B-D-GLUCOPYRANOSE CAS 60976-49-0

Introduction：Basic information about B-D-GLUCOPYRANOSE CAS 60976-49-0, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

B-D-GLUCOPYRANOSE Basic information

• Product Name: B-D-GLUCOPYRANOSE
• Synonyms: eraniin;GERANIIN;B-D-GLUCOPYRANOSE;beta-D-Glucopyranose cyclic 2-7:4-5-(3,6-dihydro-2,9,10,11,11-pentahydroxy-3-oxo-2,6-methano-2H-1-benzoxocin-5,7-dicarboxylate) cyclic 3,6-(4,4',5,5',6,6'-hexahydroxy[1,1'-biphenyl]-2,2'-dicarboxylate) 1-(3,4,5-trihydroxybenzoate) stereoisomer;3,4,4,6,7,15,16,17,18,19,20-undecahydroxy-2,9,13,22,27-pentaoxo-2,3,4,4a,9,11a,13,22,24,25,25a,27-dodecahydro-11H-3,5-epoxy-25,11-(epoxymethano)dibenzo[h,j]dibenzo[7,8:9,10][1,5]dioxacycloundecino[3,2-b][1,6]dioxacyclododecin-29-yl 3,4,5-trihydroxybenzoat;5-(3,6-dihydro-2,9,10,11,11-pentahydroxy-3-oxo-2,6-Methano-2H-1-benzoxocin-5,7-dicarboxylate)cyclic 3,6-(4,4',5,5',6,6'-hexahydroxy[1,1'-biphenyl]-2,2'-dicarboxylate)1-(3,4,5-trihydroxybenzoate), stereoisoMer;7:4®b-D-Glucopyranose, cyclic 2®
• CAS: 60976-49-0
• MF: C41H28O27
• MW: 952.64
• Product Categories: chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 60976-49-0.mol

B-D-GLUCOPYRANOSE Chemical Properties

• density: 2.25
• storage temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• solubility: DMSO : 100 mg/mL (104.97 mM; Need ultrasonic)
• form: powder
• pka: 6.35±0.70(Predicted)
• color: Light yellow
• Major Application: food and beverages
• InChIKey: JQQBXPCJFAKSPG-JAEVIPNINA-N
• SMILES: O1[C@@]2(C([C@@H]3c4c1c(c(cc4C(=O)OC5C6OC(=O)c7c(c(c(c(c7)O)O)O)c8c(cc(c(c8O)O)O)C(=O)OCC(OC5OC(=O)c9cc(c(c(c9)O)O)O)C6OC(=O)C3=CC2=O)O)O)(O)O)O

Safety Information

• WGK Germany: WGK 3
• Storage Class: 11 - Combustible Solids

B-D-GLUCOPYRANOSE Usage And Synthesis

Description

Geraniin is a tannin that has been found in P. urinaria and has diverse biological activities. It scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH; IC₅₀s = 0.92 and 1.27 μM at pH 4.5 and 7.9, respectively), superoxide (IC₅₀ = 2.65 μM), and hydroxyl radicals (IC₅₀ = 1.44 μM) in cell-free assays. Geraniin inhibits herpes simplex virus 1 (HSV-1) and HSV-2 replication in plaque reduction assays (IC₅₀s = 35 and 18.4 μM, respectively). It inhibits angiotensin-converting enzyme (ACE) in vitro (IC₅₀ = 13.22 μM) and reduces both systolic and diastolic blood pressure in spontaneously hypertensive rats when administered at a dose of 5 mg/kg. Geraniin (5, 10, and 20 μM) induces apoptosis and halts the cell cycle at the S phase in A549 lung cancer cells. It reduces tumor growth in an A549 mouse xenograft model when administered at doses of 10 and 20 mg/kg.

Chemical Properties

It is a white powder, soluble in organic solvents such as methanol, ethanol, and DMSO. It comes from the whole herb of Phyllanthus urinaria L., a plant of the Euphorbiaceae family.

Uses

Geraniin protects PC12 cells against neuronal damage and may be used in the treatment of Alzheimer’s disease/ Also is an ACE inhibitor which is useful for hypertension treatment.

Definition

ChEBI: Geraniin is a tannin.

in vivo

Treatment with Geraniin prior to application of okadaic acid delays development of tumors compared with control group, reduces the percentage of tumor bearing mice from 80.0% to 40.0%, and reduces the average numbers of tumor per mouse from 3.8 to 1.1 in week 20. It is also showed that oral administration of Geraniin to rats (50 mg/kg/d or 100 mg/kg/d) inhibit the elevation of serum total cholesterol, lipid peroxide, free fatty acid, triglyceride, glutamic oxaloacetic transaminase and glutamic pyruvic transaminase induced by treatment with peroxidized oil^[1].

References

[1] SHYR-YI LIN . Antioxidant, anti-semicarbazide-sensitive amine oxidase, and anti-hypertensive activities of geraniin isolated from Phyllanthus urinaria[J]. Food and Chemical Toxicology, 2008, 46 7: Pages 2485-2492. DOI: 10.1016/j.fct.2008.04.007
[2] CHIEN-MIN YANG . The in vitro activity of geraniin and 1,3,4,6-tetra-O-galloyl-β-d-glucose isolated from Phyllanthus urinaria against herpes simplex virus type 1 and type 2 infection[J]. Journal of ethnopharmacology, 2007, 110 3: Pages 555-558. DOI: 10.1016/j.jep.2006.09.039
[3] JIA LI. Geraniin induces apoptotic cell death in human lung adenocarcinoma A549 cells in vitro and in vivo.[J]. Canadian journal of physiology and pharmacology, 2013, 91 12: 1016-1024. DOI: 10.1139/cjpp-2013-0140