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79346

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:
Molecular Weight:
616.83
UNSPSC Code:
12352211
NACRES:
NA.25
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
2407201
Assay:
≥98.0% (TLC)
Form:
film, powder or solid (or crystals)
Quality level:
Pricing and availability is not currently available.
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Quality Level

assay

≥98.0% (TLC)

form

film, powder or solid (or crystals)

quality

synthetic

color

white

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

Application

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

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. Phorbol 12-myristate 13-acetate induces PKC localization from the cytosol, enabling the enzyme association with the cell membrane.

Other Notes

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

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1 of 1

This Item
P8139P8129P1585
form

film

form

film or powder

form

powder

form

(Lyophilisate)

assay

≥98.0% (TLC)

assay

≥99% (TLC)

assay

≥98% (TLC)

assay

≥99% (HPLC)

Quality Level

200

Quality Level

200

Quality Level

100

Quality Level

200

storage temp.

−20°C

storage temp.

−20°C

storage temp.

room temp

storage temp.

−20°C

solubility

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

solubility

DMSO: soluble, ethanol: soluble (Dissolve in water-miscible organic solvent prior to preparing aqueous solutions.)

solubility

chloroform: 50 mg/mL, clear, colorless

solubility

DMSO: soluble (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)

quality

synthetic

quality

-

quality

-

quality

-


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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

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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The calcium ATPase SERCA2 regulates desmoplakin dynamics and intercellular adhesive strength through modulation of PKCalpha signaling
Hobbs RP, et al.
Faseb Journal, 25(3), 990-1001 (2011)
E. Kontny et al.
Eur. J. Pharmacol., Molec. Pharmacol. Sec., 227, 333-333 (1992)
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



Global Trade Item Number

SKUGTIN
UPL0014-1G04061825153056
79346-5MG04061832951157
79346-1MG04061832951140
79346-25MG04061832860701

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/418/501/product-dating-information-06-25-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. 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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  5. 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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  6. 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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  7. 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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  8. 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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