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520-26-3

Basic Information
CAS No.: 520-26-3
Name: Hesperidin
Article Data: 7
Cas Database
Molecular Structure:
Molecular Structure of 520-26-3 (Hesperidin)
Formula: C28H34O15
Molecular Weight: 610.569
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;Hesperetin-7-rutinoside;(2S)-5-hydroxy-2-(3-hydroxy-4-methoxy-phenyl)-7-[(2S,4R,5R)-3,4,5-trihydroxy-6-[[(2R,4S,5S)-3,4,5-trihydroxy-6-methyl-oxan-2-yl]oxymethyl]oxan-2-yl]oxy-chroman-4-one;(2S)-5-hydroxy-2-(3-hydroxy-4-methoxy-phenyl)-7-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-oxan-2-yl]oxymethyl]oxan-2-yl]oxy-chroman-4-one;Ciratin;Glucopyranoside, hesperetin-7 6-O-(6-deoxy-alpha-L-mannopyranosyl)-, beta-D-;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;Glucopyranoside, hesperetin-7[6-O-(6-deoxy-.alpha.-L-mannopyranosyl)]-, .beta.-D-;4H-1-Benzopyran-4-one,7-[[6-O-(6-deoxy- R-L-mannopyranosyl)-a-D-glucopyranosyl]- oxy]-2,3-dihydro-5-hydroxy-2-(3-hydroxy- 4-methoxyphenyl)-,(2S)-;Hesperetin, 7-[6-O- (6-deoxy-.alpha.-L-mannopyranosyl)]-.beta.-D-glucopyranosid e);Hesper bitabs;Hesperetin, 7-(6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranoside);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)-, (2S)-;Hesperetin 7-O-rutinoside;3,5-Dihydroxy-4-methoxy-7-rutinosyloxyflavan-4-on;Hesperetin 7-rutinoside;Hesperetin 7-rhamnoglucoside;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)-;Citrus aurantium extract(synephrine,hesperidin,bioflavonoids);
EINECS: 208-288-1
Density: 1.653 g/cm3
Melting Point: 250-255 °C (dec.)(lit.)
Boiling Point: 930.067 °C at 760 mmHg
Flash Point: 305.542 °C
Solubility: Soluble in pyridine, sodium hydroxide solution, soluble in DMF, slightly soluble in methanol and hot glacial acetic acid, and very slightly soluble in ethyl ether, acetone, chloroform and benzene. Insoluble in water
Appearance: light brown powder
Hazard Symbols: IrritantXi
Risk Codes: 22-36/37/38
Safety: 22-24/25-36/37/39-27-26
Transport Information: N/A
PSA: 234.29000
LogP: -1.15660
Synthetic route
64-17-5

ethanol

50376-44-8

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

520-26-3

hesperidin

Conditions
ConditionsYield
at 22℃; Kinetics; pH 3 bis pH 8;
100-22-1

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

hesperidin radical

A

100-22-1

N,N,N',N'-tetramethyl-para-semiquinonediimine

B

520-26-3

hesperidin

Conditions
ConditionsYield
at 20℃; Equilibrium constant; pH=3.0;
at 20℃; Rate constant; Equilibrium constant; pH=13.5;

hesperidin radical

60-87-7

10-[2-(dimethylamino)propyl]phenothiazine

B

520-26-3

hesperidin

Conditions
ConditionsYield
at 20℃; Equilibrium constant; pH=3.0;
at 20℃; Rate constant; Equilibrium constant; pH=3;
hesperetin

hesperetin

hexa-O-acetyl-α-rutinosyl bromide

hexa-O-acetyl-α-rutinosyl bromide

520-26-3

hesperidin

Conditions
ConditionsYield
With quinoline; silver(l) oxide anschl. mit wss.-aethanol. NaOH;
161713-86-6

4G-α-D-glucopyranosyl hesperidin

520-26-3

hesperidin

Conditions
ConditionsYield
With small intestine homogenate of rat at 37℃; for 1h;
161713-86-6

4G-α-D-glucopyranosyl hesperidin

A

520-26-3

hesperidin

B

520-33-2

hesperetin

Conditions
ConditionsYield
With small intestine homogenate of rat at 37℃; for 4h; Title compound not separated from byproducts.;
64726-90-5

(2S)-7-[[6-O-(6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl]oxy]-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one

A

369593-42-0

(R)-hesperidin

B

520-26-3

hesperidin

Conditions
ConditionsYield
With triethylamine In methanol at 40℃; Kinetics; Temperature; Reagent/catalyst;

hesperidin

A

369593-42-0

(R)-hesperidin

B

520-26-3

hesperidin

Conditions
ConditionsYield
In methanol; formic acid; acetonitrile at 20℃; Resolution of racemate;
520-26-3

hesperidin

520-33-2

hesperetin

Conditions
ConditionsYield
With sulfuric acid; acetic acid In water for 12h; Reflux;98%
With sulfuric acid In water at 121℃; for 4h; High pressure;87%
With sulfuric acid In ethanol for 8h; Reflux;87%
520-26-3

hesperidin

520-27-4

diosmin

Conditions
ConditionsYield
With iodine In pyridine at 90℃; for 10h;89%
With morpholine; iodine at 40 - 70℃; Temperature; Reagent/catalyst; Large scale; Green chemistry;85.7%
With ethanol; iodine; sodium acetate
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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

The Hesperidin, with the CAS registry number 520-26-3, is also known as (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. It belongs to the product categories of Flavanones; Plant Extract; Antioxidant; Biochemistry; Disaccharides; Flavonoids; Glycosides; Sugars; Natural Plant Extract; Carbohydrates & Derivatives; Intermediates & Fine Chemicals; Pharmaceuticals. Its EINECS number is 208-288-1. This chemical's molecular formula is C28H34O15 and molecular weight is 610.56. What's more, its systematic name is (2S)-5-Hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxo-3,4-dihydro-2H-chromen-7-yl 6-O-(6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranoside. This chemcial is a flavanone glycoside (flavonoid) found abundantly in citrus fruits. It is believed to play a role in plant defense. Generally, it is used as an antioxidant according to in vitro studies. In human nutrition it contributes to the integrity of the blood vessels.

Physical properties of Hesperidin are: (1)ACD/LogP: -1.212; (2)# of Rule of 5 Violations: 3; (3)ACD/LogD (pH 5.5): -1.22; (4)ACD/LogD (pH 7.4): -1.65; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 5.11; (8)ACD/KOC (pH 7.4): 1.88; (9)#H bond acceptors: 15; (10)#H bond donors: 8; (11)#Freely Rotating Bonds: 15; (12)Polar Surface Area: 234.29 Å2; (13)Index of Refraction: 1.695; (14)Molar Refractivity: 141.996 cm3; (15)Molar Volume: 369.323 cm3; (16)Polarizability: 56.292×10-24cm3; (17)Surface Tension: 98.02 dyne/cm; (18)Density: 1.653 g/cm3; (19)Flash Point: 305.542 °C; (20)Enthalpy of Vaporization: 141.731 kJ/mol; (21)Boiling Point: 930.067 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

Uses of Hesperidin: it can be used to produce 5-hydroxy-2-(3-hydroxy-4-methoxy-phenyl)-7-(O6-a-L-rhamnopyranosyl-b-D-glucopyranosyloxy)-chromen-4-one at the temperature of 90 °C. It will need reagent iodine and solvent pyridine with the reaction time of 10 hours. The yield is about 89%.

Hesperidin can be used to produce 5-hydroxy-2-(3-hydroxy-4-methoxy-phenyl)-7-(O6-a-L-rhamnopyranosyl-b-D-glucopyranosyloxy)-chromen-4-one at the temperature of 90 °C

When you are using this chemical, please be cautious about it as the following:
This chemcial is irritating to eyes, respiratory system and skin. It is harmful if swallowed. You should not breathe dust. When using it, you must avoid contact with skin and eyes. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. You should take off immediately all contaminated clothing. When using it, you need to wear suitable protective clothing, gloves and eye/face protection.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C4c5c(O)cc(O[C@@H]2O[C@H](CO[C@@H]1O[C@H]([C@H](O)[C@@H](O)[C@H]1O)C)[C@@H](O)[C@H](O)[C@H]2O)cc5O[C@H](c3ccc(OC)c(O)c3)C4
(2)Std. 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
(3)Std. InChIKey: QUQPHWDTPGMPEX-QJBIFVCTSA-N

The toxicity data is as follows:  

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 1gm/kg (1000mg/kg)   National Technical Information Service. Vol. AD277-689,