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Hesperetin-7-methyl ether

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Hesperetin-7-methyl ether

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Chemical structure

Hesperetin-7-methyl ether

3D structure

Chemical Properties of Hesperetin-7-methyl ether

Cas No. N/A SDF Download SDF
PubChem ID 14157910 Appearance Powder
Formula C17H16O6 M.Wt 316.3
Type of Compound Flavonoids Storage Desiccate at -20°C
Synonyms 7-METHOXYHESPERETIN
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (2S)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-methoxy-2,3-dihydrochromen-4-one
SMILES COC1=C(C=C(C=C1)C2CC(=O)C3=C(C=C(C=C3O2)OC)O)O
Standard InChIKey LWBHKKLWSUFUNZ-HNNXBMFYSA-N
Standard InChI InChI=1S/C17H16O6/c1-21-10-6-12(19)17-13(20)8-15(23-16(17)7-10)9-3-4-14(22-2)11(18)5-9/h3-7,15,18-19H,8H2,1-2H3/t15-/m0/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Hesperetin-7-methyl ether

The peel of Citrus maxima

Biological Activity of Hesperetin-7-methyl ether

DescriptionHesperetin-7-methyl ether is a natural prooduct from Citrus maxima.
TargetsPDE

Protocol of Hesperetin-7-methyl ether

Structure Identification
J Pharm Sci. 2013 Jul;102(7):2120-7.

Inhibitory effects of hesperetin derivatives on guinea pig phosphodiesterases and their ratios between high- and low-affinity rolipram binding.[Pubmed: 23666855]

The phosphodiesterase (PDE)4 molecule exists as two distinct conformers, PDE4H and PDE4L , which have high and low affinities, respectively, for the selective PDE4 inhibitor, rolipram. The inhibition of PDE4H and PDE4L is associated with adverse responses, such as nausea, vomiting, and gastric hypersecretion, and with anti-inflammatory and bronchodilator effects, respectively.
METHODS AND RESULTS:
We determined the therapeutic (PDE4H/PDE4L) ratios of hesperetin-7-O-methylether(Hesperetin-7-methyl ether), hesperetin-5,7,3'-O-trimethylether (HTME), hesperetin-7-O-acetate, hesperetin-7,3'-O-diacetate, hesperetin-5,7,3'-O-triacetate (HTA), hesperetin-5,7,3'-O-tripropionate, hesperetin-5,7,3'-O-tributyrate, hesperetin-5,7,3'-O-triisobutyrate, and hesperetin-5,7,3'-O-tripivatate, and compared these ratios to those of hesperetin, hesperetin-7,3'-O-dimethylether, hesperidin, and hesperidin-3'-O-methylether to identify derivatives with therapeutic ratios and to characterize the structure-activity relationships among these compounds.

Hesperetin-7-methyl ether Dilution Calculator

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Preparing Stock Solutions of Hesperetin-7-methyl ether

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.1616 mL 15.8078 mL 31.6156 mL 63.2311 mL 79.0389 mL
5 mM 0.6323 mL 3.1616 mL 6.3231 mL 12.6462 mL 15.8078 mL
10 mM 0.3162 mL 1.5808 mL 3.1616 mL 6.3231 mL 7.9039 mL
50 mM 0.0632 mL 0.3162 mL 0.6323 mL 1.2646 mL 1.5808 mL
100 mM 0.0316 mL 0.1581 mL 0.3162 mL 0.6323 mL 0.7904 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Hesperetin-7-methyl ether

Inhibitory effects of hesperetin derivatives on guinea pig phosphodiesterases and their ratios between high- and low-affinity rolipram binding.[Pubmed:23666855]

J Pharm Sci. 2013 Jul;102(7):2120-7.

The phosphodiesterase (PDE)4 molecule exists as two distinct conformers, PDE4H and PDE4L , which have high and low affinities, respectively, for the selective PDE4 inhibitor, rolipram. The inhibition of PDE4H and PDE4L is associated with adverse responses, such as nausea, vomiting, and gastric hypersecretion, and with anti-inflammatory and bronchodilator effects, respectively. We determined the therapeutic (PDE4H/PDE4L) ratios of hesperetin-7-O-methylether, hesperetin-5,7,3'-O-trimethylether (HTME), hesperetin-7-O-acetate, hesperetin-7,3'-O-diacetate, hesperetin-5,7,3'-O-triacetate (HTA), hesperetin-5,7,3'-O-tripropionate, hesperetin-5,7,3'-O-tributyrate, hesperetin-5,7,3'-O-triisobutyrate, and hesperetin-5,7,3'-O-tripivatate, and compared these ratios to those of hesperetin, hesperetin-7,3'-O-dimethylether, hesperidin, and hesperidin-3'-O-methylether to identify derivatives with therapeutic ratios and to characterize the structure-activity relationships among these compounds. The activities of PDE isozymes 1 through 5 were measured using a two-step procedure using [(3)H]adenosine 3',5'-cyclic monophosphate or [(3)H]guanosine 3',5'-cyclic monophosphate as substrates. The inhibitory concentration (IC50) for 50% of PDE4 inhibition and effective concentration (EC50) for replacing 50% of [(3)H]rolipram binding on high-affinity rolipram-binding sites was taken as the PDE4L and PDE4H value, respectively. The HTME and the HTA dually inhibited PDE3 and PDE4, and displayed PDE4H/PDE4L ratios of 18.3 and 20.8, respectively, suggesting that they may be candidate drugs for treating asthma and chronic obstructive pulmonary disease (COPD) because the combined inhibition of PDE3 and PDE4 has synergistically anti-inflammatory and bronchodilator effects in COPD patients.

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