ChemicalBook >> CAS DataBase List >>PHORBOL 12-MYRISTATE 13-ACETATE
PHORBOL 12-MYRISTATE 13-ACETATE
- CAS No.
- 16561-29-8
- Chemical Name:
- PHORBOL 12-MYRISTATE 13-ACETATE
- Synonyms
- TPA;12-O-TETRADECANOYLPHORBOL 13-ACETATE;Recombinant Human Tissue Plasminogen Activator;phorbol ester;factora1;,9aalpha))-;Cocarcinogen A1;Cocarcinogen C3;pma(tumorpromoter);factora1(crotonoil)
- CBNumber:
- CB2376433
- Molecular Formula:
- C36H56O8
- Molecular Weight:
- 616.83
- MDL Number:
- MFCD00036736
- MOL File:
- 16561-29-8.mol
- MSDS File:
- SDS
Last updated:2024-04-03 15:02:28
| 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) |
| NCI Dictionary of Cancer Terms | 12-O-tetradecanoylphorbol-13-acetate; tetradecanoylphorbol acetate |
| FDA UNII | NI40JAQ945 |
| NCI Drug Dictionary | tetradecanoylphorbol acetate |
| EPA Substance Registry System | 12-O-Tetradecanoylphorbol 13-acetate (16561-29-8) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |    GHS05,GHS06,GHS08 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Danger | |||||||||
| Hazard statements | H300+H310+H330-H314-H317-H334-H351 | |||||||||
| Precautionary statements | P202-P260-P280-P303+P361+P353-P304+P340+P310-P305+P351+P338 | |||||||||
| 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 | |||||||||
| 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. | |||||||||
| NFPA 704 |
|
PHORBOL 12-MYRISTATE 13-ACETATE price More Price(67)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich | P1585 | PMA foruseinmolecularbiologyapplications,≥99%(HPLC) | 16561-29-8 | 5MG | $276 | 2024-03-01 | Buy |
| Sigma-Aldrich | 524400 | Phorbol-12-myristate-13-acetate | 16561-29-8 | 1mg | $82.8 | 2024-03-01 | Buy |
| Sigma-Aldrich | 524400 | Phorbol-12-myristate-13-acetate | 16561-29-8 | 5mg | $208 | 2024-03-01 | Buy |
| Sigma-Aldrich | 5.00582 | InSolution Phorbol-12-myristate-13-acetate - CAS 16561-29-8 - Calbiochem | 16561-29-8 | 2MG | $111 | 2024-03-01 | Buy |
| Alfa Aesar | J63916 | Phorbol 12-myristate 13-acetate, 99+% | 16561-29-8 | 1mg | $105 | 2024-03-01 | Buy |
PHORBOL 12-MYRISTATE 13-ACETATE Chemical Properties,Uses,Production
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
Raw materials
Preparation Products
Global( 239)Suppliers
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| Chengdu Biopurify Phytochemicals Ltd. | +8618080483897 | sales@biopurify.com | China | 3424 | 58 |
| Hebei Mojin Biotechnology Co., Ltd | +8613288715578 | sales@hbmojin.com | China | 12456 | 58 |
| Chongqing Zhihe Biopharmaceutical Co., Ltd. | +86-18580541567 +86-17782035140 | sales@zhswyy.com | China | 338 | 58 |
| Henan Fengda Chemical Co., Ltd | +86-371-86557731 +86-13613820652 | info@fdachem.com | China | 7845 | 58 |
| Henan Tianfu Chemical Co.,Ltd. | +86-0371-55170693 +86-19937530512 | info@tianfuchem.com | China | 21691 | 55 |
| Hangzhou FandaChem Co.,Ltd. | 008657128800458; +8615858145714 | fandachem@gmail.com | China | 9348 | 55 |
| career henan chemical co | +86-0371-86658258 | sales@coreychem.com | China | 29914 | 58 |
| Shaanxi Pioneer Biotech Co., Ltd . | +8613259417953 | sales@pioneerbiotech.com | China | 3000 | 58 |
| NanJing Spring & Autumn Biological Engineering CO., LTD. | +8613815430202 | sale02@cqherb.com | CHINA | 376 | 58 |
| BOC Sciences | +1-631-485-4226 | inquiry@bocsci.com | United States | 19553 | 58 |
View Lastest Price from PHORBOL 12-MYRISTATE 13-ACETATE manufacturers
| Image | Update time | Product | Price | Min. Order | Purity | Supply Ability | Manufacturer | |
|---|---|---|---|---|---|---|---|---|
 |
2024-04-26 | PHORBOL 12-MYRISTATE 13-ACETATE
16561-29-8
|
US $0.00-0.00 / kg | 0.10000000149011612kg | ≥98% | 20tons | Chongqing Zhihe Biopharmaceutical Co., Ltd. | |
 |
2024-04-26 | PHORBOL 12-MYRISTATE 13-ACETATE
16561-29-8
|
US $2150.00-2130.00 / gram | 20gram | 99% | 100tons | Hebei Dangtong Import and export Co LTD | |
 |
2024-04-05 | PHORBOL 12-MYRISTATE 13-ACETATE
16561-29-8
|
US $8.00-1.00 / kg | 1kg | 99% | g-kg-tons, free sample is available | Henan Fengda Chemical Co., Ltd |
-
- PHORBOL 12-MYRISTATE 13-ACETATE
16561-29-8
- US $0.00-0.00 / kg
- ≥98%
- Chongqing Zhihe Biopharmaceutical Co., Ltd.
-
- PHORBOL 12-MYRISTATE 13-ACETATE
16561-29-8
- US $2150.00-2130.00 / gram
- 99%
- Hebei Dangtong Import and export Co LTD
-
- PHORBOL 12-MYRISTATE 13-ACETATE
16561-29-8
- US $8.00-1.00 / kg
- 99%
- Henan Fengda Chemical Co., Ltd
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PHORBOL 16-HYDROXY 12-PALMITATE 13-ACETATE
1of4
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,
4BETA-PHORBOL 12-MYRISTATE 13-ACETATE
4BETA,9ALPHA,12BETA,13ALPHA,20-PENTA-HYDROXYTIGLIA-1,6-DIEN-3-ONE 12BETA-MYRISTATE 13-ACETATE
4ALPHA,9ALPHA,12BETA,13ALPHA,20-PENTAHYDROXYTIGLIA-1,6-DIEN-3-ONE 12BETA-MYRISTATE 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
12-TETRADECANOYL PHORBOL 13-ACETATE
PHORBOL 12-MYRISTATE 13-ACETATE, SYNTHET IC
PHORBOL 12-MYRISTATE 13-ACETATE,*MOLECUL AR BIOLOGY
PHORBOL 12-MYRISTATE 13-ACETATE FROM &
Tetradecanoic acid, (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-cyclopropa3,4benz1,2-eazulen-9-yl ester
4B-PHORBOL-12-MYRISTATE-13-ACETATE
2-ORTHO-TETRADECANOYL-PHORBOL-13-ACETATE
O-TETRADECANOYLPHORBOL-13-ACETATE
12-ORTHO-TETRADECANOYLPHORBOL-13-ACETATE
12-O-Tetradecanoylphorbol 13-acetate, PMA, TPA, 4β,9α,12β,13α,20-Pentahydroxytiglia-1,6-dien-3-one 12-tetradecanoate 13-acetate
Phorbol 12-myristate 13-acetate,99%
Phorbol 12-myristate 13-acetate,97%
PHORBOL(12-MYRISTOYL-13-ACETYL) ANALYTICAL GRADE
Phorbol 12-myristate 13-acetate,12-O-Tetradecanoylphorbol 13-acetate, 4β,9α,12β,13α,20-Pentahydroxytiglia-1,6-dien-3-one 12-tetradecanoate 13-acetate, PMA, TPA
Phorbol 12-Myristate 13-Acetate >99.5%
Phorbol-12-Myristate-13-acetate / 12-Tetradecanoyl phorbol-13-acetate, TPA
PMA, TPA, Cocarcinogen A1
12-O-TETRADECANOYL PHORBOL-13-ACETATE;COCARCINOGEN A1; COCARCINOGEN C3
Cocarcinogen A1
Cocarcinogen C3
(1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-9a-acetoxy-4a,7b-dihydroxy-3-(hydroxyMethyl)-1,1,6,8-tetraMethyl-5-oxo-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-1H-cyclopropa[3,4]benzo[1,2-e]azulen-9-yl tetradecanoate
12-O-tetradecanoyl phorbol-13-acetate(CAS：16561-29-8)
4β,9α,12β,13α,20-Pentahydroxytiglia-1,6-dien-3-one 12-tetradecanoate 13-acetate
PHORBOL 12-MYRISTATE 13-ACETATE, SYN
(1AR,1bS,4aR,7aS,7bS,8R,9R,9aS)
-1,1,6,8-tetramethyl-5-oxo-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-1H-cyclopropa[3,4]benzo[1,2-e]azulen-9-yl tetradecanoate
-9a-acetoxy-4a,7b-dihydroxy-3-(hydroxymethyl)
InSolution? Phorbol-12-myristate-13-acetate
PHORBOL 12-MYRISTATE 13-ACETATE
PHORBOL (12-MYRISTOYL-13-ACETYL)
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
a-tetramethyl-5h-cyclopropa(3,4)benz(1,2-e)azulen-5-one,9a-acetate
-e)azulen-9-ylester,(1ar-(1aalpha,1bbeta,4abeta,7aalpha,7balpha,8alpha,9beta
factora1
factora1(crotonoil)
factora1[crotonoil]
hydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-1h-cyclopropa(3,4)benz(1,2
myristicacid,9-esterwith1,1a-alpha,1b-beta,4,4a,7a-alpha,7b,8,9,9a-decahydr
myristicacid,9-esterwith1,1aalpha,1bbeta,4,4a,7aalpha,7b,8,9,9a-decahydro-4
o-4a-beta,7b-alpha,9-beta,9a-alpha-tetrahydroxy-3-(hydroxymethyl)-1,1,6,8-alph
pentahydroxy-tigliadienone-monoacetate(c)monomyristate(b)
phorbol12-tetradecanoate13-acetate
phorbolacetate,myristate
phorbolmonoacetatemonomyristate
phorbolmyristateacetate
pma(tumorpromoter)
tetradecanoicacid,9a-(acetyloxy)-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-4a,7b-di
tetradecanoylphorbolacetate
,9aalpha))-
1,6,8-beta-tetramethyl-l)-9a-acetate9-myristate