138-59-0

• 常用中文名：莽草酸
• 常用英文名：Shikimic acid
• CAS号：138-59-0
• 分子式：C₇H₁₀O₅
• 分子量：174.151
• 相关类别： 生物化工 天然产物
• 发布时间：2018-02-07 08:00:00
• 更新时间：2024-01-02 16:48:26
• Shikimic acid 是在微生物和植物中发现的芳香族氨基酸生物合成途径的关键代谢中间体。
• 　　莽草酸是从中药八角茴香中提取的一种单体化合物，有抗炎、镇痛作用，是抗癌药物中间体，莽草酸通过影响花生四烯酸代谢，抑制血小板聚集，抑制动、静脉血栓及脑血栓形成，莽草酸具有有抗炎、镇痛作用，莽草酸还可作为抗病毒和抗癌药物中间体。
  　　八角茴香含有一种抗亚洲禽流感病毒的重要成分莽草酸。专家称这是世界上对付禽流感的唯一武器。香产于中国和越南，是一种木兰科东方小型树种结出的果实，味道辛辣，类似甘草，是东方烹调的传统调味品，也是法国绿茴香酒和茴香甜酒等利口酒的主要香料。一般还可用来增加糖果、茴香酒和烟草的香味。八角茴香的药用价值在禽流感到来之前就已经受到了关注，包括它可能具有的抗癌功效。现在作为莽草酸的主要来源，八角茴香再次引起了重视，因为莽草酸是可有效对付致命的H5N1型禽流感病毒的药物“达菲”的重要成分。法国马赛的茴香酒制造商里卡公司的主任阿尔贝·埃尔格里西说：“治疗一个感染禽流感的患者需要10粒达菲胶囊，制造10粒达菲胶囊则需要13克八角茴香。”莽草酸每公斤的价格在200-250美元之间，质量特别好的，价格高达每克50美元。莽草酸具有抗炎、镇痛作用，莽草酸还可作为抗病毒和抗癌药物中间体。药理作用莽草酸是从中药八角茴香中提取的一种单体化合物，有抗炎、镇痛作用，是抗癌药物中间体，莽草酸通过影响花生四烯酸代谢，抑制血小板聚集，静脉血栓及脑血栓形成，莽草酸具有有抗炎、镇痛作用，莽草酸还可作为抗病毒和抗癌药物中间体。八角茴香含有一种抗亚洲禽流感病毒的重要成分莽草酸。专家称这是世界上对付禽流感的唯一武器。香产于中国和越南，是一种木兰科东方小型树种结出的果实，味道辛辣，类似甘草，是东方烹调的传统调味品，也是法国绿茴香酒和茴香甜酒等利口酒的主要香料。一般还可用来增加糖果、茴香酒和烟草的香味。八角茴香的药用价值在禽流感到来之前就已经受到了关注，包括它可能具有的抗癌功效。现在作为莽草酸的主要来源，八角茴香再次引起了重视，因为莽草酸是可有效对付致命的H5N1型禽流感病毒的药物"达菲"的重要成分。法国马赛的茴香酒制造商里卡公司的主任阿尔贝·埃尔格里西说："治疗一个感染禽流感的患者需要10粒达菲胶囊，制造10粒达菲胶囊则需要13克八角茴香。"莽草酸每公斤的价格在200-250美元之间，质量特别好的，价格高达每克50美元。

名称

• 中文名: 莽草酸
• 英文名: Shikimic acid
• 中文别名: (3R,4S,5R)-(-)-3,4,5-三羟基-1-环己烯羧酸; (3R,4S,5R)-(-)-3,4,5-三羟基-1-环己烯-1-甲酸
• 英文别名: (3R,4S,5R)-3,4,5-Trihydroxycyclohex-1-enecarboxylic acid; MFCD00066278; 3,4,5-Trihydroxycyclohex-1-enecarboxylic acid; 3,4,5-Trihydroxy-1-cyclohexenecarboxylic acid; (3R,4S,5R)-(-)-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic Acid; EINECS 205-334-2; 1-Cyclohexene-1-carboxylic acid, 3,4,5-trihydroxy-; 3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acid; (3R,4S,5R)-(−)-3,4,5-Trihydroxy-1-cyclohexenecarboxylic acid; 3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid; Shikimic Acid

物化性质

• 密度: 1.7±0.1 g/cm3
• 沸点: 400.5±45.0 °C at 760 mmHg
• 熔点: 185-187 °C(lit.)
• 分子式: C₇H₁₀O₅
• 分子量: 174.151
• 闪点: 210.1±25.2 °C
• 精确质量: 174.052826
• PSA: 97.99000
• LogP: -0.92
• 外观性状: 白色粉末
• 蒸汽压: 0.0±2.1 mmHg at 25°C
• 折射率: 1.680
• 储存条件:

  应充氩气密封于阴凉干燥处保存。

• 稳定性:

  1. 有吸湿性。能升华

  2. 存在于烟叶中。

• 水溶解性: 18 g/100 mL (20 ºC)
• 分子结构:

  分子性质数据：

  1、 摩尔折射率：38.14

  2、 摩尔体积（cm³/mol）：100.9

  3、 等张比容（90.2K）：331.7

  4、 表面张力（3.0 dyne/cm）：116.6

  5、 极化率（0.5 10^-24cm³）：15.12

• 计算化学:

  1、 疏水参数计算参考值（XlogP）：-1.7

  2、 氢键供体数量：4

  3、 氢键受体数量：5

  4、 可旋转化学键数量：1

  5、 互变异构体数量：

  6、 拓扑分子极性表面积（TPSA）：98

  7、 重原子数量：12

  8、 表面电荷：0

  9、 复杂度：222

  10、同位素原子数量：0

  11、确定原子立构中心数量：3

  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：无色或白色针状结晶。

  2. 溶解性：在20ºC水中溶解度为18%，微溶于乙醇、乙醚，几乎不溶于氯仿、苯。

  3. 沸点（ºC）：400.5

  4. 熔点（ºC）：185~187

  5. 闪点（ºC）：210.1

  6. 相对密度(d²⁰₄₎ ：1.725

生物活性

• 描述: Shikimic acid 是在微生物和植物中发现的芳香族氨基酸生物合成途径的关键代谢中间体。
• 相关类别:
  天然产物 >> 酸和醛
  研究领域 >> 其他
• 靶点:

  Human Endogenous Metabolite

• 体外研究: 莽草酸是一种重要的代谢中间体,具有多种应用。莽草酸是一种工业上重要的化合物,可作为磷酸奥司他韦等化学物质合成的前体[1]。
• 参考文献:

  [1]. Lee MY, et al. Improvement of shikimic acid production in Escherichia coli with growth phase-dependent regulation in the biosynthetic pathway from glycerol. World J Microbiol Biotechnol. 2017 Feb;33(2):25.

MSDS

Name: Shikimic Acid 98% Material Safety Data Sheet Synonym: 3,4,5-Trihydroxy-1-Cyclohexene-1-Carboxylic Acid CAS: 138-59-0 Section 1 - Chemical Product MSDS Name:Shikimic Acid 98% Material Safety Data Sheet Synonym:3,4,5-Trihydroxy-1-Cyclohexene-1-Carboxylic Acid Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS CAS# Chemical Name content EINECS# 138-59-0 Shikimic Acid 98% 205-334-2 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: Effects may be delayed. Substance may have carcinogenic potential. 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. Runoff from fire control or dilution water may cause pollution. Extinguishing Media: In case of fire, use water, dry chemical, chemical foam, or alcohol-resistant foam. 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: Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. 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. Keep container tightly closed. 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# 138-59-0: 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 minimize contact with skin. 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: white Odor: None reported. pH: Not available. Vapor Pressure: Not available. Viscosity: Not available. Boiling Point: Not available. Freezing/Melting Point: 185.00 - 187.00 deg C Autoignition Temperature: Not applicable. Flash Point: Not applicable. Explosion Limits, lower: Not available. Explosion Limits, upper: Not available. Decomposition Temperature: Solubility in water: 18g/100ml (20 c) Specific Gravity/Density: Molecular Formula: C7H10O5 Molecular Weight: 174.15 Section 10 - STABILITY AND REACTIVITY Chemical Stability: Stable under normal temperatures and pressures. Conditions to Avoid: Incompatible materials, dust generation, 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# 138-59-0: GW4600000 LD50/LC50: Not available. Carcinogenicity: Shikimic Acid - 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. 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# 138-59-0: No information available. Canada None of the chemicals in this product are listed on the DSL/NDSL list. CAS# 138-59-0 is not listed on Canada's Ingredient Disclosure List. US FEDERAL TSCA CAS# 138-59-0 is not listed on the TSCA inventory. It is for research and development use only. SECTION 16 - ADDITIONAL INFORMATION N/A

毒性和生态

毒理学数据: 急性毒性数据： 小鼠腹腔LD：1mg/kg 致肿瘤数据： 小鼠经口TDLo：4000mg/kg 小鼠腹腔TDLo：400mg/kg 致突变数据： 小鼠腹腔显性致死试验：1000mg/kg 小鼠经口显性致死试验：3200mg/kg 仓鼠肾的形态转变试验：250mg/L CHEMICAL IDENTIFICATION RTECS NUMBER : GW4600000 CHEMICAL NAME : 1-Cyclohexene-1-carboxylic acid, 3,4,5-trihydroxy- CAS REGISTRY NUMBER : 138-59-0 LAST UPDATED : 199510 DATA ITEMS CITED : 11 MOLECULAR FORMULA : C7-H10-O5 MOLECULAR WEIGHT : 174.17 WISWESSER LINE NOTATION : L6UTJ AVQ CQ DQ EQ HEALTH HAZARD DATA ACUTE TOXICITY DATA TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 1 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 - mouse DOSE/DURATION : 4000 mg/kg TOXIC EFFECTS : Tumorigenic - equivocal tumorigenic agent by RTECS criteria Gastrointestinal - tumors TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 40 mg/kg TOXIC EFFECTS : Tumorigenic - equivocal tumorigenic agent by RTECS criteria Gastrointestinal - tumors TYPE OF TEST : Dominant lethal test TYPE OF TEST : Dominant lethal test MUTATION DATA TYPE OF TEST : Morphological transformation TEST SYSTEM : Rodent - hamster Kidney DOSE/DURATION : 250 mg/L REFERENCE : TOLED5 Toxicology Letters. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1977- Volume(issue)/page/year: 19,43,1983 *** REVIEWS *** IARC Cancer Review:Animal Inadequate Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 40,47,1986 IARC Cancer Review:Human No Adequate Data IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 40,47,1986 IARC Cancer Review:Group 3 IMSUDL IARC Monographs, Supplement. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) No.1- 1979- Volume(issue)/page/year: 7,56,1987 TOXICOLOGY REVIEW CTRRDO Cancer Treatment Reports. (Washington, DC) V.60-71, 1976-87. For publisher information, see JNCIEQ. Volume(issue)/page/year: 60,1171,1976

安全

• 个人防护装备: Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
• 危害码 (欧洲): Xi: Irritant;
• 风险声明 (欧洲): R36/37/38
• 安全声明 (欧洲): S22-S24/25
• 危险品运输编码: NONH for all modes of transport
• WGK德国: 3
• RTECS号: GW4600000
• 海关编码: 29181980

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制备

莽草酸是从中药八角茴香中提取的一种单体化合物。

海关

海关编码	2918199090
中文概述	HS: 2918199090. 其他含醇基但不含其他含氧基羧酸（包括其酸酐、酰卤化物、过氧化物和过氧酸及该税号的衍生物）. 增值税率:17.0%. 退税率:9.0%. 监管条件:无. 最惠国关税:6.5%. 普通关税:30.0%
申报要素	品名, 成分含量, 用途
Summary	2918199090 other carboxylic acids with alcohol function but without other oxygen function, their anhydrides, halides, peroxides, peroxyacids and their derivatives。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:6.5%。General tariff:30.0%