Hesperidin
- Iupac Name：(2S)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxy-2,3-dihydrochromen-4-one
- CAS No.: 520-26-3
- Molecular Weight：610.56100
- Modify Date.: 2022-10-28 09:16
- Introduction: Hesperidin (HP) is a bioflavonoid that plays a role in plant defense and is abundant in citrus species, such as grapefruit, lemon and orange. Hesperidin is used effectively as a supplemental agent in complementary therapy protocols, since it possesses biological and pharmacological properties as an effective antioxidant, anti-inflammatory, anti-carcinogenic, and anti-hypertensive agent with lipid-lowering activity[1]IC50: hesperidin (IC50=116.68μmo/L))[4]in vitro: hesperidin and linarin
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1. Names and Identifiers
- 1.1 Name
- Hesperidin
- 1.2 Synonyms
(2S)-5-Hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxo-3,4-dihydro-2H-chromen-7-yl 6-O-(6-deoxyhexopyranosyl)hexopyranoside (S)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-((((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)chroma (S)-5-Hydroxy-2-(3-hydroxy-4-methoxy-phenyl)-7-[3,4,5-trihydroxy-6-(3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-2-yloxy]-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-α-L-mannopyranosyl)-β-D-glucopyranosyl]oxy]-2,3-dihydro-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one 4H-1-Benzopyran-4-one, 7-[[6-O-(6-deoxyhexopyranosyl)hexopyranosyl]oxy]-2,3-dihydro-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-, (2S)- 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 cirantin Cirontin EINECS 208-288-1 Hespeidin Hesperetin 7-rhamnoglucoside,Hesperitin-7-rutinoside Hesperetin7-rhamnoglucoside Hesperetin7-rutinoside Hesperiden Hesperidin,Hesperetin 7-rhamnoglucoside, Hesperitin-7-rutinoside Hesperidoside Hespiridin MFCD00075663 Neobiletin usafcf-3 VITAMIN P
- 1.3 CAS No.
- 520-26-3
- 1.4 CID
- 10621
- 1.5 EINECS(EC#)
- 208-288-1
- 1.6 Molecular Formula
- C28H34O15 (isomer)
- 1.7 Inchi
- InChI=1S/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
- 1.8 InChkey
- QUQPHWDTPGMPEX-QJBIFVCTSA-N
- 1.9 Canonical Smiles
- CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=CC(=C4C(=O)CC(OC4=C3)C5=CC(=C(C=C5)OC)O)O)O)O)O)O)O)O
- 1.10 Isomers Smiles
- C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC3=CC(=C4C(=O)C[C@H](OC4=C3)C5=CC(=C(C=C5)OC)O)O)O)O)O)O)O)O
2. Properties
- 2.1 Density
- 1.65 g/cm3
- 2.1 Melting point
- 250-255°C (dec.)(lit.)
- 2.1 Boiling point
- 930.1ºC at 760 mmHg
- 2.1 Refractive index
- 1.695
- 2.1 Flash Point
- 305.5ºC
- 2.1 Precise Quality
- 610.19000
- 2.1 PSA
- 234.29000
- 2.1 logP
- -1.15660
- 2.1 Appearance
- light brown powder
- 2.2 Storage
- Keep Cold. Hygroscopic.
- 2.3 Color/Form
- light brown
- 2.4 pKa
- 7.15±0.40(Predicted)
- 2.5 Water Solubility
- Solubility: Soluble in pyridine, sodium hydroxide solution, soluble in dimethylformamide, slightly soluble in methanol and hot glacial acetic acid, very slightly soluble in ether, acetone, chloroform and benzene.
- 2.6 Stability
- Stable. Incompatible with strong oxidizing agents.
- 2.7 StorageTemp
- Sealed in dry,2-8°C
3. Use and Manufacturing
- 3.1 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.
- 3.2 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
- 3.3 Usage
- Natural product food supplement.
4. Safety and Handling
- 4.1 Hazard Codes
- Xi
- 4.1 Risk Statements
- R22
- 4.1 Safety Statements
- S22-S24/25
- 4.1 RIDADR
- NONH for all modes of transport
- 4.1 WGK Germany
- 3
- 4.1 RTECS
- MK6650000
- 4.1 Report
-
Reported in EPA TSCA Inventory.
- 4.2 Safety
-
Hazard Codes of Hesperidin (CAS NO.520-26-3): 
Xi
The Risk Statements: 22-36/37/38
22: Harmful if swallowed
36/37/38: Irritating to eyes, respiratory system and skin
The Safety Statements: 22-24/25-36/37/39-27-26
22: Do not breathe dust
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
27: Take off immediately all contaminated clothing
24/25: Avoid contact with skin and eyes
36/37/39: Wear suitable protective clothing, gloves and eye/face protection
F: 3-10
Moderately toxic by intraperitoneal route. When heated to decomposition it emits acrid smoke and fumes.
- 4.3 Specification
-
General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media: Use water spray, dry chemical, carbon dioxide, or chemical foam.
Handling: Remove contaminated clothing and wash before reuse. Avoid contact with eyes, skin, and clothing. Avoid ingestion and inhalation.
Storage: Store in a cool, dry place. Keep container closed when not in use.
- 4.4 Toxicity
-
| Organism |
Test Type |
Route |
Reported Dose (Normalized Dose) |
Effect |
Source |
| mouse |
LD50 |
intraperitoneal |
1gm/kg (1000mg/kg) |
|
National Technical Information Service. Vol. AD277-689, |
5. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
Not classified.
2.2 GHS label elements, including precautionary statements
| Pictogram(s) | No symbol. |
| Signal word | No signal word. |
| Hazard statement(s) | none |
| Precautionary statement(s) | |
| Prevention | none |
| Response | none |
| Storage | none |
| Disposal | none |
2.3 Other hazards which do not result in classification
none
7. Synthesis Route
520-26-3Total: 4 Synthesis Route
-
-
|
|
 |
|
Literatures:
Yamada, Mika; Tanabe, Fujimi; Arai, Norie; Mitsuzumi, Hitoshi; Miwa, Yoshikatsu; Kubota, Michio; Chaen, Hiroto; Kibata, Masayoshi
Bioscience, Biotechnology and Biochemistry, 2006 , vol. 70, # 6 p. 1386 - 1394
Yield: null
|
-
|
|
|
|
Literatures:
Yamada, Mika; Tanabe, Fujimi; Arai, Norie; Mitsuzumi, Hitoshi; Miwa, Yoshikatsu; Kubota, Michio; Chaen, Hiroto; Kibata, Masayoshi
Bioscience, Biotechnology and Biochemistry, 2006 , vol. 70, # 6 p. 1386 - 1394
Yield: null
|
9. Other Information
- 9.0 Merck
- 14,4671
- 9.1 BRN
- 75140
- 9.2 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.
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.
- 9.3 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.
- 9.4 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.
Figure 2 Yellow powder of hesperidin
- 9.5 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.
- 9.6 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.
- 9.7 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%.
- 9.8 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.
- 9.9 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.1,2 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.1 It also is reported to produce estrogenic effects, decreasing serum and hepatic lipid concentrations and reducing osteoporosis in ovariectomized rats.1 Hesperidin produces free radical scavenging activity in various in vitro antioxidant assays.1
- 9.10 Chemical Properties
- light brown powder
- 9.11 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.
- 9.12 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.
- 9.13 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.
- 9.14 Uses
- Hesperidin is a flavoring agent that is a bioflavonoid found in citrus pulp. it has minor use as a flavorant.
- 9.15 Uses
- A flavanone found in citrus fruits, also regarded as Vitamin P.
- 9.16 Uses
- antiinflammatory, capillary protectant, hypolipidemic
- 9.17 Uses
- Anticancer
- 9.18 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.
- 9.19 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.
- 9.20 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.
- 9.21 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.
- 9.22 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.]
- 9.23 Usage
- Hesperidin which has been found to be a potent chemopreventive agent in oral, urinary bladder, and colon carcinogenesis in animal models. Applied in food field, it is used as a flavour enhancer and sweetener in a wide variety of alcoholicbeverage, dessert foods and savory foods, applied in cosmetics, it can be added into toothpaste and mouth wash, applied in pharmaceutical field, it is mainly used to reducing the bitterness of in form. It also enhance the action of Vitamin C.
10. Computational chemical data
- Molecular Weight: 610.56100g/mol
- Molecular Formula: C28H34O15
- Compound Is Canonicalized: True
- XLogP3-AA: -1.1
- Exact Mass: 610.18977037
- Monoisotopic Mass: 610.18977037
- Complexity: 940
- Rotatable Bond Count: 7
- Hydrogen Bond Donor Count: 8
- Hydrogen Bond Acceptor Count: 15
- Topological Polar Surface Area: 234
- Heavy Atom Count: 43
- Defined Atom Stereocenter Count: 11
- Undefined Atom Stereocenter Count: 0
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Isotope Atom Count: 0
- Covalently-Bonded Unit Count: 1
- CACTVS Substructure Key Fingerprint: AAADcfB4PAAAAAAAAAAAAAAAAAAAAAAAAAA0aJECAAAAAACRQAAAGgAACAAADBSwmAMyDoAABgCIAqBSAAACCAAkIAAIiAEGiMgdNzaGNRqieWOl4BUPuQfI7PzOIAABCAAIQABAAAIQABCAAAAAAAAAAA==
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