月桂酸甲酯 | 111-82-0

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 月桂酸甲酯
• 中文别名: 十二酸甲酯；十二酸
• 英文名称: methyl laurate
• 英文别名: methyl n-dodecanoate；dodecanoic acid methyl ester；methyl dodecanoate；lauric acid methyl ester
• CAS: 111-82-0
• 化学式: C₁₃H₂₆O₂
• 分子量: 214.348
• InChiKey: UQDUPQYQJKYHQI-UHFFFAOYSA-N

物化性质

• 熔点：
  4-5 °C (lit.)
• 沸点：
  262 °C/766 mmHg (lit.)
• 密度：
  0.87 g/mL at 25 °C (lit.)
• 闪点：
  >230 °F
• 溶解度：
  水：25℃时不溶0.00759g/L（实际）
• 介电常数：
  3.6000000000000001
• LogP：
  5.41 at 36℃
• 物理描述：
  Liquid
• 颜色/状态：
  COLORLESS LIQUID
• 气味：
  FATTY, FLORAL ODOR REMINISCENT OF WINE
• 味道：
  FATTY TASTE
• 蒸汽压力：
  4.11X10-3 mm Hg @ 25 °C
• 分解：
  When heated to decomposition it emits acrid smoke and irritating vapors.
• 折光率：
  Index of refraction: 1.4301 @ 25 °C/D
• 保留指数：
  1509;1507;1514;1506;1505;1509;1506;1506;1506;1509;1507;1503;1513;1514.9;1510;1518;1508;1513;1513;1501;1508;1507;1510;1508;1508;1507;1517;1505;1506;1509;1510;1507;1504.7;1507;1510;1507.4;1505.6;265.9;265.8;265.9
• 稳定性/保质期：
  • 禁止与强氧化剂接触。
  • 存在于烤烟烟叶、白肋烟烟叶、香料烟烟叶中。

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  15
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

ADMET

毒理性

• 致癌物分类

对人类不具有致癌性（未被国际癌症研究机构IARC列名）。

No indication of carcinogenicity to humans (not listed by IARC).

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 相互作用

线性饱和脂肪酸甲酯与小鼠淋巴细胞的植物凝集素共同作用，其共刺激作用的程度强烈依赖于酰基链的长度，以十四烷甲酯的作用最强。对于含有10、12或16个酰基碳原子的类似物，效果较小，而含有少于10个或超过16个酰基碳原子的类似物则无活性。/甲酯/

Linear saturated fatty acid methyl esters were comitogenic with lectins for mouse lymphocytes, the degree of comitogenicity being strongly dependent on the length of the acyl group, and maximal for methyl tetradecanoate. Lesser effects were found for analogs with 10, 12, or 16 acyl carbon atoms, whereas those with fewer than 10 or more than 16 were inactive. /Methyl esters/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 非人类毒性摘录

使用生长反应下降作为标准，研究了碳链长度为4至18的脂肪酸甲酯对必需脂肪酸缺乏的影响。在大鼠食用甲基月桂酸后观察到高死亡率。它加剧了必需脂肪酸的缺乏，因为补充导致了肝胆固醇酯的积累增加。

USING DEPRESSED GROWTH RESPONSE AS A CRITERION, THE EFFECTS OF METHYL ESTERS OF FATTY ACIDS OF CHAIN LENGTH 4 TO 18 CARBONS ON ESSENTIAL FATTY ACID DEFICIENCY WERE STUDIED. HIGH MORTALITY WAS OBSERVED IN RATS FED METHYL LAURATE. IT ACCENTUATED THE ESSENTIAL FATTY ACID DEFICIENCY BECAUSE SUPPLEMENTATION RESULTED IN AN INCR ACCUMULATION OF HEPATIC CHOLESTEROL ESTERS.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 非人类毒性摘录

静脉注射1.2毫克甲基月桂酸酯导致小鼠立即死亡。

INTRAVENOUS INJECTION OF 1.2 MG METHYL LAURATE PRODUCED IMMEDIATE DEATH IN MICE.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• TSCA：
  Yes
• 危险品标志：
  N
• 安全说明：
  S24/25
• 危险类别码：
  R50
• WGK Germany：
  1
• 海关编码：
  2915 90 30
• 危险品运输编号：
  UN 3082 9 / PGIII
• RTECS号：
  OF0670000
• 包装等级：
  III
• 危险类别：
  9
• 危险性防范说明：
  P501,P273,P260,P270,P264,P280,P391,P314,P337+P313,P305+P351+P338,P301+P312+P330
• 危险性描述：
  H302,H319,H372,H410
• 储存条件：
  以镀锌桶包装，存储于阴凉、干燥处，远离火种和热源。

SDS

Name:	Methyl laurate 96% Material Safety Data Sheet
Synonym:	Methyl dodecanoate; Lauric acid methyl este
CAS:	111-82-0

Section 1 - Chemical Product MSDS Name:Methyl laurate 96% Material Safety Data Sheet
Synonym:Methyl dodecanoate; Lauric acid methyl este

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
111-82-0	METHYL LAURATE	96%	203-911-3

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:
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.
Skin:
Get medical aid if irritation develops or persists. Flush skin with plenty of soap and water.
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. Get medical aid if cough or other symptoms appear.
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.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

---

Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation. 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:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 111-82-0: 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 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: Liquid
Color: clear, colorless
Odor: Oil,winey,fatty odor
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 262 deg C @ 766.00mm Hg
Freezing/Melting Point: 4.8 deg C
Autoignition Temperature: Not available.
Flash Point: > 112 deg C (> 233.60 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: insoluble
Specific Gravity/Density: .8700g/cm3
Molecular Formula: C13H26O2
Molecular Weight: 214.35

---

Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents - strong bases.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported.

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 111-82-0: OF0670000 LD50/LC50:
Not available.
Carcinogenicity:
METHYL LAURATE - 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# 111-82-0: 1
Canada
CAS# 111-82-0 is listed on Canada's DSL List.
CAS# 111-82-0 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 111-82-0 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

月桂酸甲酯是日用化妆香精和制皂业的重要原料，也是合成高效、安全、无毒和无污染的新型食品乳化剂——月桂酸蔗糖酯的关键成分。此外，它还可用于合成多种阴离子表面活性剂和非离子表面活性剂，并作为精细化工的重要中间体。

制备

月桂酸甲酯可通过将月桂酸与甲醇进行酯化反应制得。具体步骤为：将月桂酸、无水甲醇以及浓硫酸的混合物加热回流18小时后，倒入水中分离出酯层，并依次用清水、饱和碳酸氢钠溶液和水洗涤。干燥后再进行蒸馏，收集261-263℃馏分，即得十二酸甲酯，收率约为81%。

毒性

月桂酸甲酯被GRAS（一般认为安全）认证（FEMA编号），适用于食品工业中的使用。

使用限量

根据FEMA规定：在软饮料和冷饮中，其用量为0.50～5.0毫克/千克；糖果中为0.02～0.50毫克/千克；焙烤制品为1.0毫克/千克。而根据FDA（§172.515，2000）规定，则适度为其使用范围。

化学性质

月桂酸甲酯是一种无色、具有类似酒香及花香的油状液体，能与乙醇、乙醚、丙酮和苯等溶剂混溶。

用途

• 用作有机合成中间体。
• 由微囊化真菌孢子催化反应产生的一种风味酮，也用于生产生物柴油。
• 气相色谱固定液、食品添加剂及有机合成试剂。
• 作为气相色谱分析标准品，并应用于有机合成中。

生产方法

月桂酸甲酯可通过将月桂酸与甲醇进行酯化反应制得。具体步骤为：将月桂酸、无水甲醇和浓硫酸的混合物加热回流18小时后，倒入水中分离出酯层，并依次用水、饱和碳酸氢钠溶液和水洗涤。干燥后再进行蒸馏，收集261-263℃馏分，即得十二酸甲酯。

反应信息

• 作为反应物：
  描述：

  月桂酸甲酯 在 niobium(V) oxide 、 氨 作用下， 生成 十二腈
  参考文献：
  名称：

  脂肪酸甲酯转化为腈类：增强催化剂的酸碱性质

  摘要：

  近年来，脂肪腈已成为生物燃料框架或生物质中石油部分（如聚合物等精细化学品）的增值的关注对象。尽管酯已开发并公开了几种催化剂，但通过酯与氨的直接反应生产长链脂肪腈的方法尚未在学术上得到广泛研究。酸碱特性被隐含地认为是导致该反应的催化剂，但没有研究与酸性或碱性位点的任何性质或数量直接相关。本研究旨在了解哪个部位负责该反应，从而如何设计更好的催化剂。在300°C时，强酸与酯的转化率和腈的收率相关，表明各种催化剂之间反应的共同性质。强度上限

  DOI：

  10.1016/j.jcat.2013.05.032
• 作为产物：
  描述：

  月桂酰胺 在 盐酸 、 disodium hydrogenphosphate 作用下， 以 水 、 乙腈 为溶剂， 反应 4.0h， 生成 月桂酸甲酯
  参考文献：
  名称：

  The Conversion of Amides to Esters with Meerwein'S Reagent. Application to the Synthesis of a Carfentanil Precursor.

  摘要：

  An efficient two step transformation of 1 degrees and 2 degrees amides to methyl and ethyl esters has been developed using trimethyl- and triethyloxonium tetrafluoroborates, and dilute acid. This methodology was applied to 1-benzyl-4-phenylamino-4-piperidinecarboxamide precursor in the synthesis of carfentanil, to produce the methyl ester in 60% yield and the ethyl ester in 80% yield.

  DOI：

  10.1080/00397919708004212
• 作为试剂：
  描述：

  6-氯甲基-1,2,3,4-四氢萘 、 Sodium laurate 在 月桂酸甲酯 作用下， 生成 lauric acid-(5,6,7,8-tetrahydro-[2]naphthylmethyl ester)
  参考文献：
  名称：

  Yamashita; Ishii, Kogyo Kagaku zasshi / Journal of the Society of Chemical Industry, 1953, vol. 56, p. 547

  摘要：

  DOI：

文献信息

• [EN] SUBSTITUTED QUINAZOLINES AS FUNGICIDES<br/>[FR] QUINAZOLINES SUBSTITUÉES, UTILISÉES EN TANT QUE FONGICIDES
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：WO2010136475A1

  公开（公告）日：2010-12-02

  The present invention relates to a compound of formula (I) wherein wherein the substituents have the definitions as defined in claim 1or a salt or a N-oxide thereof, their use and methods for the control and/or prevention of microbial infection, particularly fungal infection, in plants and to processes for the preparation of these compounds.

  本发明涉及一种具有如下式（I）的化合物，其中取代基具有权利要求1中定义的定义，或其盐或N-氧化物，它们的用途以及用于控制和/或预防植物中微生物感染，特别是真菌感染的方法，以及制备这些化合物的方法。
• [EN] MICROBIOCIDAL OXADIAZOLE DERIVATIVES<br/>[FR] DÉRIVÉS D'OXADIAZOLE MICROBIOCIDES
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：WO2017157962A1

  公开（公告）日：2017-09-21

  Compounds of the formula (I) wherein the substituents are as defined in claim 1, useful as a pesticides, especially fungicides.

  式(I)的化合物，其中取代基如权利要求1所定义，作为杀虫剂特别是杀菌剂有用。
• [EN] INSECTICIDAL TRIAZINONE DERIVATIVES<br/>[FR] DÉRIVÉS DE TRIAZINONE INSECTICIDES
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：WO2013079350A1

  公开（公告）日：2013-06-06

  Compounds of the formula (I) or (I'), wherein the substituents are as defined in claim 1, are useful as pesticides.

  式(I)或(I')的化合物，其中取代基如权利要求1所定义的那样，可用作杀虫剂。
• [EN] PHENOTHIAZINE DERIVATIVES AND USES THEREOF<br/>[FR] DÉRIVÉS DE PHÉNOTHIAZINE ET LEURS UTILISATIONS
  申请人：CAMP4 THERAPEUTICS CORP

  公开号：WO2019195789A1

  公开（公告）日：2019-10-10

  The present invention provides phenothiazine compounds, processes for their preparation, pharmaceutical compositions comprising the compounds, and the use of the compounds or the compositions in the treatment of various diseases or conditions, for example ribosomal disorders and ribosomopathies, e.g. Diamond Blackfan anemia (DBA).

  本发明提供了吩噻嗪化合物，其制备方法，包含该化合物的药物组合物，以及在治疗各种疾病或症状中使用该化合物或组合物，例如核糖体紊乱和核糖体病，例如钻石-布莱克范贫血（DBA）。
• Cleavage of Carboxylic Esters by Aluminum and Iodine
  作者：Dayong Sang、Huaxin Yue、Yang Fu、Juan Tian

  DOI：10.1021/acs.joc.1c00034

  日期：2021.3.5

  A one-pot procedure for deprotecting carboxylic esters under nonhydrolytic conditions is described. Typical alkyl carboxylates are readily deblocked to the carboxylic acids by the action of aluminum powder and iodine in anhydrous acetonitrile. Cleavage of lactones affords the corresponding ω-iodoalkylcarboxylic acids. Aryl acetylates undergo deacetylation with the participation of the neighboring group

  描述了一种在非水解条件下使羧酸酯脱保护的一锅法方法。在无水乙腈中，铝粉和碘的作用下，典型的羧酸烷基酯很容易解封为羧酸。切割内酯得到相应的ω-碘代烷基羧酸。乙酸芳基酯在相邻基团的参与下进行脱乙酰化。该方法能够在芳基酯存在下选择性裂解烷基羧酸酯。

表征谱图