Ingenol-3-angelate

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). Secondarily, ingenol-3-angelate causes inflammation due, at least in part, to activation of PKC, leading to antibody-dependent cellular cytotoxicity. These actions have relevance in diminishing actinic keratosis and, possibly, other cancers of the skin.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(R). Molecular Formula: C25H34O6. Formula Weight: 430.5. Purity: >95%. Formulation: (Request formulation change), A crystalline solid. Solubility: DMF: 10 mg/ml, DMSO: 5 mg/ml, Ethanol: 10 mg/ml, PBS (pH 7.2): 0.5 mg/ml. lambdamax: 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.