A diterpene ester with anticancer activity
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20-O-Acetylingenol-3-angelate

Item No. 39904

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2Z)-2-methyl-2-butenoic acid, (1aR,2S,5R,5aS,6S,8aS,9R,10aR)-4-[(acetyloxy)methyl]-1a,2,5,5a,6,9,10,10a-octahydro-5,5a-dihydroxy-1,1,7,9-tetramethyl-11-oxo-1H-2,8a-methanocyclopenta[a]cyclopropa[e]cyclodecen-6-yl ester
CAS Number
82425-35-2
Synonyms
  • AAI
  • 3-O-Angeloyl-20-O-acetyl Ingenol
  • PEP008
Molecular Formula
C27H36O7
Formula Weight
472.6
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Acetonitrile: Slightly soluble: 0.1-1 mg/mlChloroform: Sparingly soluble: 1-10 mg/ml
SMILES
O[C@@]12[C@]3(C=C([C@@H]2OC(/C(C)=C\C)=O)C)C([C@](C=C([C@H]1O)COC(C)=O)([H])[C@@]4([H])[C@@](C4(C)C)([H])C[C@H]3C)=O
InChi Code
InChI=1S/C27H36O7/c1-8-13(2)24(31)34-23-14(3)11-26-15(4)9-19-20(25(19,6)7)18(22(26)30)10-17(12-33-16(5)28)21(29)27(23,26)32/h8,10-11,15,18-21,23,29,32H,9,12H2,1-7H3/b13-8-/t15-,18+,19-,20+,21-,23+,26+,27+/m1/s1
InChi Key
ZYCAGKYWXRKLSN-KLKWOBOISA-N
Origin
Plant/Euphorbia pekinensis Rupr.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

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    500 µg

    $109

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    1 mg

    $196

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    5 mg

    $872

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    10 mg

    $1,525

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    Product Description

    20-O-Acetylingenol-3-angelate is a diterpene ester that has been found in E. peplus and a derivative of ingenol-3-angelate (Item No. 16207) that has anticancer activity.1,2 It inhibits the growth of K562, HL-60, KT-1, MCF-7/adr, A549, and NIH3T3 cells when used at a concentration of 12.5 µM. 20-O-Acetylingenol-3-angelate (31.25-500 nM) induces cell cycle arrest at the G2/M phase, apoptosis, and necrosis in K562 cells.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Mason, S.A., Cozzi, S.-J., Pierce, C.J., et al. The induction of senescence-like growth arrest by protein kinase C-activating diterpene esters in solid tumor cells. Invest. New Drugs 28(5), 575-586 (2010).

    2. Liu, M., Chen, F., Yu, R., et al. Synthesis and cytotoxicity against K562 cells of 3-O-angeloyl-20-O-acetyl ingenol, a derivative of ingenol mebutate. Int. J. Mol. Sci. 17(8), 1348 (2016).