邻苯二甲酸单乙基己基酯 | 4376-20-9

• 物质功能分类: 分析化学 - 标准品 - 农业和环境标准品
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 邻苯二甲酸单乙基己基酯
• 中文别名: 邻苯二甲酸单(2-乙基己基)酯
• 英文名称: (2-ethylhexyl) hydrogen phthalate
• 英文别名: 2-(((2-Ethylhexyl)oxy)carbonyl)benzoic acid；2-(2-ethylhexoxycarbonyl)benzoic acid
• CAS: 4376-20-9
• 化学式: C₁₆H₂₂O₄
• mdl: MFCD00041500
• 分子量: 278.348
• InChiKey: DJDSLBVSSOQSLW-UHFFFAOYSA-N

物化性质

• 熔点：
  25-27℃
• 沸点：
  341.16°C (rough estimate)
• 密度：
  0,107 g/cm3
• 闪点：
  >93 °C
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）
• 物理描述：
  Mono(2-ethylhexyl)phthalate is a clear colorless to cloudy white viscous liquid. (NTP, 1992)
• 保留指数：
  2152
• 稳定性/保质期：
  在常温常压下，该物质保持稳定。

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

ADMET

毒理性

• 致癌物分类

对人类不具有致癌性（未被国际癌症研究机构IARC列名）。

No indication of carcinogenicity to humans (not listed by IARC).

来源:Toxin and Toxin Target Database (T3DB)

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2922509090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

制备方法与用途

生物活性

Phthalic acid mono-2-ethylhexyl ester (MEHP) 是邻苯二甲酸二己酯 (DEHP) 的主要生物活性代谢物，可抑制 CYP17 的 17,20 裂合酶活性。

靶点

Human Endogenous Metabolite

用途：DEHP的一种具有生物活性的代谢物。

反应信息

• 作为反应物：
  描述：

  邻苯二甲酸单乙基己基酯 以53%的产率得到
  参考文献：
  名称：

  SAIDO KATSUHIKO; MOTOHASHI SHIGEYASU; KUROKI TAKESHI; IKEMYRA TADASHI; SA+, CHEM. PHARM. BULL. 1979, 27, NO 12, 3140-3144

  摘要：

  DOI：
• 作为产物：
  描述：

  邻苯二甲酸二辛酯 在 Tris-HCl buffer 、 mouse hepatic microsomal esterase ES_46.5K 作用下， 以 丙酮 为溶剂， 生成 邻苯二甲酸单乙基己基酯
  参考文献：
  名称：

  Involvement of a Novel Mouse Hepatic Microsomal Esterase, ES46.5K, in the Hydrolysis of Phthalate Esters.

  摘要：

  ES46.5K 是一种来自小鼠肝脏微粒体的新型酯酶（Watanabe K. 等人，Biochem.Mol.Biol.Int.，31，25-30（1993 年））催化了邻苯二甲酸酯的水解。ES46.5K 和小鼠肝微粒体可水解邻苯二甲酸二乙基酯、二丁酯、二异丁酯、二辛酯和二乙基己酯，而具有环状结构的邻苯二甲酸二环己基酯和二苯基酯则不被酶水解。ES46.5K 对邻苯二甲酸二乙基酯、邻苯二甲酸二丁酯、邻苯二甲酸二异丁酯、邻苯二甲酸二辛酯和邻苯二甲酸二己酯的 Vmax（μmol/min/mg 蛋白）/Km（μM）比值分别为 291、2786、565、51 和 57，而微粒体的 Vmax/Km（μM）比值分别为 0.58、0.83、1.71、0.05 和 1.10。ES46.5K 的水解活性受到二异丙基氟磷酸酯和双对硝基苯磷酸酯的抑制。这些结果表明，ES46.5K 对邻苯二甲酸酯具有很高的催化活性，并在小鼠体内邻苯二甲酸酯的代谢过程中发挥一定的作用。

  DOI：

  10.1248/bpb.20.749
• 作为试剂：
  描述：

  肾上腺酮 在 邻苯二甲酸单乙基己基酯 、 β-烟酰胺腺嘌呤二核苷酸 作用下， 生成 11-去氢皮质甾酮
  参考文献：
  名称：

  Structure-dependent inhibition of human and rat 11β-hydroxysteroid dehydrogenase 2 activities by phthalates

  摘要：

  Phthalates are diesters of phthalic acid and an alcohol moiety. Phthalates have been classified as endocrine disruptors and have a broad range of effects with unknown mechanisms. Some of the effects of phthalate are consistent with disruptions of normal glucocorticoid homeostasis, and in particular, with defective function of 11 beta-hydroxysteroid dehydrogenase 2 (11 beta-HSD2). In the present study, we tested 12 phthalate diesters and four monoesters for the inhibition of human and rat kidney 11 beta-HSD2. We examined the modes of inhibition and looked for a relationship between the potency for inhibition and the chemical structures. Of the phthalate diesters we tested, dipropyl phthalate (DPrP) and di-n-butyl phthalate (DBP) significantly inhibited both human and rat 11 beta-HSD2 activities. The IC(50)s were 85.59 mu M for DPrP and 13.69 mu M for DBP when calculated for rat 11 beta-HSD2. As diesters, 8 of the phthalates did not affect 11 beta-HSD2 enzyme activity. Compared to the diesters that were inhibitory, the 8 non-inhibitory phthalates, had either fewer carbons, that is 1 or 2 carbons in the alcohol moiety, or more carbons, 5-10, as a branched or unbranched chain in the alcohol moeity. However, phthalates could be inhibitors with six carbons in the alcohol moiety if the carbons were cyclized, as in dicyclohexyl phthalate (DCHP), which inhibited rat 11 beta-HSD2 with an IC50 of 32.64 mu M. Thus, whether a phthalate is an inhibitor may reflect the size and shape of the compound. Although the diesters are the compounds used in manufacturing and present as environmental contaminants, it is the monoester metabolites that are detected in human serum and urine. We showed that mono (2-ethylhexyl) phthalate (MEHP) significantly inhibited human (IC50=110.8 +/- 10.9) and rat (121.8 +/- 8.5 mu M) 11 beta-HSD2 activity even though its parent compound, di(2-ethylhexyl) phthalate (DEHP) did not. MEHP was a competitive inhibitor of 11 beta-HSD2 enzymatic activity. We conclude that phthalates of a certain size act as competitive inhibitors. (C) 2009 Published by Elsevier Ireland Ltd.

  DOI：

  10.1016/j.cbi.2009.09.014

文献信息

• [EN] PROCESS FOR PREPARING CARBOXYLIC ACID ESTERS IN THE PRESENCE OF A TITANIUM-CONTAINING CATALYST<br/>[FR] PROCÉDÉ DE PRÉPARATION D'ESTERS D'ACIDES CARBOXYLIQUES EN PRÉSENCE D'UN CATALYSEUR CONTENANT DU TITANE
  申请人：SIBUR HOLDING PUBLIC JOINT STOCK CO

  公开号：WO2016043616A1

  公开（公告）日：2016-03-24

  The present invention relates to a process for preparing carboxylic acid esters, comprising esterification of a carboxylic acid with an alcohol in the presence of a titanium-containing catalyst selected from compounds of a general formula, Tin(OR)x(OR')xOy, wherein n is an integer from 1 to 4; у is an integer from 0 to 6; x can be the same or different and is an integer from 2 to 8; R is a linear or branched C1-C18alkyl, C3-C18cycloalkyl, R' is aryl optionally comprising an electron-donor substituent; or a mixture thereof, with the proviso that if n is 1, then x is 2 and у is 0; and if n>1, then the compounds comprise at least two alkoxy groups and two aryloxy groups. The present invention also relates to a process for preparing carboxylic acid esters, wherein a compound of general formula (I) or (II), wherein q represents an integer of 1 to 4; Y is independently R or R'; or a mixture thereof, with the proviso that the compounds comprise at least two alkoxy groups and two aryloxy groups, is used as a catalyst. The claimed process allows to reduce the amount of a used catalyst and the time of the process duration, while increasing the conversion rate of initial reagents and the yield of a target product.

  本发明涉及一种制备羧酸酯的方法，包括在存在选择自通式Tin(OR)x(OR')xOy的化合物的钛催化剂的情况下，将羧酸与醇酯化，其中n为1至4的整数；у为0至6的整数；x可以相同也可以不同，为2至8的整数；R为线性或支链的C1-C18烷基，C3-C18环烷基，R'为芳基，可包含电子给体取代基；或二者的混合物，但若n为1，则x为2且у为0；若n>1，则化合物至少包含两个烷氧基和两个芳氧基。本发明还涉及一种制备羧酸酯的方法，其中通式(I)或(II)的化合物，其中q表示1至4的整数；Y独立地为R或R'；或二者的混合物，但化合物至少包含两个烷氧基和两个芳氧基，被用作催化剂。所述方法允许减少使用的催化剂量和过程持续时间，同时提高初始试剂的转化率和目标产品的产率。
• LOW VISCOSITY LOW VOLATILITY LUBRICATING OIL BASE STOCKS AND METHODS OF USE THEREOF
  申请人：ExxonMobil Research and Engineering Company

  公开号：US20170183595A1

  公开（公告）日：2017-06-29

  A lubricating oil base stock including one or more monoesters represented by the formula (I), (II), (III) and (IV) as defined herein. The lubricating oil base stock has a high temperature high shear (HTHS) viscosity of less than about 1.7 cP as determined by ASTM D4683, and a Noack volatility from about 15 to about 90 percent as determined by ASTM D5800. A lubricating oil containing the lubricating oil base stock including one or more monoesters represented by the formula (I), (II), (III) and (IV) as defined herein. A method for improving one or more of thermal and oxidative stability, solubility and dispersancy of polar additives, deposit control and traction control in a lubricating oil by using as the lubricating oil a formulated oil containing the lubricating oil base stock including one or more monoesters represented by the formula (I), (II), (III) and (IV) as defined herein.

  一种润滑油基础油，包括根据本文所定义的公式(I)、(II)、(III)和(IV)表示的一个或多个单酯。该润滑油基础油的高温高剪切（HTHS）粘度小于约1.7厘泊，由ASTM D4683确定，挥发性从约15%到约90%，由ASTM D5800确定。一种含有根据本文所定义的公式(I)、(II)、(III)和(IV)表示的一个或多个单酯的润滑油基础油的润滑油。一种通过使用包含根据本文所定义的公式(I)、(II)、(III)和(IV)表示的一个或多个单酯的润滑油基础油的配制油来改善润滑油中的热稳定性、氧化稳定性、溶解性和分散性、沉积控制和牵引控制的方法。
• Dicarboxylic diester, process for producing the same, and refrigerating machine lubricating oil comprising the ester
  申请人：Kawahara Yasuyuki

  公开号：US20050038283A1

  公开（公告）日：2005-02-17

  A diester represented by the formula wherein A represents a cyclohexane ring, cyclohexene ring or benzene ring, X is H or methyl group, R X and R Y are the same or different and each is C3-C18 branched-chain alkyl group, C1-C18 straight-chain alkyl group, C2-C18 straight-chain alkenyl or C3-C18 cycloalkyl, provided that when A is a benzene ring, R X and R Y are different from each other and —COOR X and —COOR Y are attached to two adjacent carbon atoms of the benzene ring, and having the following properties: 1) a total acid number of 0.05 mgKOH/g or less, 2) a sulfated ash content of 10 ppm or less, 3) a sulfur content of 20 ppm or less, 4) a phosphorus content of 20 ppm or less, 5) a peroxide value of 1.0 meq/kg or less, 6) a carbonyl value of 10 or less; 7) a volume resistivity of 1×10 11 Ω·cm or more, 8) a hydroxyl value of 3 mgKOH/g or less, and 9) a water content of 100 ppm or less, a process for preparing the same and a refrigerator lubricating oil comprising the diester.

  由以下公式表示的二酯，其中A代表环己烷环、环己烯环或苯环，X为H或甲基基团，RX和RY相同或不同，且每个均为C3-C18支链烷基基团、C1-C18直链烷基基团、C2-C18直链烯基或C3-C18环烷基，前提是当A为苯环时，RX和RY彼此不同，且—COORX和—COORY连接到苯环的两个相邻碳原子，并具有以下特性：1）总酸值为0.05 mgKOH/g或更低，2）硫酸盐灰分含量为10 ppm或更低，3）硫含量为20 ppm或更低，4）磷含量为20 ppm或更低，5）过氧化值为1.0 meq/kg或更低，6）羰基值为10或更低；7）体积电阻率为1×1011Ω·cm或更高，8）羟值为3 mgKOH/g或更低，9）水含量为100 ppm或更低，制备该二酯的方法以及包含该二酯的制冷剂润滑油。
• MAKEUP COMPOSITION
  申请人：KERGOSIEN Guillaume

  公开号：US20110150805A1

  公开（公告）日：2011-06-23

  Composition for making up keratin fibres, such as eyelashes or eyebrows, having improved makeup-removing properties, containing in a continuous aqueous phase: an aqueous dispersion of a particular polyurethane present in an amount of solids greater than or equal to 5% by weight relative to the total weight of said composition, and said composition comprising an emulsifying system comprising less than 2% by weight of triethanolamine.

  用于制造角蛋白纤维（如睫毛或眉毛）的组合物，具有改善卸妆性能，包含在连续水相中：特定聚氨酯的水分散体，其含量固体物质量大于或等于所述组合物总重量的5%，以及所述组合物包括含有少于2%三乙醇胺的乳化系统。
• Ecotoxicity and biodegradation of phthalate monoesters
  作者：Norbert Scholz

  DOI：10.1016/s0045-6535(03)00668-4

  日期：2003.12

  Little is known about the fate and the effects of phthalic acid monoesters. Various of these monoesters ranging from n-butyl to isononyl monoester have been evaluated in respect to their biodegradation behaviour and their acute aquatic toxicity. All esters are readily biodegradable, achieving degradation rates of 90% and more. The acute toxicity values strongly depend on the carbon chain length of

  关于邻苯二甲酸单酯的命运和作用知之甚少。就其生物降解行为和急性水生毒性而言，已对从正丁基到异壬酰基单酯的各种单酯进行了评估。所有酯都易于生物降解，降解率达到90％或更高。急性毒性值在很大程度上取决于醇部分的碳链长度。短链样品的LC / EC50约为100 mg / l或更高，异壬基单酯的LC / EC50值稳定在30 mg / l左右。