每周分子 | Molecule of the Week

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

收录于合集 #每周分子 110个

每周分子：氯化十六烷基吡啶

Molecule of the Week:

Cetylpyridinium chloride

氯化十六烷基吡啶(CPC)是一种季铵盐防腐剂，用于许多非处方个人护理产品中：漱口水、牙膏、含片、鼻腔喷雾剂等。它也被用于局部抗感染产品中和药用防腐剂。

CPC更正式的名称是1-hexadecylpyridinium chloride，它首次出现在20世纪30年代的化学文献中。1944年，路易斯安那州(新奥尔良)泽维尔大学的药剂师C. Lee Huyck写了一篇关于CPC消毒特性的早期报道。

从危害信息表可以看出，CPC本身具有一定的危害性；但直到最近，人们还认为它在消费品中的浓度太低，不必担心。2020年，加州大学旧金山分校的Brian K. Shoichet、诺华生物医学研究所(Cambridge, MA)的Laszlo Urban及其他机构的研究人员发表的一项研究表明，一些被认为是惰性的药物添加剂(如CPC)具有潜在的生物活性。但结果并不一定意味着这些物质有毒。

然而，一些科学家对“quats”(工业上被称为季铵盐化合物)持怀疑态度。2000年代后期，弗吉尼亚理工大学的毒理学家Terry Hrubec和爱德华维亚骨科医学院(均位于弗吉尼亚州的布莱克斯堡)在一项实验室研究中注意到，两种被认为安全的quat消毒剂导致了一些对照小鼠胚胎的缺陷。从那以后，她和其他研究人员发现了更多由quat导致动物缺陷的例子。

这些研究中没有任何一项涉及CPC；暴露于含quat的产品对人体健康没有影响。但在2020年三月，已经积累了足够的证据表明，quat的累积造成了动物缺陷，美国加州公共卫生部门将这些物质添加到其生物监测项目中。

氯化十六烷基吡啶信息速览

CAS 登记号	123-03-5
SciFinder命名	Pyridinium, 1-hexadecyl-, chloride (1:1)
分子式	C₂₁H₃₈ClN
摩尔质量	339.99 g/mol
外观	白色晶体或者粉末
熔点	27 ºC
水溶性	68 g/L

氯化十六烷基吡啶危害信息

GHS*分类：急性毒性，口服，分类4
H302-吞食有害
GHS分类：皮肤腐蚀/刺激，分类2
H315-引起皮肤刺激
GHS分类：严重的眼睛损伤/眼睛刺激，分类1
H315-导致严重的眼睛损伤
GHS分类：急性毒性，吸入，分类3
H330-吸入致命
GHS分类：特定靶器官毒性，单次暴露，呼吸道刺激，分类3
H335-可能引起呼吸道刺激

【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。

Cetylpyridinium chloride (CPC) is a quaternary ammonium salt antiseptic that is used in many over-the-counter personal-care products: mouthwashes, toothpastes, lozenges, and breath and nasal sprays, to name a few. It is also used in topical anti-infective products and as a pharmaceutical preservative.

More formally known as 1-hexadecylpyridinium chloride, CPC first appeared in the chemical literature in the 1930s. An early account1 of its disinfecting properties was written by pharmacist C. Lee Huyck at Xavier University of Louisiana (New Orleans) in 1944.

As shown in the hazard information table, CPC by itself has some dangerous properties; but its concentrations in consumer products have been considered too small to be of concern—until recently. In 2020, Brian K. Shoichet at the University of California, San Francisco; Laszlo Urban at the Novartis Institutes for Biomedical Research (Cambridge, MA); and researchers at other institutions published a study showing that some supposedly inert pharmaceutical additives such as CPC have potential biological activity. But the results do not necessarily mean that the substances are toxic.

Some scientists, however, are a bit more suspicious of “quats”, as quaternary ammonium compounds are called in the industry. In the late 2000s, toxicologist Terry Hrubec at Virginia Tech and the Edward Via College of Osteopathic Medicine (both in Blacksburg, VA) noticed that some control mice embryos in a lab study acquired certain defects from two quat disinfectants, which were thought to be safe. Since then, she and other researchers have found more instances of quat-caused animal defects.

CPC has not been implicated in any of these studies; and no human health effects have been associated with exposure to quat-containing products. But this past March, enough evidence about defects in animals attributed to quats had been accumulated that the California Department of Public Health added these substances to its Biomonitoring California program.

Cetylpyridinium chloridefast facts

CAS Reg. No.	123-03-5
SciFinder nomenclature	Pyridinium, 1-hexadecyl-, chloride (1:1)
Empirical formula	C₂₁H₃₈ClN
Molar mass	339.99 g/mol
Appearance	White crystals or powder
Melting point	77 ºC
Water solubility	68 g/L

Arecoline hazard information

Hazard class: Acute toxicity, oral, category 4
H302-Harmful if swallowed
Hazard class: Skin corrosion/irritation, category 2
H315-Causes skin irritation
Hazard class: Serious eye damage/eye irritation, category 1
H315-Causes serious eye damage
Hazard class: Acute toxicity, oral, category 2
H330-Fatal if inhaled
Hazard class: Specific target organ toxicity, single exposure, respiratory tract irritation, category 3
H335-May cause respiratory irritation

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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