A PKC activator
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Ingenol

Item No. 14031

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(1aR,2S,5R,5aR,6S,8aS,9R,10aR)-1a,2,5,5a,6,9,10,10a-octahydro-5,5a,6-trihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-1H-2,8a-methanocyclopenta[a]cyclopropa[e]cyclodecen-11-one
CAS Number
30220-46-3
Molecular Formula
C20H28O5
Formula Weight
348.4
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMSO: 5 mg/mlEthanol: 10 mg/mlPBS (pH 7.2): 0.5 mg/ml
SMILES
CC([C@@H]1O)=C[C@@]23[C@]1(O)[C@H](O)C(CO)=C[C@]([C@@]4([H])[C@@](C4(C)C)([H])C[C@H]3C)([H])C2=O
InChi Code
InChI=1S/C20H28O5/c1-9-7-19-10(2)5-13-14(18(13,3)4)12(17(19)24)6-11(8-21)16(23)20(19,25)15(9)22/h6-7,10,12-16,21-23,25H,5,8H2,1-4H3/t10-,12+,13-,14+,15+,16-,19+,20-/m1/s1
InChi Key
VEBVPUXQAPLADL-POYOOMFHSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $38

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    1 mg

    $65

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    5 mg

    $274

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    10 mg

    $399

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    Product Description

    Ingenol is a diterpenoid related to phorbol, derived from the milkweed plant E. peplus.1 It is a protein kinase C activator that displays a Ki value of 30 μM and an ED50 value of 27 μM in vitro.2,3 Most ingenol esters are tumor-promoting.4 However, ingenol mebutate possesses anti-tumor activity when used topically for actinic keratosis.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Wender, P.A., Koehler, K.F., Sharkey, N.A., et al. Analysis of the phorbol ester pharmacophore on protein kinase C as a guide to the rational design of new classes of analogs. Proc. Natl. Acad. Sci. USA 83(12), 4214-4218 (1986).

    2. Hasler, C.M., Acs, G., and Blumberg, P.M. Specific binding to protein kinase C by ingenol and its induction of biological responses. Cancer Res. 52(1), 202-208 (1992).

    3. Vogg, G., Mattes, E., Rothenburger, J., et al. Tumor promoting diterpenes from Euphorbia leuconeura L. Phytochemistry 51(2), 289-295 (1999).

    4. Nelson, T.J., and Alkon, D.L. Neuroprotective versus tumorigenic protein kinase C activators. Trends Biochem. Sci. 34(3), 136-145 (2009).

    5. Lebwohl, M., Swanson, N., Anderson, L.L., et al. Ingenol mebutate gel for actinic keratosis. N. Engl. J. Med. 366(11), 1010-1019 (2012).