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Merck

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

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About This Item

Empirical Formula (Hill Notation):
C36H56O8
CAS Number:
16561-29-8
Molecular Weight:
616.83
UNSPSC Code:
12352211
NACRES:
NA.77
MDL number:
MFCD00036736

Product Name

Phorbol-12-myristate-13-acetate, InSolution, ≥98%, 10 mM in DMSO, extremely potent mouse skin tumor promoter

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

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

Quality Level

100

Related Categories

Biochem/physiol Actions

Cell permeable: yes
Primary Target
PKC
Reversible: yes
Secondary Target
Ca2+-ATPase

Disclaimer

Toxicity: Irritant (B)

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.

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.

Packaging

Packaged under inert gas

Preparation Note

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

Legal Information

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

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

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

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)

Certificates of Analysis (COA)

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Global Trade Item Number

SKUGTIN
5.00582.000104055977244977

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