153-18-4

• 常用中文名：芦丁
• 常用英文名：Rutin
• CAS号：153-18-4
• 分子式：C₂₇H₃₀O₁₆
• 分子量：610.518
• 相关类别： 原料药 维生素类与矿物质类药 维生素C类药
• 发布时间：2018-02-05 08:00:00
• 更新时间：2024-01-01 18:29:29
• Rutin是天然的黄酮苷,具有抗炎,抗氧化、抗过敏、抗病毒等功效。

名称

• 中文名: 芸香叶苷
• 英文名: rutin
• 中文别名: 芦丁三水合物; 紫皮甙三水合物; 维生素P三水合物; 芦丁
• 英文别名: 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}methyl)tetrahydro-2H-pyran-2-yl]oxy}-4H-chromen-4-one; 4H-1-Benzopyran-4-one, 3-((6-O-(6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl)oxy)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-; Tanrutin; 4H-1-Benzopyran-4-one, 3-[[6-O-(6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl]oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-; Quercetin 3-O-β-D-rutinoside; 3,3',4',5,7-Pentahydroxyflavone 3-(O-rhamnosylglucoside); Venoruton; Vitamin P trihydrate; Ilixathin; Quercetin 3-O-rutinoside; Quercetin 3-β-rutinoside; Rutinion acid; Osyritrin; 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl-6-O-(6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranoside; 3-((6-O-(6-Deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl)oxy)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one; Violaquercitrin; Rutozyd; EINECS 205-814-1; Globularicitrin; Sophorin; 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl 6-O-(6-deoxy-α-L-mannopyranosyl)-β-D-mannopyranoside; Paliuroside; 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl 6-O-(6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranoside; Eldrin; Rutabion; Rutin hydrate; Oxyritin; Rutoside; Quercetin 3-O-β-rutinoside; Rutin; Rutin trihydrate; 3-[[6-O-(6-Deoxy-a-L-mannopyranosyl)-b-D-glucopyranosyl]oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one; 3,3',4',5,7-Pentahydroxyflavone-3-rutinoside; Birutan; 4H-1-Benzopyran-4-one, 3-[[6-O-(6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl]-oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-; Melin; Osyritin; Rutinic acid; Quercetin-3-O-rutinoside; MFCD00006830; Myrticolorin

物化性质

• 密度: 1.8±0.1 g/cm3
• 沸点: 983.1±65.0 °C at 760 mmHg
• 熔点: 195 °C (dec.)(lit.)
• 分子式: C₂₇H₃₀O₁₆
• 分子量: 610.518
• 闪点: 325.4±27.8 °C
• 精确质量: 610.153381
• PSA: 269.43000
• LogP: 1.76
• 外观性状: 灰白-黄色结晶固体
• 蒸汽压: 0.0±0.3 mmHg at 25°C
• 折射率: 1.765
• 储存条件:

  1.食品级塑料袋外套牛皮纸袋密封包装，或用玻璃瓶密封包装。贮存于阴凉干燥处。不与毒害化学品共贮。

• 稳定性:

  1.常温常压下稳定。

  2.禁配物：强氧化剂
• 水溶解性: 12.5 g/100 mL
• 分子结构:

  1、 摩尔折射率：138.17

  2、 摩尔体积（cm³/mol）：334.1

  3、 等张比容（90.2K）：1117.8

  4、 表面张力（dyne/cm）：125.2

  5、 极化率（10^-24cm³）：54.77

• 计算化学:

  1.疏水参数计算参考值（XlogP）:-1.3

  2.氢键供体数量:10

  3.氢键受体数量:16

  4.可旋转化学键数量:6

  5.互变异构体数量:162

  6.拓扑分子极性表面积266

  7.重原子数量:43

  8.表面电荷:0

  9.复杂度:1020

  10.同位素原子数量:0

  11.确定原子立构中心数量:10

  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：芦丁是广泛存在于植物中的黄酮醇配糖体，两个配糖体为葡萄糖和鼠李糖。为淡黄色或淡绿色针状结晶或结晶性粉末

  2.熔点（℃）：214~215

  3.比旋光度（º,乙醇中）：13.82

  4.溶解性：能溶于吡啶、甲酰和碱液，微溶于乙醇、丙酮和乙酸乙酯，几乎不溶于水、氯仿、醚、苯、二硫化碳和石油醚。

生物活性

• 描述: Rutin是天然的黄酮苷,具有抗炎,抗氧化、抗过敏、抗病毒等功效。
• 相关类别:
  信号通路 >> 自噬 >> 自噬
  天然产物 >> 黄酮类化合物
  研究领域 >> 炎症/免疫
• 参考文献:

  [1]. E. H. Aksu, et al. Rutin ameliorates cisplatin-induced reproductive damagevia suppression of oxidative stress and apoptosis in adultmale rats. Andrologia. 2016 Apr 23.

  [2]. Han YH, et al. Lipin1-Mediated Repression of Adipogenesis by Rutin.Am J Chin Med. 2016;44(3):565-78

  [3]. Lu N, et al. Effects of rutin on the redox reactions of hemoglobin. Int J Biol Macromol. 2016 Apr 25;89:175-180.

MSDS

Name: Rutin Trihydrate 98% (Titr.) Material Safety Data Sheet Synonym: Glucopyranoside, quercetin-3 6-O-(6-deoxy-alpha-L-mannopyranosyl)-, beta-D-; 3,3',4',5,7-Pentahydroxyflavone-3-rutinoside; Quercetin rhamnoglucosin CAS: 153-18-4 Section 1 - Chemical Product MSDS Name:Rutin Trihydrate 98% (Titr.) Material Safety Data Sheet Synonym:Glucopyranoside, quercetin-3 6-O-(6-deoxy-alpha-L-mannopyranosyl)-, beta-D-; 3,3',4',5,7-Pentahydroxyflavone-3-rutinoside; Quercetin rhamnoglucosin Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS CAS# Chemical Name content EINECS# 153-18-4 Rutin, DAB 98 205-814-1 Hazard Symbols: XI Risk Phrases: 36/37/38 Section 3 - HAZARDS IDENTIFICATION EMERGENCY OVERVIEW Irritating to eyes, respiratory system and skin.Hygroscopic (absorbs moisture from the air).Light sensitive.The toxicological properties of this material have not been fully investigated. Potential Health Effects Eye: Causes eye irritation. Skin: Causes skin irritation. Ingestion: Causes gastrointestinal irritation with nausea, vomiting and diarrhea. The toxicological properties of this substance have not been fully investigated. Inhalation: Causes 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: Treat symptomatically and supportively. 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 agent most appropriate to extinguish fire. Do NOT get water inside containers. 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: Clean up spills immediately, observing precautions in the Protective Equipment section. Sweep up, then place into a suitable container for disposal. Avoid generating dusty conditions. Provide ventilation. Do not get water inside containers. 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. Keep container tightly closed. Avoid ingestion and inhalation. Store protected from light. Do not allow contact with water. Keep from contact with moist air and steam. Storage: Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Store protected from moisture. Store protected from light. 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# 153-18-4: 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: Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced. Section 9 - PHYSICAL AND CHEMICAL PROPERTIES Physical State: Powder Color: yellow to green Odor: None reported. pH: Not available. Vapor Pressure: Not available. Viscosity: Not available. Boiling Point: Decomposes Freezing/Melting Point: 195 deg C Autoignition Temperature: Not available. Flash Point: Not available. Explosion Limits, lower: Not available. Explosion Limits, upper: Not available. Decomposition Temperature: > 195 deg C Solubility in water: disulfide and benzene Specific Gravity/Density: Molecular Formula: C27H30O16.3H2O Molecular Weight: 664.58 Section 10 - STABILITY AND REACTIVITY Chemical Stability: Stable at room temperature in closed containers under normal storage and handling conditions. Conditions to Avoid: Incompatible materials, light, dust generation, moisture, excess heat, strong oxidants. Incompatibilities with Other Materials: Oxidizing agents. 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# 153-18-4: VM2975000 LD50/LC50: Not available. Carcinogenicity: Rutin, DAB - 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: XI Risk Phrases: R 36/37/38 Irritating to eyes, respiratory system and skin. Safety Phrases: S 24/25 Avoid contact with skin and eyes. S 28A After contact with skin, wash immediately with plenty of water. S 37 Wear suitable gloves. S 45 In case of accident or if you feel unwell, seek medical advice immediately (show the label where possible). WGK (Water Danger/Protection) CAS# 153-18-4: 1 Canada CAS# 153-18-4 is listed on Canada's NDSL List. CAS# 153-18-4 is not listed on Canada's Ingredient Disclosure List. US FEDERAL TSCA CAS# 153-18-4 is listed on the TSCA inventory. SECTION 16 - ADDITIONAL INFORMATION N/A

毒性和生态

毒理学数据: 1、急性毒性：大鼠腹腔LD50：2 gm/kg；小鼠腹腔LC50：200 mg/kg；小鼠静脉LC50：950 mg/kg 2、慢性毒性/致癌性：大鼠经口TDLo：973 gm/kg/3Y-C 生态学数据: 其它有害作用：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 : VM2975000 CHEMICAL NAME : Rutin CAS REGISTRY NUMBER : 153-18-4 BEILSTEIN REFERENCE NO. : 0075455 LAST UPDATED : 199701 DATA ITEMS CITED : 12 MOLECULAR FORMULA : C27-H30-O16 MOLECULAR WEIGHT : 610.57 WISWESSER LINE NOTATION : T66 BO EVJ CR CQ DQ& GQ IQ DO- BT6OTJ CQ DQ EQ F1O- BT6OTJ CQ DQ EQ F1 HEALTH HAZARD DATA ACUTE TOXICITY DATA TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 2 gm/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 200 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 950 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - guinea pig DOSE/DURATION : 2 gm/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 973 gm/kg/3Y-C TOXIC EFFECTS : Tumorigenic - neoplastic by RTECS criteria Liver - tumors TYPE OF TEST : Specific locus test MUTATION DATA TYPE OF TEST : Body fluid assay TEST SYSTEM : Rodent - rat Bacteria - Salmonella typhimurium DOSE/DURATION : 2 gm/kg REFERENCE : FCTOD7 Food and Chemical Toxicology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.20- 1982- Volume(issue)/page/year: 25,9,1987 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 80506 No. of Facilities: 68 (estimated) No. of Industries: 1 No. of Occupations: 6 No. of Employees: 2770 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 80506 No. of Facilities: 19 (estimated) No. of Industries: 1 No. of Occupations: 9 No. of Employees: 934 (estimated) No. of Female Employees: 506 (estimated)

安全

• 危害码 (欧洲): Xn: Harmful;Xi: Irritant;
• 风险声明 (欧洲): R22
• 安全声明 (欧洲): S24/25
• WGK德国: 3
• RTECS号: VM2975000
• 海关编码: 2932999099

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制备

1. 芸香苷存在于芸香叶、烟叶、橙皮、番茄等内，槐花米和荞麦花内含量尤其丰富。我国药用的芸香苷是从槐花米中提得。槐花米经洗涤后，用热水和石灰乳（调pH至7.5-8）煮沸20min，添加硼砂，在95-100℃保温半小时，趁热过滤，用盐酸将滤液调至pH6-7，冷却至30℃以下，静置析出结晶，分离，得芸香苷粗品，经溶解、再结晶、干燥即得成品。以槐花米计总收率8.3%。

2. 将原料(一般用槐花蕾)粉碎后，用热乙醇萃取，再经乙醚、热甲醇和热水多次结晶精制而得。
浸提物浓缩后所得的残留物，用溶剂将其他可溶性色素等不纯物除去后，再经乙醇、乙醚、热甲醇和热水多次结晶和活性炭精制而得高纯度物。

海关

海关编码	2932999099
中文概述	2932999099. 其他仅含氧杂原子的杂环化合物. 增值税率:17.0%. 退税率:13.0%. 监管条件:无. 最惠国关税:6.5%. 普通关税:20.0%
申报要素	品名, 成分含量, 用途
Summary	2932999099. other heterocyclic compounds with oxygen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%