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Pentamethylfuran bromate, also known as methyl myristate, molecular formula C15H30O2, CAS 124-10-7, is a colorless and transparent liquid at room temperature and pressure. Due to its low melting point, it will be in a semi-solid, semi liquid, or fully solid state when the ambient temperature is low. Can dissolve in common organic solvents such as ethanol, ethyl acetate, dichloromethane, and low polarity ether solvents. It is a saturated fatty acid methyl ester that can be used as an intermediate in organic synthesis and biochemistry.
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| Chemical Formula | C15H30O2 |
| Exact Mass | 242 |
| Molecular Weight | 242 |
| m/z | 242 (100.0%), 243 (16.2%), 244 (1.2%) |
| Elemental Analysis | C, 74.32; H, 12.48; O, 13.20 |
Application Conversion
Add pentamethylfuran bromate (1.0 mmol), PhSiH3 (108 mg, 1.0 mmol), and ruthenium catalyst (4 mg, 1 mol%) into a pressure tube equipped with a magnetic stirring rod, and then heat and stir the reaction mixture in an oil bath at (100 ° C) for 6 hours. After the reaction is complete, cool the reaction mixture to room temperature. Add 3 ml of methanol and 2 mL of 10% NaOH aqueous solution to the reaction system. Stir the obtained mixture overnight to completely hydrolyze it. Extract the organic compounds from the mixture with CH2Cl2 (3 × 12m L), dry the organic portion with Na2SO4, remove the solvent with a rotary evaporator, use silica gel as the stationary phase, and a mixture of n-hexane (3.2) as the eluent. Purify the crude product by column chromatography.
Add pentamethylfuran bromate (89.2 mg), pentafluorophenylborane (5 mol%, 2.5 mg), and CH2Cl2 (1.0 mL) into a Schlumberger tube (10 mL). Slowly add poly (methyl hydroperoxide silicone oil) (18.0 equivalents, 110 μ L) into the tube (over 5 minutes) using a syringe, stir at room temperature for 6 hours, and add triethylamine (0.1 mL) to quench the reaction. After the reaction is complete, dilute to 10 mL, then directly introduce the reaction mixture into a silica gel liquid chromatography column, and purify the product by column chromatography using petroleum ether as the eluent.
Pentamethylfuran bromate, more commonly known as methyl myristate or methyl tetradecanoate, has a CAS number of 124-10-7. This compound has a wide range of applications in multiple fields, and the following is a detailed summary of its uses:
Food essence field
Food essence additives:
Pentamethylfuran bromate is an important component of many food essence, which is often used to enhance the flavor and aroma of food. For example, in natural foods such as honey and coconut, pentamethylfuran bromate can add a unique sweet aroma, making the food more tempting.
In addition, due to its aroma similar to apple and blue cheese, pentamethylfuran bromate is widely used in various baked goods, candies, and beverages, bringing unique taste and flavor to these products.
Security and Compliance:
As a food additive, the use of pentamethylfuran bromate is strictly regulated by food safety regulations in various countries. Under reasonable dosage and usage conditions, pentamethylfuran bromate is considered safe and does not pose a risk to human health.
Daily essence
Cosmetics and personal care products:
Pentamethylfuran bromate is also widely used in cosmetics and personal care products. Because of its mild aroma and good skin compatibility, it is often used as the essence of these products to add pleasant aroma to the products.
For example, the addition of pentamethylfuran bromate in products such as shampoo, shower gel, and skincare can enhance the overall sensory experience of the product, making consumers feel more pleasant and comfortable during use.
Household cleaning products:
In addition to cosmetics and personal care products, pentamethylfuran bromate is also commonly used in household cleaning products. Its unique aroma can neutralize odors generated during the cleaning process, bringing a fresh breath to the home environment.
Research field of gas chromatography and biochemistry
Gas chromatography stationary phase:
Pentamethylfuran bromate is often used as a stationary phase in gas chromatography due to its unique physical and chemical properties. The selection of stationary phase is crucial for the separation efficiency and accuracy of analysis results in gas chromatography analysis. Methyl myristate, as a stationary phase, can provide good separation efficiency and stability, meeting the analysis needs of various complex samples.
Biochemical research reagents:
In the field of biochemical research, pentamethylfuran bromate is also commonly used as a reagent or standard substance. It can participate in the synthesis, modification, and detection of biomolecules, providing strong support for biochemical research. For example, in fatty acid metabolism research, pentamethylfuran bromate can be used as a substrate or marker to monitor changes in metabolic pathways and rates.
Other application areas
Industrial solvents:
Due to its insolubility in water but easy solubility in organic solvents, pentamethylfuran bromate can also be used as a solvent in certain industrial processes. Its good solubility and stability contribute to improving the efficiency and product quality of industrial production.
Pesticides and insecticides:In the field of pesticides and insecticides, pentamethylfuran bromate also has certain application potential.
Although its application as the main ingredient of pesticides or insecticides is relatively rare at present, it may play a certain role as an auxiliary ingredient in some formulations.
Other emerging fields:
With the continuous development of science and technology, the application fields of pentamethylfuran bromate are also constantly expanding. For example, in emerging fields such as nanotechnology and materials science, pentamethylfuran bromate may have unique properties and potential waiting for people to explore and apply.
The acyl chloride method is a commonly used method for synthesizing ester compounds, which involves converting carboxylic acids into corresponding acyl chlorides and then reacting with alcohols to obtain esters. The following are the detailed steps and corresponding chemical equations for synthesizing pentamethylfuran bromate (methyl tetradecanoate) by acyl chloride method:
matters needing attention
Acyl chlorides are highly reactive compounds that easily react with compounds containing active hydrogen such as water and alcohols, releasing a large amount of heat and gas. Therefore, when preparing and using acyl chlorides, it is necessary to strictly follow safety operating procedures and operate in a fume hood.
The purity of the raw materials has a significant impact on the reaction results. Therefore, high-purity raw materials should be used during the synthesis process, and reagents containing moisture, oxides, or other impurities should be avoided.
Factors such as reaction temperature, solvent, catalyst, etc. can all affect the rate of reaction and the yield of products. Therefore, appropriate reaction conditions should be selected and optimized according to specific circumstances during the synthesis process.
Post processing steps are crucial for obtaining high-purity products. Careful operation should be carried out in the steps of extraction, washing, drying, and solvent evaporation to ensure the purity and yield of the product.
During the synthesis process, efforts should be made to minimize the emission of harmful substances and the generation of waste. The generated exhaust gas, waste liquid, and waste residue should be properly treated to meet environmental protection requirements.
The synthesis of methyl myristate by acyl chloride method is an effective method. This method has the advantages of mild reaction conditions, easy operation, and high product purity. However, during the synthesis process, attention should be paid to factors such as safety, raw material purity, reaction conditions, and post-treatment that affect the reaction results. By optimizing the synthesis conditions and improving the operational level, the yield and purity of the product can be further improved to meet the needs of industrial production.
This substance is circulated in the chemical supply chain under the trade name "pentamethylfuran bromate", and its chemical essence is methyl myristate, a saturated fatty acid methyl ester. The following timeline is based on industry public information.
In the mid-19th century, methyl myristate was first synthesized as a simple fatty acid methyl ester, mainly by esterification of myristic acid with methanol under acid catalysis.
Large scale industrial production began in the mid-20th century, mainly used in the fields of soap and daily chemical industry.
In 1996, it was listed in Food Flavors (GB2760-1996) and approved to be used as food essence (honey, coconut and other flavors), marking its legal status in the food industry.
On July 2014, Jingzhou Yinjie Chemical Co., Ltd. was established and began to lay out the production of this product.
In August 2016, multiple chemical trading companies began to include it in their product lines.
In December 2017, Hubei Qifei Pharmaceutical and Chemical Co., Ltd. (Tianmen City) and Wuhan Penglei Biotechnology were successively established, focusing on heterocyclic compounds and spice intermediates, with pentamethylfuran bromate as one of the core products.
In 2018, there was a production record of "raw material pharmaceutical grade" in the industry, and the quality standards were upgraded from industrial grade to pharmaceutical grade.
Established in September 2019, Wuhan Kamik Technology Co., Ltd. collaborates with universities such as Wuhan University to optimize production processes and promote the development of products towards high purity (99%+).
From 2020 to 2021, the application will expand from the traditional essence field to organic synthetic intermediates, biochemical research, and gas chromatography standards.
Hubei Dahao Chemical Co., Ltd. was established in March 2022 to further enrich the supply chain.
In December 2022, the industry research literature systematically summarized its properties: melting point of 18.4-20 ℃, boiling point of 250 ℃ (760mmHg), insoluble in water, soluble in ethanol/ether/dichloromethane; And reported its high melanin induction effect in B16F10 melanoma, opening up a new direction for biomedical research.
Starting around 2023, it will serve as an upstream raw material for OLED material intermediates, pesticide intermediates, and dye intermediates, significantly expanding its application scenarios.
FAQ
What is the use of methyl myristate?
Pharmaceutical Applications: Methyl myristate is used as a solvent and carrier for active ingredients in drug formulations, improving bioavailability and stability. Food Industry: It acts as a flavoring agent and a food additive, contributing to the aroma and taste of various products.
What is methyl myristate standard?
Methyl myristate (Standard) is the analytical standard of Methyl myristate. This product is intended for research and analytical applications. Methyl myristate is a saturated fatty acid methyl ester obtained from the esterification of myristic acid. Methyl myristate shows a high melanin induction in B16F10 melanoma.
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