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5.00582

Sigma-Aldrich

InSolution Phorbol-12-myristate-13-acetate - CAS 16561-29-8 - Calbiochem

Synonym(s):
InSolution Phorbol-12-myristate-13-acetate - CAS 16561-29-8 - Calbiochem, 12-O-Tetradecanoyl-phorbol-13-acetate, PMA, TPA
Empirical Formula (Hill Notation):
C36H56O8
CAS Number:
Molecular Weight:
616.83
MDL number:

Quality Level

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

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

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 (>Cat. No. 344270, >Cat. No. 344282)-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
Secondary Target
Ca2+-ATPase
Reversible: yes
Primary Target
PKC

Packaging

Packaged under inert gas

Warning

Toxicity: Irritant (B)

Physical form

A 10 mM (2 mg/324 µL) solution of Phorbol-12-myristate-13-acetate (Cat. No. 524400) in DMSO.

Reconstitution

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

Pictograms

Skull and crossbonesHealth hazard

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Carc. 2 - Eye Irrit. 2 - Resp. Sens. 1 - Skin Irrit. 2 - Skin Sens. 1

Storage Class Code

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 2

Flash Point(F)

188.6 °F - (Dimethylsulfoxide)

Flash Point(C)

87 °C - (Dimethylsulfoxide)

Certificate of Analysis

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Certificate of Quality

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