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Isoeugenol is a chemical substance with the molecular formula C10H12O2. Light yellow slightly thick liquid with clove like odor. It is insoluble in water and glycerin, but soluble in organic solvents such as ethanol. It is found in clove, carnation, tuberose and other essential oils. It is usually a mixture of cis and trans isomers, mainly trans. It is easy to change color with alkali and iron, so it is not suitable for white flavoring products. It has soft, sweet and clear spicy fragrance, with carnation and clove flowers. It is used to prepare essence and vanillin. It can be used to prepare ylang, nutmeg and other essential oils; It can also be used to prepare edible essence with raspberry, peach, spice and clove flavor. It is the raw material of semi synthetic vanillin.
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Chemical Formula |
C10H12O2 |
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Exact Mass |
164 |
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Molecular Weight |
164 |
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m/z |
164 (100.0%), 165 (10.8%) |
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Elemental Analysis |
C, 73.15; H, 7.37; O, 19.49 |
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Isoeugenol is an organic compound with a mixed aroma of clove and vanilla, with a molecular formula of C01H21O2 and a molecular weight of 164.12. It naturally exists in more than 500 plant species such as nutmeg, basil, and bay leaves, with significant differences in content (such as 40-320 mg/kg in nutmeg). As a phenolic propane compound, it has become a core raw material in the fields of food, fragrance, medicine, industry, etc. due to its unique chemical properties.
1.1 Main agent of floral essence
It is the core ingredient of carnation essence. Its fragrance is more elegant than eugenol, and is widely used in the deployment of rose, ylang, sweet clover and other floral essence. For example:
Carnation essence: Isoeugeno accounts for 60% -70%, giving essence the symbolic sweet and clear fragrance;
Oriental Fragrance Type: Compound with Musk and Lingmao Fragrance, used for fragrance types such as Yilan, Daffodil, and White Orchid to enhance the level of aroma;
Special scenario application: In dental materials, its aroma can mask drug odors and improve patient experience.
1.2 Fruit flavor essence base
It can simulate a variety of fruit aromas, and is used to prepare banana, raspberry, strawberry, peach and other fruit flavor essence. For example:
Raspberry essence: mixed with isoamyl acetate to restore the sweet and sour characteristics of raspberry;
Nut essence: Add 0.5% -1% isoeugeno to walnut and almond essence to enhance the caramel of baked nuts.
1.3 Synergism of spicy essence
It is the key ingredient of cinnamon, nutmeg, clove and other spice essence, which can enhance the penetration of aroma. For example:
Ham essence: it is mixed with smoke liquid to make the aroma of artificial ham closer to the traditional technology;
Spice compound: Adding 0.1% -0.3% isoeugeno to five spice powder and curry powder can prolong the fragrance retention time.
2.1 Compliance Application of Edible Spices
According to GB 2760-2014 "National Food Safety Standard for the Use of Food Additives", isoeugeno is listed as a "temporarily allowed edible flavoring" and can be used in the following food categories:
Baked goods: add 0.002% -0.005% to bread and cake to give clove flavor;
Candy: Add 0.005% -0.01% to hard candy and soft candy to enhance the persistence of fruit aroma;
Beverages: Add 0.001% -0.003% to tea drinks and carbonated drinks to simulate natural vanilla aroma.
2.2 Flavor Modification and Masking
Food acceptance can be improved by masking unpleasant odors:
Aquatic products: Add 0.003% -0.005% to fish balls and crab sticks to neutralize the fishy smell;
Functional food: Add 0.001% -0.002% to protein powder and dietary fiber to mask the bean odor.
2.3 Natural equivalent spice substitution
As a natural extracted spice, it can replace some synthetic spices and meet the needs of clean labeling. For example:
Organic food: In organic yogurt and organic fruit juice, it is used as a substitute for ethyl maltol, which complies with the EU EC 1334/2008 standard;
Halal food: As a natural spice in Halal meat products, it meets the requirements of Islamic law.
3.1 Semi synthetic Vanillin Core Raw Materials
About 70% of vanillin worldwide is prepared by the isoeugenol oxidation method, with the following process route:
Isomerization: Eugenol is heated to 200-230 ℃ in potassium hydroxide pentanol solution to isomerize into isoeugeno;
Oxidation: Oxidation by nitric acid or hydrogen peroxide to produce vanillin;
Purification: White needle shaped crystals (purity ≥ 99%) are obtained through distillation and crystallization.
3.2 Market value of vanillin
Vanillin, as one of the world's largest spice producers, has an annual market size of over 1 billion US dollars and is widely used in:
Food: accounting for 65% of vanillin consumption, used for chocolate, ice cream, baked goods;
Daily chemicals: 25%, used for perfume, shampoo and laundry detergent;
Medicine: accounting for 10%, used for the synthesis of drugs such as dopa and methyldopa.
Medical field: cross-border applications from traditional to modern
4.1 Traditional Medicinal Value
Used in traditional medicine for pain relief and anti-inflammatory purposes:
Dental anesthesia: It is the main component of local dental anesthetics, and its anesthetic effect is weaker than benzocaine but lasts longer;
Skin disease treatment: In Ayurvedic medicine in India, it is used to treat eczema and dermatitis.
4.2 Modern Pharmacological Research
Biological activity attracts scientific attention:
Antioxidant: IC50 value of 12.5 μ M, capable of scavenging DPPH free radicals, used for anti-aging in skincare products;
Antibacterial: The MIC value for Staphylococcus aureus and Escherichia coli is 50-100 μ g/mL, which can be used as a food preservative;
Anti cancer: Animal experiments have shown that isoeugeno can inhibit the proliferation of liver cancer cells, but IARC lists it as a Class 2B carcinogen (possibly carcinogenic to humans), limiting its direct use in drugs.
5.1 Lipid peroxidation inhibitors
Can delay oil oxidation and extend product shelf life:
Edible oil: Adding 0.01% isoeugeno can reduce the peroxide value of soybean oil by 40%;
Coating: Adding 0.5% to epoxy coating can improve weather resistance by 30%.
5.2 Free radical scavengers
Used for stabilizing polymer materials:
Plastic: Adding 0.1% isoeugeno to PE film can prolong the thermal aging time by 50%;
Rubber: Adding 0.2% isoeugeno to SBR rubber can enhance its ozone resistance.
5.3 Environmentally friendly materials
Isoeugenol derivatives for green chemistry:
Biodegradable plastics: copolymerized with lactic acid to prepare biodegradable packaging materials;
Water treatment agent: Modified flocculant, with a removal rate of 95% for heavy metal ions.
1. At present, the synthesis methods of isoeugeno have the problems of complex production process, high production cost, or environmental pollution caused by reaction waste liquid, or high content of cis isoeugeno. A synthesis method of isoeugeno aims to solve the problems of complex production process, high production cost, environmental pollution caused by reaction waste liquid, or high content of cis isoeugeno in the current synthesis method of isoeugeno. The following steps are included:
(1) Add clove powder to 1mol/L potassium hydroxide solution and ethanol, and place for 1~2h under the condition of 100~130 ℃ and ultrasonic wave to obtain decomposition solution; Wherein, the mass volume ratio of clove powder, potassium hydroxide solution and ethanol is (20-30) kg: (5-10) L: (5-10) L;
(2) The decomposition liquid and toluene are stirred and mixed, and then heated and distilled in a vacuum state. The temperature at the heating point of the distillation is controlled to be 50~90 ℃, and the temperature at the volatile outlet of the distillation gas is controlled to be 35~45 ℃. The distillation gas is condensed and collected with a condenser to obtain low boiling point impurities; Wherein, the volume ratio of the decomposition solution to toluene is (5-10): (3-4);
(3) Continue to distill the remaining filtrate after removing the low boiling point impurities in step (2), control the temperature at the distillation heating point to be 100 ℃～ 120 ℃, and control the temperature at the distillation gas volatilization outlet to be 90 ～ 105 ℃. Condensate the distillation gas with a condenser and collect it to obtain isoeugeno.
In this method, the amount of alkali liquor required is greatly reduced, and the liquid in the reaction process can be directly used for distillation without means such as extraction and separation, and the operation is simpler; In addition, the reagents and test devices used in the invention are commonly used, and the production cost is very low; More importantly, the content of trans isoeugeno obtained by the invention in isoeugeno can reach more than 95%.
2. The invention relates to a method for preparing isoeugeno by catalytic pyrolysis of biomass with ruthenium or rhodium catalyst. According to the method provided by the invention, taking biomass as raw material, the biomass and ruthenium or rhodium catalyst are mechanically mixed in a mass ratio of (10 ∶ 1) to (1 ∶ 3), and then rapidly pyrolyzed at 250 ～ 400 ℃ under oxygen free conditions. The liquid product rich in isoeugeno can be obtained after the pyrolysis gas is condensed. The ruthenium or rhodium catalyst used in the invention can greatly promote the formation of eugenol during the pyrolysis of pine, fir, cypress or araucaceae biomass, inhibit the pyrolysis of cellulose and hemicellulose to form volatile organic products, and inhibit the pyrolysis of lignin to form other phenolic products. Therefore, the composition of the obtained liquid product is relatively simple, and the purity of isoeugenol is high, which greatly simplifies the subsequent separation and purification process. Secondly, the catalyst has stable performance and can be separated from the pyrolysis residue by mechanical method to achieve recycling. In addition, the invention controls the pyrolysis temperature at 250~400 ℃, and there are fewer pyrolysis products at lower pyrolysis temperature, which is not only conducive to controlling the product composition and further improving the selectivity of isoeugeno, but also has lower requirements for equipment and reaction conditions, which is conducive to reducing production costs.
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