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P8139

Sigma-Aldrich

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
Beilstein:
2407201
MDL number:
MFCD00036736
UNSPSC Code:
12352211
PubChem Substance ID:
24278653
NACRES:
NA.77

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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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.

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.

Caution

Photosensitive

Other Notes

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

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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

WGK

WGK 3

Personal Protective Equipment

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’.

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  1. What is the difference between Phorbol 12-myristate 13-acetate, Product P8139 and molecular biology grade Product P1585?

    Product P1585 has been tested and found suitable for stimulation of interleukin 2 production of Jurkat cells. Product P8139 has not tested in this application.

  2. Why do I not see any solid in the Phorbol 12-myristate 13-acetate bottle, Product P8139?

    Phorbol 12-myristate 13-acetate may be an invisible film in the bottle.

  3. How should Product P8139, Phorbol 12-myristate 13-acetatebe dissolved?

    Stock solutions of 20 mM can be prepared in DMSO and diluted into aqueous buffers. View more information on P8139 solubility in the product information sheet (under Documents, above).

  4. How should I store the solutions of Product P8139, Phorbol 12-myristate 13-acetate?

    Stock solutions in DMSO can be stored protected from light as aliquots at -20°C for at least 6 months, or at 2-8°C for up to 3 months.

  5. Do you have any application information for Product P8139, Phorbol 12-myristate 13-acetate?

    View the P8139 product information sheet (under Documents, above).

  6. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  7. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  8. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  9. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  10. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

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)
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)
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
Inhibition of protein kinase C results in decreased expression of bovine leukemia virus.
Jensen WA et al.
Journal of Virology, 66, 4427-4427 (1992)
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