Skip to Content
MilliporeSigma
All Photos(1)

Key Documents

79346

Sigma-Aldrich

Phorbol 12-myristate 13-acetate

synthetic, ≥98.0% (TLC)

Synonym(s):

12-O-Tetradecanoylphorbol 13-acetate, 4β,9α,12β,13α,20-Pentahydroxytiglia-1,6-dien-3-one 12-tetradecanoate 13-acetate, PMA, TPA

Sign Into View Organizational & Contract Pricing


About This Item

Empirical Formula (Hill Notation):
C36H56O8
CAS Number:
Molecular Weight:
616.83
Beilstein/REAXYS Number:
2407201
MDL number:
UNSPSC Code:
12352211
PubChem Substance ID:
NACRES:
NA.25

assay

≥98.0% (TLC)

form

film

quality

synthetic

solubility

chloroform: 10 mg/mL, clear, colorless to light yellow

storage temp.

−20°C

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

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

Looking for similar products? Visit Product Comparison Guide

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

signalword

Danger

Hazard Classifications

Acute Tox. 1 Dermal - Acute Tox. 1 Inhalation - Acute Tox. 2 Oral - Carc. 2 - Eye Dam. 1 - Resp. Sens. 1 - Skin Corr. 1B - Skin Sens. 1

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Differential effect of bryostatin 1 and phorbol 12-myristate 13-acetate on HOP-92 cell proliferation is mediated by down-regulation of protein kinase Cdelta
Choi SH, et al.
Cancer Research, 66(14), 7261-7269 (2006)
Adipose tissue-derived mesenchymal stem cells are more potent suppressors of dendritic cells differentiation compared to bone marrow-derived mesenchymal stem cells
Ivanova-Todorova E, et al.
Immunology Letters, 126(1-2), 37-42 (2009)
R D Estensen
Journal of experimental pathology, 1(2), 71-77 (1984-01-01)
Tumor promoters act on carcinogen-initiated tissues to cause phenotypic expression of malignancy. Phorbol ester tumor promoters, like hormones, act on cells and tissues at nanomolar concentrations, often producing "physiological" effects. These promoters also act on cells to produce what appear
Phorbol 12-myristate 13-acetate upregulates cyclooxygenase-2 expression in human pulmonary epithelial cells via Ras, Raf-1, ERK, and NF-kappaB, but not p38 MAPK, pathways
Chang MS, et al.
Cellular Signalling, 17(3), 299-310 (2005)
Fate of immunoprecipitable protein kinase C in GH3 cells treated with phorbol 12-myristate 13-acetate.
Ballester Roymarie and Rosen OM
The Journal of Biological Chemistry, 260(28), 15194-15199 (1985)

Articles

Cancer research has revealed that the classical model of carcinogenesis, a three step process consisting of initiation, promotion, and progression, is not complete.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service