Synthetic, pure phosphoinositol for signal transduction research
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D-myo-Inositol-1,2,6-triphosphate (sodium salt)

Item No. 10007780

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
D-myo-inositol-1,2,6-tris(hydrogen phosphate), trisodium salt
Synonyms
  • Ins(1,2,6)-P3
  • 1,2,6-IP3
Molecular Formula
C6H12O15P3 • 3Na
Formula Weight
486.0
Purity
≥98%
Formulation (Request formulation change)
A lyophilized powder
SMILES
O[C@H]1[C@@H](OP([O-])(O)=O)[C@@H](OP([O-])(O)=O)[C@H](OP([O-])(O)=O)[C@@H](O)[C@@H]1O.[Na+].[Na+].[Na+]
InChi Code
InChI=1S/C6H15O15P3.3Na/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);;;/q;3*+1/p-3/t1-,2-,3+,4?,5?,6?;;;
InChi Key
JENABGGDGLKLTB-AJBPOAAQSA-K
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    100 µg

    $63

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    500 µg

    $274

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    1 mg

    $481

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    Product Description

    D-myo-Inositol-1,2,6-phosphate (Ins(1,2,6)-P3) 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 Ins(1,4,5)-P3 to its receptor on the endoplasmic reticulum results in opening of the calcium channels and an increase in intracellular calcium.4,5 Ins(1,2,6)-P3 (tested as the D/L racemic mixture) is ~1,000-fold less potent than Ins(1,4,5)-P3 at initiating Ca2+ release when injected into Xenopus oocytes.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

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

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

    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. DeLisle, S., Radenberg, T., Wintermantel, M.R., et al. Second messenger specificity of the inositol trisphosphate receptor: Reappraisal based on novel inositol phosphates. Am. J. Physiol. 266(2 Pt 1), C429-C436 (1994).