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：2-乙酰-1-吡咯啉

Molecule of the Week:

2-Acetyl-1-pyrroline

十一月是每周分子的风味和香味月！

2-乙酰基-1-吡咯啉(2AP)是杂环化合物1-吡咯啉的酮衍生物。2AP的危害信息表显示，纯的2AP化合物具有一些危险的特性，但你很可能是因为它令人愉悦的香味而知道它的存在。

1982年，美国农业部(奥尔巴尼，美国加州)的Ron G. Buttery和Louisa C. Ling以及国际水稻研究所(洛斯巴尼奥斯，菲律宾)的Bienvenido Juliano发现2AP是米饭中重要的香味成分。2AP存在于印度香米和卡尔罗斯大米的挥发油中。研究人员们还通过催化还原2-乙酰吡咯，之后再用碳酸银氧化合成了2AP。

第二年，同样是这些作者，在热带植物Pandanus amaryllifolius的叶子中鉴定出2AP。Pandanus amaryllifolius的叶子在南亚和东南亚被用作调味剂。

20世纪80年代后期，化学家开始在烤面包的香味中鉴定2AP。1985年，慕尼黑工业大学(GARCHE，西德)的Peter Schieberle和Werner Grosch报道说，这种化合物跟其他风味和香味成分一起存在于小麦和黑麦面包的面包皮中。2AP是通过美拉德反应生成的，烘焙面包的过程中会发生美拉德反应——氨基酸和还原糖通过美拉德反应生成了面包皮的棕色成分。

令人费解的是，2AP也是几种亚洲哺乳动物(包括bintarong [Arctictis binturong; 又名bearcat] 和老虎的三个亚种[Panthera tigris] )的尿液气味来源。

2-乙酰基-1-吡咯啉信息速览

CAS 登记号	85213-22-5
SciFinder命名	Ethanone, 1-(3,4-dihydro-2H-pyrrol-5-yl)-
分子式	C₆H₉NO
摩尔质量	111.14 g/mol
外观	无色至黄色固体或液体
熔点	19°C
沸点	183°C
水溶性	易溶

2-乙酰基-1-吡咯啉危害信息

GHS*分类：易燃液体，分类2
H225-高度易燃液体和蒸气
GHS分类：吸入毒性，分类1
H304-吞咽并进入呼吸道可能致命
GHS分类：皮肤腐蚀/刺激，分类2
H315-引起皮肤刺激
GHS分类：急性毒性，吸入，分类4
H332-吸入有害
GHS分类：生殖毒性，分类2
H361-被怀疑会损害生育能力或未出生的孩子
GHS分类：特异性靶器官毒性，反复接触，分类2
H373-长期或反复接触可能对器官造成损害

【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。

November is flavor and aroma month at MOTW!

2-Acetyl-1-pyrroline (2AP) is a ketone derivative of the heterocyclic compound 1-pyrroline. The hazard information table shows that the pure compound has some dangerous properties, but you probably know it from its pleasing aroma.

In 1982, Ron G. Buttery and Louisa C. Ling at the US Department of Agriculture (Albany, CA) and Bienvenido Juliano at the International Rice Research Institute (Los Baños, Philippines) identified 2AP as an important aroma component of cooked rice. It is present in the volatile oils of basmati and Calrose rice. The researchers also synthesized 2AP via the catalytic reduction of 2-acetylpyrrole, followed by oxidation with silver carbonate.

The following year, the same authors identified 2AP in the leaves of the tropical plant pandan (Pandanus amaryllifolius). The leaves are used as a flavoring agent in south and southeast Asia.

Later in the 1980s, chemists began to identify 2AP in the aroma of baking bread. In 1985, Peter Schieberle and Werner Grosch at what is now the Technical University of Munich (Garching, West Germany) reported that the compound, in addition to other flavor and aroma ingredients, is present in the crusts of wheat and rye breads. 2AP is formed by the Maillard reaction that is characteristic of baking bread, in which amino acids and reducing sugars react to form the components of the crust’s brown color.

Curiously, on a less appealing note, 2AP also contributes to the urine odor of several Asian mammals, including the bintarong (Arctictis binturong; aka the bearcat) and three subspecies of tiger (Panthera tigris).

2-Acetyl-1-pyrrolinefast facts

CAS Reg. No.	85213-22-5
SciFinder nomenclature	Ethanone, 1-(3,4-dihydro-2H-pyrrol-5-yl)
Empirical formula	C₆H₉NO
Molar mass	111.14 g/mol
Appearance	Colorless to yellow solid or liquid
Melting point	19 °C
Boiling point	183°C
Water solubility	Soluble

2-Acetyl-1-pyrroline hazard information

Flammable liquids, category 2
H225-Highly flammable liquid and vapor
Aspiration toxicity, category 1
H304-May be fatal if swallowed and enters airways
Skin corrosion/irritation, category 1
H315-Causes skin irritation
Acute toxicity, inhalation, category 4
H332-Harmful if inhaled
Reproductive toxicity, category 2
H361-Suspected of damaging fertility or the unborn child
Specific target organ toxicity, repeated exposure, category 2
H373-May cause damage to organs through prolonged or repeated exposure

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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