowable dosage of 70 mg/kg (referring to grain food); Cocoa powder and sugary cocoa powder, chocolate, cocoa liquid block, cocoa cake, cocoa coated products (small amount for flavoring) and cream are limited to processing requirements (GMP). This product has the aroma of vanillin, but it is more elegant than vanillin, and the aroma intensity is 3-4 times higher than vanillin. Most of it is used as food spices for snacks, food, beverages, etc., and is also used on perfumes, cosmetics, and tobacco. The oral LD50 of rats is> 2000mg/kg. |
| Preparation | Ethyl vanillin can be synthesized from catechol. Catechol is ethylated to o-ethoxyphenol (1). The ether is condensed with glyoxylic acid to obtain the corresponding mandelic acid derivative (2), which is oxidized (3) and decarboxylated to finally produce ethyl vanillin (4). |
| content analysis | after the sample is dried in phosphorus pentoxide for 4 hours, the sample is accurately weighed about 300 mg, placed in a 125 ml conical flask, and dissolved in 50ml dimethylmethylamine. Add 3 drops of thymol blue test solution (TS-247) and titrate with 0.1 mol/L sodium methoxide under the measures of magnetic stirring and prevention of carbon dioxide in the atmosphere. At the same time, a blank test was made. 0.1mol/L sodium methoxide per ml is equivalent to 16.62 mg of ethyl vanillin (C9H10O3). |
| toxicity | LD50 @ 1590~2000 mg/kg (rat, oral). MNL 1000 mg/kg (rats). ADI 0~3(FAO/WHO,1995). GRAS(FDA;§ 182.60,2000). |
| usage limit | FEMA(mg/kg): soft drink 20; Cold drink 47; Candy 65; Baked food 63; Pudding 74; Gum sugar 110; Wine 100; Seasoning 250; Vanilla juice 28000; Frosting and decorating layer 140~200. |
| production method | is made from o-ethoxyphenol. This method is similar to the process of vanillin. It can also make o-ethoxyphenol react with glyoxylic acid, and then heat and oxidize with copper oxide and caustic soda aqueous solution to produce ethyl vanillin. Not only can vanillin be produced from safrole oil, but also ethyl vanillin can be produced. The alcohol solution of safrole (4-allyl-1, 2-methylenedioxybenzene) and potassium hydroxide is heated in an autoclave to destroy its dioxy ring. Then the 50% potassium hydroxide solution of sodium ethyl sulfate and the product was heated at 150-155 ℃ for 2-3h for etherification. The phenolic mixture after etherification is dissolved in 50% ethanol, and then a small amount of sulfuric acid is added to refluxing and heating to hydrolyze it to produce concentrated vanillin and isoeugenol. The former is precipitated into scaly crystals, filtered, and then recrystallized with 50% ethanol to obtain pure products. Isoeugenol-like is separated from the filtrate and dissolved in 10% sodium hydroxide solution. Sodium m-nitrobenzene sulfonate is added to reflux and heated for 3 hours. After cooling, it is acidified with dilute sulfuric acid to generate ethyl vanillin. The oil produced by acidification is extracted with benzene, then extracted with 35% sodium sulfite solution, and recrystallized after acidification to obtain the finished product. Dissolve catechol ether and sodium hydroxide in water, gradually add chloroform, boil to remove excess chloroform, the solution is acidified and the resin is precipitated, filtered, the filter residue is extracted with ether, and then purified by heavy sulfite method, and obtained by removing impurities with high-pressure steam. Dissolve protocatechuic aldehyde in anhydrous ethanol, add potassium hydroxide ethanol solution and ethyl sodium sulfate, and heat it to 130 ℃ in a pressure kettle. After removing alcohol, extract with ether, and then treat with sodium hydroxide solution to remove impurities. It is formed by condensation of o-ethoxyphenol, p-nitroso dimethylaniline hydrochloride and hexamethylenetetramine. using protocatechuic aldehyde as raw material, protocathuic aldehyde is dissolved in absolute ethanol, sodium ethyl sulfate and potassium hydroxide ethanol solution are added, and ethyl vanillin is generated by heating to 135 ℃ in an autoclave. After distillation and recovery of ethanol, the finished product is obtained by extraction and fractionation with ether. Synthesis of o-ethoxyphenol (see Synthesis of Vanillin 22017) Phase transfer catalysis method uses o-ethoxyphenol and chloroform as raw materials, adds appropriate amount of 95% ethanol, tertiary amine and sodium hydroxide, and synthesizes ethyl vanillin through Reimer-Tieman reaction. Glyoxylic acid method o-ethoxyphenol is condensed with glyoxylic acid, and then heated and oxidized in copper oxide and caustic soda aqueous solution to produce ethyl vanillin. The nitroso method is obtained by the condensation of o-ethoxyphenol, urotropine and p-nitroso dimethylphenylamine hydrochloride. The reaction mixture is extracted with benzene, and the extraction liquid is distilled under reduced pressure to obtain crude ethyl vanillin, and the finished ethyl vanillin is recrystallized with ethanol. The method has many side effects, serious pollution and high raw material cost. This method has a short process route and easy control of reaction conditions. This method is mostly used in industry. The one-way yield of the product is 64.4%. Trichloroacetaldehyde method o-ethoxyphenol is condensed with trichloroacetaldehyde to obtain 3-ethoxy-4-hydroxytrichloromethyl methanol, alkaline hydrolysis, and then chlorination to obtain ethyl vanillin. The methanol solution of safrole (4-allyl-1, 2-methylenedioxybenzene) and potassium hydroxide was synthesized from safrole as raw material and heated in an autoclave to destroy its dioxygen ring. Then etherification was carried out by heating the 50% potassium hydroxide solution of sodium ethyl sulfate and the product at 150~155 ℃ for 2~3h. The etherate is dissolved in 50% ethanol solution, and then a small amount of sulfuric acid is added to heat and reflux to hydrolyze it to generate ethyl vanillin and isoeugenol. The former forms scaly crystals and precipitates. After filtration and 50% ethanol recrystallization, pure ethyl vanillin is obtained. Isolated from the filtrate to obtain isoeugenol, dissolved in 10% sodium hydroxide solution, added with sodium m-nitrobenzene sulfonate, heated and refluxed for 3 hours, and then acidified with dilute sulfuric acid to generate ethyl vanillin. First, benzene is used for extraction, then the extraction solution is extracted with 35% sodium heavy sulfite solution, and then the finished product is obtained by acidification and recrystallization. The method is rich in raw materials, but the route is long, the process is complex, there is a by-product isoethyl vanillin generation, the yield is low. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 21:11:58
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Raw Materials for Ethyl protal