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Hesperidin

Catalog Number
ACM520263-4
CAS
520-26-3
Structure
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]oxymethyl]oxan-2-yl]oxy-2,3-dihydrochromen-4-one
Synonyms
Atripliside B
Molecular Weight
610.56
Molecular Formula
C28H34O15
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
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
InChI Key
QUQPHWDTPGMPEX-QJBIFVCTSA-N
Boiling Point
576.16 °C
Melting Point
250-255 °C(lit.)
Flash Point
305.5 °C
Purity
95%
Density
1.3290 g/cm³
Solubility
Insoluble in water, soluble in organic solvents
Appearance
Light brown powder
Storage
Sealed in dry, 2-8 °C
Active Content
95%
Physical State
Solid
Typical Applications
Use as antioxidant.
Spec Sheet
Case Study

Preparation of Modified Silica Dioxide and Hesperidin Complexes

Preparation of Modified Silica Dioxide and Hesperidin Complexes Binkowska, I. Hesperidin: synthesis and characterization of bioflavonoid complex, SN Appl. Sci. 2 (2020) 445.

Silica-based materials are suitable for oral drug delivery. The advantage of silica dioxide is that chemical modification is simple due to the presence of hydroxyl groups on the internal and external surfaces. Hesperidin complexes can improve the physicochemical and pharmacological properties of hesperidin.
Modification of Silica Dioxide and Preparation of Its Complexes with Hesperidin
Various amounts (0.1, 0.2, and 0.3 mL) of (3-aminopropyl)trimethoxysilane were added dropwise to a suspension of 0.5 g of silica dioxide in 60 mL of dry toluene. The mixture was then heated under reflux for 8 hours. The product was filtered and washed several times with toluene and methanol. The samples labeled as AMS-1, AMS-2, and AMS-3 were then dried overnight at 100 °C.
The complexes of amino-functionalized silica dioxide and hesperidin were prepared using different hesperidin/silica dioxide ratios (1/1, 1/2, and 2/1). A calculated amount of hesperidin was dissolved in methanol, and then the modified silica dioxide was added. The mixture was stirred on a magnetic stirrer at room temperature for 24 hours. The samples were then filtered and washed with methanol. The samples labeled as HESP-AMS-1, HESP-AMS-2, and HESP-AMS-3 were dried for 12 hours at 100 °C. The percentage of hesperidin attached to the amino-functionalized silica dioxide was calculated using spectrophotometric and thermogravimetric analyses.

Protective Effect of Hesperidin Against Tert-butyl Hydroperoxide-induced Oxidative Stress in Human Hepatocytes

Protective Effect of Hesperidin Against Tert-butyl Hydroperoxide-induced Oxidative Stress in Human Hepatocytes Chen, Mingcang, et al. Food and Chemical Toxicology 48.10 (2010): 2980-2987.

Hesperidin is a natural flavonoid found in fruits and vegetables, and it has been reported to possess a wide range of pharmacological properties, including antioxidant, anti-inflammatory, anti-hypercholesterolemic, and anti-cancer activities.
Protective Effect of Hesperidin Against t-BuOOH-induced Cytotoxicity
This study assessed the potential of hesperidin in protecting cells from tert-butyl hydroperoxide (t-BuOOH)-induced damage by boosting the cellular antioxidant defense mechanism. Hesperidin significantly protected hepatocytes against t-BuOOH-induced cytotoxicity, such as mitochondrial membrane potential (MMP) depletion and lactate dehydrogenase (LDH) release. Hesperidin also significantly inhibited oxidative stress indicators in a dose-dependent manner, such as ROS and lipid peroxidation levels. Western blot analysis showed that hesperidin promoted the phosphorylation of ERK/MAPK, which appears to be the reason for Nrf2 nuclear translocation, thereby inducing the expression of the cytoprotective heme oxygenase-1 (HO-1). According to the findings presented above, hesperidin shows promise as a therapeutic option for protecting hepatocytes against oxidative stress-induced damage and improving liver function.

Custom Q&A

What is the chemical formula of hesperidin?

The chemical formula of hesperidin is C28H34O15.

What is the molecular weight of hesperidin?

The molecular weight of hesperidin is 610.6 g/mol.

Where is hesperidin typically found?

Hesperidin is found in citrus fruits.

What is the IUPAC name of hesperidin?

The IUPAC name of hesperidin is (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]oxymethyl]oxan-2-yl]oxy-2,3-dihydrochromen-4-one.

What are some synonyms for hesperidin?

Some synonyms for hesperidin include hesperidin, Cirantin, Hesperidoside, and Hesper bitabs.

What is the InChIKey of hesperidin?

The InChIKey of hesperidin is QUQPHWDTPGMPEX-QJBIFVCTSA-N.

What is the CAS number of hesperidin?

The CAS number of hesperidin is 520-26-3.

In which species is hesperidin a natural product?

Hesperidin is a natural product found in Ficus erecta var. beecheyana, Citrus tankan, and other organisms.

What is the role of hesperidin in biological processes?

Hesperidin has a role as a mutagen.

What is the ChEMBL ID of hesperidin?

The ChEMBL ID of hesperidin is CHEMBL449317.

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