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P8139

Sigma-Aldrich

Phorbol 12-myristate 13-acetate

≥99% (TLC), film or powder

Synonym(s):
12-O-Tetradecanoylphorbol 13-acetate, PMA, TPA, 4β,9α,12β,13α,20-Pentahydroxytiglia-1,6-dien-3-one 12-tetradecanoate 13-acetate
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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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 for the stimulation of various cells including spleen cells, quiescent lymphocytes and fetal thymocytes. It has also been used 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 Germany

WGK 3

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

  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.

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