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| | PHORBOL 12-MYRISTATE 13-ACETATE Basic information |
| Product Name: | PHORBOL 12-MYRISTATE 13-ACETATE | | Synonyms: | 13-o-acetylphorbol12-myristate;4)benz(1,2-e)azulen-5-one9a-acetate,(+)-ethyl-5h-cyclopropa(;5h-cyclopropa(3,4)benz(1,2-e)azulen-5-one,1,1a-beta,1b-alpha,4,4a,7a-beta,7b,;12-O-Tetradecanoyl-Phorbol-13-Acetate(TPA, MPA) 16561-29-8;12-O-tetradecanoyl phorbol-13-acetate (PMA);Phorbol-12-myristate-13-acetate - CAS 16561-29-8 - Calbiochem;InSolution Phorbol-12-myristate-13-acetate - CAS 16561-29-8 - Calbiochem;4BETA-PHORBOL 12-MYRISTATE 13-ACETATE | | CAS: | 16561-29-8 | | MF: | C36H56O8 | | MW: | 616.83 | | EINECS: | 605-413-5 | | Product Categories: | Activator;enzyme;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;Protein Kinase;Signalling;standardized herbal extract;Diterpenoids | | Mol File: | 16561-29-8.mol |  |
| | PHORBOL 12-MYRISTATE 13-ACETATE Chemical Properties |
| Melting point | 65-79oC | | Boiling point | 571.87°C (rough estimate) | | density | 1.17±0.1 g/cm3 (20 ºC 760 Torr) | | refractive index | 1.4900 (estimate) | | storage temp. | -20°C | | solubility | DMSO: DMSO solutions can be stored dark at −20°C for at least six months.soluble | | pka | 11.19±0.70(Predicted) | | form | Fine Crystalline Powder | | color | Off-white to light yellow | | Water Solubility | Very soluble in methanol, soluble in DMSO, chloroform, ethanol or acetone, ether, ethyl acetate, DMF or acetonitrile. Insoluble in water. | | Sensitive | Light Sensitive | | BRN | 2407201 | | Stability: | Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 2 months. | | InChIKey | PHEDXBVPIONUQT-RGYGYFBISA-N | | CAS DataBase Reference | 16561-29-8(CAS DataBase Reference) | | EPA Substance Registry System | 12-O-Tetradecanoylphorbol 13-acetate (16561-29-8) |
| Hazard Codes | Xi | | Risk Statements | 38-36/37/38 | | Safety Statements | 36/37-26 | | RIDADR | 2928 | | WGK Germany | 3 | | RTECS | QH4377000 | | F | 8-10 | | HazardClass | 6.1(a) | | PackingGroup | II | | HS Code | 29153900 | | Hazardous Substances Data | 16561-29-8(Hazardous Substances Data) | | Toxicity | Diesters of
phorbol, particularly 12-O-tetradecanoylphorbol 13-acetate, also
known as phorbol myristate acetate, have been identified as the
potent, highly lipophilic tumor-promoting components in croton
oil. They are potent promoters of skin tumors in vivo and have
been shown to transform cultured fibroblasts and embryonic cells
previously exposed to polycyclic aromatic hydrocarbon carcinogens in vitro. The structure of phorbol, the parent alcohol is
shown below. Phorbol esters also have important effects on leukocytes and on the immune system of the intact animal. There
appears to be a specific receptor for phorbol esters on T cells, a
finding that may account for the selective toxicity of phorbol
esters for T cells. The mechanism of tumor promotion by phorbol
esters is still largely unknown, but findings suggest an initial cell
membrane interaction (often with stimulation of second messenger synthesis and increased protein kinase activity), with subsequent effects on nuclear regulatory events. |
| | PHORBOL 12-MYRISTATE 13-ACETATE Usage And Synthesis |
| Description | Phorbol 12-myristate-13-acetate (16561-29-8) activates protein kinase C (10-100 ng/ml)1. May display PKC-independent effects in various cell types2. Warning: Phorbol 12-myristate-13-acetate is a skin irritant. Avoid contact with this compound. | | Chemical Properties | white to off-white solid | | Uses | 4β-Phorbol 12-Myristate 13-Acetate is used in the activation of certain pyruvate kinases as well as protein kinases. | | Definition | ChEBI: Phorbol 13-acetate 12-myristate is a phorbol ester that is phorbol in which the hydroxy groups at the cyclopropane ring juction (position 13) and the adjacent carbon (position 12) have been converted into the corresponding acetate and myristate esters. It is a major active constituent of the seed oil of Croton tiglium. It has been used as a tumour promoting agent for skin carcinogenesis in rodents and is associated with increased cell proliferation of malignant cells. However its function is controversial since a decrease in cell proliferation has also been observed in several cancer cell types. It has a role as a protein kinase C agonist, an antineoplastic agent, a reactive oxygen species generator, a plant metabolite, a mitogen, a carcinogenic agent and an apoptosis inducer. It is an acetate ester, a tetradecanoate ester, a diester, a tertiary alpha-hydroxy ketone and a phorbol ester. | | General Description | White crystals. | | Air & Water Reactions | Practically water insoluble. | | Reactivity Profile | PHORBOL 12-MYRISTATE 13-ACETATE is sensitive to acids and alkalis. . | | Fire Hazard | Flash point data for PHORBOL 12-MYRISTATE 13-ACETATE are not available; however, PHORBOL 12-MYRISTATE 13-ACETATE is probably combustible. | | Biological Activity | Extensively used phorbol ester activator of protein kinase C; tumor promoter. Binds to PKC with a K i value of 2.6 nM as measured by displacement of [ 3 H]phorbol 12,13-dibutyrate binding in rat cortex synaptosomal membranes. | | Biochem/physiol Actions | Cell permeable: yes | | target | PKC | AP-1 | | storage | -20°C (protect from light) | | References | 1) Saraiva et al. (2004), Characterization of phorbol esters activity on individual mammalian protein kinase C isoforms, using the yeast phenotypic assay; Eur. J. Pharmacol., 491 101
2) Doerner et al. (1990), Protein kinase C-dependent and independent effects of phorbol esters on hippocampal calcium channel current; J. Neurosci., 10 1699
3) Merck Index 14:7332 |
| | PHORBOL 12-MYRISTATE 13-ACETATE Preparation Products And Raw materials |
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