5.00582

Phorbol 12-Myristate 13-Acetate

≥98% (HPLC), liquid, PKC activator, Calbiochem^®

• Synonym(s): InSolution Phorbol-12-myristate-13-acetate, 12-O-Tetradecanoyl-phorbol-13-acetate, PMA, TPA
• Empirical Formula (Hill Notation): C₃₆H₅₆O₈
• CAS Number: 16561-29-8
• Molecular Weight: 616.83
• UNSPSC Code: 12352211
• NACRES: NA.77
• MDL number: MFCD00036736
• Assay: ≥98% (HPLC)
• Form: liquid
• Storage condition: OK to freeze, avoid repeated freeze/thaw cycles, desiccated (hygroscopic), protect from light

Properties

• Product Name: Phorbol-12-myristate-13-acetate, InSolution, ≥98%, 10 mM in DMSO, extremely potent mouse skin tumor promoter
• Quality Segment: 100
• assay: ≥98% (HPLC)
• form: liquid
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze, avoid repeated freeze/thaw cycles, desiccated (hygroscopic), protect from light
• storage temp.: −70°C
• SMILES string: O([C@]21[C@H]([C@H]3[C@@]([C@H]4[C@](CC(=C3)CO)(C(=O)C(=C4)C)O)([C@@H]([C@H]2OC(=O)CCCCCCCCCCCCC)C)O)C1(C)C)C(=O)C
• 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

Description

General description

Most commonly-used phorbol ester. Extremely potent mouse skin tumor promoter. Activates protein kinase C in vivo and in vitro, even at nM concentrations. Promotes the expression of iNOS in cultured hepatocytes. Activates Ca²⁺-ATPase and potentiates forskolin-induced cAMP formation. Inhibits apoptosis induced by the Fas antigen, but induces apoptosis in HL-60 promyelocytic leukemia cells. Its binding is reversible.

Biochem/physiol Actions

Cell permeable: yes

Primary Target
PKC

Reversible: yes

Secondary Target
Ca²⁺-ATPase

Packaging

Packaged under inert gas

Preparation Note

Following initial thaw, aliquot and freeze (-70°C). Use only fresh DMSO for preparing further dilutions.

Other Notes

Powell, D.J., et al. 2003. Mol. Cell Biol.23, 7794.
Tepper, C.G., et al. 1995. Proc. Natl. Acad. Sci. USA92, 8443.
Oishi, K., and Yamaguchi, M. 1994. J. Cell. Biochem.55, 168.
Macfarlane, D.E., and O′Donnell, P.S. 1993. Leukemia7, 1846.
Ghandi, V.C. and Jones, D.J., 1992. Neuropharmacol.31, 1101.
Hortelano, S., et al. 1992. J. Biol. Chem.267, 24937.
Kontny, E., et al. 1992. Eur. J. Pharmacol.227, 333.
Zanaboni, P.B., et al. 1992. J. Appl. Physiol.73, 2011.
Saltis, J., et al. 1991. J. Biol. Chem.266, 261.
Beguinot, L., et al. 1985. Proc. Natl. Acad. Sci. USA82, 2774.
Perchellet, J. 1985. Carcinogenesis6, 567.
Nishizuka, Y. 1984. Science255, 1365.
Mastro, A. 1982. Lymphokines6, 263.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Irritant (B)

Safety Information

• pictograms: GHS06,GHS08
• signalword: Danger
• pcodes: P202 - P280 - P302 + P352 + P312 - P304 + P340 + P311 - P305 + P351 + P338 - P308 + P313
• Hazard Classifications: Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Carc. 2 - Eye Irrit. 2 - Resp. Sens. 1 - Skin Irrit. 2 - Skin Sens. 1
• wgk: WGK 2
• hcodes: H311 + H331,H315,H317,H319,H334,H351
• Storage Class: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• flash_point_f: 188.6 °F - closed cup - (Dimethylsulfoxide)
• flash_point_c: 87 °C - closed cup - (Dimethylsulfoxide)