HESPERIDIN

PRODUCT IDENTIFICATION

CAS NO. 520-26-3

HESPERIDIN  

EINECS NO.

208-288-1

FORMULA C28H34O15
MOL WT. 610.57

H.S. CODE

2940.00.6000

TOXICITY

 

SYNONYMS Hesperidoside; Cirantin; Hesperidin;
Hesperitin-7-rutinoside; Hesperitin-7-rhamnoglucoside; Hesperetin 7-rutinoside; Hesperetin 7-rhamnoglucoside; (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; Cirantin; Hesperetin-7 6-O-(6-deoxy-alpha-L-mannopyranosyl)-, beta-D-Glucopyranoside; Vitamin P; 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; 5-Hydroxy-2-(3-hydroxy-4-methoxyphenyl)- 7-((6-O-alpha-L-rhamnopyranosyl- beta- D-glucopyranosyl)oxy)-4-chromanon; Other CAS RN: 106904-63-6, 15512-51-3, 16643-24-6, 17654-22-7, 28283-75-2, 30927-97-0, 32737-61-4
SMILES

C1[C@@H](c2cc(c(OC)cc2)O)Oc2cc(O[C@@H]3O[C@H](CO[C@H]4[C@@H] ([C@@H]([C@@H](O)[C@@H](O4)C)O)O)[C@@H](O)[C@@H]([C@H]3O)O) cc(c2C1=O)O

CLASSIFICATION

Vitamin, Flavanone glycoside, Flavonoid, Bitter compound

EXTRA NOTES

A flavanone glycoside found in citrus fruit peels.
Biochem/physiol Actions: Flavonoid phytochemical extracted from citrus species. It is the rhamnoglucoside (rutinoside) of hesperetin.

PHYSICAL AND CHEMICAL PROPERTIES

PHYSICAL STATE white to yellow powder
MELTING POINT 257 - 262 C
BOILING POINT  
SPECIFIC GRAVITY  
SOLUBILITY IN WATER Soluble
pH  
VAPOR DENSITY  

AUTOIGNITION

 

NFPA RATINGS

 

REFRACTIVE INDEX

 
FLASH POINT  
STABILITY

Stable under ordinary conditions. Hygroscopic, light sensitive.

EXTERNAL LINKS & GENERAL DESCRIPTION

Wikipedia Linking - Hesperidin

Google Scholar Search - Hesperidin

Drug Information Portal (U.S. National Library of Medicine) - Hesperidin

PubChem Compound Summary - Hesperidin

Drug Bank -  Hesperidin

KEGG (Kyoto Encyclopedia of Genes and Genomes) - Hesperidin

http://www.ebi.ac.uk/ - Hesperidin

http://www.ncbi.nlm.nih.gov/ - Hesperidin

Material Safety Data Sheet

Local:
Hesperidin, a polyphenolic bioflavonoid, is a water-soluble pigment synthesized or naturally occurring as a glycoside in orange peel or other citrus fruits. It, chemically (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, is a white to yellow crystalline powder melting at ca 260 C. Bioflavonoids are called phytochemicals, Vitamin P, and Vitamin C2. There are about 2000 known bioflavonoids including  catechin, citrin, eriodictin, hesperetin, hesperidin, nobiletin, quercetin, rutin, sinensetin, and tangeretin. Vitamin P is not a dietary essential but is known to have the effect on capillary disorders.  It increases the strength of the walls of the blood capillaries and regulates their permeability. It may have an contribution to the total antioxidant activity and detoxifiers. It may enhance the action of Vitamin C. It is  considered that it lowers down cholesterol levels if it taken with Vitamin C. It is also know to have pharmacological action as an anti-inflammatory ,antihistaminic and antiviral agent. Hesperidin is the predominant flavonoid in lemons and sweet oranges.

Rutin, the glycoside form of quercetin, is a bioflavonol having aromatic trimeric heterocyclic structure. It is a naturally occurring pigment. It, chemically 3-[[6-O-(6-deoxy-alpha-L- mannopyranosyl )-beta-D-glucopyranosyl] oxy]-2- (3,4-dihydroxyphenyl) -5,7-dihydroxy-4H- 1-Benzopyran-4-one, is a yellow to greenish crystalline powder melting at 190 C. Rutin is classified as vitamin P which increases the strength of the walls of the blood capillaries and regulates their permeability. Others classified as vitamin P are catechin, citrin, eriodictin, hesperetin, hesperidin, nobiletin, quercetin,  sinensetin, and tangeretin. It is not a dietary essential but is known to have the effect on capillary disorders. It may also have an contribution to the total antioxidant activity and detoxifiers. It is also know to have pharmacological action as an anti-inflammatory ,antihistaminic and antiviral agent.

Members of rutin molecules

Product

CAS RN

Rutinose 90-74-4
Rutin 153-18-4
Hesperidin 520-26-3
Narcissin 604-80-8
Tetra(hydroxyethyl)rutoside 6980-20-7
Troxerutin 7085-55-4
Ascorutin 8067-12-7
Rutin sodium sulfate 12768-44-4
Eriocitrin 13463-28-0
Narirutin 14259-46-2
Tamarixetin 7-rutinoside 14265-53-3
Delphinidin-3-rutinoside 15674-58-5
Kaempferol 7-neohesperidoside 17353-03-6
Keracyanin 18719-76-1
Monoxerutin 23869-24-1
Veronicastroside 25694-72-8
Ethoxazorutoside 30851-76-4
Isorhamnetin-3-O-rutinoside-7-O-glucoside 55481-91-9
Rutin S 64755-26-6
Diethanolamine-rutin 69344-84-9
Rutin-N-mustard 85625-48-5
Nirurin 96253-68-8
Rutin sulfate 108916-86-5
Isorhamnetin-3-O-rutinoside-4'-O-glucoside 111393-97-6
Violdelphin 126417-59-2
Swertiamacroside 128585-97-7
D-Glucose-rutin 130603-71-3
Rutin butyryl ester 131981-32-3
2',5,5',7-Tetrahydroxy-flavanone-7-O-rutinoside 153286-43-2
Rutin hydrate 207671-50-9

Rutin trihydrate

250249-75-3

SALES SPECIFICATION

APPEARANCE

yellow powder

ASSAY

93.0% - 98.0 %
IDENTIFICATION

Pass

OPTICAL ROTATION

-65° ~ -70° (C=2 Pyridine)

LOSS ON DRYING

5.0% max

QUERCETIN

5.0% max

HEAVY METALS

10ppm max

TRANSPORTATION
PACKING  
HAZARD CLASS Not regulated
UN NO.  
OTHER INFORMATION
Hazard Symbols: XI, Risk Phrases: 36/37/38, Safety Phrases: 24/25/28A/37/45

GENERAL DESCRIPTION OF FLAVONOID

Flavonoid is any member of a class of widely distributed biological natural products containing aromatic heterocyclic skeleton of flavan (2-Phenylbenzopyran) but no nitrogen in plants. Generally, flavonoids are biological pigments providing colours from red to blue in flowers, fruit and leaves. Besides their coloring in plants, flavonoids have important roles in the growth and development of plants; protection against UV-B radiation; forming antifungal barriers; antimicrobial, insecticidal and oestrogenic activities; plant reproduction. Flavonoids also exhibit a wide range of biological properties including anti-microbial, insecticidal and oestrogenic activities. Flavonoids are usually classified into main 6 subgroups as below plus flavans, neoflavonoids, flavonols, aurons, catechins according to the structural patterns.
  • Flavonols (Hydroxy derivatives of flavone): Fisetin, Galangin, Kaempferide, Kaempferol, Morin, Myricetin, Myricitrin, Quercetin, Quercetrin, Rhamnetin, Robinin, Rutin, Spirenoside
  • Flavones (skeleton: 2-phenylchromen-4-one): Apigenin, Baicalein, Chrysin, Diosmetin, Diosmin, Flavone, Luteolin, Rpoifolin,Tangeretin, Techtochrysin, Rhamnazin, Nobiletin, Natsudaidain.
  • Isoflavones (skeleton: 3-phenylchromen-4-one): Daidzin, Genistein, Irilone, Luteone, Prunetin, Pratensein,
  • Flavonones (derivation by reduction of the 2(3) C=C bond): Eriodictyol, Hesperidin, Hesperetin, Likvirtin, Naringin; Naringenin; Pinocembrin
  • Flavanols (derivation by reduction of the keto group):(+)-Catechin, (+)-Gallocatechin, (-)-Epicatechin (EC), (-)-Epigallocatechin (EGC), (-)-Epicatechin 3-gallate (ECG), (-)-Epigallocatechin 3-gallate (EGCG), Theaflavin, Theaflavin 3-gallate, Theaflavin 3'-gallate, Theaflavin 3,3' digallate, Thearubigins
  • Anthocyanidins (aglycones of the glycoside anthocyanins): Apigeninidin, Cyanidin, Delphinidin, Diosmetinidin, Guibourtinidin, Fisetinidin, Luteolinidin, Malvidin, Pelargonidin, Peonidin, Robinetinidin, Tricetinidin, Capensinidin, Petunidin, Europinidin, Aurentinidin, Columnidin, 5-Desoxy-malvidin, 5-Desoxy-peonidin, Hirsutinidin, Rosinidin