(E)-C-HDMAPP (ammonium salt)
Item № 13151
CAS № 933030-60-5
Purity ≥95%
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500 µg $61.00 $0.00
1 mg $116.00 $0.00
5 mg $488.00 $0.00
10 mg $854.00 $0.00

Pricing updated 2016-02-06. Prices are subject to change without notice.

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  • (​E)-5-hydroxy-4-methylpent-3-enyl pyrophosphate

Synthetic and natural alkyl phosphates, also known as phosphoantigens, stimulate the proliferation of γδ-T lymphocytes.1 Isopentenyl pyrophosphate, and related derivatives including (E)-hydroxy-dimethyl-allyl pyrophosphate ((E)-HDMAPP), are particularly effective activators of γδ-T cells.23 (E)-C-HDMAPP is the pyrophosphonate form of (E)-HDMAPP. The pyrophosphonate moiety in (E)-C-HDMAPP is much less susceptible to chemical or enzymatic hydrolysis than its pyrophosphate counterpart. As a result, (E)-C-HDMAPP is much more stable in solution and in vascular circulation.4 (E)-C-HDMAPP possesses comparable activity to (E)-HDMAPP, which is the most potent of the isoprenoid phosphoantigens. (E)-C-HDMAPP stimulates the synthesis of tumor necrosis factor (TNF-α) by γδ-T lymphocytes with an IC50 value of 0.91 nM.4 (E)-C-HDMAPP also significantly increases the number of circulating γδ-T cells in vivo, in cynomolgus monkeys.4

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Technical Information
Formal Name P’-[(3E)-5-hydroxy-4-methyl-3-penten-1-yl]-isohypophosphoric acid, triammonium salt
CAS Number 933030-60-5
  • (​E)-5-hydroxy-4-methylpent-3-enyl pyrophosphate
Molecular Formula C6H14O7P2 • 3NH4
Formula Weight 311.2
Purity ≥95%
Formulation A crystalline solid
SMILES [O-]P(OP([O-])(CC/C=C(CO)\C)=O)([O-])=O.[NH4+].[NH4+].[NH4+]
InChI Code 1S/C6H14O7P2.3H3N/c1-6(5-7)3-2-4-14(8,9)13-15(10,11)12;;;/h3,7H,2,4-5H2,1H3,(H,8,9)(H2,10,11,12);3*1H3/b6-3+;;;

WARNING - This product is not for human or veterinary use.

Shipping & Storage
Storage -20°C
Shipping Wet ice in continental US; may vary elsewhere
Stability 2 years
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Download Safety Data Sheet (SDS) 23 Kb PDF

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Additional Information

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References & Background Reading
Product Description References

1. Tanaka, Y., Sano, S., Nieves, E., et al. Nonpeptide ligands for humanγδT cells. Proc Natl Acad Sci USA 91 8175-8179 (1994).

2. Poupot, M., and Fournié, J. Non-peptide antigens activating human Vg9/Vd2 T lymphocytes. Immunol Lett 95 129-138 (2004).

3. Tanaka, Y., Morita, C.T., Tanaka, Y., et al. Natural and synthetic non-peptide antigens recognized by humanγδT cells. Nature 375 155-158 (1995).

4. Boëdec, A., Sicard, H., Dessolin, J., et al. Synthesis and biological activity of phosphonate analogues and geometric isomers of the highly potent phosphoantigen (E)-1-hydroxy-2-methylbut-2-enyl 4-diphosphate. J Med Chem 51 1747-1754 (2008).

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