每周分子 | Molecule of the Week

Original ACS美国化学会 ACS美国化学会 2022-07-01

每周分子: ‍缩水甘油

Molecule of the Week: Glycidol

缩水甘油是一种环氧化物和醇，因此是高活性化合物。它可与水混溶，但也会与水发生反应。在大气压下蒸馏时会分解。

1909年，华沙理工大学的化学家Nikolai Prilezhaev用过氧苯甲酸环氧化烯丙醇制备了缩水甘油。该反应在当时是一个突破，并被称为Prilezhaev氧化。现在，缩水甘油的生产方法仍然大同小异；但在2018年，一些公司在英国蒂赛德建立了一个试验工厂，通过“绿色”工艺生产缩水甘油。

缩水甘油具有手性中心，但常生产和应用的是其外消旋混合物。它可用作化学中间体、也可用于生产洗涤剂、保健品、工业油漆和涂料。

如危害信息表所示，缩水甘油具有异常多的健康风险。当美国食品药品监督管理局确认19种物质是尼古丁传输系统（“电子烟”和“电子液体”）的潜在有害成分时，这些因素最近得到了确认。缩水甘油，以及之前的“每周分子”二乙酰和乙二醇，都是FDA清单中的重要物质。FDA要求生产商和进口商在运输这些物质时，要报告其产品中每种化合物的浓度。

缩水甘油信息速览

CAS登记号	556-52-5
分子式	C₃H₆O₂
摩尔质量	74.08g/mol
外观	无色粘性液体
熔点	167 ºC (dec.)
水溶性	混溶

缩水甘油危害信息

GHS 分类*: 易燃液体，分类4
H227—可燃液体
GHS 分类: 自反应物质和混合物; 和有机过氧化物，C型
H242—加热可能引起火灾
GHS 分类: 急性毒性，口服，分类4
H302—吞咽有害
GHS 分类: 急性毒性，皮肤，分类4
H312—与皮肤接触有害
GHS 分类: 皮肤腐蚀/刺激，分类2
H315—引起皮肤刺激
GHS 分类: 严重眼损伤/眼刺激，分类1
H318—造成严重眼损伤
GHS 分类: 急性毒性，吸入，分类3
H331—吸入会中毒
GHS 分类: 特定目标器官毒性，单次接触，呼吸道刺激，分类3
H335—可能引起呼吸道刺激
GHS 分类: 生殖细胞致突变性，分类2
H341—怀疑导致遗传缺陷
GHS 分类: 致癌性，分类1B
H350—可能导致癌症
HS 分类: 生殖毒性，分类1B
H360—可能会损害生育能力或胎儿

【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SciFinder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。

Glycidol is an epoxide and an alcohol, and as such is a highly reactive compound. It is miscible with water but also reacts with it. It decomposes when distilled at atmospheric pressure.

In 1909, chemist Nikolai Prilezhaev at the Warsaw University of Technology prepared glycidol by epoxidizing allyl alcohol with peroxybenzoic acid. This reaction was a breakthrough at the time and became known as the Prilezhaev oxidation. Glycidol is still manufactured in much the same way; but in 2018, a group of companies built a pilot plant in Teesside, UK, to make it via a “green” process.

Glycidol has a chiral center, but it is generally produced and used as the racemic mixture. It is used as a chemical intermediate and in the production of detergents, healthcare products, and industrial paints and coatings.

As shown in the hazard information table, glycidol presents an unusually large number of health risks. These factors were recently acknowledged when the US Food and Drug administration identified 19 substances as potentially harmful constituents of nicotine delivery systems (“e-cigarettes” and “e-liquids”). Glycidol, along with former Molecules of the Week diacetyl and ethylene glycol, is prominent in the FDA list. The agency now requires manufacturers and importers of the delivery systems to report the concentrations of each compound in its products.

Glycidol fast facts

CAS Reg. No.	556-52-5
Empirical formula	C₃H₆O₂
Molar mass	74.08 g/mol
Appearance	Colorless viscous liquid
Melting point	167 ºC (dec.)
Water solubility	Miscible

Glycidol hazard information

GHS classification*: flammable liquids, category 4
H227—Combustible liquid
GHS classification: self-reactive substances and mixtures; and organic peroxides, type C
H242—Heating may cause a fire
GHS classification: acute toxicity, oral, category 4
H302—Harmful if swallowed
GHS classification: acute toxicity, dermal, category 4
H312—Harmful in contact with skin
GHS classification: skin corrosion/irritation, category 2
H315—Causes skin irritation
GHS classification: serious eye damage/eye irritation, category 1
H318—Causes serious eye damage
GHS classification: acute toxicity, inhalation, category 3
H331—Toxic if inhaled
GHS classification: specific target organ toxicity, single exposure, respiratory tract irritation, category 3
H335—May cause respiratory irritation
GHS classification: germ cell mutagenicity, category 2
H341—Suspected of causing genetic defects
GHS classification: carcinogenicity, category 1B
H350—May cause cancer
HS classification: reproductive toxicity, category 1B
H360—May damage fertility or the unborn child

*Globally Harmonized System of Classification and Labeling of Chemicals. Explanation of pictograms.

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 SciFinder. Each record displays the registry number, index name and synonyms, bibliographic information, and more. Send us a molecule suggestion at motw@acs.org.

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