每周分子 | Molecule of the Week

Original ACS 美国化学会 ACS美国化学会 2022-07-01

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每周分子：甲基苯基缩水甘油酸乙酯

Molecule of the Week:

Ethyl methylphenylglycidate

甲基苯基缩水甘油酸乙酯是一种芳香族有机化合物，具有酯和环氧化物两个官能团。它也被称为“草莓醛” ，然而它并不存在于草莓中，也不包含醛基。该化合物含有两个不对称中心；其商品是所有四种立体异构体的外消旋体。

第一个已知的甲基苯基缩水甘油酯的合成方法，是由德国柏林大学的Rainer Ludwig Claisen于1905年在一篇题为“关于利用氨基钠的一些合成”的长篇文章中报道的。Claisen是一位因开发了以其名字命名的缩合和重排反应而闻名的先驱化学家。

我们现在使用的甲基苯基缩水甘油酸乙酯的合成方法是由日本京都大学的Keiiti Sisido、Osamu Nakanisi和Hitosi Nozaki于1961年报道的。他们利用酮(该例中是苯乙酮)与α-卤代酯(氯乙酸乙酯) 发生Darzens缩合反应形成环氧环。

甲基苯基缩水甘油酸乙酯的风味和香气会让人联想到草莓，因此而得名“草莓醛”。它不仅被用作人造草莓调味剂，还被用于香精工业，尤其是用于香水、个人护理用品、肥皂和洗涤剂中。

甲基苯基缩水甘油酸乙酯信息速览

CAS 登记号	77-83-8
CAS SciFinder命名	2-Oxiranecarboxylic acid, 3-methyl-3-phenyl-, ethyl ester
分子式	C₁₂H₁₄O₃
摩尔质量	206.24 g/mol
外观	无色至浅黄色液体
沸点	272–275 °C
水溶性	<1 g/L

甲基苯基缩水甘油酸乙酯危害信息

GHS*分类：皮肤腐蚀/刺激，分类2
H315-引起皮肤刺激
GHS分类：皮肤致敏，分类1B
H317-可能引起皮肤过敏
GHS分类：严重眼损伤/眼刺激，分类2A
H319-会引起严重的眼刺激
GHS分类：短期(急性)水生危害，分类2
H401-对水生生物有毒
GHS分类：长期(慢性)水生危害，分类2
H411-对水生生物有长期毒害影响

【关于每周分子】

自2001年以来，“每周分子”已成为广受欢迎的栏目。多数分子由读者推荐。每个结构都经由科学家审查，并以3-D和平面图像的形式显示，同时附有该分子简介。可以通过美国化学文摘社 (CAS) 提供的CAS SciFinderⁿ中的CAS REGISTRY获取“每周分子”的更多信息。CAS REGISTRY中的每条物质信息都展示了物质的CAS登记号、索引名、通用名、商品名、书目信息等其他更多信息。发送邮件至motw@acs.org推荐您感兴趣的分子吧。

Ethyl methylphenylglycidate is an aromatic organic compound with two functional groups, an ester and an epoxide. It is also known as “strawberry aldehyde” even though it is not found in strawberries and does not contain an aldehyde group. The compound contains two asymmetric centers; the article of commerce is a racemate of all four stereoisomers.

The first known synthesis of ethyl methylphenylglycidate was reported in 1905 by Rainer Ludwig Claisen at the University of Berlin in a lengthy article titled “About some syntheses using sodium amide”. Claisen was a pioneering chemist primarily known for developing condensation and rearrangement reactions that bear his name.

Today, ethyl methylphenylglycidate is synthesized by a method reported in 1961 by Keiiti Sisido, Osamu Nakanisi, and Hitosi Nozaki at Kyoto University (Japan). They used the Darzens condensation, in which a ketone (acetophenone in this case) is treated with an α-haloester (ethyl chloroacetate) to form the epoxide ring.

Ethyl methylphenylglycidate’s flavor and aroma are reminiscent of strawberries, hence its nickname. It is used not only as an artificial strawberry-flavoring agent, but also in the fragrance industry, particularly in perfumes, personal care products, soaps, and detergents.

Ethyl methylphenylglycidatefast facts

CAS Reg. No.	77-83-8
SciFinder nomenclature	2-Oxiranecarboxylic acid, 3-methyl-3-phenyl-, ethyl ester
Empirical formula	C₁₂H₁₄O₃
Molar mass	206.24 g/mol
Appearance	Colorless to pale yellow liquid
Boiling point	272–275 °C
Water solubility	<1 g/L

Ethyl methylphenylglycidate hazard information

Skin corrosion/irritation, category 2
H315-Causes skin irritation
Skin sensitization, category 1B
H317-May cause an allergic skin reaction
Serious eye damage/irritation, category 2A
H319-Causes serious eye irritation
Short-term (acute) aquatic hazard category 2
H401-Toxic to aquatic life
Long-term (chronic) aquatic hazard, category 2
H411-Toxic to aquatic life with long-lasting effects

About Molecule of the Week

MOTW has been a popular feature on ACS website since 2001. Many molecules are suggested by our website visitors. Every structure is reviewed by a scientist and displayed in 3-D and flat images with a brief description. Each week’s molecule also links to a sample record from the CAS REGISTRY, which is searched using CAS SciFinderⁿ. Each record displays the registry number, index name and synonyms, bibliographic information, and more. Send us a molecule suggestion at motw@acs.org.

往期回顾：

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