Synonym: 12-O-Tetradecanoylphorbol 13-acetate; 4β,9α,12β,13α,20-Pentahydroxytiglia-1,6-dien-3-one 12-tetradecanoate 13-acetate; PMA; TPA
CAS Number: 16561-29-8
Empirical Formula (Hill Notation): C36H56O8
Molecular Weight: 616.83
MDL Number: MFCD00036736
Linear Formula: C36H56O8
Product Type: Chemical
| assay |
≥98.0% (TLC) |
| form |
film |
| InChI |
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 |
| quality |
synthetic |
| Quality Level |
200  |
| SMILES string |
CCCCCCCCCCCCCC(=O)O[C@@H]1[C@@H](C)[C@@]2(O)C(C=C(CO)C[C@@]3(O)C2C=C(C)C3=O)C4C(C)(C)[C@]14OC(C)=O |
| solubility |
chloroform: 10 mg/mL, clear, colorless to light yellow |
| storage temp. |
−20°C |
| Application: |
Phorbol 12-myristate 13-acetate has been used to stimulate the in vitro production of interleukin (IL)-18, IL-10 and macrophages. It has also been used to induce protein kinase C activity. |
| Biochem/physiol Actions: |
Phorbol 12-myristate 13-acetate is a potent tumor promoter and activates protein kinase C in vivo and in vitro. It is a phorbol ester that is associated with many cellular responses including gene transcription, cell division and differentiation, apoptosis and immune response. It is also involved in protein kinase C (PKC) mediated receptor desensitization. Phorbol 12-myristate 13-acetate induces PKC localization from the cytosol, enabling the enzyme association with the cell membrane. |
| Other Notes: |
Activates protein kinase C in vivo and in vitro at nanomolar concentrations; Highly potent tumor promotor and mitogen: active principle of croton oil. Review |
| Packaging: |
1, 5, 25 mg in glass bottle |
| Purity |
≥98.0% (TLC) |
| Storage Temp. |
−20°C |
| UNSPSC |
12352211 |
GHS05,GHS06,GHS08