10083-24-6
Piceatannol
CAS: 10083-24-6
Molecular Formula: C14H12O4
10083-24-6 - Names and Identifiers
| Name | Piceatannol |
| Synonyms | Piceatannol PICEATANNOL (E)-Piceatannol Trans-Piceatannol trans-Piceatannol 3,3',4,5'-Tetrahydroxystilbene (E)-3,3',4,5'-Tetrahydroxystilbene TRANS-3,3',4,5'-TETRAHYDROXYSTILBENE Trans-3,3',4,5'-Tetrahydroxystilbene 3,3',4,5'-Tetrahydroxy-Trans-Stilbene 3,4,3',5'-Tetrahydroxy-Trans-Stilbene PICEATANNOL (3,3',4,5'-TETRAHYDROXY-TRAN Piceatannol (3,3',4,5'-Tetrahydroxy-Tran 4-[2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,2-diol 4-[2-(3,5-Dihydroxyphenyl)Ethenyl]Benzene-1,2-Diol (e)-4-[2-(3,5dihydroxyphenyl)ethenyl]1,2-benzenediol (E)-4-[2-(3,5Dihydroxyphenyl)Ethenyl]1,2-Benzenediol 4-[(E)-2-(3,5-Dihydroxyphenyl)Ethenyl]Benzene-1,2-Diol 4-[(1E)-2-(3,5-Dihydroxyphenyl)Ethenyl]-1,2-Benzenediol |
| CAS | 10083-24-6 |
| EINECS | 600-132-4 |
| InChI | InChI=1/C14H12O4/c15-11-5-10(6-12(16)8-11)2-1-9-3-4-13(17)14(18)7-9/h1-8,15-18H/b2-1+ |
10083-24-6 - Physico-chemical Properties
| Molecular Formula | C14H12O4 |
| Molar Mass | 244.24 |
| Density | 1.1245 (rough estimate) |
| Melting Point | 223.0-227.0 °C |
| Boling Point | 108°C/0.04mmHg(lit.) |
| Flash Point | 252.2°C |
| Solubility | Soluble in methanol, acetone, DMSO, benzene, toluene and other solvents, insoluble in petroleum ether. |
| Vapor Presure | 6.51E-11mmHg at 25°C |
| Appearance | White crystal |
| Color | light tan to yellow |
| Maximum wavelength(λmax) | ['323nm(MeOH)(lit.)'] |
| pKa | 9.17±0.10(Predicted) |
| Storage Condition | 2-8°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 | 1.5190 (estimate) |
| MDL | MFCD00221715 |
| Physical and Chemical Properties | Solubility: H2O: 0.5 mg/mL storage condition: 2-8 ℃ WGK Germany:3 |
| In vitro study | Piceatannol is about 10 times more selective for Syk than Lyn. Piceatannol treatment in RBL-2H3 cells strongly inhibited antigen-stimulated phosphorylation of Syk and most other cellular proteins, but had no effect on phosphorylation of receptor β or γ isoforms, in a dose-dependent manner. Piceatannol is also a potent inhibitor of histamine release in mast cells. Selective inhibition of Syk by Piceatannol in mast cells can block receptor-mediated downstream cellular responses, including inhibition of 1,4,5-IP 3 synthesis, secretion, membrane rim fluctuations, and trafficking. Piceatannol also effectively inhibited PKA, PKC, MLCK, and CDPK, with IC50 of 3 μm, 8 μm, 12 μm, and 19 μm, respectively. Piceatannol selectively inhibited IFNα-induced tyrosine phosphorylation of STAT3 and 5 but had no effect on STAT1 and 2, while selectively inhibited Tyrosine dephosphorylation of Jak1 and IFNAR1 but had no effect on Tyk2 and ifnar2. Piceatannol can effectively induce apoptosis in BJAB Burkitt-like lymphoma cells with an ED50 of 25 μm, this process is achieved through activation of caspase 3 and alterations in mitochondrial permeability independent of the CD95/Fas signaling pathway. Piceatannol inhibits TNF, H 2 O 2 , PMA, NF-κB activation induced by LPS, okadaic acid and ceramide. Piceatannol inhibits TNF-induced NF-κB-dependent reporter gene expression by blocking TNF-induced phosphorylation of IκB α of, p65 phosphorylation, p65 nuclear translocation and activation of IκBα kinase to inhibit expression of matrix metalloproteinase-9, cyclooxygenase-2, and cyclin D1, independent of tyrosine kinases. Piceatannol directly binds to PI3K in an ATP-competitive manner and inhibits PI3K activity, which is more effective than resveratrol in anti-atherosclerosis. Piceatannol inhibits androgen-dependent or-Independent CaP cell proliferation while decreasing the expression of mTOR and its key effectors, AKT and eIF4EBP-1 |
| In vivo study | Oral administration of Piceatannol in BALB/c mice with dextran sodium sulfate-induced colitis can significantly improve the destruction of colon structure, induce a significant decrease in colonic myeloperoxidase (MPO) activity and the production of inflammatory mediators, such as nitric oxide (NO), prostaglandin (PG) E 2, and pro-inflammatory cytokines. In a db/db mouse model of type 2 diabetes, Piceatannol inhibits the rise in blood glucose levels in the early stages and improves impaired glucose tolerance in the late stages. |
10083-24-6 - Risk and Safety
| Safety Description | 24/25 - Avoid contact with skin and eyes. |
| WGK Germany | 3 |
| HS Code | 29072990 |
10083-24-6 - Reference
| Reference Show more | 1. Liu Wenjing, Gao Jinxian, Qian Qian, Pu Junfeng, Shi Lei, Wu Shujin. Leucotaxol inhibits endoplasmic reticulum stress to protect acute liver injury induced by carbon tetrachloride in mice [J]. Chinese patent medicine, 2020,42(12):3158-3165. 2. Jiang mengdan, Xia pengguo, Liang zongsuo, Xu xinhan, Chen xiliang, Han ruilian. Feasibility study on the use of three leaves of green fibrous root based on microstructure, antioxidant activity and chemical composition [J]. Shi Zhen Chinese medicine, 2020,31(10):2492-2495. 3. [IF = 5.279] Tong Zhu et al."Effects of White LED Light and UV-C Radiation on Stilbene Biosynthesis and Phytochemicals Accumulation Identified by UHPLC-MS/MS duration Peanut (Arachis hypogaea L.) Germination." J Agr Food Chem. 2020;68(21):5900-5909 4. [IF = 4.142] Wang Chenxi et al."Systematic quality evaluation of Peiyuan Tongnao capsule by offline two-dimensional liquid chromatography/quadrupole-Orbitrap mass spectrometry and adjusted parallel reaction monitoring of quality markers." Anal Bioanal Chem. 2019 Nov;4 5. [IF = 4.074] Jia Li et al."Omics and Transgenic Analyses Reveal that Salvianolic Acid B Exhibits its Anti-Inflammatory Effects through Inhibiting the Mincle-Syk-Related Pathway in Macrophages." J Proteome Res. 2021;XXXX(XXX):XXX-XXX 6. [IF = 2.354] Zhu Tong et al."Light radiation promoted stilbene accumulation in peanut sprouts: a response of the reestablishment of oxidant-antioxidant homeostasis." Acta Physiol Plant. 2021 Oct;43(10):1-14 |
10083-24-6 - Reference Information
| Plant source: | Rhubarb |
| Use and preparation method of whitebark cedar | whitebark cedar is a chemical structure similar to resveratrol The compound is widely found in fruits and vegetables such as grapes, blueberries, and passion fruits. It can inhibit the growth and development of immature fat cells, thereby achieving the purpose of weight loss. In addition, white cedar also helps prevent cancer, heart disease and neurological diseases. In early April 2012, Purdue University in the United States published a new study in the journal Biochemistry found that white cedar delays the production of new fat cells and inhibits the growth of immature fat cells into mature cells, thus helping to control obesity. The researchers also said that although this study shows that red wine can help lose weight, further research is needed to improve the stability and solubility of white cedar to maximize its effect. laboratory preparation method: using 3, 4-dimethoxybenzyl alcohol as raw material, the target product (E)-3,3 ', 4,5'-tetrahydroxystilbene, namely whitebark cedar, is obtained through bromination, Arbuzov rearrangement reaction, Wittig-Horner reaction and demethylation reaction. |
| biological activity | Piceatannol is a natural stilbene and a selective Syk inhibitor, which is about 10 times more selective than Lyn. |
| Target | Value |
| Syk (Cell-free assay) | |
| Lyn (Cell-free assay) | |
| cAK (Cell-free assay) | 3 μM |
| PKC (Cell-free assay) | 8 μM |
| MLCK (Cell-free assay) | 12 μM |
| use | used for content determination/identification/pharmacological experiments, etc. Pharmacological effects: It has anti-leukemia, inhibition of non-receptor activating enzymes, spleen butyric acid kinase and lymphocyte-specific protein tyrosine kinase activity, which helps to delay the production of immature new adipocytes. antioxidant, anti-inflammatory, anti-thrombotic, anti-cancer, anti-cancer, anti-hyperlipidemia, antibacterial and other activities |
Last Update：2024-04-09 21:54:55
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