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Merck

P8139

Phorbol 12-myristate 13-acetate

≥99% (TLC), film or powder, PKC activator

Synonym(s):

12-O-Tetradecanoylphorbol 13-acetate, 4β,9α,12β,13α,20-Pentahydroxytiglia-1,6-dien-3-one 12-tetradecanoate 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
NACRES:
NA.77
PubChem Substance ID:
24278653
UNSPSC Code:
12352211
MDL number:
MFCD00036736
Beilstein/REAXYS Number:
2407201

Key Documents

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Product Name

Phorbol 12-myristate 13-acetate, ≥99% (TLC), film or powder

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

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 key

PHEDXBVPIONUQT-RGYGYFBISA-N

assay

≥99% (TLC)

form

film or powder

solubility

DMSO: soluble
ethanol: soluble (Dissolve in water-miscible organic solvent prior to preparing aqueous solutions.)

storage temp.

−20°C

Quality Level

200

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Application

Phorbol 12-myristate 13-acetate has been used:
  • to induce differentiation of THP-1monocytes to macrophage.
  • to stimulate the proliferation of peripheral blood lymphocytes.
  • to induce respiratory bursts and enhance the generation of ultra-weak photon emission (UPE) from the neutrophil-like cells derived from HL-60 cells.
  • in conjugation with Ionomycin calcium salt to stimulate T-cell activation
  • for the stimulation of various cells including spleen cells, quiescent lymphocytes, and fetal thymocytes.
  • for the activation of PKC (protein kinase C) in cells.

Disclaimer

Photosensitive

Features and Benefits

This compound is featured on the PKC page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

General description

Dissolve in water-miscible organic solvent prior to preparing aqueous solutions. DMSO solutions can be stored dark at -20 °C for at least six months.
Phorbol 12-myristate 13-acetate (PMA) exhibits high inflammatory properties. It stimulates protein kinase C (PKC) activity. PMA induces the release of proteases, cytokines, and NADPH oxidases, leading to tissue damage or histamine production, and promoting vascular remodeling, redness, heat, and tumor promotion. Additionally, it enhances reactive oxygen species (ROS) production and decreases enzymes involved in ROS detoxification. PMA also inhibits the basal level of superoxide dismutase (SOD), catalase, and glutathione peroxidase.
Phorbol 12-myristate 13-acetate is a phorbol ester. It works as a tumor promoter and is involved in gene transcription, cell growth, differentiation, programmed cell death, immune pathway and receptor desensitization via protein kinase C (PKC) signaling pathways. Phorbol 12-myristate 13-acetate is also a model agent to study growth factors-, hormones-, and cytokines-mediated regulation of cellular growth and differentiation.

Other Notes

2024 CiteAb Award Winner for Supplier Succeeding in Parkinson′s Research

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

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCQ9869
MKCQ9867
MKCQ9865
MKCQ6732
MKCQ2981

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Inhibition of protein kinase C results in decreased expression of bovine leukemia virus.
Jensen WA et al.
Journal of Virology, 66, 4427-4427 (1992)
Cytokine requirements for the growth and development of mouse NK cells in vitro.
Toomey JA et al.
Journal of Leukocyte Biology, 74, 233-233 (2003)
NGFI-A gene expression is necessary for T lymphocyte proliferation.
Perez-Castillo A et al.
The Journal of Biological Chemistry, 268, 19445-19445 (1993)
Liwang Liu et al.
Journal of biophotonics, 12(8), e201900045-e201900045 (2019-05-31)
Advances in microscopy with new visualization possibilities often bring dramatic progress to our understanding of the intriguing cellular machinery. Picosecond optoacoustic micro-spectroscopy is an optical technique based on ultrafast pump-probe generation and detection of hypersound on time durations of picoseconds
Rejection of H-Y disparate skin grafts by monospecific CD4+ Th1 and Th2 cells: no requirement for CD8+ T cells or B cells.
Zelenika D, et al.
Journal of Immunology, 161, 1868-1868 (1998)
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