CAS 520-26-3|(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-be...

General Information

Structure

Molecular Formula

C₂₈H₃₄O₁₅

Molecular Mass

610.56056

Exact Mass

610.18977039

Charge

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

Canonic 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

Isomeric 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

Calculated Properties

JChem

LogD (pH = 7.4)

-0.34

LogD (pH = 5.5)

-0.31

Log P

-0.31

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

false

Acid pKa

8.61

Polar Surface Area

234.29

Polarizability

59.91

Molar Refractivity

140.77

LOG S

-2.59

Data Source

Names and Identifiers

IUPAC Traditional name

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

Synonyms

HesperidinHesperitin-7-rutinosideHesperetin 7-rhamnoglucosideHesperidin(2S)-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-oneNSC 44184Hesperetin 7-RutinosideAtripliside BCirantinHesperidinehesperidinCirantinHesperidoside(S)-(-)-hesperidin(2S)-hesperidinHesperetin 7-O-rutinosideCiratinHesperidin

Names and Identifiers

Registration numbers

CAS Number

MDL Number

Beilstein Number

EC Number

PubChem SID

2489568016203786926744171

Unique Ingredient Identifier

E750O06Y6O

CHEBI ID

28775CHEBI:24530CHEBI:28775CHEBI:5682

Chemspider ID

CHEMBL

Wikipedia Title

PubChem CID

KEGG ID

Patent number

WO2007103555WO2007136428US2007197648EP1652527WO2007123338US2004023890US2007270358EP1568283US2006270009EP1369489EP1600143EP0920870EP1834636EP1514540

MetaCyc Database

CPD-7075

BRENDA Database

3.2.1.1667.6.2.22.4.1.3843.2.1.B281.2.3.13.2.1.1682.7.11.183.2.1.402.4.1.192.6.1.13.4.21.51.14.18.12.4.1.B531.20.4.3

Rhea Database

RHEA:28134

SureChEMBL Database

SCHEMBL94586

MetaboLights Database

MTBLS2096MTBLS406MTBLS4820MTBLS3943

KEGG DRUG Database

HMDB Database

BKMS React Database

CompTox Database

BRENDA Ligand Database

LINCS Database

ACToR Database

NMRShiftDB Database

KNApSAcK Database

IntEnz Database

Reaxys Registry

BindingDB Database

DrugBank ID

Registration numbers

Properties

Safety Information

Storage Condition

-20°C

-20°C Freezer

German water hazard class

Storage Temperature

2-8°C

Personal Protective Equipment

Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

MSDS Link

Download link

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule 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]

Wikipedia

Hesperidin

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

52040

50162

TRC

H281185

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

ChEBI

CHEBI:28775

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.

Molecule Details

References

PubChem Literature

From Data Sources

• Guzmán-Gutiérrez SL et al. Planta Med. 2009 Mar;75(4):295-301.

• Cejudo B., et al.: J. Agric. Food Chem., 58, 11814 (2009)

• Ananth, V., et al.: J. Pharm. Res., 2, 1739 (2009)

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

IUPAC Traditional name

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

Synonyms

Molecule Details

S2309

H5254

52040

50162

TRC

H281185

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

ChEBI

CHEBI:28775

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.

Bioactivity

PubChem BioAssay