5,7-Dihydroxy-2-(4-methoxyphenyl)-4H-chromen-4-one
Acacetin
CAS: 480-44-4
Molecular Formula: C16H12O5
5,7-Dihydroxy-2-(4-methoxyphenyl)-4H-chromen-4-one - Names and Identifiers
| Name | Acacetin |
| Synonyms | Abietic ACACETIN 480-44-4 Acacetin LINARIGENIN METHYL-4'-APIGENIN ACACETIN WITH HPLC Apigenin-4'-methyl Ether 5,7-DIHYDROXY-4'-METHOXYFLAVONE ACACETIN(METHYL-4'-APIGENIN)(RG) 5,7-dihydroxy-2-(4-methoxyphenyl)-4-benzopyrone 5,7-Dihydroxy-2-(4-méthoxyphényl)-4H-chromén-4-one 5,7-Dihydroxy-2-(4-methoxyphenyl)-4H-chromen-4-one 5,7-Dihydroxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one |
| CAS | 480-44-4 |
| EINECS | 207-552-3 |
| InChI | InChI=1/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 |
| InChIKey | DANYIYRPLHHOCZ-UHFFFAOYSA-N |
5,7-Dihydroxy-2-(4-methoxyphenyl)-4H-chromen-4-one - Physico-chemical Properties
| Molecular Formula | C16H12O5 |
| Molar Mass | 284.26 |
| Density | 1.2160 (rough estimate) |
| Melting Point | 260-265°C(lit.) |
| Boling Point | 346.76°C (rough estimate) |
| Flash Point | 198.2°C |
| Solubility | Soluble in hot ethanol, insoluble in ether, soluble in alkaline solution. |
| Vapor Presure | 2.25E-11mmHg at 25°C |
| Appearance | Yellow needle crystal |
| Color | Light Yellow to Green-Yellow to Dark Yellow |
| Maximum wavelength(λmax) | ['335nm(EtOH)(lit.)'] |
| Merck | 14,13 |
| BRN | 277879 |
| pKa | 6.51±0.40(Predicted) |
| Storage Condition | 2-8°C |
| Refractive Index | 1.6200 (estimate) |
| MDL | MFCD00016936 |
| Physical and Chemical Properties | Yellow needle-like crystals, soluble in methanol, ethanol, DMSO and other organic solvents, from eupatorium, Thistle, Acacia. |
5,7-Dihydroxy-2-(4-methoxyphenyl)-4H-chromen-4-one - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. |
| WGK Germany | 3 |
| RTECS | DJ3002000 |
| FLUKA BRAND F CODES | 3-8-10 |
| HS Code | 29329990 |
5,7-Dihydroxy-2-(4-methoxyphenyl)-4H-chromen-4-one - Reference
| Reference Show more | 1. Hu Ruirui, Wang Li, Zhang Hongqin. Preparation and in vivo pharmacokinetic evaluation of farnesin polylactic acid nanoparticles [J]. Chinese herbal medicines, 2018, 041(005):1170-1172. 2. Han Xing, Li Xueyan, Yang Haiyang, et al. Screening of quality control components of Chrysanthemum Water extract and its network pharmacological effects [J]. China Pharmacy, 2019, 030(023):3258-3265. 3. Lili, Chen Yong, Zhang Mengwei, Huang Hongxia, Gao Shouhong, Chen Wansheng. Determination of 11 main components in UHPLC-MS experience prescription cold dampness lung decoction by Novel coronavirus pneumonia (COVID-19)/MS [J]. Journal of Pharmaceutical Practice, 2021,39(02):148-151 156. 4. Jiang, Yanfeng Yang, et al. "Gene mining and identification of a flavone synthase II involved in flavones biosynthesis by transcriptomic analysis and targeted flavonoid profiling in chrysanthemum indicum L." Industrial Crops and Products 134 (2019): 244-256 5. [IF=4.411] Li Jia et al."Systematic Profiling of the Multicomponents and Authentication of Erzhi Pill by UHPLC/Q-Orbitrap-MS Oriented Rapid Polarity-Switching Data-Dependent Acquisition and Selective Monitoring of the Chemical Markers Deduced from Fingerprint Analys 6. [IF=5.645] Yanfengyang Jiang et al."Gene mining and identification of a flavone synthase II involved in flavones biosynthesis by transcriptomic analysis and targeted flavonoid profiling in Chrysanthemum indicum L.."Ind Crop Prod. 2019 Aug;134:244 7. [IF=1.402] Wei Yaxin et al."Acacetin improves endothelial dysfunction and aortic fibrosis in insulin-resistant SHR rats by estrogen receptors."Mol Biol Rep. 2020 Sep;47(9):6899-6918 8. [IF=3.935] Junmao Li et al."Comprehensive chemical profiling of the flowers of Citrus aurantium L. var. amara Engl. and uncovering the active ingredients of lipid lowering."J Pharmaceut Biomed. 2022 Mar;211:114621 9. [IF=7.46] Shuo Wang et al."A novel visual sensing method based on Al@AuNCs for rapid identification of Chrysanthemum morifolium from different origins."Sensor Actuat B- Chem. 2022 Apr;356:131307 10. [IF=4.36] Zhenhui Guo et al."Study on the mechanism of Cortex Lycii on lung cancer based on network pharmacology combined with experimental validation."J Ethnopharmacol. 2022 Apr;:115280 |
5,7-Dihydroxy-2-(4-methoxyphenyl)-4H-chromen-4-one - Reference Information
| plant source: | chrysanthemum |
| Plant source | Acacia farnesiana (Linn.) Willd.) (Mimosa) Leguminosae. Shrubs, 2-4 m high; branches with spines, spines up to 1-2cm long. Two pinnate compound leaves, pinna 4-8 pairs, each pinna 10-20 pairs of leaflets, small leaves linear oblong. The flower heads are axillary, 1.5cm in diameter, often in clusters. The pod is cylindrical, 3-7cm long and 8-15mm in diameter. Seeds are mostly black. The flowers are extremely fragrant for extracting essence. Thorn irrigation or small trees, two pinnate compound leaves, flower heads clustered in leaf axils, when in full bloom, like golden pompoms. |
| biological activity | Acacetin (5,7-Dihydroxy-4 '-methoxyflavone) is an orally effective flavonoid from Tephroseris kirilowii (Turcz.) Holub. Acacetin stopped in the ATP binding pocket of PI3Kγ. Acacetin leads to arrest of cancer cell cycle and induces apoptosis and autophagy. Acacetin has effective anti-cancer and anti-inflammatory activities and has the potential to be used in the research of pain-related diseases. |
| Cell Line: | Breast cancer MCF-7 cells, hepatocellular carcinoma SMMC-7721 cells, lung adenocarcinoma A549 cells, esophageal carcinoma Eca109 cells MDA-MB-231 cells MDA-MB-231 cells MDA-MB-231 cells MDA-MB-231 cells |
| Concentration: | 10, 20, 40, 60, 80, 100, 150, 200 μM 50, 100, 150 μM 50, 100, 150 μM 50, 100, 150 μM 50, 100, 150 μM |
| Incubation Time: | 24 hours 24 hours 24 hours 24 hours 24 hours |
| Result: | Decreased cancer cell viabilities in a dose-dependent manner. Had IC 50 values of 82.75 μM, 103.9 μM, 157.4 μM, 54.7 μM in MDA-MB-231, MCF-7, A549, Eca109 cells, respectively. Resulted in increase in percentage of cells at G2/M phase and decrease in percentage of cells at G1 and S phase in a dose-dependent manner. Induced apoptosis. Induced autophagy. Resulted in marked increases in EGFP-LC3 puncta formation and a dose-dependent accumulation of LC3-II. Resulted in decrease in levels of Bcl-2 and Bcl-xL and increase in levels of p53. Led to decreases in levels of PI3Kγ-p110, p-AKT, p-mTOR, p-p70S6K, and p-ULK in a dose-dependent manner. Had little or no effect on expression of PI3Kα, PI3Kβ, PI3Kδ, p-ERK, p-p38, and p-JNK. Significantly suppressed microglial activation in an LPS-induced (ip; 5mg/kg) neuroinflammation mouse model. |
| Animal Model: | Male C57BL/6 mice, 7 weeks of age |
| Dosage: | 5, 20 mg/kg |
| Administration: | Orally; once a day for 3 days |
| use | acacia has sedative and anti-cancer effects. used for content determination/identification/pharmacological experiment, etc. Pharmacological effects: the effects of relaxing depression, rationing qi, calming the nerves, and activating collaterals. |
Last Update：2024-04-09 20:02:46
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Spot supply
Product Name: Acacetin Visit Supplier Webpage Request for quotationCAS: 480-44-4
Tel: 0714-3999186
Email: 2853786052@qq.com
Mobile: 86+15671228036
QQ: 2853786052
Wechat: 15671228036
Multiple SpecificationsSpot supply
Product Name: Acacetin Visit Supplier Webpage Request for quotationCAS: 480-44-4
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409
Wechat: 18301782025
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