PHORBOL 12-MYRISTATE 13-ACETATE
PHORBOL 12-MYRISTATE 13-ACETATE
CAS: 16561-29-8
Molecular Formula: C36H56O8
PHORBOL 12-MYRISTATE 13-ACETATE - Names and Identifiers
PHORBOL 12-MYRISTATE 13-ACETATE - Physico-chemical Properties
| Molecular Formula | C36H56O8 |
| Molar Mass | 616.83 |
| Density | 1.17±0.1 g/cm3 (20 ºC 760 Torr) |
| Melting Point | 65-79oC |
| Boling Point | 571.87°C (rough estimate) |
| Water Solubility | Very soluble in methanol, soluble in DMSO, chloroform, ethanol or acetone, ether, ethyl acetate, DMF or acetonitrile. Insoluble in water. |
| Appearance | Form Fine Crystalline Powder, color Off-white to light yellow |
| Storage Condition | -20°C |
| 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. |
| Refractive Index | 1.4900 (estimate) |
| MDL | MFCD00036736 |
| Physical and Chemical Properties | The bioactive Phorbol 12-myristate 13-acetate (PMA, 12-O-Tetradecanoylphorbol-13-acetate, TPA) is an effective PKC activator with active effects in the nanomolar concentration range. Phorbol 12-myristate 13-acetate (PMA) induces sphingosine-1-phosphate (S1P). |
PHORBOL 12-MYRISTATE 13-ACETATE - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | R38 - Irritating to the skin R36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S36/37 - Wear suitable protective clothing and gloves. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| UN IDs | 2928 |
| WGK Germany | 3 |
| RTECS | QH4377000 |
| FLUKA BRAND F CODES | 8-10 |
| HS Code | 29153900 |
| Hazard Class | 6.1(a) |
| Packing Group | II |
| 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 - Reference
| Reference Show more | 1. Su Yang, Ren Wenchen, Li Shanshan, et al. Effect of yangjinhua on intestinal Th17/Treg axis in mice with psoriasis based on intestinal-immune-skin axis [J]. Modern Chinese medicine research and practice, 2018, 32(05):31-34. 2. Shen Nan, Yu Xiao, Miao Hongyu, etc. Protective Mechanism of Jiangzhi granule on intestinal mucosal immune barrier in rats with nonalcoholic steatohepatitis. Journal of Shanghai University of Traditional Chinese Medicine. |
PHORBOL 12-MYRISTATE 13-ACETATE - Nature
| Solubility | DMSO: DMSO solutions can be stored dark at −20?#x00b0;C for at least six months.soluble |
| Sensitivity | Light Sensitive |
| BRN | 2407201 |
| EPA chemical information | 12-O-Tetradecanoylphorbol 13-acetate (16561-29-8) |
Last Update：2024-04-10 22:29:15
PHORBOL 12-MYRISTATE 13-ACETATE - Security information
| toxic substance data | 16561-29-8(Hazardous Substances Data) |
Last Update：2024-04-10 22:29:15
PHORBOL 12-MYRISTATE 13-ACETATE - Uses and synthesis methods
phorbol ester
phorbol ester, also known as phorbol ester and euphorbia diterpene alcohol ester, is a component of croton oil, an ester formed by decadecanoic acid and phorbol. It has been proved to be a cancer promoter. Its cancer-promoting activity varies in size. The highest activity is 12-o-decanoyl Euphorbia diterpene alcohol -13-acetate (TPA), and the rest are Euphorbia diterpene alcohol -12,13-didecanoate, Euphorbia diterpene alcohol -12,13-bisbutyrate, 4-o-methyl Euphorbia diterpene acid -12-decanoyl -13-acetate, Euphorbia diterpene alcohol -12,13-Didecanoate. The mechanism of cancer promotion is not very clear. Recently, it is believed that it is related to initiating cell membrane interaction, promoting the synthesis of second messengers and increasing protein kinase activity. phorbol ester can activate the signaling pathway that leads to cell proliferation or differentiation and can promote cell carcinogenesis. Among them, the highest activity is 12-o -14-alkanoyl phorbol -13-acetate.
Target
PKC
11.7 nM (EC 50 )
in vitro studies
In order to examine the role of PKC in p38MAPK phosphorylation, the cells are stimulated with the PKC activator, PMA (100 nM), which mimics the binding of DAG, the natural activator of PKC, to the C1 region of the PKCs. p38MAPK phosphorylation by PMA is observed in the two cell types similar to that observed by GnRH in αT3-1 cells, that is, a slow sustained activation (3.2-fold and 3.6-fold, respectively at 30 min). The paradoxical findings that PKCs activated by GnRH and PMA play a differential role in p38MAPK phosphorylation may be explained by differential localization of the PKCs. Basal, GnRH- and PMA- stimulation of p38MAPK phosphorylation in αT3-1 cells is mediated by Ca 2 influx via voltage-gated Ca 2 channels and Ca 2 mobilization, while in the differentiated LβT2 gonadotrope cells it is mediated only by Ca 2 mobilization.
THP-1 cells are differentiated into macrophage-like cells (THP-1 macrophages) by incubation in the presence of PMA (200 ng/mL; 1-5 days), which leads to a macrophage-like phenotype characterized by changes in morphology and increased cell surface expression of CD11 and CD14.
In the monocytic cell line THP-1, PMA results in a more differentiated phenotype than VD3, according to adherence, loss of proliferation, phagocytosis of latex beads, and expression of CD11b and CD14.
In vivo studies
PMA is a PKC agonist, which reverses the damage induced by 5-hydroxydecanoic acid (5-HD). Thus, activation of the mitoKATP protected mitochondrial function in SOD and MDA via the PKC pathway.
category
Toxic substances
Toxicity classification
Highly toxic
Acute toxicity
intravenous-mouse LD50: 0.309 mg/kg
flammability hazard characteristics
Flammable, hot and irritating smoke from the fire site
storage and transportation features
The warehouse is ventilated and dry at low temperature; stored and transported separately from food
Fire extinguishing agent
Water, sand, foam
Last Update：2024-04-09 21:11:58
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Spot supply
Product Name: Phorbol 12-Myristate 13-Acetate Visit Supplier Webpage Request for quotationCAS: 16561-29-8
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409
Wechat: 18301782025
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