Isoescin IA

CAS# 219944-39-5

Isoescin IA

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Chemical structure

Isoescin IA

3D structure

Chemical Properties of Isoescin IA

Cas No. 219944-39-5 SDF Download SDF
PubChem ID 6476032 Appearance White - beige powder
Formula C55H86O24 M.Wt 1131.3
Type of Compound Triterpenoids Storage Desiccate at -20°C
Synonyms Aescin C; Escin IVa
Solubility Soluble in methanol; slightly soluble in water
Chemical Name (2S,3S,4S,5R,6R)-6-[[(3S,4S,4aR,6aR,6bS,8R,8aR,9R,10R,12aS,14aR,14bR)-8a-(acetyloxymethyl)-8,9-dihydroxy-4-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-10-[(E)-2-methylbut-2-enoyl]oxy-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-4-hydroxy-3,5-bis[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]oxane-2-carboxylic acid
SMILES CC=C(C)C(=O)OC1C(C2(C(CC1(C)C)C3=CCC4C5(CCC(C(C5CCC4(C3(CC2O)C)C)(C)CO)OC6C(C(C(C(O6)C(=O)O)OC7C(C(C(C(O7)CO)O)O)O)O)OC8C(C(C(C(O8)CO)O)O)O)C)COC(=O)C)O
Standard InChIKey YOSIWGSGLDDTHJ-IVKVKCDBSA-N
Standard InChI InChI=1S/C55H86O24/c1-10-23(2)46(71)79-44-43(68)55(22-72-24(3)59)26(17-50(44,4)5)25-11-12-30-51(6)15-14-32(52(7,21-58)29(51)13-16-53(30,8)54(25,9)18-31(55)60)75-49-41(77-48-38(66)36(64)34(62)28(20-57)74-48)39(67)40(42(78-49)45(69)70)76-47-37(65)35(63)33(61)27(19-56)73-47/h10-11,26-44,47-49,56-58,60-68H,12-22H2,1-9H3,(H,69,70)/b23-10+/t26-,27+,28+,29+,30+,31+,32-,33+,34+,35-,36-,37+,38+,39-,40-,41+,42-,43-,44-,47-,48-,49+,51-,52+,53+,54+,55-/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 Isoescin IA

The herbs of Aesculus hippocastanum L.

Biological Activity of Isoescin IA

DescriptionEscin Ia and Isoescin IA have been traditionally used clinically as the chief active ingredients of escin, a major triterpene saponin isolated from horse chestnut (Aesculus hippocastanum) seeds for the treatment of chronic venous insufficiency, hemorrhoids, inflammation and edema.
In vivo

Comparative pharmacokinetics and bioavailability of escin Ia and isoescin Ia after administration of escin and of pure escin Ia and isoescin Ia in rat.[Pubmed: 22094055 ]

J Ethnopharmacol. 2012 Jan 6;139(1):201-6.

Escin Ia and Isoescin IA have been traditionally used clinically as the chief active ingredients of escin, a major triterpene saponin isolated from horse chestnut (Aesculus hippocastanum) seeds for the treatment of chronic venous insufficiency, hemorrhoids, inflammation and edema. To establish a sensitive LC-MS/MS method and investigate the pharmacokinetic properties of escin Ia and Isoescin IA in rats and the pharmacokinetics difference of sodium escinate with pure escin Ia and Isoescin IA. The absolute bioavailability of escin Ia and Isoescin IA and the bidirectional interconversion of them in vivo were also scarcely reported.
METHODS AND RESULTS:
Wister rats were administrated an intravenous (i.v.) dose (1.7 mg/kg) of sodium escinate (corresponding to 0.5mg/kg of escin Ia and 0.5mg/kg of Isoescin IA, respectively) and an i.v. dose (0.5mg/kg) or oral dose (4mg/kg) of pure escin Ia or Isoescin IA, respectively. At different time points, the concentrations of escin Ia and Isoescin IA in rat plasma were determined by LC-MS/MS method. Main pharmacokinetic parameters including t(1/2), MRT, CL, V(d), AUC and F were estimated by non-compartmental analysis using the TopFit 2.0 software package (Thomae GmbH, Germany) and statistical analysis was performed using the Student's t-test with P<0.05 as the level of significance. After administration of sodium escinate, the t(1/2) and MRT values for both escin Ia and Isoescin IA were larger than corresponding values for the compounds given alone. Absorption of escin Ia and Isoescin IA was very low with F values both <0.25%. Escin Ia and Isoescin IA were found to form the other isomer in vivo with the conversion of escin Ia to Isoescin IA being much extensive than from Isoescin IA to escin Ia.
CONCLUSIONS:
Comparison of the pharmacokinetics of escin Ia and Isoescin IA given alone and together in rat suggest that administration of herbal preparations of escin for clinical use may provide longer duration of action than administration of single isomers. The interconversion of escin Ia and Isoescin IA when given alone indicates that administration of one isomer leads to exposure to the other.

Protocol of Isoescin IA

Structure Identification
Adv Pharm Bull. 2015 Nov;5(4):587-91.

Determination of Four Major Saponins in Skin and Endosperm of Seeds of Horse Chestnut (Aesculus Hippocastanum L.) Using High Performance Liquid Chromatography with Positive Confirmation by Thin Layer Chromatography.[Pubmed: 26819933]

To separate and quantify four major saponins in the extracts of the skin and the endosperm of seeds of horse chestnut (Aesculus hippocastanum L.) using ultrasonic solvent extraction followed by a high performance liquid chromatography-diode array detector (HPLC-DAD) with positive confirmation by thin layer chromatography (TLC).
METHODS AND RESULTS:
The saponins: escin Ia, escin Ib, Isoescin IA and isoescin Ib were extracted using ultrasonic extraction method. The optimized extraction conditions were: 70% methanol as extraction solvent, 80 °C as extraction temperature, and the extraction time was achieved in 4 hours. The HPLC conditions used: Zorbax SB-ODS-(150 mm × 2.1 mm, 3 μm) column, acetonitrile and 0.10% phosphoric acid solution (39:61 v/v) as mobile phase, flow rate was 0.5 mL min-1 at 210 nm and 230 nm detection. The injection volume was 10 μL, and the separation was carried out isothermally at 30 °C in a heated chamber. Results: The results indicated that the developed HPLC method is simple, sensitive and reliable. Moreover, the content of escins in seeds decreased by more than 30% in endosperm and by more than 40% in skin upon storage for two years.
CONCLUSIONS:
This assay can be readily utilized as a quality control method for horse chestnut and other related medicinal plants.

Isoescin IA Dilution Calculator

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Isoescin IA Molarity Calculator

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Preparing Stock Solutions of Isoescin IA

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 0.8839 mL 4.4197 mL 8.8394 mL 17.6788 mL 22.0985 mL
5 mM 0.1768 mL 0.8839 mL 1.7679 mL 3.5358 mL 4.4197 mL
10 mM 0.0884 mL 0.442 mL 0.8839 mL 1.7679 mL 2.2098 mL
50 mM 0.0177 mL 0.0884 mL 0.1768 mL 0.3536 mL 0.442 mL
100 mM 0.0088 mL 0.0442 mL 0.0884 mL 0.1768 mL 0.221 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 Isoescin IA

Determination of Four Major Saponins in Skin and Endosperm of Seeds of Horse Chestnut (Aesculus Hippocastanum L.) Using High Performance Liquid Chromatography with Positive Confirmation by Thin Layer Chromatography.[Pubmed:26819933]

Adv Pharm Bull. 2015 Nov;5(4):587-91.

PURPOSE: To separate and quantify four major saponins in the extracts of the skin and the endosperm of seeds of horse chestnut (Aesculus hippocastanum L.) using ultrasonic solvent extraction followed by a high performance liquid chromatography-diode array detector (HPLC-DAD) with positive confirmation by thin layer chromatography (TLC). METHODS: The saponins: escin Ia, escin Ib, Isoescin IA and isoescin Ib were extracted using ultrasonic extraction method. The optimized extraction conditions were: 70% methanol as extraction solvent, 80 degrees C as extraction temperature, and the extraction time was achieved in 4 hours. The HPLC conditions used: Zorbax SB-ODS-(150 mm x 2.1 mm, 3 mum) column, acetonitrile and 0.10% phosphoric acid solution (39:61 v/v) as mobile phase, flow rate was 0.5 mL min(-1) at 210 nm and 230 nm detection. The injection volume was 10 muL, and the separation was carried out isothermally at 30 degrees C in a heated chamber. RESULTS: The results indicated that the developed HPLC method is simple, sensitive and reliable. Moreover, the content of escins in seeds decreased by more than 30% in endosperm and by more than 40% in skin upon storage for two years. CONCLUSION: This assay can be readily utilized as a quality control method for horse chestnut and other related medicinal plants.

Comparative pharmacokinetics and bioavailability of escin Ia and isoescin Ia after administration of escin and of pure escin Ia and isoescin Ia in rat.[Pubmed:22094055]

J Ethnopharmacol. 2012 Jan 6;139(1):201-6.

ETHNOPHARMACOLOGICAL RELEVANCE: Escin Ia and Isoescin IA have been traditionally used clinically as the chief active ingredients of escin, a major triterpene saponin isolated from horse chestnut (Aesculus hippocastanum) seeds for the treatment of chronic venous insufficiency, hemorrhoids, inflammation and edema. AIM OF THE STUDY: To establish a sensitive LC-MS/MS method and investigate the pharmacokinetic properties of escin Ia and Isoescin IA in rats and the pharmacokinetics difference of sodium escinate with pure escin Ia and Isoescin IA. The absolute bioavailability of escin Ia and Isoescin IA and the bidirectional interconversion of them in vivo were also scarcely reported. MATERIALS AND METHODS: Wister rats were administrated an intravenous (i.v.) dose (1.7 mg/kg) of sodium escinate (corresponding to 0.5mg/kg of escin Ia and 0.5mg/kg of Isoescin IA, respectively) and an i.v. dose (0.5mg/kg) or oral dose (4mg/kg) of pure escin Ia or Isoescin IA, respectively. At different time points, the concentrations of escin Ia and Isoescin IA in rat plasma were determined by LC-MS/MS method. Main pharmacokinetic parameters including t(1/2), MRT, CL, V(d), AUC and F were estimated by non-compartmental analysis using the TopFit 2.0 software package (Thomae GmbH, Germany) and statistical analysis was performed using the Student's t-test with P<0.05 as the level of significance. RESULTS: After administration of sodium escinate, the t(1/2) and MRT values for both escin Ia and Isoescin IA were larger than corresponding values for the compounds given alone. Absorption of escin Ia and Isoescin IA was very low with F values both <0.25%. Escin Ia and Isoescin IA were found to form the other isomer in vivo with the conversion of escin Ia to Isoescin IA being much extensive than from Isoescin IA to escin Ia. CONCLUSION: Comparison of the pharmacokinetics of escin Ia and Isoescin IA given alone and together in rat suggest that administration of herbal preparations of escin for clinical use may provide longer duration of action than administration of single isomers. The interconversion of escin Ia and Isoescin IA when given alone indicates that administration of one isomer leads to exposure to the other.

Description

Isoescin IA is a triterpenoid saponin isolated from the seeds of Aesculus chinensis. Isoescin IA has anti-HIV-1 protease activity.

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