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P8139

Sigma-Aldrich

Phorbol 12-myristate 13-acetate

≥99% (TLC), film or powder

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Synonym(s):
12-O-Tetradecanoylphorbol 13-acetate, 4β,9α,12β,13α,20-Pentahydroxytiglia-1,6-dien-3-one 12-tetradecanoate 13-acetate, PMA, TPA
Empirical Formula (Hill Notation):
C36H56O8
CAS Number:
Molecular Weight:
616.83
Beilstein:
2407201
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

Assay

≥99% (TLC)

form

film or powder

solubility

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

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

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This Item
79346P15855.00582
PMA for use in molecular biology applications, ≥99% (HPLC)

Sigma-Aldrich

P1585

PMA

form

film or powder

form

film

form

film

form

liquid

solubility

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

solubility

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

solubility

DMSO: soluble (DMSO solutions can be stored dark at −20 °C for at least six months.), ethanol: soluble (Dissolve in water-miscible organic solvent prior to preparing aqueous solutions)

solubility

-

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−70°C

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

100

General description

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.

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.

Biochem/physiol Actions

Potent tumor promoter; activates protein kinase C in vivo and in vitro.

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.

Caution

Photosensitive

Signal Word

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 Code

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

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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