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(Synonyms: 芦笋酸) 目录号 : GC30004

Asparagusicacid是芦笋的特异性产物,是导致吃芦笋后尿液味道异常的主要成分。

Asparagusic acid Chemical Structure

Cas No.:2224-02-4

规格 价格 库存 购买数量
10mM (in 1mL DMSO)
¥835.00
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5mg
¥758.00
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10mg
¥1,205.00
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50mg
¥3,481.00
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100mg
¥5,534.00
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Sample solution is provided at 25 µL, 10mM.

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产品描述

Asparagusic acid (1,2-dithiolane-4-carboxylic acid) is unique to asparagus. The compound is responsible for the odorous urine excreted after eating asparagus. Its derivatives ihydroasparagusic acid have anti-inflammatory effect.

[1]. Mitchell SC et al. Asparagusic acid. Phytochemistry. 2014 Jan;97:5-10.

Chemical Properties

Cas No. 2224-02-4 SDF
别名 芦笋酸
Canonical SMILES O=C(O)C1CSSC1
分子式 C4H6O2S2 分子量 150.22
溶解度 DMSO : ≥ 46 mg/mL (306.22 mM) 储存条件 Store at -20°C
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储备液的保存方式和期限:-80°C 储存时,请在 6 个月内使用,-20°C 储存时,请在 1 个月内使用。
为了提高溶解度,请将管子加热至37℃,然后在超声波浴中震荡一段时间。
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溶解性数据

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1 mg 5 mg 10 mg
1 mM 6.6569 mL 33.2845 mL 66.569 mL
5 mM 1.3314 mL 6.6569 mL 13.3138 mL
10 mM 0.6657 mL 3.3285 mL 6.6569 mL
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Research Update

Asparagusic acid

Phytochemistry 2014 Jan;97:5-10.24099657 10.1016/j.phytochem.2013.09.014

Asparagusic acid (1,2-dithiolane-4-carboxylic acid) is a simple sulphur-containing 5-membered heterocyclic compound that appears unique to asparagus, though other dithiolane derivatives have been identified in non-food species. This molecule, apparently innocuous toxicologically to man, is the most probable culprit responsible for the curious excretion of odorous urine following asparagus ingestion. The presence of the two adjacent sulphur atoms leads to an enhanced chemical reactivity, endowing it with biological properties including the ability to substitute potentially for α-lipoic acid in α-keto-acid oxidation systems. This brief review collects the scattered data available in the literature concerning Asparagusic acid and highlights its properties, intermediary metabolism and exploratory applications.

Comparison of lipoic and Asparagusic acid for surface-initiated disulfide-exchange polymerization

Chemistry 2013 Aug 26;19(35):11558-63.23893874 10.1002/chem.201301567

Bring it on: Organic chemistry on surfaces and in solution is not the same; this study offers a perfect example that small changes (from 27 to 35°; see graphic) can result in big consequences. Strained cyclic disulfides from asparagusic, but not lipoic acid, are ideal for growing functional architectures directly on surfaces; for the substrate-initiated synthesis of cell-penetrating poly(disulfide)s in solution, exactly the contrary is true.

Synthesis, characterization and biological investigation of platinum(ii) complexes with Asparagusic acid derivatives as ligands

Dalton Trans 2019 Jan 15;48(3):936-944.30565617 10.1039/c8dt02553c

After more than 50 years of platinum-based anticancer research only three compounds are in clinical use worldwide. The use of the well-known lead compound of this class of anticancer agents, cisplatin, is limited by its side effects and varying resistance mechanisms. Therefore, we report on platinum(ii) compounds with Asparagusic acid derivatives as ligands which show interesting anticancer results on cisplatin resistant cell lines.

Preparation and determination of Asparagusic acid

Methods Enzymol 1979;62:181-4.440100 10.1016/0076-6879(79)62216-4

Asparagus, urinary odor, and 1,2-dithiolane-4-carboxylic acid

Perspect Biol Med 2013 Summer;56(3):341-51.24375116 10.1353/pbm.2013.0031

The derivatives of 1,2-dithiolane are scattered widely throughout the natural world where they are generally exploited for their biocidal properties. One of these, known as Asparagusic acid (1,2-dithiolane-4-carboxylic acid), is present in the frequently consumed vegetable, asparagus, and though apparently innocuous toxicologically, it may be responsible for the distinctive urine odor produced after consuming this food. This review collects together, for the first time, historical observations associating asparagus ingestion with this unique odor-producing phenomenon and collates data implicating a 1,2-dithiolane structure as the major chemical precursor responsible.