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Catalog No. BCN2511
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5mg $490 In stock
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Quality Control of 12-O-tetradecanoylphorbol-13-acetate

Chemical structure


Biological Activity of 12-O-tetradecanoylphorbol-13-acetate

Extensively used phorbol ester activator of protein kinase C; tumor promoter. Binds to PKC with a Ki value of 2.6 nM as measured by displacement of [3H]phorbol 12,13-dibutyrate binding in rat cortex synaptosomal membranes.

12-O-tetradecanoylphorbol-13-acetate Dilution Calculator

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Chemical Properties of 12-O-tetradecanoylphorbol-13-acetate

Cas No. 16561-29-8 SDF Download SDF
Synonyms PMA
Chemical Name (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
SMILES CCCCCCCCCCCCCC(=O)O[C@@H]1[C@H]([C@]2([C@@H](C=C(C[C@]3([C@H]2C=C(C3=O)C)O)CO)[C@H]4[C@@]1(C4(C)C)OC(=O)C)O)C
Standard InChI 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
Type of Compound Diterpenoids Appearance White powder
Formula C36H56O8 M.Wt 616.83
Solubility Soluble to 100 mM in DMSO
Storage Desiccate at -20°C
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other courier with RT , or blue ice upon request.

Preparing Stock Solutions of 12-O-tetradecanoylphorbol-13-acetate

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.6212 mL 8.106 mL 16.2119 mL 32.4238 mL 40.5298 mL
5 mM 0.3242 mL 1.6212 mL 3.2424 mL 6.4848 mL 8.106 mL
10 mM 0.1621 mL 0.8106 mL 1.6212 mL 3.2424 mL 4.053 mL
50 mM 0.0324 mL 0.1621 mL 0.3242 mL 0.6485 mL 0.8106 mL
100 mM 0.0162 mL 0.0811 mL 0.1621 mL 0.3242 mL 0.4053 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

Preparation of 12-O-tetradecanoylphorbol-13-acetate

This product is isolated and purified from the seeds of Euphorbia lathyris L.

References on 12-O-tetradecanoylphorbol-13-acetate

Differential 12-O-Tetradecanoylphorbol-13-acetate-induced activation of rat mammary carcinoma susceptibility Fbxo10 variant promoters via a PKC-AP1 pathway.[Pubmed: 24008983]

12-O-tetradecanoylphorbol-13-acetate (TPA) induced activation of a 4.2 kb WF Fbxo10 promoter region, but lower levels of activation of the homologous WKY Fbxo10 promoter region. Using general and specific protein kinase inhibitors, we identified a protein kinase C (PKC) pathway that mediated 12-O-tetradecanoylphorbol-13-acetate activation. We narrowed the possible PKCs to a member of the atypical PKC isoforms, namely PKCµ. We also determined that activator protein 1 (AP1) family member c-Fos mediated 12-O-tetradecanoylphorbol-13-acetate activation of the 4.2 kb WF Fbxo10 promoter. 12-O-tetradecanoylphorbol-13-acetate was shown to induce endogenous FBXO10 mRNA and FBXO10 protein in Jurkat cells, a human T cell line, with a maximal level of expression from 1.5 to 2.5 h after exposure. These results indicate that FBXO10/Fbxo10 expression is regulated by a PKC-dependent pathway acting through c-Fos, which binds AP1-specific DNA elements in Mcs5a1.

Structure-dependent inhibitory effects of synthetic cannabinoids against 12-O-tetradecanoylphorbol-13-acetate-induced inflammation and skin tumour promotion in mice.[Pubmed: 23837590]

METHODS: Twenty-three analogues of synthetic cannabinoids were isolated from, and identified as adulterants in, illegal drugs distributed in the Tokyo metropolitan area, and were examined for their inhibitory effects on the induction of oedema in mouse ears by 12-O-tetradecanoylphorbol-13-acetate (TPA). Furthermore, selected cannabinoids, JWH-018, -122 and -210, were studied for their effects on carcinogenesis induced in mouse skin initiated with 7,12-dimethylbenz[a]anthracene (DMBA) and promoted by 12-O-tetradecanoylphorbol-13-acetate. KEY FINDINGS: Among cannabinoids, naphthoylindoles mostly exhibited superior inhibitory effects against 12-O-tetradecanoylphorbol-13-acetate-induced ear oedema and, especially, JWH-018, -122 and -210 showed potent activity with 50% inhibitory dose (ID50) values of 168, 346 and 542 nm, respectively (an activity corresponding to that of indometacin (ID50 = 908 nm)). Furthermore these three compounds also markedly suppressed the tumour-promoting activity of 12-O-tetradecanoylphorbol-13-acetate. CONCLUSIONS: This is the first report indicating the structure-activity relationships for the anti-inflammatory activity of synthetic cannabinoids on 12-O-tetradecanoylphorbol-13-acetate-induced inflammation in mice. Naphthoylindoles, JWH-018, -122 and -210, had the most potent anti-inflammatory activity and also markedly inhibited tumour promotion by 12-O-tetradecanoylphorbol-13-acetate in the two-stage mouse skin carcinogenesis model. The present results suggest that synthetic cannabinoids, such as JWH-018, -122 and -210, may be used as cancer chemopreventive agents in the future.

12-O-tetradecanoylphorbol-13-acetate promotes breast cancer cell motility by increasing S100A14 level in a Kruppel-like transcription factor 4 (KLF4)-dependent manner.[Pubmed: 24532790]

We determined that 12-O-tetradecanoylphorbol-13-acetate (TPA) up-regulated the expression of KLF4 and facilitated its binding directly to two conserved GC-rich DNA segments within the S100A14 promoter, which is essential for the transactivation of KLF4 induced S100A14 expression. Furthermore, stable silencing of KLF4 significantly suppressed breast cancer cell migration induced by TPA. Collectively, these results offer insights into the fact that 12-O-tetradecanoylphorbol-13-acetate provokes cell motility through regulating the expression and function of S100A14 in a KLF4-dependent manner.

Tumor promotion by 12-O-tetradecanoylphorbol-13-acetate in an ultra-short-term skin carcinogenesis bioassay using rasH2 mice.[Pubmed: 23610217]

Assessment of the skin tumor-promoting potential of 12-O-tetradecanoylphorbol-13-acetate (TPA) after initiation with 7,12-dimethylbenz[a]anthracene (DMBA) was conducted using rasH2 transgenic (Tg) mice and their nontransgenic (non-Tg) littermates. Mice were treated with DMBA (50 μg/100 μL acetone) on clipped back skin at the commencement of the study, and 1 week thereafter, 12-O-tetradecanoylphorbol-13-acetate was applied at 8 μg/200 μL or 4 μg/200 μL acetone, once or twice weekly, for 7 weeks.In conclusion, skin promotion effects could be detected within only 8 weeks in the rasH2 mice, and the concentration of 4 μg 12-O-tetradecanoylphorbol-13-acetate once weekly was sufficient as a positive control. This short-term skin carcinogenesis bioassay using rasH2 mice could represent a useful tool for the assessment of drug and chemical safety with cutaneous treatment.


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