|
Phorbol 12-myristate 13-acetate
Cayman Chemical Item Number 10008014
Description
Phorbol 12-myristate 13-acetate (PMA) is a phorbol ester that is commonly used to activate certain types of protein kinase C (PKC), including group A (α, βI, βII, γ) and group B (δ, ε, η, θ) isoforms.1↗ Phorbol esters, including PMA, are structurally analogous to diacylglycerol and activate PKC isoforms by associating with their C1 domains.2↗ Through PKC, PMA also activates certain MAP kinase pathways.3↗ Prolonged treatment of cells with PMA at high concentrations results in the downregulation of total PKC activity and is tumorigenic, whereas lower concentrations may be protective.4↗,5↗ In addition, PMA promotes hematopoietic differentiation.6↗,7↗ The aqueous solubility of PMA is about 10-fold better than that of phorbol-12,13-dibutyrate, indicating that PMA is preferable in cell-based studies.
Synonyms TPA PMA 12-O-Tetradecanoylphorbol-13-acetate
Formal Name
(1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-9a-(acetyloxy)-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-4a,7b-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-1H-cyclopropa[3,4]benz[1,2-e]azulen-9-yl ester tetradecanoic acid
CAS Number 16561-29-8
Molecular Formula C36H56O8
Formula Weight 616.8
Formulation A crystalline solid
Purity ≥98%
Stability 2 years
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES O=C(CCCCCCCCCCCCC)O[C@H]1[C@](C2(C)C)(OC(C)=O)[C@]2([H])[C@@](C=C(CO)C[C@@]3(O)[C@@]4([H])C=C(C)C3=O)([H])[C@]4(O)[C@@H]1C
InCHI Code 1S/C36H56O8/c1-7-8-9-10-11-12-13-14-15-16-17-18-29(39)43-32-24(3)35(42)27(30-33(5,6)36(30,32)44-25(4)38)20-26(22-37)21-34(41)28(35)19-23(2)31(34)40/h19-20,24,27-28,30,32,37,41-42H,7-18,21-22H2,1-6H3/t24-,27+,28-,30-,32-,34-,35-,36-/m1/s1
InCHI Key PHEDXBVPIONUQT-RGYGYFBISA-N |