1490-04-6

• 常用中文名：薄荷脑
• 常用英文名：Menthol
• CAS号：1490-04-6
• 分子式：C₁₀H₂₀O
• 分子量：156.265
• 相关类别： 原料药 人工合成抗感染类药 消毒防腐药
• 发布时间：2018-02-04 08:00:00
• 更新时间：2024-01-03 13:08:16
• Menthol 是个天然的止痛剂。Menthol 通过抑制神经元细胞膜的 Ca++ 电流,刺激冷感受器,从而产生凉的感觉。
• 1、薄荷脑和消旋薄荷脑均用作牙膏、香水、饮料和糖果等的赋香剂。
  在医药上用作刺激药，作用于皮肤或粘膜，有清凉止痒作用；内服可作为驱风药，用于头痛及鼻、咽、喉炎症等。其酯用于香料和药物。 2、广泛用于日用香精、食用香精、烟用香精。
  3、有杀菌和防腐作用。
  4、用作疗效性化妆品的特殊添加剂。用于花露水等。

名称

• 中文名: 薄荷脑
• 英文名: 2-Isopropyl-5-methylcyclohexanol
• 英文别名: (1R,2S,5R)-(−)-Menthol; levo-menthol; EINECS 216-074-4; (-)-(1R,3R,4S)-Menthol; (−)-menthol; (-)-trans-p-Methan-cis-3-ol; (1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol; Levomenthol; L-Menthol; (-)-(1R,2S,5R)-Menthol; (-)-MENTHYL ALCOHOL; (1R)-(-)-Menthol; (R)-(-)-Menthol; DL-Menthol; (1R,2S,5R)-5-methyl-2-propan-2-yl-cyclohexan-1-ol; [1R-(1a,2b,5a)]-5-Methyl-2-(1-methylethyl)cyclohexanol; (-)-p-Menthan-3-ol; Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1R,2S,5R)-; (-)-Menthol; UNII:YS08XHA860; Menthol, l-; Menthol; (1R,2S,5R)-(-)-Menthol; MFCD00001484

物化性质

• 密度: 0.9±0.1 g/cm3
• 沸点: 215.4±8.0 °C at 760 mmHg
• 熔点: 34-36 ℃(lit.)
• 分子式: C₁₀H₂₀O
• 分子量: 156.265
• 闪点: 93.3±0.0 °C
• 精确质量: 156.151413
• PSA: 20.23000
• LogP: 3.20
• 蒸汽压: 0.0±0.9 mmHg at 25°C
• 折射率: 1.457
• 稳定性: Stable. Combustible. Incompatible with strong oxidizing agents.

生物活性

• 描述: Menthol 是个天然的止痛剂。Menthol 通过抑制神经元细胞膜的 Ca++ 电流,刺激冷感受器,从而产生凉的感觉。
• 相关类别:
  信号通路 >> 其他 >> 其他
  研究领域 >> 神经疾病
• 参考文献:

  [1]. NicolettaGaleotti, et al. Menthol: a natural analgesic compound. Neuroscience Letters. 2002 Apr.

MSDS

Name: DL-Menthol 99% Material Safety Data Sheet Synonym: p-Menthan-3-o CAS: 1490-04-6 Section 1 - Chemical Product MSDS Name:DL-Menthol 99% Material Safety Data Sheet Synonym:p-Menthan-3-o Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS CAS# Chemical Name content EINECS# 1490-04-6 DL-Menthol 99 216-074-4 Hazard Symbols: XI Risk Phrases: 36/37/38 Section 3 - HAZARDS IDENTIFICATION EMERGENCY OVERVIEW Irritating to eyes, respiratory system and skin.The toxicological properties of this material have not been fully investigated. Potential Health Effects Eye: May cause eye irritation. The toxicological properties of this material have not been fully investigated. Skin: May cause skin irritation. The toxicological properties of this material have not been fully investigated. Ingestion: May cause gastrointestinal irritation with nausea, vomiting and diarrhea. 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: Not available. 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. 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. 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 fog, dry chemical, carbon dioxide, or regular 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 or absorb material, then place into a suitable clean, dry, closed container for disposal. Section 7 - HANDLING and STORAGE Handling: Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use only in a well-ventilated area. Avoid contact with eyes, skin, and clothing. Avoid ingestion and inhalation. Storage: Keep container closed when not in use. Store in a cool, dry, well-ventilated area away from incompatible substances. Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION Engineering Controls: Use adequate ventilation to keep airborne concentrations low. Exposure Limits CAS# 1490-04-6: 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: white Odor: None reported. pH: Not available. Vapor Pressure: Not available. Viscosity: Not available. Boiling Point: Not available. Freezing/Melting Point: 28.00 - 30.00 deg C Autoignition Temperature: Not available. Flash Point: 93 deg C ( 199.40 deg F) Explosion Limits, lower: Not available. Explosion Limits, upper: Not available. Decomposition Temperature: Solubility in water: soluble in alcohol, chloroform and ether Specific Gravity/Density: .8900g/cm3 Molecular Formula: C10H20O Molecular Weight: 156.27 Section 10 - STABILITY AND REACTIVITY Chemical Stability: Stable under normal temperatures and pressures. Conditions to Avoid: Incompatible materials. Incompatibilities with Other Materials: Strong oxidizing agents. Hazardous Decomposition Products: Carbon monoxide, carbon dioxide. Hazardous Polymerization: Has not been reported. Section 11 - TOXICOLOGICAL INFORMATION RTECS#: CAS# 1490-04-6: GW0554000 LD50/LC50: Not available. Carcinogenicity: DL-Menthol - 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. WGK (Water Danger/Protection) CAS# 1490-04-6: 1 Canada CAS# 1490-04-6 is listed on Canada's DSL List. CAS# 1490-04-6 is not listed on Canada's Ingredient Disclosure List. US FEDERAL TSCA CAS# 1490-04-6 is listed on the TSCA inventory. SECTION 16 - ADDITIONAL INFORMATION N/A

毒性和生态

CHEMICAL IDENTIFICATION RTECS NUMBER : GW0554000 CHEMICAL NAME : Cyclohexanol, 5-methyl-2-(1-methylethyl)- CAS REGISTRY NUMBER : 1490-04-6 LAST UPDATED : 199701 DATA ITEMS CITED : 2 MOLECULAR FORMULA : C10-H20-O

安全

• 符号: GHS05, GHS07
• 信号词: Danger
• 危害声明: H315-H318-H335
• 警示性声明: P280-P305 + P351 + P338 + P310
• 危害码 (欧洲): Xn,Xi
• 风险声明 (欧洲): 37/38-41-48/20/22-40-22
• 安全声明 (欧洲): 36/37/39-36-26
• 危险品运输编码: UN 1888 6.1/PG 3
• WGK德国: 2
• RTECS号: OT0525000

制备

  工业上从薄荷中提取薄荷油和薄荷脑采用水蒸汽蒸馏法和有机溶剂提取法，前者提取效率低，后者存在有机溶剂残留的毒性。采用超临界二氧化碳从薄荷中提取的薄荷脑（薄荷醇），则可消除上述两种方法所产生的弊端。其得率比水蒸汽蒸馏法约高5倍，比有机溶剂法约高3倍，产品保持纯天然特征，质量好，纯度高，无溶剂残留毒性，易达到出口要求，具有更好的竞争力，可以占领市场。薄荷脑可由天然薄荷原油提纯也可用合成法制取。唇形科植物薄荷的地上部分（茎；枝；叶和花序）经水蒸气蒸馏所得的精油称薄荷原油，得油率为0.5-0.6。合成薄合脑的方法有多种。 
从香茅醛中制造 
利用香茅醛易环化成异胡薄荷醇的性质，将右旋香茅醛用酸催化剂（如硅胶）环化成左旋异胡薄荷脑，分出左旋异胡薄荷脑，氢化生成左旋薄荷。其立体异构体经热裂解可部分地遭到转变成右旋香茅醛，再循环使用。
从百里酚中制造 
在间甲酚铝存在情况下，对间甲酚进行烷基化反应生成百里酚。经催化加氢得所有四对薄荷脑立体异构体（即消旋薄荷脑；消旋新薄荷脑；消旋异薄荷醇和消旋新异薄荷脑）。将其进行蒸馏，取消旋薄荷醇馏分，制造酯后反复重结晶，进行异构体的分离和光学拆分。分离出来的左旋薄荷醇酯，经皂化后得薄荷脑。
消旋薄荷脑可用蒸馏法与其他三对异构体分开，剩下的异构体混合物在百里酚氢化条件下可平衡成消旋薄荷脑，消旋新薄荷脑，消旋异薄荷脑，比例为 6：3：1，新异薄荷脑含量很少，可不计。从以上混合物可再分出消旋薄荷脑。消旋薄荷醇经苯甲酸酯饱和溶液或其超冷混合物以左旋酯接种结晶，分开后皂化，得纯左旋薄荷脑；不要的右旋薄荷脑及其他异构体，可再按氢化条件平衡转变为消旋薄荷脑。 
从薄荷油制造
将薄荷油冷冻后析出结晶，离心所得结晶用低沸溶剂重结晶得纯左旋薄荷醇。除去结晶后的母液仍含薄荷醇40%～50%，还含较大量的薄荷酮，经氢化转变为左旋薄荷醇和右旋新薄荷醇的混合物。将酯的部分皂化，经结晶、蒸馏或制成其硼酸酯后分去薄荷油中的其他部分，可得到更多的左旋薄荷醇。
鉴别
（1） 取本品1g，加硫酸20ml使溶解，即显橙红色，24小时后析出无薄荷脑香气的无色油层（与麝香草酚的区别）。
（2） 取本品50mg，加冰醋酸1ml 使溶解，加硫酸6 滴与硝酸1 滴的冷混合液，仅显淡黄色（与麝香草酚的区别）。 （药物作用）薄荷脑能选择性地刺激人体皮肤或黏膜的冷觉感受器，产生冷觉反射和冷感，引起皮肤黏膜血管收缩（实际上皮肤保持正常），对深部组织的血管也可引起收缩而产生治疗作用。外用可以消炎，止痛，止痒，促进血液循环，减轻浮肿等；内服以复方制剂中可缓解局部炎症（咽喉炎）及治疗感冒，并有健胃，驱风作用。（适应症状）外用用于局部止痛，止痒，头痛，眩晕，蚊虫叮咬；滴鼻用于伤风鼻塞，吸入或喷雾用于咽喉炎；口服可以健胃。