4H-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)-, (S)-

Base Information

• Chemical Name: 4H-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)-, (S)-
• CAS No.: 520-26-3
• Molecular Formula: C28H34O15
• Molecular Weight: 610.569
• Hs Code.: HESPERIDIN PRODUCT IDENTIFICATION
• NSC Number: 44184
• DSSTox Substance ID: DTXSID50859444
• Wikidata: Q104196220
• Metabolomics Workbench ID: 123605
• ChEMBL ID: CHEMBL1535112
• Mol file: 520-26-3.mol

Synonyms:2S, Hesperidin;4H-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)-, (S)-;7-Rhamnoglucoside, Hesperetin;Hesperetin 7 Rhamnoglucoside;Hesperetin 7 Rutinoside;hesperetin 7-rhamnoglucoside;Hesperetin-7-Rutinoside;Hesperidin;Hesperidin 2S

Chemical Property of 4H-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)-, (S)-

Chemical Property:

• Appearance/Colour: light brown powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 250-255 °C (dec.)(lit.)
• Refractive Index: 1.695
• Boiling Point: 930.067 °C at 760 mmHg
• PKA: 7.15±0.40(Predicted)
• Flash Point: 305.542 °C
• PSA: 234.29000
• Density: 1.653 g/cm³
• LogP: -1.15660
• Storage Temp.: 2-8°C
• Sensitive.: Hygroscopic
• Solubility.: DMSO (Slightly), Pyridine (Slightly, Sonicated)
• Water Solubility.: Insoluble in water. Soluble in organic solvents such as DMSO.
• XLogP3: -1.1
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 15
• Rotatable Bond Count: 7
• Exact Mass: 610.18977037
• Heavy Atom Count: 43
• Complexity: 940

Purity/Quality:

99%, ^*data from raw suppliers

Hesperidin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 22-36/37/38
• Safety Statements: 22-24/25-36/37/39-27-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• 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
• Recent NIPH Clinical Trials: A verification study of safety evaluation of excessive consumption of the test food to consume 5 times more than regular daily intake in healthy subjects: an open-label trial
• 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. 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. Hesperidin is a flavoring agent that is a bioflavonoid found in citrus pulp. it has minor use as a flavorant. A flavanone found in citrus fruits, also regarded as Vitamin P. antiinflammatory, capillary protectant, hypolipidemic Anticancer
• 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. 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 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.
• 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.
• 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.
• 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.

Technology Process of 4H-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)-, (S)-

There total 9 articles about 4H-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)-, (S)- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

hesperidin → (R)-hesperidin (369593-42-0) + hesperidin (520-26-3)

Guidance literature:

In methanol; formic acid; acetonitrile; at 20 ℃; Resolution of racemate;

DOI:10.1002/chir.23147

Reference yield:

4G-α-D-glucopyranosyl hesperidin (161713-86-6) → hesperidin (520-26-3)

Guidance literature:

With small intestine homogenate of rat; at 37 ℃; for 1h;

DOI:10.1271/bbb.50657

Reference yield:

4G-α-D-glucopyranosyl hesperidin (161713-86-6) → hesperidin (520-26-3) + hesperetin (520-33-2,41001-90-5,69097-99-0)

Guidance literature:

With small intestine homogenate of rat; at 37 ℃; for 4h; Title compound not separated from byproducts.;

DOI:10.1271/bbb.50657

upstream raw materials:

ethanol

3,2',6'-trihydroxy-4-methoxy-4'-(O⁶-α-L-rhamnopyranosyl-β-D-glucopyranosyloxy)-trans-chalcone

N,N,N',N'-tetramethyl-para-phenylenediamine

10-[2-(dimethylamino)propyl]phenothiazine

Downstream raw materials:

3''-O-butanoylhesperidin

4^G-α-D-glucopyranosyl hesperidin

(Ξ)-2-(3-ethoxycarbonyloxy-4-methoxy-phenyl)-5-hydroxy-7-(O⁶-α-L-rhamnopyranosyl-β-D-glucopyranosyloxy)-chroman-4-one

D-Glucose

Refernces

• 1、 Belboukhari, Nasser,Cheriti, Abdelkrim,Roussel, Christian,Vanthuyne, Nicolas. "Chiral separation of hesperidin and naringin and its analysis in a butanol extract of Launeae arborescens". scheme or table. p. 669 - 681. Retrieved 2010/08/20.
• 2、 Jovanovic, Slobodan V.,Steenken, Steen,Hara, Yukihiko,Simic, Michael G.. "Reduction potentials of flavonoid and model phenoxyl radicals. Which ring in flavonoids is responsible for antioxidant activity?". . p. 2497 - 2504. Retrieved 2007/10/03.