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Eriodictyol powder, light yellow crystalline powder, easily soluble in methanol, slightly soluble in boiling water, hot ethanol, ether, and glacial acetic acid, and soluble in dilute alkali. Polyphenols and flavonoids are widely distributed in fruits and vegetables, mainly in lemon and peanuts. It has the functions of anti-oxidation, anti-inflammatory, analgesic, and improving diabetes and diabetes complications.
It comes from the holy grass of the Tianma family. It has antioxidant, anti-inflammatory, and analgesic It can improve diabetes and complications of diabetes. Some studies have found that it can effectively protect keratinocytes from UV-induced death by inhibiting the cleavage of pro-caspase-3 or pro-caspase-9 and the release of cytochrome c. it can resist bacteria and inflammation and plays a crucial role in the pathogenesis of diabetes. It can inhibit type I allergic reaction induced by immunoglobulin E (Ig E) /antigen (Ag), At the same time, it has analgesic and warming effects.
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Chemical Formula |
C15H12O6 |
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Exact Mass |
288 |
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Molecular Weight |
288 |
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m/z |
288 (100.0%), 289 (16.2%), 290 (1.2%), 290 (1.2%) |
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Elemental Analysis |
C, 62.50; H, 4.20; O, 33.30 |
Eriodictyol powder is a naturally occurring flavonoid, belonging to the flavone subclass of flavonoids, widely distributed in various plants, particularly in citrus fruits such as lemons, limes, and oranges. This compound is recognized for its potent antioxidant and anti-inflammatory properties, making it a subject of interest in the fields of nutrition, herbal medicine, and pharmaceutical research.
Structurally, eriodictyol features a backbone of two aromatic rings linked by a three-carbon bridge, with hydroxyl groups attached to several positions, conferring its hydrophilic nature and enhancing its ability to scavenge free radicals. These free radical-scavenging capabilities are crucial in mitigating oxidative stress, a precursor to numerous chronic diseases including cancer, cardiovascular ailments, and neurodegenerative conditions.
Beyond its antioxidant activities, eriodictyol has demonstrated promising effects in modulating immune responses and exhibiting antimicrobial properties, potentially useful in combating infections. Studies suggest it may also play a role in regulating blood sugar levels and improving insulin sensitivity, which is beneficial for diabetes management.
Moreover, eriodictyol's anti-inflammatory actions have been investigated for their potential to alleviate conditions like asthma, rheumatoid arthritis, and inflammatory bowel disease. Its ability to modulate signaling pathways involved in inflammation highlights its therapeutic potential.
In summary, eriodictyol, with its multifaceted biological activities, stands out as a valuable natural compound for promoting health and wellness.
Ongoing research continues to unravel additional mechanisms through which this flavonoid exerts its beneficial effects, paving the way for potential applications in functional foods, dietary supplements, and pharmaceutical preparations.
in the cosmetics industry
1. Antioxidant function
It has received widespread attention due to its powerful antioxidant function. Free radicals are one of the main culprits of skin aging, which can damage skin cells and lead to aging phenomena such as sagging, increased wrinkles, and deepening pigmentation. As an antioxidant, it can effectively eliminate free radicals, protect skin cells from oxidative damage, and thus delay the process of skin aging. Adding it to cosmetics can help keep the skin youthful, reduce the appearance of fine lines and wrinkles, and also help fade pigmentation and brighten the complexion.
2. Antibacterial effect
It also has antibacterial properties and can inhibit the growth of various bacteria and fungi. Adding it to cosmetics can help reduce the number of bacteria and fungi on the surface of the skin, preventing the occurrence of skin infections.
3. Anti inflammatory effect
It also has significant anti-inflammatory effects. When the skin is exposed to external stimuli such as ultraviolet radiation, chemicals, pollutants, etc., an inflammatory response can occur, leading to discomfort symptoms such as redness, swelling, stinging, itching, etc. It can inhibit the release of inflammatory factors, reduce skin inflammation, and alleviate skin discomfort symptoms. Adding it to cosmetics can help sensitive and damaged skin quickly recover to a healthy state, reduce discomfort symptoms such as redness, swelling, and stinging, and also help improve skin tolerance.
4. Improve skin quality
It can also improve skin quality, making the skin more delicate, smooth, and elastic. It can promote the renewal and metabolism of skin cells, accelerate the shedding of aging cells, and also help promote the synthesis and secretion of collagen, making the skin firmer and more elastic.
Anti aging products
In anti-aging products, it is usually one of the main antioxidant ingredients. For example, some high-end brands have added anti wrinkle essence, face cream and other products. These products can penetrate deep into the skin, effectively eliminate free radicals, reduce the appearance of fine lines and wrinkles, and also help brighten skin tone and fade pigmentation.
Sensitive skin products
In products targeting sensitive skin, Eriodictyol powder is often used as the main soothing ingredient. For example, some face cream, lotion and other products specially designed for sensitive skin have added products. These products can alleviate skin inflammation, relieve discomfort symptoms such as redness, swelling, and stinging, while also helping to improve skin tolerance.
Antibacterial products
In antibacterial products, it is usually used together with other antibacterial ingredients to enhance the antibacterial effect of the product. For example, some cleansers, toners, and other products with antibacterial properties have added sage phenols. These products can reduce the number of bacteria and fungi on the surface of the skin, preventing the occurrence of skin infections.
Improve skin quality products
It is often used as the main active ingredient in products that improve skin quality. For example, some products with whitening, moisturizing, exfoliating and other effects have added products. These products can promote the renewal and metabolism of skin cells, accelerate the shedding of aging cells, and also help promote the synthesis and secretion of collagen, making the skin more delicate, smooth, and elastic.
in the food industry
Eriodictyol powder is an effective antioxidant that can eliminate free radicals, prevent oxidation reactions of lipids, proteins, carbohydrates, etc. in food, thereby extending the shelf life of food and maintaining its nutritional value. In the process of food production and processing, coumarin is often added to easily oxidizable foods such as oils, meats, dairy products, baked goods, etc. to slow down oxidation reactions and maintain the freshness and quality of food.
1. Oil antioxidant
Oils and fats are important components in food, but they are prone to oxidation reactions, leading to a decrease in quality and loss of nutritional value. As an antioxidant, holy grass phenol can effectively inhibit the oxidation reaction of oil and prolong the shelf life of oil. For example, adding holy grass phenol to edible vegetable oil can slow down the oxidation and decomposition of the oil, prevent the production of bad flavors and harmful substances, and maintain the clarity and stability of the oil.
2. Meat preservation
Meat products are easily affected by factors such as oxidation and microbial contamination during storage and processing, leading to a decrease in quality and a shortened shelf life. As an antioxidant and antibacterial agent, holy grass phenol can inhibit the oxidation reaction and microbial growth of meat, prolong the shelf life of meat, and maintain its freshness. For example, adding resveratrol to meat products can reduce fat oxidation and protein denaturation, prevent odor and discoloration, while inhibiting bacterial growth and extending the shelf life of meat products.
3. Antioxidant properties of dairy products
Dairy products such as milk, yogurt, cheese, etc. are rich in protein and lipids, which are prone to oxidation reactions, leading to a decrease in quality and nutritional value. Shengcao phenol, as an antioxidant, can be added to dairy products to inhibit the oxidation reactions of lipids and proteins, maintaining the freshness and nutritional value of dairy products. For example, adding resveratrol to milk can slow down fat oxidation and protein denaturation, prevent milk from producing odors and layering, while maintaining the milk's milky whiteness and taste.
4. Antioxidant properties in baked goods
Baked foods such as bread and cakes are rich in oil and sugar, which can easily undergo oxidation and browning reactions, leading to a decrease in quality and a deterioration in taste. Shengcao phenol, as an antioxidant, can be added to baked goods to inhibit oxidation and browning reactions, maintaining the freshness and taste of baked goods. For example, adding resveratrol to bread can slow down oil oxidation and sugar browning, prevent bread from producing odors and hardening, while maintaining the softness and aroma of the bread.
Adding Holy Grass Phenol to Edible Vegetable Oil
In the production process of edible vegetable oil, adding resveratrol as an antioxidant to the oil can significantly improve its stability and extend its shelf life. A certain edible oil production enterprise added a certain amount of holy grass phenol to soybean oil during production. After experimental comparison, it was found that the oxidation degree of soybean oil with added holy grass phenol was significantly reduced during storage, and the color and flavor remained good. The shelf life was extended to more than 18 months.
Adding Holy Grass Phenol to Meat Products
In the production process of meat products, adding resveratrol as an antioxidant and antibacterial agent can significantly improve the quality and shelf life of meat products. A certain meat product manufacturing enterprise added a certain amount of holy grass phenol to sausages during production. After experimental comparison, it was found that the addition of holy grass phenol significantly reduced the degree of fat oxidation during storage, maintained good color and taste, and inhibited bacterial growth, extending the shelf life of sausages to more than 3 months.
Adding Holy Grass Phenol to Dairy Products
In the production process of dairy products, adding resveratrol as an antioxidant can significantly improve the quality and nutritional value of dairy products. A certain dairy production enterprise added a certain amount of holy grass phenol to milk during milk production. After experimental comparison, it was found that the addition of holy grass phenol significantly reduced the degree of fat oxidation during storage, maintained good milk whiteness and taste, and maintained the stability of nutrients such as calcium and vitamin D in milk.
Adding phenol to baked goods
Adding resveratrol as an antioxidant to baked goods during the production process can significantly improve the quality and taste of baked goods. A certain baking food production enterprise added a certain amount of holy grass phenol to bread during production. After experimental comparison, it was found that the bread with added holy grass phenol had a significantly reduced degree of oil oxidation during storage, maintained good softness in taste, and maintained the aroma and color of the bread.
Adding Holy Grass Phenol to Beverages
Adding resveratrol as an antioxidant to beverages during the production process can significantly enhance their color and nutritional value. A certain beverage production enterprise added a certain amount of resveratrol to fruit juice during production. After experimental comparison, it was found that the degree of oxidation and decomposition of vitamin C in fruit juice with added resveratrol was significantly reduced during storage, and the color and flavor remained good, while maintaining the acidity, sourness, and taste of the juice.
Synthesis methods
Eriodictyol is a kind of flavonoid compound that can be isolated from herbal medicine, which has the functions of anti-oxidation, anti-inflammation, analgesia, and improvement of diabetes and diabetic complications. There are mainly two synthetic methods reported in the literature at present:
The first one uses luteolin as a raw material, methanol as a solvent, and uses gigantic carbon hydrogenation to reduce the double bond, and then needs to be purified by a silica gel column for post-treatment to obtain eriodictol. The reaction formula is as follows:
The second one uses hesperetin as a raw material, uses pine as a solvent, adds anhydrous aluminum chloride and heats at 70°C, and then treats with hydrochloric acid to obtain eriodictyol. The reaction formula is as follows:
Using hesperetin as a raw material, adding anhydrous aluminum chloride (AlCl3) to the vine solvent, heating to 70 degrees Celsius, and treating with hydrochloric acid to obtain eriodictyol. The following is a detailed step-by-step description:
Chemical formula:
C16H14O6 + 3 AlCl3 → intermediate product
Intermediate + HCl → C15H12O6 + AlCl3 + H2O
Reaction system preparation
Dissolve an appropriate amount of hesperetin in pyridine, ensuring full dissolution.
Add Anhydrous Aluminum Chloride
Slowly add anhydrous aluminum chloride (AlCl3) to the reaction system while mixing the reactants with magnetic stirring to ensure uniform mixing.
Heating the reaction
The reaction system was heated to 70 degrees Celsius, and reacted at this temperature for a certain period of time. The heating process can use heating plate or oil bath to control the temperature.
Hydrochloric acid treatment
After the reaction was completed, the reaction mixture was cooled to room temperature, and dilute hydrochloric acid (HCl) was slowly added dropwise while stirring to neutralize the inorganic salt product in the reaction system and precipitate it.
Isolation and Purification
The resulting precipitate is separated by centrifugation or filtration, and washed and purified with an appropriate solvent. The eriodictol product with higher purity can be obtained by column chromatography, crystallization and other methods.
Solubility and Stability
In terms of solubility, Eriodictyol powder has low solubility in water, is slightly soluble in DMSO, very slightly soluble in methanol, and practically insoluble in non-polar organic solvents. DMSO is commonly used as the solvent to prepare stock solutions in experiments. Regarding stability, the powder is sensitive to light and high temperature, and is prone to racemization in solution; although the natural enantiomer is predominant, its stability is limited. It is relatively stable in solid form, and strict storage conditions are required to prevent degradation and ensure that its physicochemical properties and activity are unaffected.
The powder is slightly irritating, classified as skin irritant (Category 2) and eye irritant (Category 2A), and may also cause respiratory irritation, with a hazard symbol of Xi. Avoid inhalation of dust and contact with skin and eyes during handling. Wear protective gloves, goggles and other protective equipment, and clean the skin thoroughly after operation. Handling should be performed in a well-ventilated environment. Its hazard code is R36/37/38 and safety statements are S26 and S37/39. In case of spillage, collect the dust for proper disposal to avoid environmental contamination.
Bioactive Properties
It possesses a variety of pharmacological activities and is a bitter-masking dietary flavonoid. It can be slowly absorbed by the human body and exists in plasma and urine as its conjugated form, homoeriodictyol. It exhibits significant antioxidant and anti-inflammatory effects, as well as anticancer, antidiabetic and anti-obesity activities. In addition, it provides neuroprotective, cardiovascular protective and hepatoprotective effects. It exerts neuroprotective effects by activating the Nrf2/ARE signaling pathway, and also acts as an inhibitor of influenza RNA-dependent RNA polymerase, with an IC50 value of 18 nM.
Indigenous peoples of California, North America, have long used the leaves of yerba santa (Eriodictyon californicum) for herbal remedies. By chewing or decocting the leaves, they relieved respiratory discomforts such as cough and asthma, whose soothing effects are closely associated with eriodictyol contained in the leaves. In 1890, yerba santa was officially recognized as a medicinal plant by being included in the United States Pharmacopoeia, laying the foundation for subsequent research on its chemical constituents. In the late 19th century, the scientific community began to focus on the active ingredients of yerba santa; however, limited by separation technologies, only crude extracts could be obtained, and the effective monomers could not be identified.
In 1906, American chemists F. B. Power and T. A. Tutin first reported the isolation of two crystalline phenolic substances from the leaves of yerba santa at a meeting of the American Pharmaceutical Association in Indianapolis. In 1907, the two researchers formally published their findings, naming one compound with the molecular formula C₁₅H₁₂O₆ Eriodictyol and its homologue Homoeriodictyol. In 1909, they further refined the isolation method to obtain sufficient samples, confirmed the basic chemical properties of eriodictyol, and completed the scientific "discovery" and naming of the substance.
From 1909 to 1910, through hydrolysis, derivatization and other experiments, Power and Tutin gradually elucidated the flavone core structure of eriodictyol, identified it as a flavanone compound, and determined the substitution positions of hydroxyl groups in the molecule. In 1940, T. A. Geissman published an improved isolation process. By optimizing extraction and recrystallization procedures, the extraction efficiency and purity of eriodictyol were greatly enhanced, providing technical support for subsequent powdered preparation. During this period, the chemical structure of eriodictyol was fully clarified, removing obstacles for its pulverization and standardized production.
In the late 20th century, with the maturity of natural product extraction and purification technologies, it was produced on a large scale, transitioning from laboratory research to industrial manufacturing. As a bitterness inhibitor and antioxidant, it has been widely used in food and health products. Meanwhile, the academic community has continued to explore its pharmacological activities such as anti-inflammatory and neuroprotective effects, promoting it from a traditional herbal extract to a modern functional ingredient with continuously expanding application value.
FAQ
What is eriodictyol?
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Eriodictyol is a flavonoid that belongs to a subclass of flavanones and is widespread in citrus fruits, vegetables, and medicinally important plants. Eriodictyol has been anticipated to explain the method of its activity via multiple cellular signaling cascades.
What is the structure of Eriodictyol?
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On the basis of the above-cited spectroscopic data, the structure of eriodictyol was unambiguously identified as (S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychroman-4-one (4).
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