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
• Empirical Formula (Hill Notation): C₃₆H₅₆O₈
• CAS Number: 16561-29-8
• Molecular Weight: 616.83
• Beilstein: 2407201
• MDL number: MFCD00036736
• UNSPSC Code: 12352211
• PubChem Substance ID: 24278653
• NACRES: NA.77

Properties

• Product Name: Phorbol 12-myristate 13-acetate, ≥99% (TLC), film or powder
• Quality Level: 200
• 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
• 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

Description

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.[1]

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.[2]

Application

Phorbol 12-myristate 13-acetate has been used:

• to induce differentiation of THP-1monocytes to macrophage.[3]
• to stimulate the proliferation of peripheral blood lymphocytes.[4]
• to induce respiratory bursts and enhance the generation of ultra-weak photon emission (UPE) from the neutrophil-like cells derived from HL-60 cells.[5]
• in conjugation with Ionomycin calcium salt to stimulate T-cell activation[6]
• for the stimulation of various cells including spleen cells, quiescent lymphocytes, and fetal thymocytes.[7][8][9]
• for the activation of PKC (protein kinase C) in cells.[10]

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

Other Notes

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

Safety Information

• Pictograms: GHS06,GHS08,GHS05
• Signal Word: Danger
• Hazard Statements: H300 + H310 + H330,H314,H317,H334,H351
• Precautionary Statements: P202 - P260 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338
• 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