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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:
Molecular Weight:
616.83
Beilstein:
2407201
MDL number:
UNSPSC Code:
12352211
PubChem Substance ID:
NACRES:
NA.25
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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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1 of 4

This Item
SAB2108392HPA075251HPA019502
biological source

rabbit

biological source

rabbit

biological source

rabbit

biological source

rabbit

species reactivity

rat, human, mouse

species reactivity

goat, rabbit, bovine, rat, mouse, guinea pig, human, horse

species reactivity

human

species reactivity

human

Gene Information

human ... S100B(6285)

Gene Information

human ... S100B(6285)
rat ... S100b(25742)

Gene Information

human ... S100P(6286)

Gene Information

human ... S100P(6286)

clone

monoclonal

clone

polyclonal

clone

polyclonal

clone

polyclonal

technique(s)

immunohistochemistry: 1:50-1:200, western blot: 1:500-1:2000

technique(s)

immunoblotting: suitable

technique(s)

immunofluorescence: 0.25-2 μg/mL (ICC-IF)

technique(s)

immunohistochemistry: 1:2500- 1:5000

shipped in

wet ice

shipped in

wet ice

shipped in

wet ice

shipped in

wet ice

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; Highly potent tumor promotor and mitogen: active principle of croton oil.

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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    Yu-Ying Chao et al.
    Journal of cellular physiology (2022-10-18)
    Pancreatic ductal adenocarcinoma (PDAC) is one of the most lethal cancers because of its late diagnosis and chemoresistance. Primary cilia, the cellular antennae, are observed in most human cells to maintain development and differentiation. Primary cilia are gradually lost during

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