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Home > Products >  China Largest Factory manufacturer supply 90% 92% 95% 98% Hesperidin CAS 520-26-3

China Largest Factory manufacturer supply 90% 92% 95% 98% Hesperidin CAS 520-26-3 CAS NO.520-26-3

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Keywords

  • Hesperidin
  • Hesperidin
  • 520-26-3

Quick Details

  • ProName: China Largest Factory manufacturer sup...
  • CasNo: 520-26-3
  • Molecular Formula: 520-26-3
  • Appearance: dendritic needle crystal
  • Application: Pharm chemicals industry
  • DeliveryTime: 3-5 days
  • PackAge: 25KG/Drum
  • Port: Shanghai Guangzhou Qingdao Shenzhen
  • ProductionCapacity: 200 Metric Ton/Month
  • Purity: 99%
  • Storage: 2-8°C
  • Transportation: By air /Sea/ coruier
  • LimitNum: 1 Kilogram
  • Ash Content: 10
  • Heavy Metal: 10
  • Voluntary Standards: QS
  • Valid Period: 2
  • Color: white
  • Melting point: ≥350°C
  • Boiling point: 363.24°C (rough estimate)
  • density: 1.667
  • solubility: 1 M NaOH: 10 mg/mL, dark green
  • Water Solubility: <0.1 g/100 mL at 21 oC
  • Stability: Stable. Combustible. Incompatible with...

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                                  PRODUCT DETAILS   

Hesperidin

【Product name】 Hesperidin 

 【CAS NOe】520-62-3

【Alias】Hesperidin, Hesperidin, Hesperidin

【Molecular formula and molecular weight】C28H34O15 ; 610.55

【Source】 This product is the dried young fruit extract of Citrus aurantium L. and its cultivars or Citrus sinensis Osbeck

【Product Specifications】90% 92% 95% 98%

【Product Property】Thin dendritic needle crystal

【Product Uses】as raw materials for medicine or cosmetics.

【Product packaging 25 kg cardboard drum (diameter 37 cm, height 50 cm).

【Solvent】water, ethanol

                       

Hesperidin Basic information
Hesperidin Pharmacological activity Industry Status Chemical Properties Uses 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;HESPERIDIN, HPLC WS-10001-(HD-0489)-2002 90%;HESPERIDIN HEAVY 92% BY HPLC;(S)-7-[[6-O-(6-Deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl]oxy]-2,3-dihydro-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one;7-[6-O-(6-Deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyloxy]-2α-(3-hydroxy-4-methoxyphenyl)-5-hydroxy-2,3-dihydro-4H-1-benzopyran-4-one;Hesperidin,97%,includes analogeous compounds;Hesperidin ,98%;Hesperidin,Hesperetin 7-rhamnoglucoside, Hesperitin-7-rutinoside
CAS: 520-26-3
MF: C28H34O15
MW: 610.56
EINECS: 208-288-1
Product Categories: natural product;plant extract;Flavanones;Antioxidant;Biochemistry;Disaccharides;Flavonoids;Glycosides;Sugars;Natural Plant Extract;chemical reagent;pharmaceutical intermediate;phytochemical;Inhibitors;Carbohydrates & Derivatives;Intermediates & Fine Chemicals;Pharmaceuticals;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
Mol File: 520-26-3.mol
Hesperidin Structure
 
Hesperidin Chemical Properties
Melting point  250-255 °C (dec.)(lit.)
alpha  -76 º (c=2,pyridine)
Boiling point  576.16°C (rough estimate)
density  1.3290 (rough estimate)
refractive index  1.5940 (estimate)
storage temp.  Sealed in dry,2-8°C
solubility  DMSO (Slightly), Pyridine (Slightly, Sonicated)
pka 7.15±0.40(Predicted)
form  Powder
color  light brown
Water Solubility  Insoluble in water. Soluble in organic solvents such as DMSO.
Sensitive  Hygroscopic
Merck  14,4671
BRN  75140
Stability: Stable. Incompatible with strong oxidizing agents.
InChIKey QUQPHWDTPGMPEX-QJBIFVCTSA-N
CAS DataBase Reference 520-26-3(CAS DataBase Reference)
EPA Substance Registry System Hesperidin (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
TSCA  Yes
HS Code  29389090
MSDS Information
Provider Language
Hesperidin English
SigmaAldrich English
ACROS English
 
Hesperidin Usage And Synthesis
Hesperidin Hesperidin (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 activity 1. 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 Status Hesperidin 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 Properties It 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.
Uses The 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 method The 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%.
Description Hesperidin exists mainly in the peel of lemon, orange, and Seville orange flower, which belong to facilitating medicine. These Chinese medicines are warm and fragrant with the function of eliminating depression and knots. They cure abdominal distension, belching swallow acid pain, nausea and vomiting, diarrhea or constipation caused by the spleen, and stomach qi zhi; and they also cure depression, hernia, breast pain, and menoxenia caused by liver qi; moreover, they cure chest pain, cough, and asthma, which are caused by lung qi.
Modern research has shown that li qi medicines have an extensive effect, such as regulatory effect on the digestive system, and they control the bronchial smooth muscle, the uterus smooth muscle, and the cardiovascular system. The base of the effect of li qi medicines in inverse, anti-nausea, antidiarrheal, and analgesia pharmacological effects is its effect in inhibiting gastric bowel movement; its exciting gastrointestinal movement is the foundation to eliminate swelling; its effect in relaxation of the bronchial smooth muscle is the foundation of pharmacological effects in antinausea. The intravenous injection to treat shock effect is the new development of li qi medicine.
Description Hesperidin is a flavanone rutinoside first isolated from citrus peels. It is metabolized by intestinal bacteria to an aglycone form, hesperetin (Item No. 10006084), which is thought to be more bioavailable due to reduced polarity that allows for increased cell permeability. At 100 μM, hesperidin has been shown to increase the cytotoxicity of doxorubicin (Item No. 15007) on MCF-7 and HeLa cancer cells in vitro by inhibiting cell cycle progression and upregulating apoptosis. It also is reported to produce estrogenic effects, decreasing serum and hepatic lipid concentrations and reducing osteoporosis in ovariectomized rats. Hesperidin produces free radical scavenging activity in various in vitro antioxidant assays.
Chemical Properties light brown powder
Physical properties Appearance: fine dendritic crystal (precipitation at pH 6–7), odorless, tasteless. Melting point: 258–262 °C (softening at 250 °C). Solubility: 1 g of hesperidin can be soluble in 50 l of water. Hesperidin dissolves in dimethyl formamide and formamide at 60 °C. It is slightly soluble in methanol and hot ice acetic acid and hardly soluble in acetone, benzene, and chloroform and is soluble in dilute alkali and pyridine.
History Hesperidin is the glycoside in the form of hesperidin and rubiose and is a derivative of dihydroflavonoids. It widely exists in legume, birch, lip flower, butterfly flower, Rutaceae, and citrus plants. Hesperidin is an important composition of citrus pulp and peel; most of hesperidin exists in citrus processing waste such as skin and fruit bag. Mature skin and tissue have the highest content of hesperidin (30–50% in endocarp; 30–50% in orange collaterals, nuclear, and pulp; and 10–20% in exo_x005fcarp); the content of hesperidin is relatively low in juice and orange bag, which is about 1–5%. The crude extracts of hesperidin was first discovered in 1827 by Lebreton. Then the Hungarian scholar Albert Szent-Gyorgi discovered that the flavonoids have a protective microvascular effect in 1936, which is similar to that of vitamin P. Preparation of vitamin P was made in 1938. It was not until 1949 that it was discovered that vitamin P was made up of two flavonoids, luteolin and hesperidin, which are believed to be vitamin active. This substance, which was later named as vitamin P, was designed to reduce blood vessel permeability and brittleness, as well as alleviate bad blood and vitamin C deficiency. It was later discovered that the substance had an antioxidant effect, so the name of vitamin P was abandoned. Due to the widespread distribution of hesperidin in plant medicine, the research and development have been widely followed.
Uses vitamin P is considered a vascular protector and an anti-inflammatory agent, vitamin P is said to promote capillary health and increase resistance to collagen destruction. Vitamin P is a bioflavonoid that can work in conjunction with vitamin C, helping prevent oxidation of the latter. Vitamin P is found in such food sources as apricots, broccoli, citrus fruit pulp, grapes, prunes, and spinach.
Uses Hesperidin is a flavoring agent that is a bioflavonoid found in citrus pulp. it has minor use as a flavorant.
Uses A flavanone found in citrus fruits, also regarded as Vitamin P.
Uses antiinflammatory, capillary protectant, hypolipidemic
Uses Anticancer
Definition ChEBI: A disaccharide derivative that consists of hesperetin substituted by a 6-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage.
Indications Hesperidin can be used for cardiovascular disease prevention and treatment, blood sugar and blood lipid and blood pressure regulation, circulatory system regulation, and body regulation, and it can also be used as an antibacterial, anti-inflammatory, and antiviral.
Pharmacology The pharmacological effect of hesperidin is widespread, and people thought it was vitamin P in the early days, but in recent years, people found that it has other functions such as controlling blood pressure, antiallergic, reducing bone mineral density and cholesterol, improving enzyme activity and microcirculation, antibacterial, anti-inflammatory, anti-hepatitis B, antitumor, and other pharmacological effects.Hesperidin has the function of vitamin P, which can reduce capillary permeability and prevent microvascular hemorrhage. Intraperitoneal injection of hesperidin at 175–250 mg/kg in mice could increase permeability of blood vessels by antihistamine and inhibiting hemolytic lecithin. Hesperidin has antiviral and antimicrobial effect, and preincubation with hesperidin at 200 mg/ml protects the cells from viruses. One to 10 μg/ml of hesperidin effectively inhibits the growth of the fungus. It has the effect of maintaining the normal osmotic pressure of the blood vessels, reducing the shortness of blood vessels, shortening bleeding time, reducing blood fat, and preventing atherosclerosis; hesperidin has an effect on the gastrointestinal tract, which can excite the smooth muscle transiently and then inhibit it, and it is a major component of the diet drug; hesperidin has an effect of anti-lipid peroxidation and scavenging hydroxyl radical. Hesperidin is a newly discovered flavonoid compound which has an effect in the central nervous system; it has a sedative effect. At the same time, hesperidin has the effect of lowering cholesterol, curing rheumatism, and inhibiting skin pigmentation. Hesperidin is a strong affinity for estrogen receptors, which can be used in estrogen receptors to prevent bone loss and reduce the number of osteoblasts.
Hesperidin has a significant inhibitory effect on human lung cancer, colorectal cancer, kidney cancer, and human breast cancer cells, which can be used for cancer prevention.
Clinical Use Hesperidin has the effect to maintain osmotic pressure, strengthen the capillary toughness, shorten the bleeding time, lower cholesterol, and so on. Although hesperidin cannot be used as independent medication, it is recorded in the pharmacopoeia that hesperidin, as auxiliary materials, is widely used to aid in the treatment of cardiovascular system; it can be configured as a variety of drugs to prevent hardening of the arteries and myocardial infarction. It is one of the main raw materials of medicine “pulse.” Hesperidin is used as auxiliary materials for the treatment of vascular brittleness, bedsore, rheumatoid arthritis, vitamin C deficiency disease, trauma, obstetric disease, gum inflammation, edema, and gastrointestinal tract disease in the world. Hesperidin can be used to produce an anticancer drug called diosmin. Natural antioxidant is available in the food industry. It is also used in the cosmetics industry.
Purification Methods Dissolve hesperidine in dilute aqueous alkali and precipitate it by adjusting the pH to 6-7. [Beilstein 18 III/IV 3219, 18/5 V 218.]
 
Hesperidin Preparation Products And Raw materials
Raw materials LIMONIN(SH)-->Polyurethane foam plastic-->HIDE POWDER
Preparation Products ETHYL LINOLEATE-->BETA-PHENYLPROPIOPHENONE
 

 

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Leader Biochemical Group is a large leader incorporated industry manufacturers and suppliers of advanced refined raw materials From the year of 1996 when our factory was put into production to year of 2020, our group has successively invested in more than 52 factories with shares and subordinates.We focus on manufacture Pharm & chemicals, functional active ingredients, nutritional Ingredients, health care products, cosmetics, pharmaceutical and refined feed, oil, natural plant ingredients industries to provide top quality of GMP standards products.All the invested factories' product lines cover API and intermediates, vitamins, amino acids, plant extracts, daily chemical products, cosmetics raw materials, nutrition and health care products, food additives, feed additives, essential oil products, fine chemical products and agricultural chemical raw materials And flavors and fragrances. Especially in the field of vitamins, amino acids, pharmaceutical raw materials and cosmetic raw materials, we have more than 20 years of production and sales experience. All products meet the requirements of high international export standards and have been recognized by customers all over the world. Our manufacture basement & R&D center located in National Aerospace Economic & Technical Development Zone Xi`an Shaanxi China. Now not only relying on self-cultivation and development as well as maintains good cooperative relations with many famous research institutes and universities in China. Now, we have closely cooperation with Shanghai Institute of Organic Chemistry of Chinese Academy of Science, Beijing Institute of Material Medical of Chinese Academy of Medical Science, China Pharmaceutical University, Zhejiang University. Closely cooperation with them not only integrating Science and technology resources, but also increasing the R&D speed and improving our R&D power. Offering Powerful Tech supporting Platform for group development. Keep serve the manufacture and the market as the R&D central task, focus on the technical research.  Now there are 3 technology R & D platforms including biological extract, microorganism fermentation and chemical synthesis, and can independently research and develop kinds of difficult APIs and pharmaceutical intermediates. With the strong support of China State Institute of Pharmaceutical Industry (hereinafter short for CSIPI), earlier known as Shanghai Institute of Pharmaceutical Industry (SIPI), we have unique advantages in the R & D and industrialization of high-grade, precision and advanced products.  Now our Group technical force is abundant, existing staff more that 1000 people, senior professional and technical staff accounted for more than 50% of the total number of employees, including 15 PhD research and development personnel, 5 master′ S degree in technical and management personnel 9 people. We have advanced equipment like fermentation equipment and technology also extraction, isolation, purification, synthesis with rich production experience and strict quality control system, According to the GMP required, quickly transforming the R&D results to industrial production in time, it is our advantages and our products are exported to North and South America, Europe, Middle East, Africa, and other five continents and scale the forefront in the nation, won good international reputation.  We believe only good quality can bring good cooperation, quality is our key spirit during our production, we are warmly welcome clients and partner from all over the world contact us for everlasting cooperation, Leader will be your strong, sincere and reliable partner in China.

 

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Hesperidin

【Product name】 Hesperidin 

 【CAS NOe】520-62-3

【Alias】Hesperidin, Hesperidin, Hesperidin

【Molecular formula and molecular weight】C28H34O15 ; 610.55

【Source】 This product is the dried young fruit extract of Citrus aurantium L. and its cultivars or Citrus sinensis Osbeck

【Product Specifications】90% 92% 95% 98%

【Product Property】Thin dendritic needle crystal

【Product Uses】as raw materials for medicine or cosmetics.

【Product packaging 25 kg cardboard drum (diameter 37 cm, height 50 cm).

【Solvent】water, ethanol

                       

Hesperidin Basic information
Hesperidin Pharmacological activity Industry Status Chemical Properties Uses 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;HESPERIDIN, HPLC WS-10001-(HD-0489)-2002 90%;HESPERIDIN HEAVY 92% BY HPLC;(S)-7-[[6-O-(6-Deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl]oxy]-2,3-dihydro-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one;7-[6-O-(6-Deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyloxy]-2α-(3-hydroxy-4-methoxyphenyl)-5-hydroxy-2,3-dihydro-4H-1-benzopyran-4-one;Hesperidin,97%,includes analogeous compounds;Hesperidin ,98%;Hesperidin,Hesperetin 7-rhamnoglucoside, Hesperitin-7-rutinoside
CAS: 520-26-3
MF: C28H34O15
MW: 610.56
EINECS: 208-288-1
Product Categories: natural product;plant extract;Flavanones;Antioxidant;Biochemistry;Disaccharides;Flavonoids;Glycosides;Sugars;Natural Plant Extract;chemical reagent;pharmaceutical intermediate;phytochemical;Inhibitors;Carbohydrates & Derivatives;Intermediates & Fine Chemicals;Pharmaceuticals;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
Mol File: 520-26-3.mol
Hesperidin Structure
 
Hesperidin Chemical Properties
Melting point  250-255 °C (dec.)(lit.)
alpha  -76 º (c=2,pyridine)
Boiling point  576.16°C (rough estimate)
density  1.3290 (rough estimate)
refractive index  1.5940 (estimate)
storage temp.  Sealed in dry,2-8°C
solubility  DMSO (Slightly), Pyridine (Slightly, Sonicated)
pka 7.15±0.40(Predicted)
form  Powder
color  light brown
Water Solubility  Insoluble in water. Soluble in organic solvents such as DMSO.
Sensitive  Hygroscopic
Merck  14,4671
BRN  75140
Stability: Stable. Incompatible with strong oxidizing agents.
InChIKey QUQPHWDTPGMPEX-QJBIFVCTSA-N
CAS DataBase Reference 520-26-3(CAS DataBase Reference)
EPA Substance Registry System Hesperidin (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
TSCA  Yes
HS Code  29389090
MSDS Information
Provider Language
Hesperidin English
SigmaAldrich English
ACROS English
 
Hesperidin Usage And Synthesis
Hesperidin Hesperidin (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 activity 1. 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 Status Hesperidin 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 Properties It 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.
Uses The 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 method The 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%.
Description Hesperidin exists mainly in the peel of lemon, orange, and Seville orange flower, which belong to facilitating medicine. These Chinese medicines are warm and fragrant with the function of eliminating depression and knots. They cure abdominal distension, belching swallow acid pain, nausea and vomiting, diarrhea or constipation caused by the spleen, and stomach qi zhi; and they also cure depression, hernia, breast pain, and menoxenia caused by liver qi; moreover, they cure chest pain, cough, and asthma, which are caused by lung qi.
Modern research has shown that li qi medicines have an extensive effect, such as regulatory effect on the digestive system, and they control the bronchial smooth muscle, the uterus smooth muscle, and the cardiovascular system. The base of the effect of li qi medicines in inverse, anti-nausea, antidiarrheal, and analgesia pharmacological effects is its effect in inhibiting gastric bowel movement; its exciting gastrointestinal movement is the foundation to eliminate swelling; its effect in relaxation of the bronchial smooth muscle is the foundation of pharmacological effects in antinausea. The intravenous injection to treat shock effect is the new development of li qi medicine.
Description Hesperidin is a flavanone rutinoside first isolated from citrus peels. It is metabolized by intestinal bacteria to an aglycone form, hesperetin (Item No. 10006084), which is thought to be more bioavailable due to reduced polarity that allows for increased cell permeability. At 100 μM, hesperidin has been shown to increase the cytotoxicity of doxorubicin (Item No. 15007) on MCF-7 and HeLa cancer cells in vitro by inhibiting cell cycle progression and upregulating apoptosis. It also is reported to produce estrogenic effects, decreasing serum and hepatic lipid concentrations and reducing osteoporosis in ovariectomized rats. Hesperidin produces free radical scavenging activity in various in vitro antioxidant assays.
Chemical Properties light brown powder
Physical properties Appearance: fine dendritic crystal (precipitation at pH 6–7), odorless, tasteless. Melting point: 258–262 °C (softening at 250 °C). Solubility: 1 g of hesperidin can be soluble in 50 l of water. Hesperidin dissolves in dimethyl formamide and formamide at 60 °C. It is slightly soluble in methanol and hot ice acetic acid and hardly soluble in acetone, benzene, and chloroform and is soluble in dilute alkali and pyridine.
History Hesperidin is the glycoside in the form of hesperidin and rubiose and is a derivative of dihydroflavonoids. It widely exists in legume, birch, lip flower, butterfly flower, Rutaceae, and citrus plants. Hesperidin is an important composition of citrus pulp and peel; most of hesperidin exists in citrus processing waste such as skin and fruit bag. Mature skin and tissue have the highest content of hesperidin (30–50% in endocarp; 30–50% in orange collaterals, nuclear, and pulp; and 10–20% in exo_x005fcarp); the content of hesperidin is relatively low in juice and orange bag, which is about 1–5%. The crude extracts of hesperidin was first discovered in 1827 by Lebreton. Then the Hungarian scholar Albert Szent-Gyorgi discovered that the flavonoids have a protective microvascular effect in 1936, which is similar to that of vitamin P. Preparation of vitamin P was made in 1938. It was not until 1949 that it was discovered that vitamin P was made up of two flavonoids, luteolin and hesperidin, which are believed to be vitamin active. This substance, which was later named as vitamin P, was designed to reduce blood vessel permeability and brittleness, as well as alleviate bad blood and vitamin C deficiency. It was later discovered that the substance had an antioxidant effect, so the name of vitamin P was abandoned. Due to the widespread distribution of hesperidin in plant medicine, the research and development have been widely followed.
Uses vitamin P is considered a vascular protector and an anti-inflammatory agent, vitamin P is said to promote capillary health and increase resistance to collagen destruction. Vitamin P is a bioflavonoid that can work in conjunction with vitamin C, helping prevent oxidation of the latter. Vitamin P is found in such food sources as apricots, broccoli, citrus fruit pulp, grapes, prunes, and spinach.
Uses Hesperidin is a flavoring agent that is a bioflavonoid found in citrus pulp. it has minor use as a flavorant.
Uses A flavanone found in citrus fruits, also regarded as Vitamin P.
Uses antiinflammatory, capillary protectant, hypolipidemic
Uses Anticancer
Definition ChEBI: A disaccharide derivative that consists of hesperetin substituted by a 6-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage.
Indications Hesperidin can be used for cardiovascular disease prevention and treatment, blood sugar and blood lipid and blood pressure regulation, circulatory system regulation, and body regulation, and it can also be used as an antibacterial, anti-inflammatory, and antiviral.
Pharmacology The pharmacological effect of hesperidin is widespread, and people thought it was vitamin P in the early days, but in recent years, people found that it has other functions such as controlling blood pressure, antiallergic, reducing bone mineral density and cholesterol, improving enzyme activity and microcirculation, antibacterial, anti-inflammatory, anti-hepatitis B, antitumor, and other pharmacological effects.Hesperidin has the function of vitamin P, which can reduce capillary permeability and prevent microvascular hemorrhage. Intraperitoneal injection of hesperidin at 175–250 mg/kg in mice could increase permeability of blood vessels by antihistamine and inhibiting hemolytic lecithin. Hesperidin has antiviral and antimicrobial effect, and preincubation with hesperidin at 200 mg/ml protects the cells from viruses. One to 10 μg/ml of hesperidin effectively inhibits the growth of the fungus. It has the effect of maintaining the normal osmotic pressure of the blood vessels, reducing the shortness of blood vessels, shortening bleeding time, reducing blood fat, and preventing atherosclerosis; hesperidin has an effect on the gastrointestinal tract, which can excite the smooth muscle transiently and then inhibit it, and it is a major component of the diet drug; hesperidin has an effect of anti-lipid peroxidation and scavenging hydroxyl radical. Hesperidin is a newly discovered flavonoid compound which has an effect in the central nervous system; it has a sedative effect. At the same time, hesperidin has the effect of lowering cholesterol, curing rheumatism, and inhibiting skin pigmentation. Hesperidin is a strong affinity for estrogen receptors, which can be used in estrogen receptors to prevent bone loss and reduce the number of osteoblasts.
Hesperidin has a significant inhibitory effect on human lung cancer, colorectal cancer, kidney cancer, and human breast cancer cells, which can be used for cancer prevention.
Clinical Use Hesperidin has the effect to maintain osmotic pressure, strengthen the capillary toughness, shorten the bleeding time, lower cholesterol, and so on. Although hesperidin cannot be used as independent medication, it is recorded in the pharmacopoeia that hesperidin, as auxiliary materials, is widely used to aid in the treatment of cardiovascular system; it can be configured as a variety of drugs to prevent hardening of the arteries and myocardial infarction. It is one of the main raw materials of medicine “pulse.” Hesperidin is used as auxiliary materials for the treatment of vascular brittleness, bedsore, rheumatoid arthritis, vitamin C deficiency disease, trauma, obstetric disease, gum inflammation, edema, and gastrointestinal tract disease in the world. Hesperidin can be used to produce an anticancer drug called diosmin. Natural antioxidant is available in the food industry. It is also used in the cosmetics industry.
Purification Methods Dissolve hesperidine in dilute aqueous alkali and precipitate it by adjusting the pH to 6-7. [Beilstein 18 III/IV 3219, 18/5 V 218.]
 
Hesperidin Preparation Products And Raw materials
Raw materials LIMONIN(SH)-->Polyurethane foam plastic-->HIDE POWDER
Preparation Products ETHYL LINOLEATE-->BETA-PHENYLPROPIOPHENONE

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