S-(2-羧基乙基)-N-乙酰半胱氨酸 | 51868-61-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: S-(2-羧基乙基)-N-乙酰半胱氨酸
• 中文别名: 2-噻唑丙醛,b-羰基-
• 英文名称: N-acetyl-S-(2-carboxyethyl)-L-cysteine
• 英文别名: (2R)-2-acetamido-3-(2-carboxyethylsulfanyl)propanoic acid
• CAS: 51868-61-2
• 化学式: C₈H₁₃NO₅S
• 分子量: 235.261
• InChiKey: CLQPFBSYILTXKI-LURJTMIESA-N

物化性质

• 熔点：
  167-173°C
• 沸点：
  576.4±50.0 °C(Predicted)
• 密度：
  1.382±0.06 g/cm3(Predicted)
• 溶解度：
  甲醇（微溶）、水（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  129
• 氢给体数：
  3
• 氢受体数：
  6

安全信息

• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  甲醇 、 S-(2-羧基乙基)-N-乙酰半胱氨酸 在 盐酸 作用下， 反应 1.0h， 生成 (R)-2-Acetylamino-3-(2-methoxycarbonyl-ethylsulfanyl)-propionic acid methyl ester
  参考文献：
  名称：

  Identification of Novel Metabolites of Butadiene Monoepoxide in Rats and Mice

  摘要：

  Differences in the metabolism of 1,3-butadiene (Bd) in rats and mice may account for the observed species difference in carcinogenicity. Previous studies of the metabolic fate of Ed have identified epoxide formation as a key metabolic transformation which gives 1,2-epoxy-3-butene (BMO), although some evidence of aldehyde metabolites is reported. In this study, male Sprague-Dawley rats and male B6C3F1 mice received single doses of [4-C-14]BMO at 1, 5, 20, and 50 mg/kg of body weight (0.014, 0.071, 0.286, and 0.714 mmol/kg of body weight). Analysis of urinary metabolites indicated that both species preferentially metabolize BMO by direct reaction with GSH when given by ip administration. The excretion of (R)-2-(N-acetyl-L-cystein-S-yl)-1-hydroxybut-3-ene (IIa), 1-(N-acetyl-L-cystein-S-yl)-2-(S)-hydroxybut-3-ene (IIb), 1-(N-acetyl-L-cystein-S-yl)-2-(R)-hydroxybut-3-ene (IIc), and (S)-2-(N-acetyl-L-cystein-S-yl)- 1-hydroxybut-3-ene (IId) accounted for 48-64% of urinary radioactivity in rats and 46-54% in mice. The metabolites originating from the R-stereoisomer of BMO (IIc and IId) predominated over those arising from the S-stereoisomer (IIa and IIb) in both species. IIc was formed preferentially in mice and IId in rats. The corresponding mercaptoacetic acids, S-(1-hydroxybut-3-en-2-yl)mercaptoacetic acid (IIf) and S-(2-hydroxybut-3-en-1-yl)mercaptoacetic acid (IIg), were identified only in mouse urine (ca. 20% of the recovered radioactivity,, 4-(N-Acetyl-L-cystein-S-yl)- 1,2-dihydroxybutane (Ia), a metabolite derived from hydrolysis of BMO, accounted for 10-17% of the radioactivity in rat and 6-10% in mouse urine. 4-(N-Acetyl-L-cystein-S-yl)-2-hydroxybutanoic acid (1b), 3-(N-acetyl-L-cystein-S-yl)propan-1-ol (Ic), and 3-(N-acetyl-L-cystein-S-yl)propanoic acid (Id:). also derived from the hydrolysis of RR IO, were only present in the rat. Metabolites of 1,2,3,4-diepoxybutane (DEB) were not detected after administration of BMO in rat or mouse urine. This study showed both quantitative and qualitative differences in the metabolism of BMO with varying doses and between species. The data aid in the safety evaluation of Ed and contribute to the interpretation of mathematical models developed for quantitative risk assessment and extrapolation of animals to humans.

  DOI：

  10.1021/tx970175v
• 作为产物：
  描述：

  N-乙酰-L-半胱氨酸 在 谷胱甘肽 、 水 、 三乙胺 作用下， 以 甲醇 、 aq. phosphate buffer 为溶剂， 反应 24.0h， 生成 S-(2-羧基乙基)-N-乙酰半胱氨酸
  参考文献：
  名称：

  硫醇基迈克尔型加成。系统评估其控制因素

  摘要：

  本文是关于控制这种流行的生物共轭反应动力学和产物稳定性的因素。我们证明a）硫醇pKa，即硫醇盐的量，是亲核试剂反应动力学的唯一决定因素；b）产物降解主要通过水解（而非硫醇交换）发生，并且对于反应最迅速的亲电试剂更为突出。在分子设计方面，丙烯酰胺和低pKa硫醇作为反应伙伴出现，为稳定性和反应速率提供了最佳折衷方案。

  DOI：

  10.1016/j.tet.2020.131637

文献信息

• COMBINATIONS OF N-ACETYL CYSTEINE DERIVATIVES AND CRANBERRY POLYPHENOLS IN COMPOSITIONS AND METHODS FOR PREVENTING AND TREATING PERIODONTAL DISEASES AND PERI-IMPLATITIS
  申请人：Dentalmed Pharm Holding Ltd.

  公开号：EP2976061B1

  公开（公告）日：2019-10-16
• METHODS OF TREATING ORGANIC ACIDEMIAS
  申请人：Hemoshear Therapeutics, Inc.

  公开号：EP3937922A1

  公开（公告）日：2022-01-19
• DIAGNOSTIC TEST FOR DISTINGUISHING THE SMOKING STATUS OF A SUBJECT
  申请人：PHILIP MORRIS PRODUCTS S.A.

  公开号：US20200141933A1

  公开（公告）日：2020-05-07

  There is disclosed herein a device for determining the smoking status of a subject, wherein said device comprises a plurality of different specific binding molecules deposited to a solid phase to detect specifically the presence of two or three tobacco smoke exposure biomarkers in a biological sample, said biomarkers consisting of: (i) cotinine and total 4-(methylnitrosamino)-1-(3-, pyridyl)-1-butanol (NNAL); (ii) cotinine and N-acetyl-S-[2-carboxyethyl]-L-cysteine (CEMA); or (iii) cotinine and NNAL and CEMA.
• [EN] COMBINATIONS OF N-ACETYL CYSTEINE DERIVATIVES AND CRANBERRY POLYPHENOLS IN COMPOSITIONS AND METHODS FOR PREVENTING AND TREATING PERIODONTAL DISEASES AND PERI-IMPLATITIS<br/>[FR] COMBINAISON DE DÉRIVÉS DE N-ACÉTYLCYSTÉINE ET DE POLYPHÉNOLS DE CANNEBERGE DANS DES COMPOSITIONS ET DES PROCÉDÉS POUR PRÉVENIR ET TRAITER DES MALADIES PARODONTIQUES ET UNE PÉRI-IMPLANTITE
  申请人：DENTALMED PHARM HOLDING LTD

  公开号：WO2014147613A1

  公开（公告）日：2014-09-25

  The present invention relates to combined compositions comprising a combination of N-acetyl cysteine (NAC), or any derivatives thereof, and polyphenols, specifically cranberry polyphenols. The invention further provides methods and uses of said combined compositions for treating and preventing periodontal diseases, specifically gingivitis, periodontitis and peri-implantitis.
• [EN] DIAGNOSTIC TEST FOR DISTINGUISHING THE SMOKING STATUS OF A SUBJECT<br/>[FR] TEST DE DIAGNOSTIC POUR DISTINGUER LE STATUT DE FUMEUR D'UN SUJET
  申请人：PHILIP MORRIS PRODUCTS SA

  公开号：WO2018211126A1

  公开（公告）日：2018-11-22

  There is disclosed herein a device for determining the smoking status of a subject, wherein said device comprises a plurality of different specific binding molecules deposited to a solid phase to detect specifically the presence of two or three tobacco smoke exposure biomarkers in a biological sample, said biomarkers consisting of: (i) cotinine and total 4- (methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL); (ii) cotinine and N-acetyl-S-[2- carboxyethyl]-L-cysteine (CEMA); or (iii) cotinine and NNAL and CEMA.