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
• Empirical Formula (Hill Notation): C₃₆H₅₆O₈
• CAS Number: 16561-29-8
• Molecular Weight: 616.83
• Beilstein/REAXYS Number: 2407201
• MDL number: MFCD00036736
• UNSPSC Code: 12352211
• PubChem Substance ID: 57652787
• NACRES: NA.25

Properties

• 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

Description

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

Safety Information

• pictograms: GHS06,GHS08,GHS05
• signalword: Danger
• hcodes: H300 + H310 + H330,H314,H317,H334,H351
• pcodes: P202 - P260 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338
• 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