528-48-3

• 常用中文名：漆黄素
• 常用英文名：Fisetin
• CAS号：528-48-3
• 分子式：C₁₅H₁₀O₆
• 分子量：286.236
• 相关类别： 生物化工 天然产物
• 发布时间：2018-08-04 12:07:45
• 更新时间：2024-01-02 16:40:25
• Fisetin是一种在许多水果和蔬菜中发现的天然黄酮醇,具有多种益处,如抗氧化,抗癌,神经保护作用。

名称

• 中文名: 漆黄素
• 英文名: fisetin
• 中文别名: 漆树黄酮; 非瑟酮; 3,3',4',7-四羟基黄酮
• 英文别名: 5-Deoxyquercetin; 4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-; Fisetin; Viset; 3,3',4',7-tetrahydroxyflavone; MFCD00006829; Fustet; Superfustel; Cotinin; Fustel; Fisidenolon 1521; 5-Desoxyquercetin; 3,7-Dihydroxy-2-(3,4-dihydroxyphenyl)-4H-1-benzopyran-4-one; 2-(3,4-Dihydroxyphenyl)-3,7-dihydroxy-4H-chromen-4-one; 2-(3,4-dihydroxyphenyl)-3,7-dihydroxychromen-4-one; Fietin; EINECS 208-434-4; 3,7,3',4'-Tetrahydroxyflavone; Fisetholz

物化性质

• 密度: 1.7±0.1 g/cm3
• 沸点: 599.4±50.0 °C at 760 mmHg
• 熔点: 330ºC
• 分子式: C₁₅H₁₀O₆
• 分子量: 286.236
• 闪点: 233.0±23.6 °C
• 精确质量: 286.047729
• PSA: 111.13000
• LogP: 2.52
• 外观性状: 黄色至棕色结晶粉末
• 蒸汽压: 0.0±1.8 mmHg at 25°C
• 折射率: 1.785
• 储存条件:

  -20°C下冷藏保存

• 稳定性:

  按规格使用和贮存，不会发生分解，避免与氧化物接触

• 水溶解性: 水溶性：实际上不溶；可溶于：丙酮,甲醇；极微溶：氯仿,苯,乙醚
• 分子结构:

  1、 摩尔折射率：71.43

  2、 摩尔体积（m³/mol）：169.5

  3、 等张比容（90.2K）：534.6

  4、 表面张力（dyne/cm）：98.9

  5、 极化率（10^-24cm³）：28.32

• 计算化学:

  1.疏水参数计算参考值（XlogP）:2

  2.氢键供体数量:4

  3.氢键受体数量:6

  4.可旋转化学键数量:1

  5.互变异构体数量:211

  6.拓扑分子极性表面积107

  7.重原子数量:21

  8.表面电荷:0

  9.复杂度:459

  10.同位素原子数量:0

  11.确定原子立构中心数量:0

  12.不确定原子立构中心数量:0

  13.确定化学键立构中心数量:0

  14.不确定化学键立构中心数量:0

  15.共价键单元数量:1

• 更多:

  1. 性状：未确定

  2. 密度（g/ cm³,25/4℃）：未确定

  3. 相对蒸汽密度（g/cm³,空气=1）：未确定

  4. 熔点（ºC）：300

  5. 沸点（ºC,常压）：未确定

  6. 沸点（ºC,8kPa）：未确定

  7. 折射率：未确定

  8. 闪点（ºC）：未确定

  9. 比旋光度（º）：未确定

  10. 自燃点或引燃温度（ºC）：未确定

  11. 蒸气压（kPa,25ºC）：未确定

  12. 饱和蒸气压（kPa,55.1ºC）：未确定

  13. 燃烧热（KJ/mol）：未确定

  14. 临界温度（ºC）：未确定

  15. 临界压力（KPa）：未确定

  16. 油水（辛醇/水）分配系数的对数值：未确定

  17. 爆炸上限（%,V/V）：未确定

  18. 爆炸下限（%,V/V）：未确定

  19. 溶解性：难溶于水

生物活性

• 描述: Fisetin是一种在许多水果和蔬菜中发现的天然黄酮醇,具有多种益处,如抗氧化,抗癌,神经保护作用。
• 相关类别:
  信号通路 >> 细胞周期/DNA损伤 >> PPAR
  信号通路 >> 细胞周期/DNA损伤 >> 抗衰老酶
  信号通路 >> 表观遗传学 >> 抗衰老酶
  信号通路 >> 细胞凋亡 >> TNF受体
  天然产物 >> 黄酮类化合物
  研究领域 >> 癌症
  研究领域 >> 炎症/免疫
  研究领域 >> 代谢疾病
  研究领域 >> 神经疾病
• 靶点:

  Sirtuin, PPAR, TNF-alpha[1][2]

• 体外研究: 非瑟酮抑制脂质积累并抑制3T3-L1细胞中PPARγ的表达。非瑟酮抑制前脂肪细胞分化的早期阶段,并诱导Sirt1的表达。非瑟酮促进Sirt1介导的PPARγ和FoxO1的去乙酰化,并增强Sirt1与PPARγ启动子的结合,导致PPARγ转录活性的抑制,从而抑制脂肪形成[1]。非瑟酮与微管蛋白结合并稳定微管,其结合特性远远优于紫杉醇。人前列腺癌细胞的非瑟酮治疗导致微管相关蛋白(MAP)-2和-4的强烈上调。非瑟酮显着抑制PCa细胞增殖,迁移和侵袭。 Nudc是一种与微管运动动力蛋白/ dynactin复合物相关的调节微管动力学的蛋白质,用非瑟酮处理抑制[2]。
• 体内研究: 对UVB暴露的小鼠的非瑟酮治疗导致增加的减少并减少炎性细胞的浸润。非瑟酮治疗还减少炎症介质,例如COX-2,PGE2及其受体(EP1-EP4)和MPO活性。此外,非瑟酮降低UVB暴露皮肤中炎性细胞因子TNFα,IL-1β和IL-6的水平。 Fisetin治疗还可以减少细胞增殖标记以及DNA损伤,这可以通过增加p53和p21蛋白的表达来证明[3]。
• 细胞实验: 用报告载体转染3T3-L1细胞，用TransIT-LT1转染表达质粒。 24小时后，用病毒上清液替换培养基。感染15-18小时后，用DMI，0.1μM曲格列酮和非瑟酮（50μM）替换培养基。加入分化刺激物两天后，使用细胞培养裂解缓冲液裂解细胞。荧光素酶活性使用分析发光光度计[1]确定。
• 动物实验: 小鼠：将小鼠分成六组，每组八只动物。第一组小鼠用0.2mL丙酮局部处理，并用作载体对照。第二组和第三组中的小鼠分别在其背部皮肤上接受Fisetin 250nmol / 0.2mL丙酮/小鼠和500nmol / 0.2mL丙酮/小鼠的局部治疗，并用作药剂对照。第四，第五和第六组中的小鼠暴露于UVB。第四组中的小鼠在指定为载体对照的UVB暴露15分钟后接受0.2mL丙酮的局部施用。第5组和第6组小鼠在UVB暴露15分钟后分别局部应用Fisetin 250 nmol / 0.2 mL丙酮/小鼠和500 nmol / 0.2 mL丙酮/小鼠处理其背部皮肤[3]。
• 参考文献:

  [1]. Kim SC, et al. Fisetin induces Sirt1 expression while inhibiting early adipogenesis in 3T3-L1 cells. Biochem Biophys Res Commun. 2015 Nov 27;467(4):638-44.

  [2]. Mukhtar E, et al. Dietary flavonoid fisetin binds to β-tubulin and disrupts microtubule dynamics in prostate cancer cells. Cancer Lett. 2015 Oct 28;367(2):173-83.

MSDS

Name: Fisetin tech. 70% Material Safety Data Sheet Synonym: 3,3',4',7-Tetrahydroxyflavone; 4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-; 5-Desoxyquercetin; C.I. 75620; C.I. Natural Brown 1; Flavone, 3,3',4',7-tetrahydroxy CAS: 528-48-3 Section 1 - Chemical Product MSDS Name:Fisetin tech. 70% Material Safety Data Sheet Synonym:3,3',4',7-Tetrahydroxyflavone; 4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-; 5-Desoxyquercetin; C.I. 75620; C.I. Natural Brown 1; Flavone, 3,3',4',7-tetrahydroxy Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS CAS# Chemical Name content EINECS# 528-48-3 4H-1-benzopyran-4-one,2-(3,4-dihydroxy 70 208-434-4 Hazard Symbols: None Listed. Risk Phrases: None Listed. Section 3 - HAZARDS IDENTIFICATION EMERGENCY OVERVIEW The toxicological properties of this material have not been fully investigated. Potential Health Effects Eye: May cause eye irritation. Skin: May cause skin irritation. Ingestion: May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated. Inhalation: May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. Chronic: No information found. Section 4 - FIRST AID MEASURES Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid. Skin: Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse. Ingestion: Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water. Inhalation: Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid. Notes to Physician: Section 5 - FIRE FIGHTING MEASURES General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Extinguishing Media: Use water spray, dry chemical, carbon dioxide, or appropriate foam. Section 6 - ACCIDENTAL RELEASE MEASURES General Information: Use proper personal protective equipment as indicated in Section 8. Spills/Leaks: Sweep up, then place into a suitable container for disposal. Avoid generating dusty conditions. Provide ventilation. Section 7 - HANDLING and STORAGE Handling: Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Avoid ingestion and inhalation. Storage: Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION Engineering Controls: Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low. Exposure Limits CAS# 528-48-3: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166. Skin: Wear appropriate protective gloves to prevent skin exposure. Clothing: Wear appropriate protective clothing to prevent skin exposure. Respirators: A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use. Section 9 - PHYSICAL AND CHEMICAL PROPERTIES Physical State: Solid Color: ochre Odor: none reported pH: Not available. Vapor Pressure: Not available. Viscosity: Not available. Boiling Point: Not available. Freezing/Melting Point: > 330 deg C Autoignition Temperature: Not applicable. Flash Point: Not applicable. Explosion Limits, lower: Not available. Explosion Limits, upper: Not available. Decomposition Temperature: Not available. Solubility in water: Not available. Specific Gravity/Density: Not available. Molecular Formula: C15H10O6 Molecular Weight: 286.23 Section 10 - STABILITY AND REACTIVITY Chemical Stability: Stable under normal temperatures and pressures. Conditions to Avoid: Incompatible materials, dust generation, strong oxidants. Incompatibilities with Other Materials: Strong oxidizing agents, strong bases. Hazardous Decomposition Products: Carbon monoxide, irritating and toxic fumes and gases, carbon dioxide. Hazardous Polymerization: Has not been reported Section 11 - TOXICOLOGICAL INFORMATION RTECS#: CAS# 528-48-3: LK9250000 LD50/LC50: Not available. Carcinogenicity: 4H-1-benzopyran-4-one,2-(3,4-dihydroxyphenyl)-3,7-dihydroxy- - Not listed by ACGIH, IARC, or NTP. Other: See actual entry in RTECS for complete information. Section 12 - ECOLOGICAL INFORMATION Section 13 - DISPOSAL CONSIDERATIONS Dispose of in a manner consistent with federal, state, and local regulations. Section 14 - TRANSPORT INFORMATION IATA Not regulated as a hazardous material. IMO Not regulated as a hazardous material. RID/ADR Not regulated as a hazardous material. Section 15 - REGULATORY INFORMATION European/International Regulations European Labeling in Accordance with EC Directives Hazard Symbols: Not available. Risk Phrases: Safety Phrases: S 24/25 Avoid contact with skin and eyes. WGK (Water Danger/Protection) CAS# 528-48-3: No information available. Canada CAS# 528-48-3 is listed on Canada's NDSL List. CAS# 528-48-3 is not listed on Canada's Ingredient Disclosure List. US FEDERAL TSCA CAS# 528-48-3 is listed on the TSCA inventory. SECTION 16 - ADDITIONAL INFORMATION N/A

毒性和生态

生态学数据: 该物质对环境可能有危害，对水体应给予特别注意。 CHEMICAL IDENTIFICATION RTECS NUMBER : LK9250000 CHEMICAL NAME : Flavone, 3,3',4',7-tetrahydroxy- CAS REGISTRY NUMBER : 528-48-3 BEILSTEIN REFERENCE NO. : 0292829 LAST UPDATED : 199701 DATA ITEMS CITED : 5 MOLECULAR FORMULA : C15-H10-O6 MOLECULAR WEIGHT : 286.25 HEALTH HAZARD DATA ACUTE TOXICITY DATA TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 180 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value MUTATION DATA TYPE OF TEST : DNA inhibition TEST SYSTEM : Human Fibroblast DOSE/DURATION : 50 mg/L REFERENCE : BCPCA6 Biochemical Pharmacology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.1- 1958- Volume(issue)/page/year: 33,3823,1984

安全

• 危害码 (欧洲): Xi
• 风险声明 (欧洲): R36/37/38
• 安全声明 (欧洲): S24/25
• WGK德国: 3
• RTECS号: LK9250000
• 海关编码: 2914501900

合成路线

58544-90-4 ~% 528-48-3

文献：Hasan, Aurangzeb; Sadiq; Abbas; Mughal; Khan, Khalid M.; Ali, Muhammad Natural Product Research, 2010 , vol. 24, # 11 p. 995 - 1003

4382-36-9 ~% 528-48-3

文献：Zanarotti, Antonio Heterocycles, 1982 , vol. 19, # 9 p. 1585 - 1586

93322-61-3 ~% 528-48-3

文献：Bellino; Venturella Annali di Chimica (Rome, Italy), 1958 , vol. 48, p. 111,118

109688-49-5 ~% 528-48-3

文献：Bellino; Venturella Annali di Chimica (Rome, Italy), 1958 , vol. 48, p. 111,118

上下游产品

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58544-90-4 4382-36-9 109688-49-5
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制备

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海关

海关编码	2914501900
中文概述	2914501900 其他酮酚。监管条件:无。增值税率:17.0%。退税率:9.0%。最惠国关税:5.5%。普通关税:30.0%
申报要素	品名, 成分含量, 用途, 丙酮报明包装
Summary	2914501900 other ketone-phenols。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:5.5%。General tariff:30.0%