dodecyltetraoxyethyleneoxyacetaldehyde diethyl acetal | 202408-17-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: dodecyltetraoxyethyleneoxyacetaldehyde diethyl acetal
• 英文别名: 1-[2-[2-[2-[2-(2,2-diethoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]dodecane
• CAS: 202408-17-1
• 化学式: C₂₆H₅₄O₇
• 分子量: 478.711
• InChiKey: GMZAFBNYHPAZDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.39
• 重原子数：
  33.0
• 可旋转键数：
  29.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  64.61
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  dodecyltetraoxyethyleneoxyacetaldehyde diethyl acetal 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以80%的产率得到dodecyltetraoxyethyleneoxyacetaldehyde
  参考文献：
  名称：

  Contact Allergens from Surfactants. Atmospheric Oxidation of Polyoxyethylene Alcohols, Formation of Ethoxylated Aldehydes, and Their Allergenic Activity

  摘要：

  Ethoxylated surfactants are susceptible to oxidation upon air exposure. We have previously studied the rate of peroxidation and formaldehyde formation in the chemically well-defined ethoxylated alcohol C12H25(OCH2CH2)(5)OH. Formaldehyde is a common cause of contact allergy. The aim of the present study was to identify other oxidation products that could be formed upon air exposure of the ethoxylated alcohol and to determine their allergenic activity. It was shown that air oxidation of C12H25(OCH2CH2)(5)OH gave all the theoretically possible aldehydes of the general formula C12H25(OCH2 CH2)(n)OCH2CHO (n = 0-4) and that the major oxidation product was C12H25(OCH2CH2)(4)OCH2CHO, dodecyltetraoxyethyleneoxyacetaldehyde. The structure elucidation and synthesis of these aldehydes are here presented for the first time. The major aldehyde was shown to be a contact allergen with the same sensitizing capacity as that of formaldehyde. A dose-response relationship was observed in the sensitization studies. The allergens were formed from the surfactant itself and the skin reactions cannot be explained due to any impurities that may be present in a technical quality of the surfactant. Cases of allergic contact dermatits to ethoxylated surfactants have been reported. To avoid the formation of allergenic oxidation products it is important to control the conditions for storage, handling, and transportation of ethoxylated surfactants.

  DOI：

  10.1021/js9704036
• 作为产物：
  描述：

  三缩四乙二醇 在 sodium hydride 作用下， 以 二甲基亚砜 为溶剂， 反应 48.0h， 生成 dodecyltetraoxyethyleneoxyacetaldehyde diethyl acetal
  参考文献：
  名称：

  Contact Allergens from Surfactants. Atmospheric Oxidation of Polyoxyethylene Alcohols, Formation of Ethoxylated Aldehydes, and Their Allergenic Activity

  摘要：

  Ethoxylated surfactants are susceptible to oxidation upon air exposure. We have previously studied the rate of peroxidation and formaldehyde formation in the chemically well-defined ethoxylated alcohol C12H25(OCH2CH2)(5)OH. Formaldehyde is a common cause of contact allergy. The aim of the present study was to identify other oxidation products that could be formed upon air exposure of the ethoxylated alcohol and to determine their allergenic activity. It was shown that air oxidation of C12H25(OCH2CH2)(5)OH gave all the theoretically possible aldehydes of the general formula C12H25(OCH2 CH2)(n)OCH2CHO (n = 0-4) and that the major oxidation product was C12H25(OCH2CH2)(4)OCH2CHO, dodecyltetraoxyethyleneoxyacetaldehyde. The structure elucidation and synthesis of these aldehydes are here presented for the first time. The major aldehyde was shown to be a contact allergen with the same sensitizing capacity as that of formaldehyde. A dose-response relationship was observed in the sensitization studies. The allergens were formed from the surfactant itself and the skin reactions cannot be explained due to any impurities that may be present in a technical quality of the surfactant. Cases of allergic contact dermatits to ethoxylated surfactants have been reported. To avoid the formation of allergenic oxidation products it is important to control the conditions for storage, handling, and transportation of ethoxylated surfactants.

  DOI：

  10.1021/js9704036