28841-62-5

Basic information

• Product Name: inositol 1,2,6-triphosphate
• Synonyms: inositol 1,2,6-triphosphate;Altrinositol;D-myo-Inositol-1,2,6-triphosphoric acid;myo-Inositol 1,2,6-triphosphoric acid;PP-56;α-Trinositol;inositol 1,2,6-trisphosphate
• CAS NO: 28841-62-5
• Molecular Formula: C₆H₁₅O₁₅P₃
• Molecular Weight: 420.091
• Mol File: 28841-62-5.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 839.2°Cat760mmHg
• Flash Point: 461.3°C
• Appearance: /
• Density: 2.25g/cm³
• Vapor Pressure: 1.04E-32mmHg at 25°C
• Refractive Index: 1.635
• CAS DataBase Reference: inositol 1,2,6-triphosphate(CAS DataBase Reference)
• NIST Chemistry Reference: inositol 1,2,6-triphosphate(28841-62-5)
• EPA Substance Registry System: inositol 1,2,6-triphosphate(28841-62-5)

Safety Data

• Hazardous Substances Data: 28841-62-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C6H15O15P3/c7-1-2(8)4(19-22(10,11)12)6(21-24(16,17)18)5(3(1)9)20-23(13,14)15/h1-9H,(H2,10,11,12)(H2,13,14,15)(H2,16,17,18)/t1?,2-,3+,4-,5-,6?/m1/s1

Upstream product

• 26326-85-2 Ins(1,2,3,4,6)P5 
• 454199-95-2 L-1,2,6-tri-O-benzoyl-3,4-O-isopropylidene-myo-inositol 
• 454200-06-7 L-1,6-di-O-benzoyl-3,4-O-isopropylidene-myo-inositol 
• 455268-36-7 L-1,2,6-tri-O-benzoyl-myo-inositol 
• 165883-87-4 L-1,6-di-O-benzoyl-myo-inositol 
• 142630-99-7 1D-3,4,5-O-tribenzoyl-myo-inositol 
• 26326-86-3 Ins(1,2,3,4,5)P₅ 
• 83-86-3 phytic acid 

Downstream Products

• 166660-37-3 1D-3,4,5-tri-O-propanoyl-myo-inositol-1,2,6-tris(dihydrogenphosphate) 
• 194786-37-3 6-O-(1'-ethoxyethyl)-1,2-O-isopropylidene-4,5,6-tri-O-(N-phenylcarbamoyl)-myo-inositol 
• 194786-36-2 (+)-D-1,2-O-isopropylidene-3,4,5-tri-O-(N-phenylcarbamoyl)-myo-inositol 
• 194786-39-5 (3aR,4R,5S,6S,7R,7aS)-4,5,6-Tris-benzyloxy-7-(1-ethoxy-ethoxy)-2,2-dimethyl-hexahydro-benzo[1,3]dioxole 
• 172219-04-4 (+)-D-3,4,5-tri-O-phenylcarbamoyl myo-inositol 
• 131233-69-7 3,4,5-tri-O-benzyl-D-myo-inositol 
• 166660-36-2 (+)-D-3,4,5-tri-O-(N-phenylcarbamoyl)-myo-inositol-1,2,3-tris(phosphate) 

Relevant articles and documents

INOSITOL DERIVATIVES AND PHARMACEUTICAL COMPOSITIONS COMPRISING THEM

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Pathway of dephosphorylation of myo-inositol hexakisphosphate by phytases of legume seeds

Using a combination of high-performance ion chromatography analysis and kinetic studies, the pathway of dephosphorylation of myo-inositol hexakisphosphate by the phytases purified from faba bean and lupine seeds, respectively, was established. The data demonstrate that the legume seed phytases under investigation dephosphorylate myo-inositol hexakisphosphate in a stereospecific way. The phytase from faba bean seeds and the phytase LP2 from lupine seeds degrade phytate by sequential removal of phosphate groups via D-Ins(1,2,3,5,6)P5, D-Ins(1,2,5,6)P4, D-Ins(1,2,6)P3, and D-Ins(1,2)P2 to finally Ins(2)P, whereas the phytases LP11 and LP12 from lupine seeds generate the final degradation product Ins(2)P via D-Ins(1,2,4,5,6)P5, D-Ins(1,2,5,6)P4, D-Ins(1,2,6)P3, and D-Ins(1,2)P2.

Enzyme assisted synthesis of D-myo-inositol-1,2,6-trisphosphate

The title compound is prepared in enantiomerically pure form via a facile enzyme assisted route. Essential for the success of the described method were a) the highly enantioselective esterification of 4,6-O-dibenzoyl-myo-inositol 2, b) the selective acylation of the axial hydroxyl function in 3 and c) the selective, base catalysed methanolysis of one benzoate group in 5. The obtained, selectively protected 1,2,6-triol 6 was converted into the title compound 7 by phosphorylation using N,N-dimethyl dibenzyl phosphoamidite followed by deprotection.