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Eugenol powder (English name: Eugenol), chemical name: 4-allyl-2-methoxyphenol. It is a kind of liquid with lilac flower taste, the chemical formula is C10H12O2 CAS 97-53-0, and it is colorless or light yellow liquid. It is miscible with alcohol, ether, chloroform and volatile oil, soluble in glacial acetic acid and caustic solution, and insoluble in water. It has the functions of bacteriostasis and virus killing. It can be used as soap and perfume, and can also be made into a single essential oil of many flowers. It can be used to prepare star shaped spices, and to prepare fragrant dried fruits.
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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 |
Eugenol is a natural active ingredient extracted from plants such as cloves, with a chemical formula of C ₁₀ H ₁₂ O ₂ and a molecular weight of 164.21. It is a colorless to light yellow viscous liquid with a strong aroma of eugenol.
1. Anti-inflammatory and antibacterial
Eugenol has a significant inhibitory effect on common pathogenic bacteria such as Staphylococcus aureus, Escherichia coli, Klebsiella pneumoniae, and Shigella, and can inhibit their growth by disrupting bacterial cell membranes. In oral care, eugenol is commonly used to treat oral diseases such as pulpitis and periapical periodontitis, with an antibacterial rate of over 90%. For example, mouthwash containing eugenol can reduce the number of oral bacteria by 75%, while relieving toothache and gum swelling.
Dingxiangphenol also has inhibitory effects on fungi such as Candida albicans, and can be used to treat oral candidiasis and skin fungal infections (such as tinea corporis and tinea pedis), with a cure rate of 91.67%, which is better than traditional clotrimazole ointment.
2. Analgesic anesthesia
Eugenol has local analgesic and anesthetic effects, and can reduce pain signal transmission by binding to nerve endings. In dental treatment, liquid clove oil is often used as an analgesic for acute pulpitis, while zinc oxide clove oil cement is used for deep caries filling and temporary sealing of cavities. Its anesthesia has high safety and can reduce the occurrence of drug-induced periapical periodontitis, especially suitable for root canal disinfection of recurrent periapical periodontitis, with an effective rate of 98.48%.
Animal experiments have shown that intravenous injection of eugenol in rabbits can produce anesthetic, blood pressure lowering, respiratory depression, and anticonvulsant effects, but subcutaneous injection in mice does not produce anesthetic effects.
3. Promote digestion
Eugenol can warm the middle and dispel cold, improve gastrointestinal discomfort symptoms, and enhance digestive ability. 5% eugenol emulsion can significantly increase gastric mucus secretion without increasing acidity, which helps to repair gastrointestinal function caused by cold infections and accelerate waste discharge.
Eugenol can also inhibit excessive stomach acid, alleviate symptoms such as stomach pain, gastric ulcers, and duodenal ulcers. For example, gastric medicine containing eugenol can increase the healing rate of gastric ulcers by 30% and reduce the recurrence rate.
4. Cardiovascular protection
Eugenol has the effect of dilating blood vessels and lowering blood pressure, and can improve blood circulation by regulating smooth muscle contraction of blood vessels. Experiments have shown that after taking preparations containing eugenol, hypertensive patients experience an average decrease of 15-20 mmHg in systolic blood pressure and 10-15 mmHg in diastolic blood pressure.
Eugenol can also inhibit platelet aggregation, prevent thrombosis, and have a certain effect on preventing cardiovascular and cerebrovascular diseases. Its antioxidant properties can clear free radicals and delay the process of atherosclerosis.
5. Other medical purposes
Transdermal absorption enhancer: Eugenol can promote the transdermal absorption of drugs such as 5-fluorouracil, increase local drug concentration, and enhance therapeutic efficacy.
Mosquito repellent: Eugenol has a good mosquito repellent effect, is non irritating to the skin, and can alleviate itching and redness after mosquito bites.
Antitumor adjuvant: Eugenol has an inhibitory effect on NO induced tumors, possibly by regulating immune responses or directly inhibiting tumor cell proliferation.
Food sector
1. Natural preservatives
As a natural preservative, eugenol can extend the shelf life of food. Its antibacterial mechanism is achieved by disrupting bacterial cell membranes, with an inhibitory concentration of 1:2000-1:8000 against common food spoilage bacteria such as Escherichia coli and Staphylococcus aureus. For example, adding 0.1% eugenol to meat products can extend the shelf life by 3-5 days.
Eugenol can also inhibit the growth of mold and prevent food from becoming moldy. Adding 0.05% eugenol to baked goods such as bread and cakes can reduce mold growth by 60%.
2. Food flavoring
Eugenol is a permitted food flavor specified in GB2760-96, which is mainly used to prepare essence such as smoked ham, nuts and spices. Its unique clove aroma can enhance food flavor and increase product appeal.
Eugenol can also be used to synthesize vanillin (an important artificial flavoring agent), which is converted into vanillin through acetylation reaction and widely used in foods such as chocolate and ice cream.
Spice and daily chemical industry
1. Essence blending
Eugenol is the blending basis of Kangjiji essence, and it is used in the blending of essence such as cosmetics, soap and food. Its strong carnation musk smell can be used as a modifier and fixative to enhance the stability and durability of essence.
Eugenol is widely used to prepare carnation flower fragrance, rose fragrance and other floral essence, as well as spicy, woody, oriental and aromatic essence. Among tobacco essence, eugenol can improve the taste and reduce irritation.
2. Chemical products for daily use
Eugenol can be used in the formulation of daily chemical products such as perfume, skin care products, shampoo, etc., to provide lasting clove fragrance. Its antibacterial properties can also extend the shelf life of products and prevent microbial contamination.
Eugenol can also be used as a soap flavoring to enhance the cleaning power and aroma of soap. For example, soap containing eugenol can extend the fragrance retention time after hand washing to more than 4 hours.
1. Spice intermediates
Eugenol is an intermediate for synthesizing other fragrances, and its derivatives include isoeugenol, methyl eugenol, acetyl eugenol, etc. For example, eugenol can be rearranged into isoeugenol by heating in potassium hydroxide, and further acetylated to obtain vanillin (an important artificial flavoring agent).
Eugenol can also be used to manufacture isoniazid, a special drug for treating tuberculosis. Eugenol is converted into isoniazid through chemical synthesis, and then reacted with hydrazine to produce isoniazid.
2. Agricultural applications
Eugenol can be used as a pesticide additive to enhance efficacy and reduce toxicity. Its derivatives have good control effects on plant diseases such as gray mold, blight, leaf mold, powdery mildew, and are environmentally friendly.
Eugenol can also be used as a fish anesthetic to reduce stress reactions and lower mortality rates during transportation. For example, after anesthetizing carp with eugenol, their oxygen consumption can be reduced by 50% and ammonia nitrogen emissions can be reduced by 30%.
3. Research application
Eugenol is often used as a model compound in scientific research to study the chemical properties and biological activities of phenolic substances. The phenolic hydroxyl and allyl side chains in its structure provide sites for chemical modification, which can be used to synthesize novel bioactive molecules.
Eugenol can also be used in cell experiments and animal experiments to study its antibacterial, anti-inflammatory, antioxidant and other mechanisms. For example, muscle specimen experiments have shown that eugenol has strong anti histamine effects and can alleviate allergic reactions.
Preparation of eugenol
1. Natural eugenol mainly uses the volatile oil obtained from the distillation of the dried flower bud of myrtle clove, which is rich in clove oil. Then, it is obtained through extraction (dissolution and separation of phenol and non phenol oil in sodium hydroxide solution with fixed content), petroleum ether extraction, acidification, neutralization, rectification and other steps.
2. Eugenol is prepared by synthesis, using guaiacol as raw material, allyl chloride, allyl alcohol, etc.
3. In industry, it can be isolated from natural essential oil or chemically synthesized. However, the isomers produced by chemical synthesis have very close boiling points and are extremely difficult to separate. At present, the single separation method is mainly used.
(1) Natural essential oil separation method
The mixture of essential oil and water was obtained from perennial subshrub Syringa basil by steam distillation. Add 20% sodium hydroxide into the oil-water mixture, and then conduct steam distillation to remove the non acid substances. Add 30% sulfuric acid to the obtained eugenol sodium solution at 50 ℃, stir and neutralize it to Ph=2-3 (water layer). After standing, the crude clove oil in the lower layer is separated, and the finished product of eugenol is obtained by vacuum distillation.
(2) Chemical synthesis method
Allyl bromide, o-methoxyphenol, anhydrous acetone and anhydrous potassium carbonate are added into the reactor, heated and refluxed for several hours. Dilute with water after cooling, and then extract with ether. The extract was washed with 10% sodium hydroxide and dried with anhydrous potassium carbonate. After recovering ether and acetone by atmospheric distillation, conduct vacuum distillation to collect the fraction at 110~113 ℃ (1600Pa), which is o-methoxyphenylallyl ether. Boil it and reflux for 1h, then cool it down. The obtained oil is dissolved with ether, and then extracted with sodium hydroxide solution. The extract is acidified with hydrochloric acid and then extracted with ether. The extracted liquid is dried with anhydrous sodium sulfate, and the finished clove powder is obtained after ether is recovered by atmospheric distillation. It can also be further reacted with o-methoxyphenol and allyl chloride under the catalysis of copper and 100 ℃ to obtain the finished product.
4. Syringa oil and other essential oils containing a large amount of eugenol shall be treated with 30% sodium hydroxide solution, and then separated with inorganic acid or carbon dioxide gas. Or it can be added with sodium acetate to make it free and then distilled with steam to obtain pure product.
5. Although eugenol can also be prepared by synthesis, it is generally separated from plants or aromatic oils in industry. Clove basil can be used as raw material. Clove basil is originally produced in Seychelles and Comoros. In 1965, the former Soviet Union was introduced into China. In the south of the Yangtze River basin, it is cultivated as a multiple sub shrub. Syringa basil oil content in flower spike is the highest, followed by leaves and stems. The main component in the oil is eugenol. It accounts for 60-70%, including linalool, paracymosin, and basilene. The synthetic eugenol is obtained by the reaction of o-methoxyphenol and bromopropyl, and then by heating rearrangement.
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