Glochicoccin D

CAS# 927812-23-5

Glochicoccin D

Catalog No. BCN4471----Order now to get a substantial discount!

Product Name & Size Price Stock
Glochicoccin D: 5mg $886 In Stock
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Quality Control of Glochicoccin D

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Chemical structure

Glochicoccin D

3D structure

Chemical Properties of Glochicoccin D

Cas No. 927812-23-5 SDF Download SDF
PubChem ID 91895381 Appearance Powder
Formula C21H24O10 M.Wt 436.4
Type of Compound Miscellaneous Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (2S,3aR,4S,4'S,5'R,6S,7aR)-3a,4-dihydroxy-4'-(4-hydroxybenzoyl)oxy-5'-methyl-3-oxospiro[5,6,7,7a-tetrahydro-4H-1-benzofuran-2,2'-oxane]-6-carboxylic acid
SMILES CC1COC2(CC1OC(=O)C3=CC=C(C=C3)O)C(=O)C4(C(CC(CC4O2)C(=O)O)O)O
Standard InChIKey ABMLTSFSLUQUFY-XUAJAPSHSA-N
Standard InChI InChI=1S/C21H24O10/c1-10-9-29-20(8-14(10)30-18(26)11-2-4-13(22)5-3-11)19(27)21(28)15(23)6-12(17(24)25)7-16(21)31-20/h2-5,10,12,14-16,22-23,28H,6-9H2,1H3,(H,24,25)/t10-,12+,14+,15+,16-,20+,21-/m1/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 Glochicoccin D

The fruits of Phyllanthus emblica L.

Biological Activity of Glochicoccin D

DescriptionStandard reference
In vitro

Anti-hepatitis B virus activities and absolute configurations of sesquiterpenoid glycosides from Phyllanthus emblica.[Pubmed: 25268491]

Org Biomol Chem. 2014 Nov 21;12(43):8764-74.


METHODS AND RESULTS:
During the process exploring anti-viral compounds from Phyllanthus species, eight new highly oxygenated bisabolane sesquiterpenoid glycoside phyllaemblicins G1–G8 (1–8) were isolated from Phyllanthus emblica, along with three known compounds, phyllaemblicin F (9), phyllaemblic acid (10) and Glochicoccin D (11). Phyllaemblicin G2 (2), bearing a tricyclo [3.1.1.1] oxygen bridge ring system, is an unusual sesquiterpenoid glycoside, while phyllaemblicins G6–G8 (6–8) are dimeric sesquiterpenoid glycosides with two norbisabolane units connecting through a disaccharide. All the structures were elucidated by the extensive analysis of HRMS and NMR data. The relative configuration of phyllaemblicin G2 was constructed based on heteronuclear coupling constants measurement, and the absolute configurations for all new compounds were established by calculated electronic circular dichroism (ECD) using time dependent density functional theory.
CONCLUSIONS:
The sesquiterpenoid glycoside dimers 6–9 displayed potential anti-hepatitis B virus (HBV) activities, especially for the new compound 6 with IC50 of 8.53 ± 0.97 and 5.68 ± 1.75 μM towards the HBV surface antigen (HBsAg) and HBV excreted antigen (HBeAg) secretion, respectively.

Protocol of Glochicoccin D

Structure Identification
J Org Chem. 2010 Nov 5;75(21):7461-4.

Stereoselective α,α'-annelation reactions of 1,3-dioxan-5-ones.[Pubmed: 20936869 ]


METHODS AND RESULTS:
Pyrrolidine enamines derived from three 1,3-dioxan-5-ones undergo α,α'-annelation reactions with methyl α-(bromomethyl)acrylate to produce bridged 2,4-dioxabicyclo[3.3.1]nonane ring systems with complete stereocontrol. Stereochemical outcomes have been rationalized based on steric and stereoelectronic interactions in intermediate boat-like conformations of the 1,3-dioxane ring and subsequent kinetic protonation to set an axial ester group on the cyclohexanone ring.
CONCLUSIONS:
Base-mediated ester epimerization provides the stereochemical array found in the highly oxygenated cyclohexane ring of phyllaemblic acid and glochicoccin B and Glochicoccin D.

Glochicoccin D Dilution Calculator

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Glochicoccin D Molarity Calculator

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Preparing Stock Solutions of Glochicoccin D

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.2915 mL 11.4574 mL 22.9148 mL 45.8295 mL 57.2869 mL
5 mM 0.4583 mL 2.2915 mL 4.583 mL 9.1659 mL 11.4574 mL
10 mM 0.2291 mL 1.1457 mL 2.2915 mL 4.583 mL 5.7287 mL
50 mM 0.0458 mL 0.2291 mL 0.4583 mL 0.9166 mL 1.1457 mL
100 mM 0.0229 mL 0.1146 mL 0.2291 mL 0.4583 mL 0.5729 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 Glochicoccin D

Anti-hepatitis B virus activities and absolute configurations of sesquiterpenoid glycosides from Phyllanthus emblica.[Pubmed:25268491]

Org Biomol Chem. 2014 Nov 21;12(43):8764-74.

During the process exploring anti-viral compounds from Phyllanthus species, eight new highly oxygenated bisabolane sesquiterpenoid glycoside phyllaemblicins G1-G8 (1-8) were isolated from Phyllanthus emblica, along with three known compounds, phyllaemblicin F (9), phyllaemblic acid (10) and Glochicoccin D (11). Phyllaemblicin G2 (2), bearing a tricyclo [3.1.1.1] oxygen bridge ring system, is an unusual sesquiterpenoid glycoside, while phyllaemblicins G6-G8 (6-8) are dimeric sesquiterpenoid glycosides with two norbisabolane units connecting through a disaccharide. All the structures were elucidated by the extensive analysis of HRMS and NMR data. The relative configuration of phyllaemblicin G2 was constructed based on heteronuclear coupling constants measurement, and the absolute configurations for all new compounds were established by calculated electronic circular dichroism (ECD) using time dependent density functional theory. The sesquiterpenoid glycoside dimers 6-9 displayed potential anti-hepatitis B virus (HBV) activities, especially for the new compound 6 with IC50 of 8.53 +/- 0.97 and 5.68 +/- 1.75 muM towards the HBV surface antigen (HBsAg) and HBV excreted antigen (HBeAg) secretion, respectively.

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