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Acacetin is a novel and potent Flavonoid that is derived from Dendranthema morifolium. Acacetin causes cell cycle arrest, apoptosis, and autophagy in cancer cells by docking in the ATP-binding pocket of PI3Kγ . Acacetin can be used for research on diseases associated with pain because it has potential anti-inflammatory and anti-cancer activity.
Physicochemical Properties
| Molecular Formula | C16H12O5 |
| Molecular Weight | 284.267 |
| Exact Mass | 284.068 |
| Elemental Analysis | C, 67.60; H, 4.26; O, 28.14 |
| CAS # | 480-44-4 |
| Related CAS # | 480-44-4 |
| PubChem CID | 5280442 |
| Appearance | Light yellow to yellow solid powder |
| Density | 1.4±0.1 g/cm3 |
| Boiling Point | 518.6±50.0 °C at 760 mmHg |
| Melting Point | 260-265 °C(lit.) |
| Flash Point | 198.3±23.6 °C |
| Vapour Pressure | 0.0±1.4 mmHg at 25°C |
| Index of Refraction | 1.669 |
| LogP | 3.15 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 2 |
| Heavy Atom Count | 21 |
| Complexity | 424 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | O1C(=C([H])C(C2=C(C([H])=C(C([H])=C12)O[H])O[H])=O)C1C([H])=C([H])C(=C([H])C=1[H])OC([H])([H])[H] |
| InChi Key | DANYIYRPLHHOCZ-UHFFFAOYSA-N |
| InChi Code | InChI=1S/C16H12O5/c1-20-11-4-2-9(3-5-11)14-8-13(19)16-12(18)6-10(17)7-15(16)21-14/h2-8,17-18H,1H3 |
| Chemical Name | 5,7-dihydroxy-2-(4-methoxyphenyl)chromen-4-one |
| Synonyms | NSC 76061; Acacetin |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| ln Vitro |
Acacetin (5,7-Dihydroxy-4'-methoxyflavone; 10-200 μM; 24 hours) decreases cell viabilities in a dose-dependent manner. Human normal glial cell line HEB and non-tumorigenic epithelial cell line MCF-10A are not significantly affected by acetin[1]. Acacetin (50-150 μM; 24 hours) induces apoptosis and autophagy and causes G2/M cell cycle arrest[1]. Acacetin (50-150 μM; 24 hours) causes dose-dependent reductions in the levels of PI3Kγ-p110, p-AKT, p-mTOR, p-p70S6K and p-ULK. |
| ln Vivo |
Acacetin (5,7-Dihydroxy-4'-methoxyflavone; 5, 20 mg/kg/day; orally; for 3 days) significantly suppresses microglial activation in an LPS-induced neuroinflammation mouse model[2]. Acacetin (25 mg/kg/day; orally; for 3 days) lowers neuronal cell death in an animal model of ischemia[2]. Acacetin (1.8-56.2 mg/kg/day; intraperitoneal; single dose) reduces visceral and inflammatory nociception and prevents the formalin-induced oedema[3]. |
| Animal Protocol |
Male C57BL/6 mice, 7 weeks of age[2] 5, 20 mg/kg Orally; once a day for 3 days |
| References |
[1]. Hong-Wei Zhang, et al. Flavonoids inhibit cell proliferation and induce apoptosis and autophagy through downregulation of PI3Kγ mediated PI3K/AKT/mTOR/p70S6K/ULK signaling pathway in human breast cancer cells. Sci Rep. 2018 Jul 26;8(1):11255. [2]. Sang Keun Ha, et al. Acacetin attenuates neuroinflammation via regulation the response to LPS stimuli in vitro and in vivo. Neurochem Res. 2012 Jul;37(7):1560-7. [3]. A I Carballo-Villalobos, et al. Evidence of mechanism of action of anti-inflammatory/antinociceptive activities of acacetin. Eur J Pain. 2014 Mar;18(3):396-405. |
| Additional Infomation |
5,7-dihydroxy-4'-methoxyflavone is a monomethoxyflavone that is the 4'-methyl ether derivative of apigenin. It has a role as an anticonvulsant and a plant metabolite. It is a dihydroxyflavone and a monomethoxyflavone. It is functionally related to an apigenin. It is a conjugate acid of a 5-hydroxy-2-(4-methoxyphenyl)-4-oxo-4H-chromen-7-olate. Acacetin has been reported in Caragana frutex, Crocus heuffelianus, and other organisms with data available. |
Solubility Data
| Solubility (In Vitro) | DMSO: ~125 mg/mL (~439.7 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (7.32 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. Solubility in Formulation 2: 5 mg/mL (17.59 mM) in 50% PEG300 50% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 3: 10 mg/mL (35.18 mM) in 0.5% CMC-Na/saline water (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 4: 2.5 mg/mL (8.79 mM) in 0.5% CMC/saline water (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.5178 mL | 17.5889 mL | 35.1778 mL | |
| 5 mM | 0.7036 mL | 3.5178 mL | 7.0356 mL | |
| 10 mM | 0.3518 mL | 1.7589 mL | 3.5178 mL |