A natural cytotoxic diterpene ester
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Ingenol-3-angelate

Item No. 16207

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2Z-methyl-2-butenoic acid, (1aR,2S,5R,5aS,6S,8aS,9R,10aR)-1a,2,5,5a,6,9,10,10a-octahydro-5,5a-dihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-11-oxo-1H-2,8a-methanocyclopenta[a]cyclopropa[e]cyclodecen-6-yl ester
CAS Number
75567-37-2
Synonyms
  • Ingenol Mebutate
  • 3-Ingenyl Angelate
  • PEP005
  • Picato®
Molecular Formula
C25H34O6
Formula Weight
430.5
Purity
≥95%
Formulation (Request formulation change)
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
λmax
210 nm
SMILES
CC([C@@H]1OC(/C(C)=C\C)=O)=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/C25H34O6/c1-7-12(2)22(29)31-21-13(3)10-24-14(4)8-17-18(23(17,5)6)16(20(24)28)9-15(11-26)19(27)25(21,24)30/h7,9-10,14,16-19,21,26-27,30H,8,11H2,1-6H3/b12-7-/t14-,16+,17-,18+,19-,21+,24+,25+/m1/s1
InChi Key
VDJHFHXMUKFKET-WDUFCVPESA-N
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

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    500 µg

    $46

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    1 mg

    $86

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    5 mg

    $271

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    10 mg

    $451

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    Product Description

    Ingenol-3-angelate is a hydrophobic diterpene ester that can be isolated from the euphorb E. peplus. It rapidly induces cell death in proliferating keratinocytes through plasma membrane and mitochondrial disruption, although it can also initiate apoptosis in some cancer cell lines (LD90 = ~190 µM).1 Secondarily, ingenol-3-angelate causes inflammation due, at least in part, to activation of PKC, leading to antibody-dependent cellular cytotoxicity.2,3,4 These actions have relevance in diminishing actinic keratosis and, possibly, other cancers of the skin.5,6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Ogbourne, S.M., Suhrbier, A., Jones, B., et al. Antitumor activity of 3-ingenyl angelate: Plasma membrane and mitochondrial disruption and necrotic cell death. Cancer Res. 64(8), 2833-2839 (2004).

    2. Gillespie, S.K., Zhang, X.D., and Hersey, P. Ingenol 3-angelate induces dual modes of cell death and differentially regulates tumor necrosis factor-related apoptosis-inducing ligand-induced apoptosis in melanoma cells. Mol. Cancer Ther. 3(12), 1651-1658 (2004).

    3. Li, L., Shukla, S., Lee, A., et al. The skin cancer chemotherapeutic agent ingenol-3-angelate (PEP005) is a substrate for the epidermal multidrug transporter (ABCB1) and targets tumor vasculature. Cancer Res. 70(11), 4509-4519 (2010).

    4. 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).

    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).

    6. Micali, G., Lacarrubba, F., Nasca, M.R., et al. Topical pharmacotherapy for skin cancer. Part I. Pharmacology. J. Am. Acad. Dermatol. 70(6), 965.e961-956.e912 (2014).

    Product Citations

    Isotani, R., Igarashi, M., Miura, M., et al. Nicotine enhances the stemness and tumorigenicity in intestinal stem cells via Hippo-YAP/TAZ and Notch signal pathway. Elife 13, RP95267 (2025).