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P8139

Phorbol 12-myristate 13-acetate

Name: Phorbol 12-myristate 13-acetate
Brand: SIGMA

≥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

Assay:

≥99% (TLC)

Form:

film or powder

Quality level:

200

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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

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Bioactive Small Molecules

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.

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.

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.

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.

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.

Other Notes

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

Disclaimer

Photosensitive

pictograms

GHS06,GHS08,GHS05

signalword

Danger

hcodes

H300 + H310 + H330,H314,H317,H334,H351

pcodes

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

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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Phorbol 12-Myristate 13-Acetate Induced Toxicity Study and the Role of Tangeretin in Abrogating HIF-1 alpha-NF-kappa B Crosstalk In Vitro and In Vivo

Chang SN, et al.

International Journal of Molecular Sciences (2020)

Inhibition of protein kinase C results in decreased expression of bovine leukemia virus.

Jensen WA et al.

Journal of Virology, 66, 4427-4427 (1992)

Optical spectral analysis of ultra-weak photon emission from tissue culture and yeast cells

Nerudova M, et al.

Journal of Separation Science, 9450, 162-168 (2015)

Phorbol 12-myristate 13-acetate up-regulates the transcription of MUC2 intestinal mucin via Ras, ERK, and NF-kappa B.

Lee HW et al.

The Journal of Biological Chemistry, 277, 32624-32624 (2002)

Label-free multi-parametric imaging of single cells: dual picosecond optoacoustic microscopy.

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

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Global Trade Item Number

SKU	GTIN
P8139-10MG	04061835558759
P8139-25MG	04061835546343
P8139-5MG	04061835558766
P8139-1MG	04061835518241

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