41001-90-5

Basic information

• Product Name: HESPERETIN
• Synonyms: 2,3-DIHYDRO-5,7-DIHYDROXY-2S-(3-HYDROXY-4-METHOXPHENYL)-4H-1-BENZOPYRAN-4-ONE;5,7,3'-TRIHYDROXY-4'-METHOXYFLAVANONE;(+/-)-3',5,7-TRIHYDROXY-4'-METHOXYFLAVANONE;3',5,7-TRIHYDROXY-4'-METHOXYFLAVANONE;3',5,7-TRIHYDROXY-4-METHOXYFLAVANONE;HESPERETINE
• CAS NO: 41001-90-5
• Molecular Formula: C16H14O6
• Molecular Weight: 302.28
• EINECS: 208-290-2
• Mol File: 41001-90-5.mol

Chemical Properties

• Boiling Point: 586.2°C at 760 mmHg
• Flash Point: 223°C
• Appearance: /
• Density: 1.458g/cm³
• Vapor Pressure: 2.45E-14mmHg at 25°C
• Refractive Index: 1.664
• Storage Temp.: 2-8°C
• CAS DataBase Reference: HESPERETIN(CAS DataBase Reference)
• NIST Chemistry Reference: HESPERETIN(41001-90-5)
• EPA Substance Registry System: HESPERETIN(41001-90-5)

Safety Data

• Statements: R36/37/38:Irritating to eyes, respiratory system and skin.
• Safety Statements: S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.; S36:Wear suitable prot
• WGK Germany: 3
• Hazardous Substances Data: 41001-90-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Hesperetin is used as a therapeutic agent for its protective effects against various diseases such as diabetes, cardiovascular diseases, and neurodegenerative disorders. Its antioxidant and anti-inflammatory properties contribute to its efficacy in these applications.
Used in Nutraceutical Industry:
Hesperetin is used as a dietary supplement to promote overall health and well-being. Its potential to improve vascular function and reduce the risk of atherosclerosis makes it a valuable addition to health-conscious diets.
Used in Cosmetic Industry:
Hesperetin is used as an ingredient in skincare products for its antioxidant properties, which can help protect the skin from environmental damage and promote a youthful appearance.
Used in Weight Management:
Hesperetin is used as a weight loss aid due to its potential to promote weight loss and improve metabolic health.
Used in Athletic Performance Enhancement:
Hesperetin is used as a performance-enhancing supplement for athletes, as it may help improve vascular function and reduce inflammation, thereby enhancing athletic performance.

InChI:InChI=1/C16H14O6/c1-21-13-3-2-8(4-10(13)18)14-7-12(20)16-11(19)5-9(17)6-15(16)22-14/h2-6,14,17-19H,7H2,1H3/t14-/m0/s1

Upstream product

• 520-26-3 hesperidin 
• 6198-24-9 2',4'-bis-β-D-glucopyranosyloxy-3,6'-dihydroxy-4-methoxy-trans-chalcone 
• 107-21-1 ethylene glycol 
• 520-33-2 hesperetin 
• 520-33-2 (S)-2,3-dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-benzopyrone 
• 161713-86-6 4^G-α-D-glucopyranosyl hesperidin 
• 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 
• 6157-13-7 1-[2-hydroxy-4,6-bis-(tetra-O-acetyl-β-D-glucopyranosyloxy)-phenyl]-ethanone 
• 621-59-0 isovanillin 
• 108-73-6 3,5-dihydroxyphenol 
• 49806-44-2 3-ethoxycarbonyloxy-4-methoxy-cinnamoyl chloride 
• 75679-30-0 Hesperetin chalcone 
• 485-80-3 S-adenosyl-L-methionine 
• 552-58-9 eriodictyol 

Downstream Products

• 70987-96-1 5-hydroxy-3′4′7-trimethoxy flavanone 
• 6274-73-3 (S)-5,7-diacetoxy-2-(3-acetoxy-4-methoxy-phenyl)-chroman-4-one 
• 6033-54-1 (-)-hesperetin oxime 
• 675139-61-4 Hesperetin 7-O-sulfate 
• 945038-48-2 Hesperetin 3'-O-sulfate 
• 29080-58-8 5-hydroxy-3',4',7-trimethoxyflavone 
• 1638743-78-8 6-(N,N-dimethylaminomethyl)-5-hydroxy-7,3',4'-trimethoxyflavone 
• 1638743-79-9 6-(N,N-diethylaminomethyl)-5-hydroxy-7,3',4'-trimethoxyflavone 
• 1638743-80-2 6-(pyrrolidin-1-yl)methyl-5-hydroxy-7,3',4'-trimethoxyflavone 
• 1638743-81-3 6-(morpholin-1-yl)methyl-5-hydroxy-7,3',4'-trimethoxyflavone 
• 1638743-82-4 6-(piperidin-1-yl)methyl-5-hydroxy-7,3',4'-trimethoxyflavone 
• 1638743-83-5 6-(N-methylpiperazin-1-yl)methyl-5-hydroxy-7,3',4'-trimethoxyflavone 
• 10496-67-0 3-(3,4-dimethoxyphenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)prop-2-en-1-one 
• 75917-11-2 5-hydroxy-6,3',4'-trimethoxyflavanone 

Relevant articles and documents

Bioavailability of glucosyl hesperidin in rats

Glucosyl hesperidin (G-hesperidin) is a water-soluble derivative of hesperidin. We compared the absorption and metabolism of G-hesperidin with those of hesperidin in rats. After oral administration of G-hesperidin or hesperidin to rats, hesperetin was detected in sera hydrolyzed with β-glucuronidase, but it was not detectable in unhydrolyzed sera. Serum hesperetin was found more rapidly in rats administered G-hesperidin than in those administered hesperidin. The area under the concentration-time curve for hesperetin in the sera of rats administered G-hesperidin was approximately 3.7-fold greater than that of rats administered hesperidin. In the urine of both administration groups, hesperetin and its glucuronide were found. Urinary excretion of metabolites was higher in rats administered G-hesperidin than in those administered hesperidin. These results indicate that G-hesperidin presents the same metabolic profile as hesperidin. Moreover, it was concluded that G-hesperidin is absorbed more rapidly and efficiently than hesperidin, because of its high water solubility.

Enhanced antioxidant activity, antibacterial activity and hypoglycemic effect of luteolin by complexation with manganese(II) and its inhibition kinetics on xanthine oxidase

The present study aims to improve the biological activities of luteolin by complexation with manganese(ii). UV-visible spectroscopy, infrared spectroscopy, thermogravimetric analysis and elemental analysis were adopted to assess the relevant interaction of luteolin and manganese(ii) ions and the chelation sites. The antioxidant activity, hypoglycemic effect and antimicrobial activity of luteolin-manganese(ii) complex with respect to its parent luteolin and the inhibition effect of which on xanthine oxidase were investigated and compared. The spectroscopic data indicated that luteolin reacts with manganese(ii) cations through the chelation sites of 5-hydroxy and 4-carbonyl in two luteolin molecules. Antioxidant and antibacterial activity were enhanced after the complexation of manganese(ii) cations with luteolin. An inhibition effect assay found that luteolin and luteolin-manganese(ii) complex reversibly inhibited xanthine oxidase in a competitive manner. Luteolin-manganese(ii) complex had a more remarkable hypoglycemic effect than luteolin by increasing the glucose consumption in liver tissue.

In vivo pharmacokinetics of hesperidin are affected by treatment with glucosidase-like BglA protein isolated from yeasts

Hesperidin is an abundant flavanone glycoside in citrus fruits and has been reported to possess a wide range of biological activities. However, hesperidin has poor bioavailability. Here, we tested the hypothesis that hesperetin found in chenpi will have a better bioavailability than hesperidin and that treatment of hesperidin with the glucosidase-like yeast Bg1A protein will increase its bioavailability. The results indicate that hesperidin in pure or extract form is hydrolyzed by BglA protein extracted from Sporobolomyces singularis or expressed in Escherichia coli BL21 (DE3). This biotransformation affected the plasma pharmacokinetics of total hesperetin in rats, in that the plasma T max was significantly shorter after administration of BglA protein-treated hesperidin than after administration of hesperidin extract. In addition, the area under the curve values for total hesperetin after administration of Bg1A-treated hesperidin were ～4-fold higher by oral administration and 3-fold higher by intravenous administration, respectively. In contrast, the plasma clearance value and volume of distribution after administration of Bg1A-treated hesperidin extract or pure hesperetin were significantly smaller than after administration of untreated hesperidin extract or pure hesperidin. This is the first study that systemically determines the absolute bioavailability of hesperidin and hesperetin simultaneously, shows clearly that hesperetin is more bioavailable than hesperidin regardless of the route of administration, and shows that prior transformation of hesperidin to hesperetin via fermentation should significantly increase its bioavailability because of the action of the yeast glycosidase-like protein BglA.

Statin-like principles of bergamot fruit (Citrus bergamia): Isolation of 3-hydroxymethylglutaryl flavonoid glycosides

The 3-hydroxy-3-methylglutaryl neohesperidosides of hesperetin (brutieridin, 1) and naringenin (melitidin, 2) were isolated and detected from the fruits of bergamot (Citrus bergamia). The structures of these compounds were determined by spectroscopic and

Hesperetin as an inhibitor of the snake venom serine protease from Bothrops jararaca

The majority (90%) of the snakebite envenomation in Brazil accounts for Bothrops from the Viperidae family. Some snake venom serine proteases provoke blood coagulation in ophidian accident victims because of their fibrinolytic activity, one of those proteases from Bothrops jararaca (B. jararaca) has been chosen for this study. Our objectives were to isolate and characterize the target serine protease; isolate, purify, and characterize the orange bagasse flavone (hesperetin, Hst), and investigate the interactions between the targets, enzyme, and hesperetin. The purified serine protease was named BjSP24 because of its molecular mass and proteolytic activity. BjSP24 was folded and characterized using circular dichroism and showed low alpha-helix contents (7.7%). BjSP24 exhibited sequence similarity to other known snake venom serine proteases as measured in the enzyme tryptic peptides' LC-MS/MS run. Hesperetin was obtained within the expected yield and with the predominance of 2S isomer (82%). It acted as a mixed inhibitor for the serine protease (SVSP) from Bothrops jararaca snake venom observed in three different in vitro experiments, fluorescence, kinetics, and SSTD-NMR. It is still to determine if hesperetin might aid-in reverting the on site blood clotting problems just after snakebite accidents.

Enhanced antioxidant, anti-inflammatory and α-glucosidase inhibitory activities of citrus hesperidin by acid-catalyzed hydrolysis

Hesperidin hydrolysates (HHS) was produced by the hydrolysis of hesperidin (HDN) in previous studies. The potential components in HHS were identified by LC-MS, and minor components (MCS) in HHS were isolated. Antioxidant activities by radical-scavenging capacities, reducing capacity and β-carotene-linoleate assay, anti-inflammatory effects by inhibiting NO production of RAW 264.7 cells, and α-glucosidase inhibitory effects of HDN, HHS, MCS and henperetin (HTN) were investigated in present study. HHS showed higher radical scavenging activities, higher reducing capacity, and higher inhibitory activity in the β-carotene-linoleate assay than HDN. HHS inhibited the production of NO and pro-inflammatory cytokines of RAW 264.7 cells more strongly than HDN. HHS also intensively inhibited α-glucosidase activity whereas HDN showed little activity. In addition, the effects of MCS on above activities showed it play a synergistic part with HTN. This work suggested that hydrolyzation of HDN enhance the activities, and provided valuable information on effective utilization of HDN.

Design, synthesis and investigation of the potential anti-inflammatory activity of 7-O-amide hesperetin derivatives

To develop new anti-inflammatory agents, a series of 7-O-amide hesperetin derivatives was designed, synthesized and evaluated for anti-inflammatory activity using RAW264.7 cells. All compounds showed inhibitory effect on LPS-induced NO production. Among them, 7-O-(2-(Propylamino)-2-oxoethyl)hesperetin (4d) and 7-O-(2-(Cyclopentylamino)-2-oxoethyl)hesperetin (4k) with hydrophobic side chains exhibited the most potent NO inhibitory activity (IC50 = 19.32 and 16.63 μM, respectively), showing stronger inhibitory effect on the production of pro- inflammatory cytokines tumor necrosis factor (TNF-α), interleukin-6 (IL-6) and interleukin-1β (IL-1β) than indomethacin and celecoxib at 10 μM. The structure-activity relationships (SARs) suggested that the 7-O-amide unit was buried in a medium-sized hydrophobic cavity of the bound receptor. Furthermore, compound 4d could also significantly suppress the expression of inducible nitric oxide synthase enzymes (iNOS) and cyclooxygenase-2 (COX-2), through the nuclear factor-kappa B (NF-κB) signaling pathway.

Hesperetin derivatives: Synthesis and anti-inflammatory activity

Sixteen novel hesperetin derivatives containing Mannich base moiety were designed and synthesized and their anti-inflammatory activities were evaluated by inhibiting tumor necrosis factor-α (TNF-α) and interleukin-6 (IL-6) in mouse RAW264.7 macrophages. Compounds 3a-3k showed better hydrophilic, while compounds 3l-3p with aromatic groups was hydrophobic. The anti-inflammatory activity of title compounds was correlated with log P values, among them, compounds 3c, 3e and 3i with minus log P values exhibited best anti-inflammatory activity through decreasing both IL-6 and TNF-α. Furthermore, the expression of LPS-induced notch1 and inos was reduced by compounds 3c, 3e, and 3i, and compound 3e attenuated LPS-induced inos protein levels in a dose-dependent manner.

Flavonoids with an oligopolysulfated moiety: A new class of anticoagulant agents

Polysulfated (oligo)flavonoids were synthesized and assayed for their in vitro and in vivo anticoagulant activities. The approach was based on molecular hybridization of two classes of anticoagulants, sulfated polysaccharides and sulfated flavonoids. The synthesis was optimized using microwave-assisted sulfation with triethylamine-sulfur trioxide. The obtained polysulfated flavonosides were highly effective in increasing clotting times and able to completely block the clotting process, in contrast to their corresponding aglycones. The thromboelastography proved that polysulfated flavonosides possess good whole blood anticoagulation activity. The following structure-activity relationships were found: 3-O-rutinosides (10, 13) were direct inhibitors of FXa, while 7-O-rutinosides (7, 8) showed inhibition of FXa by ATIII activation. Furthermore, compounds 7 and 13 were stable in plasma and active in vivo and preliminary toxicity studies would lead us to rule out acute side effects. From the overall results, the polysulfated flavonosides showed the potential as new effective and safe agents for anticoagulant therapy.

New potent antioxidative hydroxyflavanones produced with Aspergillus saitoi from flavanone glycoside in citrus fruit.

Potent antioxidative hydroxyflavanones were produced with Aspergillus saitoi from hesperidin or naringin, which are flavanone glycosides in citrus fruit with weak antioxidative activity. The hydroxyflavanone produced from hesperidin was identified as 8-hydroxyhesperetin (8-HHE), a novel substance, and those from naringin were identified as carthamidin (6-hydroxynaringenin) and isocarthamidin (8-hydroxynaringenin) by FAB-MS, 1H-NMR and 13C-NMR analyses. The antioxidative activity of these hydroxyflavanones was examined by using the free radical-scavenging system of 1,1-diphenyl-2-picrylhydrazyl (DPPH) and the methyl linoleate oxidation system. The hydroxyflavanones (8-HHE, carthamidin, and isocarthamidin) exhibited stronger activity than the flavanone glycosides (hesperidin or naringin) and their aglycones (hesperetin or naringenin). The activity of 8-HHE and isocarthamidin was comparable to that of alpha-tocopherol, and that of carthamidin was weaker than that of isocarthamidin. The hydroxyflavanones, which were hydroxylated on A ring of flavanone by Aspergillus saitoi, were obtained as potent antioxidants.