(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]oxy}methyl)oxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4-one

• ChemBase ID: 72949
• Molecular Formular: C28H34O15
• Molecular Mass: 610.56056
• Monoisotopic Mass: 610.18977039
• SMILES: [C@H]1([C@H]([C@@H]([C@H]([C@@H](O1)Oc1cc(c2c(c1)O[C@@H](CC2=O)c1ccc(c(c1)O)OC)O)O)O)O)CO[C@H]1[C@H](O)[C@@H]([C@H]([C@@H](O1)C)O)O
• Canonical SMILES: COc1ccc(cc1O)[C@@H]1CC(=O)c2c(O1)cc(cc2O)O[C@@H]1O[C@H](CO[C@@H]2O[C@@H](C)[C@@H]([C@H]([C@H]2O)O)O)[C@H]([C@@H]([C@H]1O)O)O
• 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
• InChIKey: QUQPHWDTPGMPEX-QJBIFVCTSA-N

NAMES AND DATABASE IDS

Names

• 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]oxy}methyl)oxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4-one
• IUPAC Traditional name: hesperidin
• Synonyms: Hesperidin; Hesperetin 7-rhamnoglucoside; Hesperitin-7-rutinoside; Hesperidin; (2S)-7-[[6-O-(6-Deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl]oxy]-2,3-dihydro-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-1-benzopyran-4-one; (2S)-Hesperidin; Atripliside B; Cirantin; Hesperetin 7-Rutinoside; NSC 44184; Hesperidine

Database IDs

• CAS Number: 520-26-3
• EC Number: 208-288-1
• MDL Number: MFCD00075663
• Beilstein Number: 75140
• PubChem SID: 24895680; 162037869
• PubChem CID: 10621
• CHEBI ID: 28775
• CHEMBL: 449317
• Chemspider ID: 10176
• Unique Ingredient Identifier: E750O06Y6O
• Wikipedia Title: Hesperidin

CALCULATED PROPERTIES

• Acid pKa: 8.609446
• H Acceptors: 15
• H Donor: 8
• LogD (pH = 5.5): -0.31489173
• LogD (pH = 7.4): -0.34045622
• Log P: -0.314557
• Molar Refractivity: 140.767 cm^3
• Polarizability: 56.677265 Å^3
• Polar Surface Area: 234.29 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Pyridine
• Apperance: light brown; Powder; Yellow Solid
• Melting Point: 233-236°C; 250-255 °C (dec.)(lit.)
• Optical Rotation: [α]20/D -75±5°, c = 1% in pyridine (dry matter)

Safety Information

• Storage Condition: -20°C; -20°C Freezer
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ~90% (HPLC); ≥80%; ≥97.0% (HPLC)
• Grade: analytical standard
• Salt Data: Free Base
• Description: Stereoisomers
• Shelf Life: (limited shelf life, expiry date on the label)
• Loss on Drying: ≤5% loss on drying, 110 °C
• Empirical Formula (Hill Notation): C28H34O15
• Classification: Genuine Natural Compounds

DETAILS

Selleck Chemicals - S2309

Research Area: Cardiovascular Disease , Inflammation
Biological Activity:
Hesperidin is a flavanone glycoside found abundantly in citrus fruits. It is believed to play a role in plant defense. It acts as an antioxidant according to in vitro studies. [1] In human nutrition, it contributes to the integrity of the blood vessels. Various preliminary studies reveal novel pharmaceutical properties. It reduced cholesterol and blood pressure in rats. In a mouse study, large doses of the glucoside hesperidin decreased bone density loss. Another animal study showed protective effects against sepsis. Hesperidin has anti-inflammatory effects. It is also a potential sedative, possibly acting through opioid or adenosine receptors. [2][3]

Sigma Aldrich - H5254

Biochem/physiol Actions
Flavonoid phytochemical extracted from citrus species. It is the rhamnoglucoside (rutinoside) of hesperetin.2
Application
Studies of the behavior of hesperidin and hesperetin (the aglycone) with DMPC liposomes find the aglycone penetrates more deeply and binds more strongly to the "membrane." This may explain the better bioavailability of bioflavonoid aglycones in general.1

Sigma Aldrich - 50162

Biochem/physiol Actions
Flavonoid phytochemical extracted from citrus species. It is the rhamnoglucoside (rutinoside) of hesperetin.2
Application
Studies of the behavior of hesperidin and hesperetin (the aglycone) with DMPC liposomes find the aglycone penetrates more deeply and binds more strongly to the "membrane." This may explain the better bioavailability of bioflavonoid aglycones in general.1

Sigma Aldrich - 52040

Biochem/physiol Actions
Flavonoid phytochemical extracted from citrus species. It is the rhamnoglucoside (rutinoside) of hesperetin.2
Application
Studies of the behavior of hesperidin and hesperetin (the aglycone) with DMPC liposomes find the aglycone penetrates more deeply and binds more strongly to the "membrane." This may explain the better bioavailability of bioflavonoid aglycones in general.1

Toronto Research Chemicals - H281185

A flavanone found in citrus fruits, also regarded as Vitamin P.

REFERENCES

• Guzmán-Gutiérrez SL et al. Planta Med. 2009 Mar;75(4):295-301.
• Ananth, V., et al.: J. Pharm. Res., 2, 1739 (2009)
• Cejudo B., et al.: J. Agric. Food Chem., 58, 11814 (2009)