(E)-C-HDMAPP (ammonium salt)
Item № 13151
CAS № 933030-60-5
Purity ≥95%
product image
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 2015-10-06. Prices are subject to change without notice.

Bulk Inquiry Form


Enter number, size, and select unit. Example: 2 x 500 mg

Please indicate any analytical testing requirements, special handling, packaging, or delivery requirements.

  • (​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

Download Product Insert Download Safety Data Sheet (SDS)

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
Product Downloads & Resources
Product Downloads

Download Product Insert 107 Kb PDF

Download Safety Data Sheet (SDS) 23 Kb PDF

Download free InChI Key generation software

Additional Information

View the Cayman Structure Database for chemical structure definitions for many Cayman products

Get Batch-Specific Data and Documents by Batch Number

Separate multiple batch numbers with commas

QC Sheets
Certificates of Analysis
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).

Technical Support
Contact Us
  • To streamline the process attach the appropriate questionnaire to your inquiry.

  • Toll Free Phone (USA and Canada Only): (888) 526-5351
  • Direct Phone: (734) 975-3888
Contract Research Services

We offer you the deep and diverse knowledge of more than 100 in-house scientists and the expertise that comes from more than three decades of designing and developing the tools to advance biomedical research.

Cayman is know as a partner to scientists worldwide, responding to your needs with services in:

Cayman Chemical

1180 East Ellsworth Road

Ann Arbor, Michigan 48108 USA


Please wait...