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79346

Sigma-Aldrich

Phorbol 12-myristate 13-acetate

synthetic, ≥98.0% (TLC)

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Synonym(s):
12-O-Tetradecanoylphorbol 13-acetate, 4β,9α,12β,13α,20-Pentahydroxytiglia-1,6-dien-3-one 12-tetradecanoate 13-acetate, PMA, TPA
Empirical Formula (Hill Notation):
C36H56O8
CAS Number:
Molecular Weight:
616.83
Beilstein/REAXYS Number:
2407201
MDL number:
PubChem Substance ID:
NACRES:
NA.25

Quality Level

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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This Item
P8139P1585P8629
vibrant-m

79346

Phorbol 12-myristate 13-acetate

vibrant-m

P8139

Phorbol 12-myristate 13-acetate

vibrant-m

P1585

PMA

vibrant-m

P8629

5β-Pregnane-3α,17α,20α-triol

assay

≥98.0% (TLC)

assay

≥99% (TLC)

assay

≥99% (HPLC)

assay

≥98.00% (TLC)

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

room temp

solubility

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

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.)

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)

solubility

chloroform: methanol (1:1): 19.60-20.40 mg/mL, clear, colorless

quality

synthetic

quality

-

quality

-

quality

-

Application

Phorbol 12-myristate 13-acetate has been used to stimulate the in vitro production of interleukin (IL)-18, IL-10 and macrophages. 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. Review

signalword

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_germany

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves


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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
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)
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)

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