| Identification | More | [Name]
PHORBOL 12-MYRISTATE 13-ACETATE | [CAS]
16561-29-8 | [Synonyms]
12-O-TETRADECANOYLPHORBOL 13-ACETATE
12-TETRADECANOYL PHORBOL 13-ACETATE
(1AR,1BS,4AR,7AS,7BS,8R,9R,9AS)-9A-(ACETYLOXY)-1A,1B,4,4A,5,7A,7B,8,9,9A-DECAHYDRO-4A,7B-DIHYDROXY-3-(HYDROXYMETHYL)-1,1,6,8-TETRAMETHYL-5-OXO-1H-CYCLOPROPA[3,4]BENZ[1,2-E]AZULEN-9-YL TETRADECANOATE
4ALPHA,9ALPHA,12BETA,13ALPHA,20-PENTAHYDROXYTIGLIA-1,6-DIEN-3-ONE 12BETA-MYRISTATE 13-ACETATE
4BETA,9ALPHA,12BETA,13ALPHA,20-PENTA-HYDROXYTIGLIA-1,6-DIEN-3-ONE 12BETA-MYRISTATE 13-ACETATE
4BETA-PHORBOL 12-MYRISTATE 13-ACETATE
PHORBOL 12-MYRISTATE 13-ACETATE
PHORBOL (12-MYRISTOYL-13-ACETYL)
PMA
TPA
,9aalpha))-
1,6,8-beta-tetramethyl-l)-9a-acetate9-myristate
12-o-tetradecanoylphorbolacetate
12-o-tetradekanoylphorbol-13-acetat
12-tetradecanoylphorbol13-monoacetate
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,
8,9,9a-decahydro-4a-alpha,7b-beta,9-alpha,9a-beta-tetrahydroxy-3-(hydroxymethy
abeta,7balpha,9beta,9aalpha-tetrahydroxy-3-(hydroxymethyl)-1,1,6,8alpha-tetram | [EINECS(EC#)]
605-413-5 | [Molecular Formula]
C36H56O8 | [MDL Number]
MFCD00036736 | [Molecular Weight]
616.83 | [MOL File]
16561-29-8.mol |
| Chemical Properties | Back Directory | [Appearance]
white to off-white solid | [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?#x00b0;C for at least six months.soluble
| [form ]
Fine Crystalline Powder | [pka]
11.19±0.70(Predicted) | [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) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R38:Irritating to the skin. | [Safety Statements ]
S36/37:Wear suitable protective clothing and gloves . | [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. |
| Hazard Information | Back Directory | [General Description]
White crystals. | [Reactivity Profile]
12-O-TETRADECANOYLPHORBOL-13-ACETATE(16561-29-8) is sensitive to acids and alkalis. . | [Air & Water Reactions]
Practically water insoluble. | [Fire Hazard]
Flash point data for this chemical are not available; however, 12-O-TETRADECANOYLPHORBOL-13-ACETATE is probably combustible. | [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. | [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]
4°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 |
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