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Hesperidin

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Hesperidin Basic information
Hesperidin Pharmacological activity Industry Status Chemical Properties Application Production method
Product Name:Hesperidin
Synonyms:(s)-7-[[6-o-(6-deoxy-alpha-l-mannopyranosyl)-beta-d-glucopyranosyl]oxy]-2,3-dihydro-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4h-1-benzopyran-4-one;VITAMIN P;7-(2-o-(6-deoxy-alpha-l-mannopyranosyl)-beta-d-glucopyranosyloxy)-2,3-dihydro-4',5,7-trihydroxyflavone;7-[[2-O-(6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl]oxy]-5-hydroxy-2(S)-(4-hydroxyphenyl)-4H-1-benzopyran-4-one;CITRUS-HESPERIDIN;HESPERITIN-7-RUTINOSIDE;HESPERIDIN;HESPERIDINE
CAS:520-26-3
MF:C28H34O15
MW:610.56
EINECS:208-288-1
Product Categories:Flavanones;plant extract;Antioxidant;Biochemistry;Disaccharides;Flavonoids;Glycosides;Sugars;Natural Plant Extract;Carbohydrates & Derivatives;Intermediates & Fine Chemicals;Pharmaceuticals;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;natural product;Inhibitors
Mol File:520-26-3.mol
Hesperidin Structure
Hesperidin Chemical Properties
mp 250-255 °C (dec.)(lit.)
alpha -76 º (c=2,pyridine)
storage temp. 2-8°C
color light brown
Merck 4671
Stability:Stable. Incompatible with strong oxidizing agents.
CAS DataBase Reference520-26-3(CAS DataBase Reference)
EPA Substance Registry System4H-1-Benzopyran- 4-one, 7-[[6-O-(6-deoxy-.alpha.-L- mannopyranosyl)-.beta.-D- glucopyranosyl]oxy]-2,3-dihydro- 5-hydroxy-2-(3-hydroxy-4- methoxyphenyl)-, (2S)-(520-26-3)
Safety Information
Hazard Codes Xi
Risk Statements 22-36/37/38
Safety Statements 22-24/25-36/37/39-27-26
WGK Germany 3
RTECS MK6650000
3-10
MSDS Information
ProviderLanguage
Hesperidin English
SigmaAldrich English
ACROS English
Hesperidin Usage And Synthesis
HesperidinHesperidin (glycoside) is a flavonoid substance which has flavanone oxygen glycoside structure. It is weakly acidic with pure being white needle-like crystals. It is also the main component of vitamin P.
the molecular structure of hesperidin
Figure 1 the molecular structure of hesperidin.
After the hydrogenation, hesperidin becomes a natural sweetener, dihydrochalcone, whose sweetness is 1,000 times as high as sucrose. It can be used as a functional food for application. Hesperidin has a variety of biological characteristics. Modern research has found that: hesperidin has various effects such as antioxidant, anti-cancer, anti-mildew, anti-allergy, lowering blood pressure, inhibiting oral cancer and esophageal cancer, maintenance of osmotic pressure, increasing capillary toughness, and lowering cholesterol. Related studies have shown that hesperidin has broad antibacterial spectrum on common food contamination. It has significant inhibitory effect on Bacillus subtilis, Salmonella typhimurium, Shigella bacteria, hemolytic streptococcus and Vibrio cholerae. Therefore, it is widely applied in food additives and food processing.
Pharmacological activity1. Hesperidin is a kind of drug for treatment of hypertension and myocardial infarction. It is used as the pharmaceutical raw material in the pharmaceutical industry and is one of the main components of a Chinese patent medicine, beniol.
2. Hesperidin has various effects such as anti-lipid oxidation, scavenging oxygen free radicals, and anti-inflammatory, anti-viral, anti-bacterial. Long-term use can delay aging and cancer. In short, hesperidin is a kind of flavonoids with clear defined pharmacological activity as well as extensive function of flavonoids. In addition to its application in medicine, it also has wide application in sports pharmacy and sports nutrition and therefore has broad prospects of development and utilization. Its related research work is expected to subject to further deepening.
Industry StatusHesperidin has various effects such as maintaining osmotic pressure, increasing capillary toughness, shortening the bleeding time, and reducing the cholesterol. It is clinically used for the adjuvant treatment of cardiovascular diseases. It can be used for cultivating various kinds of drugs for preventing arteriosclerosis and myocardial infarction. It is one of the major raw materials for synthesizing Chinese patent medicine “beniol”. It can be used as natural antioxidants in the food industry and can also be used in the cosmetics industry.
Hesperidin is mostly presented in the waste of citrus processing such as fruit skin and fruit bag with the highest content being presented in mature skin and tissue (30% -50% in the peel, orange envelope, nuclear, pulp contains 30% -50%, epicarp contains 10%-20%). Orange juice and capsule contain a relative low amount being 1% to 5%. Extraction methods of hesperidin include solvent extraction, alkaline extraction and acid precipitation, carbon adsorption, ion exchange, wherein the alkali extraction and acid precipitation method is simple, low-cost, and has a high extraction rate. Hesperidin can be dissolved in dilute alkali and pyridine as well as hot water (over 70 °C). It is also slightly soluble in methanol but almost insoluble in acetone, benzene and chloroform. The extraction of hesperidin mainly take advantage of its two phenolic hydroxyl groups which under alkaline conditions, has reaction with the sodium ion in the solution to generate sodium salt to be dissolved out; then acidify, cool to precipitate it from solution. Extraction of hesperidin from citrus peels commonly adopts heat extraction and soaks extraction method with a non-idea yield. In recent years, studies on the ultrasonic extraction of the effective components from natural plants (especially herbs) have been widely carried out, and have already obtained some progress. The extraction is first based on the hesperidins’ ring-opening dissolution under alkaline conditions and then further loop closure precipitation for being separated out under acidic conditions. During the extraction process, increasing the amount of the alkali can reduce the necessary amount of ethanol. But it is not recommended to apply a relative large amount of alkaline otherwise hesperidin is easily susceptible to oxidation damage.
Yellow powder of hesperidin
Figure 2 Yellow powder of hesperidin
The above information is edited by the Chemicalbook of Dai Xiongfeng.
Chemical PropertiesIt is light yellow crystalline powder with melting point being 258-262 °C (soften at 252 °C). It is easily soluble in pyridine, sodium hydroxide solution; soluble in dimethyl formamide; slightly soluble in methanol and hot glacial acetic acid; very slightly soluble in ether, acetone, chloroform and benzene.1g of this product can be dissolved in 50L water. It is odorless and tasteless.
ApplicationThe product is a vitamin P type medicine. It is mainly used to enhance the toughness of capillaries. The derivative of hesperidin, methyl hesperidin is also vitamin P type medicine. It has been listed in as a variety in Japan's《Japanese Standard of food additives》.
It is a vitamin drug which can reduce the fragility of capillary used for the adjuvant treatment of hypertension.
Production methodThe product is presented in the pericarp of lemon, citrus, and Citus aurantium. In citrus, the developed system of the mesocarp (white spongy tissue) mostly contains citrus glycosides.。 Instead thinner system of mesocarp mostly contains hesperidin. The product is mainly extracted from the dried, ripe orange peel. Crush the dry orange peel; add 3-6 times the amount of water to soak for about 0.5h to make it soft. Then add 4-10% of the amount of lime and 7-12 times the amount of water; stir uniformly and check the pH. The pH value should reach 11.5-12, otherwise we should supplement lime or sodium hydroxide. After soaking for 1.5-2h, centrifuge and filter with the residues adding 5-7 times the amount of water and further adjust to pH 11.5-12 with proper amount of lime; continue soaking and centrifuge and filter again. After the clarification of the filtrate, add diluted hydrochloric acid for adjusting pH to 5; stand for 2d; collect the precipitate and wash with water to nearly neutral which give the crude product. Add 1% of sodium hydroxide and 50% of ethanol to dissolve the crude product; filter and adjust the filtrate to pH 5 with dilute hydrochloric acid, stand overnight, and collect the precipitate; first wash once with 50% ethanol, and then wash with water to nearly neutral; dry at 70 °C; pulverize and sieve to obtain hesperidin with the total yield being 0.6-1.8%.
Chemical Propertieslight brown powder
UsageA flavanone found in citrus fruits, also regarded as Vitamin P.
Usageantiinflammatory, capillary protectant, hypolipidemic
UsageAnticancer
Hesperidin Preparation Products And Raw materials
Raw materialsLIMONIN(SH)-->Polyurethane foam plastic-->HIDE POWDER
Preparation ProductsETHYL LINOLEATE-->BETA-PHENYLPROPIOPHENONE
Tag:Hesperidin(520-26-3) Related Product Information
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