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hesperidin

Hesperiden

CAS: 520-26-3

Molecular Formula: C28H34O15

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hesperidin - Names and Identifiers

Name Hesperiden
Synonyms NSC44184
Cirantin
Usaf cf-3
Vitamin P
Hesperidin
Hesperiden
Hesperidine
Hesperidoside
Glucopyranoside
(2S)-Hesperidin
S)-(-)-Hesperidine
Hesperetin 7-rutinoside
Hesperetin-7-rutinoside
Hesperitin-7-rhamnoglucoside
Hesperetin 7-rhamnoglucoside
hesperetin-7[6-O-(6-deoxy-.alpha.-L-mannopyranosyl)]-beta-D-
Hesperidin,Hesperetin 7-rhamnoglucoside, Hesperitin-7-rutinoside
Hesperetin 7-[6-O- (6-deoxy-.alpha.-L-mannopyranosyl)]-.beta.-D-gluco pyranosid e)
5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxo-3,4-dihydro-2H-chromen-7-yl 6-O-(6-deoxyhexopyranosyl)hexopyranoside
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
(2S)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxo-3,4-dihydro-2H-chromen-7-yl 6-O-(6-deoxy-beta-L-mannopyranosyl)-beta-D-glucopyranoside
(2S)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxo-3,4-dihydro-2H-chromen-7-yl 6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranoside
(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
5-hydroxy-2-(3-hydroxy-4-methoxy-phenyl)-7-[3,4,5-trihydroxy-6-[(3,4,5 -trihydroxy-6-methyl-oxan-2-yl)oxymethyl]oxan-2-yl]oxy-chroman-4-one
(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
(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
(2S)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxo-3,4-dihydro-2H-chromen-7-yl 6-O-(6-deoxy-alpha-L-erythro-hexopyranosyl)-beta-D-threo-hexopyranoside
7-[[6-O-(6-deoxy-.alpha.-L-mannopyranosyl)-.be ta.-D-glucopyranosyl ]oxy]-2,3-dihydro-5-hydroxy-2-(3-hydroxy-4-methox yphenyl)-, (S)-, 4H-1-Benzopyran-4-one, 7-[[6-O- (6-deoxy-.alpha.-L-mannopyranosyl-.bet a.-D-glucopyranosyl] oxy]-2,3-dihydro-5-hydr
CAS 520-26-3
EINECS 208-288-1
InChI InChI=1/C28H34O15/c1-10-21(32)23(34)25(36)27(40-10)39-9-19-22(33)24(35)26(37)28(43-19)41-12-6-14(30)20-15(31)8-17(42-18(20)7-12)11-3-4-16(38-2)13(29)5-11/h3-7,10,17,19,21-30,32-37H,8-9H2,1-2H3/t10?,17-,19?,21-,22+,23-,24-,25?,26?,27+,28+/m0/s1
InChIKey QUQPHWDTPGMPEX-QJBIFVCTSA-N

hesperidin - Physico-chemical Properties

Molecular FormulaC28H34O15
Molar Mass610.56
Density1.3290 (rough estimate)
Melting Point250-255°C (dec.)(lit.)
Boling Point576.16°C (rough estimate)
Specific Rotation(α)-76 º (c=2,pyridine)
Flash Point305.5°C
Water SolubilityInsoluble in water. Soluble in organic solvents such as DMSO.
Solubility Almost insoluble in acetone, benzene, chloroform, slightly soluble in methanol, hot glacial acetic acid, soluble in formamide, dimethylamide, easily soluble in dilute alkali solution.
Vapor Presure0mmHg at 25°C
AppearanceWhite to light brown powder
Colorlight brown
Merck14,4671
BRN75140
pKa7.15±0.40(Predicted)
Storage ConditionSealed in dry,2-8°C
StabilityStable. Incompatible with strong oxidizing agents.
SensitiveHygroscopic
Refractive Index1.5940 (estimate)
MDLMFCD00075663
Physical and Chemical PropertiesDerived from pericarpium citri reticulatae
UseVitamin drugs, can reduce the fragility of the capillary, for the adjuvant treatment of hypertension

hesperidin - Risk and Safety

Hazard SymbolsXi - Irritant
Irritant
Risk CodesR22 - Harmful if swallowed
R36/37/38 - Irritating to eyes, respiratory system and skin.
Safety DescriptionS22 - Do not breathe dust.
S24/25 - Avoid contact with skin and eyes.
S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection.
S27 - Take off immediately all contaminated clothing.
S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
WGK Germany3
RTECSMK6650000
FLUKA BRAND F CODES3-10
TSCAYes
HS Code29389090

hesperidin - Nature

Open Data Verified Data
It is essentially insoluble in water, ether, acetone, chloroform and benzene, and 1g of hesperidin is soluble in 50L of water. The specific optical rotation was -76. (2%, pyridine). Has the effect of strengthening the vascular wall of the fur.

Last Update：2024-01-02 23:10:35

hesperidin - Preparation Method

Open Data Verified Data

mainly lemon, citrus, instead of flowers and other fruit peel as raw material preparation.

Last Update：2022-01-01 11:13:51

hesperidin - Application

Open Data Verified Data

can be used as a nutrition fortifier.

Last Update：2025-08-19 16:24:40

hesperidin - Reference Information

LogP0.3 at 25℃
EPA chemical information Information provided by: ofmpub.epa.gov (external link)
introduction hesperidin (glycoside) is a kind of flavonoid substance with dihydroflavonoid glycoside structure and weakly acidic. Pure product is a white needle-like crystal, which is the main component of vitamin P.
After hydrogenation of hesperidin, it is a natural sweetener dihydrochar ketone. Its sweetness is 1000 times that of sucrose. It can be used as a functional food. Hesperidin has a variety of biological characteristics. Modern research has found that hesperidin can resist oxidation and cancer, prevent mildew, anti-allergy, lower blood pressure, inhibit oral cancer and esophageal cancer, maintain osmotic pressure, enhance capillary toughness, and lower cholesterol. Relevant studies have shown that hesperidin has a broad-spectrum antibacterial effect on common food contaminated bacteria, and has a significant inhibitory effect on Bacillus subtilis, Salmonella typhimurium, Shigella freund, Streptococcus hemolyticus and Vibrio cholerae. Therefore, it is widely used in food additives and food processing.
pharmacological activity (1) hesperidin is a drug for the treatment of hypertension and myocardial infarction. it is used as a raw material in the pharmaceutical industry and is one of the main components of the proprietary Chinese medicine maitong.
(2) Hesperidin has anti-lipid oxidation, scavenging oxygen free radicals, anti-inflammatory, anti-viral, antibacterial effects, long-term use can delay aging and anti-cancer. In a word, hesperidin is a kind of flavonoid compound with definite pharmacological activity and wide function. Besides its medical use, hesperidin also has a wide range of uses in sports pharmacy and sports nutrition, so it has broad development and utilization prospects, and its related research work is expected to be further carried out systematically.
Application Hesperidin has the effects of maintaining osmotic pressure, enhancing capillary toughness, shortening bleeding time, lowering cholesterol, etc. It is clinically used for adjuvant treatment of cardiovascular diseases. It can cultivate a variety of drugs to prevent arteriosclerosis and myocardial infarction. It is one of the main raw materials of the patent medicine "Mai Tong. It can be used as a natural antioxidant in the food industry. It can also be used in the cosmetics industry.
Relevant studies have shown that hesperidin has a broad-spectrum antibacterial effect on common food contaminated bacteria, and has a significant inhibitory effect on Bacillus subtilis, Salmonella typhimurium, Shigella freund, Streptococcus hemolyticus and Vibrio cholerae. Therefore, it is widely used in food additives and food processing.
use hesperidin is an important natural phenolic compound considered to be beneficial to health. it can reduce the fragility and permeability of capillaries and is used for adjuvant treatment of hypertension and capillary hemorrhagic diseases. It has an improving effect on the reduction of capillary resistance (enhancing the effect of vitamin C), has anti-inflammatory, anti-viral, and has the effect of preventing frostbite and inhibiting the aldehyde reductase of the rat eye lens.
Vitamin drugs can reduce the fragility of capillaries and are used for adjuvant treatment of hypertension
This vitamin P drugs are used to enhance the toughness of capillaries. Methyl hesperidin, a derivative of hesperidin, is also a vitamin P drug, which is a variety included in Japan's "Food Additives.
Vitamin medicine. Can reduce the brittleness and permeability of the capillary.
a flavonoid phytochemical extracted from citrus.
extraction process hesperidin is mostly found in citrus processing waste. if the content of hesperidin in skin and fruit capsule is the highest in mature peel and tissue (endocarp 30%-50%, pericarp, kernel and pulp 30%-50%, exocarp 10%-20%), and the content in juice and orange capsule is lower by 1%-5%. The extraction methods of hesperidin include solvent extraction, alkali extraction and acid precipitation, carbon powder adsorption and ion exchange. The alkali extraction and acid precipitation method is simple, low cost and high extraction rate. Hesperidin is soluble in dilute alkali and pyridine and hot water above 70 ℃, slightly soluble in methanol, almost insoluble in acetone, benzene and chloroform.
The extraction of hesperidin is mainly to use the two phenolic hydroxyl groups contained in it under alkaline conditions to react with sodium ions in the solution to generate sodium salt and dissolve, and then acidify and cool to make it separate out of the solution. Hesperidin extracted from citrus peel is generally extracted by thermal extraction and immersion extraction, and the yield is not ideal. In recent years, ultrasonic extraction of effective components from natural plants (especially Chinese herbal medicines) has been widely carried out and some progress has been made. The use of hesperidin in alkaline conditions under open-loop dissolution for extraction, acidic conditions under closed-loop precipitation for separation, extraction when increasing the amount of alkali, can reduce the amount of ethanol, but alkaline should not be too large, otherwise, hesperidin is easy to be destroyed by oxidation.
production method this product is contained in the peel of lemon, citrus, substitute flower, etc. In the genus Citrus (Cirtus), the mesocarp (white spongy tissue) developed system contains more citrus glycosides, and the mesocarp thinner system contains more hesperidin. This line is extracted from dry, mature orange peel. Chop the dried orange peel roughly and soak it in 3-6 times of water for about 0.5h to make it soft. Add 4-10% amount of lime and 7-12 times the amount of water, stir evenly, and check the pH value. The pH value is required to reach 11.5-12, otherwise lime or sodium hydroxide should be added. After soaking for 1.5-2h, centrifugally filter, add 5-7 times the amount of water to the filter residue, adjust the pH to 11.5-12 with appropriate amount of lime, continue soaking and centrifugally filter. After the filtrate is clear, add dilute hydrochloric acid to adjust the pH to 5, let stand for 2 days, collect the precipitate, and wash with water until it is close to neutral to obtain crude product. Dissolve the crude product with a mixture of 1% sodium hydroxide and 50% ethanol, filter, adjust the pH to 5 with dilute hydrochloric acid, let it stand overnight, collect the sediment, wash it with 50% ethanol once, then wash it with water until it is close to neutral, dry at 70 ℃, crush and sift to obtain hesperidin. The total yield of orange peel powder was 0.6-1.8%.
Last Update：2024-04-09 21:54:55
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