7681-93-8

• 常用中文名：纳他霉素
• 常用英文名：Pimaricin
• CAS号：7681-93-8
• 分子式：C₃₃H₄₇NO₁₃
• 分子量：665.725
• 相关类别： 原料药 抗生素类药物 其它抗生素类药
• 发布时间：2018-07-23 23:19:07
• 更新时间：2024-01-02 19:24:27
• Natamycin (pimaricin)是抗真菌化合物。

名称

• 中文名: 那他霉素
• 英文名: natamycin
• 中文别名: 游霉素; 纳他霉素; 匹马霉素
• 英文别名: Natamycin; Synogil; Pimaricin; EINECS 231-683-5; PIMAFUCIN; myprozine; MFCD00135085; delvocid; antibiotic A 5283; mycophyt; delvopos; (8E,14E,16E,18E,20E)-(1R,3S,5R,7R,12R,22R,24S,25R,26S)-22-(3-amino-3,6-dideoxy-β-D-mannopyranosyloxy)-1,3,26-trihydroxy-12-methyl-10-oxo-6,11,28-trioxatricyclo[22.3.1.05,7]octacosa-8,14,16,18,20-pentaene-25-carboxylic acid; natacyn; delvolan; cl12,625; (1R,3S,5R,7R,8E,12R,14E,16E,18E,20E,22R,24S,25R,26S)-22-[(3-amino-3,6-dideoxy-β-D-mannopyranosyl)oxy]-1,3,26-trihydroxy-12-methyl-10-oxo-6,11,28-trioxatricyclo[22.3.1.05,7]octacosa-8,14,16,18,20-pentaene-25-carboxylic acid

物化性质

• 密度: 1.4±0.1 g/cm3
• 沸点: 952.2±65.0 °C at 760 mmHg
• 熔点: 2000ºC
• 分子式: C₃₃H₄₇NO₁₃
• 分子量: 665.725
• 闪点: 529.7±34.3 °C
• 精确质量: 665.304749
• PSA: 230.99000
• LogP: 0.74
• 外观性状: 白色至灰白色固体
• 蒸汽压: 0.0±0.6 mmHg at 25°C
• 折射率: 1.620
• 储存条件:

  2-8℃

• 分子结构:

  1、 摩尔折射率：167.73

  2、 摩尔体积（m³/mol）：477.4

  3、 等张比容（90.2K）：1385.8

  4、 表面张力（dyne/cm）：71.0

  5、 极化率（10^-24cm³）：66.49

• 更多:

  1. 性状：近白色到奶油黄色粉末，几乎无臭无味

  2. 密度（g/mL 25ºC）：1

  3. 相对蒸汽密度（g/mL,空气=1）：未确定

  4. 熔点（ºC）：2000

  5. 沸点（ºC，常压）：未确定

  6. 沸点（ºC,5.2kPa）：未确定

  7. 折射率（n20/D）：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,60ºC）：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（25℃）：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(mg/mL)：几不溶于水，微溶于甲醇，溶于冰醋酸和二甲基亚砜

生物活性

• 描述: Natamycin (pimaricin)是抗真菌化合物。
• 相关类别:
  信号通路 >> 抗感染 >> 真菌
  研究领域 >> 感染
  天然产物 >> 其他
• 参考文献:

  [1]. Wu H, et al. SlnM gene overexpression with different promoters on natamycin production in Streptomyces lydicus A02. J Ind Microbiol Biotechnol. 2014 Jan;41(1):163-72.

  [2]. Eady RA, et al. A pilot trial of natamycin. A topical antifungal agent. Practitioner. 1969 Nov;203(217):670-3.

MSDS

Name: Pimafucin (pimaricin in a 2.5% sterile water suspension) Material Safety Data Sheet Synonym: Pimaricin; Devolan; Myprozine; Natacyn; Tennecefin; Natamycin CAS: 7681-93-8 Section 1 - Chemical Product MSDS Name:Pimafucin (pimaricin in a 2.5% sterile water suspension) Material Safety Data Sheet Synonym:Pimaricin; Devolan; Myprozine; Natacyn; Tennecefin; Natamycin Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS CAS# Chemical Name content EINECS# 7681-93-8 Pimaricin ca.98.0 231-683-5 Hazard Symbols: None Listed. Risk Phrases: None Listed. Section 3 - HAZARDS IDENTIFICATION EMERGENCY OVERVIEW Light sensitive. Potential Health Effects Eye: May cause eye irritation. Skin: May cause skin irritation. Ingestion: May cause irritation of the digestive tract. Inhalation: May cause respiratory tract irritation. 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 immediately. Skin: Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Remove contaminated clothing and shoes. Ingestion: If victim is conscious and alert, give 2-4 cupfuls of milk or water. Never give anything by mouth to an unconscious person. Get medical aid immediately. Inhalation: Get medical aid immediately. Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Notes to Physician: Treat symptomatically and supportively. Antidote: None reported. 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. Substance is noncombustible. Extinguishing Media: Use agent most appropriate to extinguish fire. 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 or absorb material, then place into a suitable clean, dry, closed 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. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation. Use with adequate ventilation. Storage: Keep container closed when not in use. Store in a cool, dry, well-ventilated area away from incompatible substances. Keep refrigerated. (Store below 4C/39F.) Keep containers tightly closed. Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION Engineering Controls: Use process enclosure, local exhaust ventilation, or other engineering controls to control airborne levels. Exposure Limits CAS# 7681-93-8: CAS# 7732-18-5: 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: Solid Color: Not available. Odor: Not available. pH: Not available. Vapor Pressure: Not available. Viscosity: Not available. Boiling Point: @ 760.00mm Hg Freezing/Melting Point: 200 deg C Autoignition Temperature: Not available. Flash Point: Not available. Explosion Limits, lower: N/A Explosion Limits, upper: N/A Decomposition Temperature: Solubility in water: ketones, cyclohexanols Specific Gravity/Density: 1.01 Molecular Formula: C33H47NO13 Molecular Weight: 665.72 Section 10 - STABILITY AND REACTIVITY Chemical Stability: Stable under normal temperatures and pressures. Conditions to Avoid: Incompatible materials, light, dust generation, strong oxidants. Incompatibilities with Other Materials: Strong oxidizing agents. Hazardous Decomposition Products: Carbon monoxide, oxides of nitrogen, irritating and toxic fumes and gases, carbon dioxide. Hazardous Polymerization: Has not been reported Section 11 - TOXICOLOGICAL INFORMATION RTECS#: CAS# 7681-93-8: TK3325000 CAS# 7732-18-5: ZC0110000 LD50/LC50: CAS# 7681-93-8: Oral, mouse: LD50 = 1500 mg/kg; Oral, rabbit: LD50 = 1420 mg/kg; Oral, rat: LD50 = 2730 mg/kg. CAS# 7732-18-5: Oral, rat: LD50 = >90 mL/kg. Carcinogenicity: Pimaricin - Not listed by ACGIH, IARC, or NTP. Water - Not listed by ACGIH, IARC, or NTP. Other: See actual entry in RTECS for complete information. Section 12 - ECOLOGICAL INFORMATION Other No information available. 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# 7681-93-8: No information available. CAS# 7732-18-5: No information available. Canada CAS# 7732-18-5 is listed on Canada's DSL List. CAS# 7681-93-8 is not listed on Canada's Ingredient Disclosure List. CAS# 7732-18-5 is not listed on Canada's Ingredient Disclosure List. US FEDERAL TSCA CAS# 7681-93-8 is not listed on the TSCA inventory. It is for research and development use only. CAS# 7732-18-5 is listed on the TSCA inventory. SECTION 16 - ADDITIONAL INFORMATION N/A

毒性和生态

毒理学数据: 急性毒性：LD50：4000mg/Kg（大鼠经口）；4720mg/Kg（兔经皮）。 LC50：9400mg/m3，2小时（小鼠吸入） CHEMICAL IDENTIFICATION RTECS NUMBER : TK3325000 CHEMICAL NAME : Pimaricin CAS REGISTRY NUMBER : 7681-93-8 LAST UPDATED : 199801 DATA ITEMS CITED : 27 MOLECULAR FORMULA : C33-H47-N-O13 MOLECULAR WEIGHT : 665.81 WISWESSER LINE NOTATION : T3-25- BO DV SOV IU KU MU OU UUTJ EVQ FQ R1 C&YQ1Q C&Q HO- BT5OTJ CQ DZ EYQ1 HEALTH HAZARD DATA ACUTE TOXICITY DATA TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 2730 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 - rat DOSE/DURATION : 85 mg/kg TOXIC EFFECTS : Lungs, Thorax, or Respiration - other changes TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 190 mg/kg TOXIC EFFECTS : Lungs, Thorax, or Respiration - other changes TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 36 mg/kg TOXIC EFFECTS : Behavioral - convulsions or effect on seizure threshold TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intramuscular SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 128 mg/kg TOXIC EFFECTS : Behavioral - tolerance TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 1500 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 - mouse DOSE/DURATION : 40 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 : Subcutaneous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 180 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 : >5 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 : Oral SPECIES OBSERVED : Mammal - dog DOSE/DURATION : >300 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 : Mammal - dog DOSE/DURATION : 18 mg/kg TOXIC EFFECTS : Behavioral - convulsions or effect on seizure threshold TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Mammal - cat DOSE/DURATION : >300 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 : Mammal - cat DOSE/DURATION : 75 mg/kg TOXIC EFFECTS : Lungs, Thorax, or Respiration - other changes TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intramuscular SPECIES OBSERVED : Mammal - cat DOSE/DURATION : 90 mg/kg TOXIC EFFECTS : Lungs, Thorax, or Respiration - other changes TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - rabbit DOSE/DURATION : 1420 mg/kg TOXIC EFFECTS : Gastrointestinal - hypermotility, diarrhea TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - rabbit DOSE/DURATION : 68 mg/kg TOXIC EFFECTS : Lungs, Thorax, or Respiration - other changes TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - rabbit DOSE/DURATION : 180 mg/kg TOXIC EFFECTS : Lungs, Thorax, or Respiration - other changes TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - rabbit DOSE/DURATION : 20 mg/kg TOXIC EFFECTS : Behavioral - convulsions or effect on seizure threshold TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intramuscular SPECIES OBSERVED : Rodent - rabbit DOSE/DURATION : 120 mg/kg TOXIC EFFECTS : Lungs, Thorax, or Respiration - other changes TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - guinea pig DOSE/DURATION : 450 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 : 90 mg/kg TOXIC EFFECTS : Lungs, Thorax, or Respiration - other changes TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - guinea pig DOSE/DURATION : 160 mg/kg TOXIC EFFECTS : Lungs, Thorax, or Respiration - other changes TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intramuscular SPECIES OBSERVED : Rodent - guinea pig DOSE/DURATION : 130 mg/kg TOXIC EFFECTS : Lungs, Thorax, or Respiration - other changes TYPE OF TEST : LD30 - Lethal Dose ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Mammal - species unspecified DOSE/DURATION : 500 mg/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 : 34104 mg/kg/2Y-C TOXIC EFFECTS : Nutritional and Gross Metabolic - weight loss or decreased weight gain TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 7 gm/kg/2W-I TOXIC EFFECTS : Gastrointestinal - hypermotility, diarrhea Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death MUTATION DATA TYPE OF TEST : Sex chromosome loss and nondisjunction TEST SYSTEM : Mold - Aspergillus nidulans DOSE/DURATION : 30 mg/L REFERENCE : MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 79,169,1980

安全

• 个人防护装备: Eyeshields;Gloves
• 危害码 (欧洲): Xn: Harmful;
• 风险声明 (欧洲): R22
• 安全声明 (欧洲): S24/25
• 危险品运输编码: NONH for all modes of transport
• WGK德国: 2
• RTECS号: TK3325000

合成路线

127-09-3 ~% 85496-13-5 7681-93-8

文献：EP1862467 A2, ; Page/Page column 5; 24; 29 ;

42752-07-8 ~% 85496-13-5 7681-93-8

文献：EP1862467 A2, ; Page/Page column 5; 24; 29 ;

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制备

由游链霉菌(Streptomyces natalensis)受控发酵制得