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5.00582

Phorbol 12-Myristate 13-Acetate

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

Synonyme(s) :

InSolution Phorbol-12-myristate-13-acetate, 12-O-Tetradecanoyl-phorbol-13-acetate, PMA, TPA

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A propos de cet article

Formule empirique (notation de Hill) :
C36H56O8
Numéro CAS:
16561-29-8
Poids moléculaire :
616.83
UNSPSC Code:
12352211
NACRES:
NA.77
MDL number:
MFCD00036736
Assay:
≥98% (HPLC)
Form:
liquid
Quality level:
100
Storage condition:
OK to freeze, avoid repeated freeze/thaw cycles, desiccated (hygroscopic), protect from light
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Nom du produit

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

Quality Level

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

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)

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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

wgk

WGK 2

Classe de stockage

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)

Certificats d'analyse (COA)

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Numéro d'article de commerce international

RéférenceGTIN
5.00582.000104055977244977