A synthetic, pure phosphoinositol for signal transduction research
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D-myo-Inositol-2,5,6-triphosphate (sodium salt)

Item No. 10008424

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
D-myo-inositol-2,5,6-tris(dihydrogen phosphate), trisodium salt
Synonyms
  • Ins(2,5,6)P3 (sodium salt)
  • 2,5,6-IP3 (sodium salt)
Molecular Formula
C6H12O15P3 • 3Na
Formula Weight
486.0
Purity
≥98%
Formulation (Request formulation change)
A lyophilized powder
SMILES
O[C@@H]1[C@@H](O)[C@@H](OP([O-])(O)=O)[C@@H](O)[C@H](OP([O-])(O)=O)[C@H]1OP([O-])(O)=O.[Na+].[Na+].[Na+]
InChi Code
InChI=1S/C6H15O15P3.3Na/c7-1-2(8)5(20-23(13,14)15)6(21-24(16,17)18)3(9)4(1)19-22(10,11)12;;;/h1-9H,(H2,10,11,12)(H2,13,14,15)(H2,16,17,18);;;/q;3*+1/p-3/t1-,2-,3-,4?,5?,6?;;;/m1.../s1
InChi Key
ZVCVTWVBDIPWPZ-XIEXOYEMSA-K
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

    100 µg

    $69

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    500 µg

    $297

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    1 mg

    $525

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    Product Description

    Ins(2,5,6)P3 (sodium salt) is a member of the inositol phosphate (InsP) family of second messengers that play a critical role in the transmission of cellular signals.1,2 The most studied InsP, Ins(1,4,5)P3 is a second messenger produced in cells by phospholipase C (PLC)-mediated hydrolysis of phosphatidylinositol-4,5-biphosphate.3,4 Binding of the Ins(1,4,5)P3 to its receptor on the endoplasmic reticulum results in opening of calcium channels and an increase in intracellular calcium.4,5 Ins(2,5,6)P3 is a less potent inducer of calcium release from permeabilized rat basophilic leukemia cells with an EC50 value of 110 µM compared to Ins(1,4,5)P3, which has an EC50 value of 0.17 µM.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Berridge, M.J. Inositol trisphosphate and calcium signalling. Nature 361(6410), 315-325 (1993).

    2. Majerus, P.W. Inositol phosphate biochemistry. Annu. Rev. Biochem. 61, 225-250 (1992).

    3. Streb, H., Irvine, R.F., Berridge, M.J., et al. Release of Ca2+ from a nonmitochondrial intracellular store in pancreatic acinar cells by inositol-1,4,5-trisphosphate. Nature 306(5938), 67-69 (1983).

    4. Yoshida, Y., and Imai, S. Structure and function of inositol 1,4,5-triphosphate receptor. Jpn. J. Pharmacol. 74(2), 125-137 (1997).

    5. Exton, J.H. Regulation of phosphoinositide phospholipases by hormones, neurotransmitters, and other agonists linked to G proteins. Annu. Rev. Pharmacol. Toxicol. 36, 481-509 (1996).

    6. Tegge, W., Denis, G.V., and Ballou, C.E. Synthesis and Ca2+-release activity of D- and L-myo-inositol 2,4,5-trisphosphate and D- and L-chiro-inositol 1,3,4-trisphosphate. Carbohydr. Res. 217, 107-116 (1991).