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79346

Sigma-Aldrich

Phorbol 12-myristate 13-acetate

synthetic, ≥98.0% (TLC)

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:
57652787
NACRES:
NA.25
Pricing and availability is not currently available.

Quality Level

200

Assay

≥98.0% (TLC)

form

film

quality

synthetic

solubility

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

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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Application

Phorbol 12-myristate 13-acetate has been used to stimulate the in vitro production of interleukin (IL)-18, IL-10[1] and macrophages.[2] It has also been used to induce protein kinase C activity.[3]

Biochem/physiol Actions

Phorbol 12-myristate 13-acetate is a potent tumor promoter and activates protein kinase C in vivo and in vitro. It is a phorbol ester that is associated with many cellular responses including gene transcription, cell division and differentiation, apoptosis and immune response. It is also involved in protein kinase C (PKC) mediated receptor desensitization.[4] Phorbol 12-myristate 13-acetate induces PKC localization from the cytosol,[5] enabling the enzyme association with the cell membrane.[6]

Other Notes

Activates protein kinase C in vivo and in vitro at nanomolar concentrations[7]; Highly potent tumor promotor and mitogen: active principle of croton oil. Review[8]

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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Certificates of Analysis (COA)

Lot/Batch Number
MKCX2109
MKCT9147
MKCT0603
MKCT6145
MKCT6146

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Phorbol 12-myristate 13-acetate upregulates cyclooxygenase-2 expression in human pulmonary epithelial cells via Ras, Raf-1, ERK, and NF-kappaB, but not p38 MAPK, pathways
Chang MS, et al.
Cellular Signalling, 17(3), 299-310 (2005)
Fate of immunoprecipitable protein kinase C in GH3 cells treated with phorbol 12-myristate 13-acetate.
Ballester Roymarie and Rosen OM
The Journal of Biological Chemistry, 260(28), 15194-15199 (1985)
Adipose tissue-derived mesenchymal stem cells are more potent suppressors of dendritic cells differentiation compared to bone marrow-derived mesenchymal stem cells
Ivanova-Todorova E, et al.
Immunology Letters, 126(1-2), 37-42 (2009)
Differential effect of bryostatin 1 and phorbol 12-myristate 13-acetate on HOP-92 cell proliferation is mediated by down-regulation of protein kinase Cdelta
Choi SH, et al.
Cancer Research, 66(14), 7261-7269 (2006)
R D Estensen
Journal of experimental pathology, 1(2), 71-77 (1984-01-01)
Tumor promoters act on carcinogen-initiated tissues to cause phenotypic expression of malignancy. Phorbol ester tumor promoters, like hormones, act on cells and tissues at nanomolar concentrations, often producing "physiological" effects. These promoters also act on cells to produce what appear
View All Related Papers

Articles

Carcinogenesis and Epigenetics

Cancer research has revealed that the classical model of carcinogenesis, a three step process consisting of initiation, promotion, and progression, is not complete.

Questions

1–8 of 8 Questions  

  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  3. How many ML of DMSO should I use to dilute each milligram of phorbol?

    1 answer

    1. This product can be solubilized in DMSO at 10 mg/mL.

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  4. What is the difference between product 79346, Phorbol 12-myristate 13-acetate - synthetic, and molecular biology grade product P1585?

    1 answer

    1. Product P1585 has been tested and found suitable for stimulation of interleukin 2 production of Jurkat cells. Product 79346 has not tested in this application.

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  5. How should Product 79346, Phorbol 12-myristate 13-acetate - synthetic, be dissolved?

    1 answer

    1. PMA is soluble in acetone, DMSO, ethyl acetate, ethanol and methylene chloride, but is practically insoluble in water. The solubility of 79346 has been tested in chloroform at a concentration of 10 mg/mL.  Stock solutions of 20 mM can be prepared in DMSO and diluted into aqueous buffers.

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  6. How can I store the Product 79346, Phorbol 12-myristate 13-acetate - synthetic (PMA), solution solution?  How long?

    1 answer

    1. 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.

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

    1 answer

    1. 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.

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  8. Why do I not see any solid in the bottle of Product 79346, Phorbol 12-myristate 13-acetate - synthetic?

    1 answer

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

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