2-(异丁氧基羰基)苯甲酸 | 30833-53-5

• 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: 2-(异丁氧基羰基)苯甲酸
• 中文别名: 苯二甲酸单异丁酯；苯二甲酸单异丁酯(MIBP)
• 英文名称: phtalic acid mono-iso-butyl ester
• 英文别名: phthalic acid isobutyl ester；mono-(2-isobutyl) phthalate；mono-iso-butyl phthalate；mono-isobutyl phthalate；monoisobutyl phthalate；isobutyl phthalate；2-(2-methylpropoxycarbonyl)benzoic acid
• CAS: 30833-53-5
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: RZJSUWQGFCHNFS-UHFFFAOYSA-N

物化性质

• 熔点：
  78-80°C
• 沸点：
  283.41°C (rough estimate)
• 密度：
  1.0643 (rough estimate)
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）
• 物理描述：
  Solid
• 保留指数：
  1771

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

ADMET

毒理性

• 毒性总结

邻苯二甲酸盐是一类能够干扰内分泌系统的合成工业化合物。邻苯二甲酸盐是最常见的能够破坏内分泌系统的化学化合物。在生殖道发育的关键时期，邻苯二甲酸盐会干扰雄激素信号通路。胎儿睾丸发育不良综合征，在啮齿动物中也被称为“邻苯二甲酸盐综合征”，是由于胎儿睾酮、胰岛素样生长因子-3（IGF-3）和卵泡刺激激素（FSH）水平降低的结果。观察到母乳中的水平与婴儿的自由睾酮之间存在负相关，而单乙基邻苯二甲酸盐（MEP）和单丁基（MBP）与性激素结合球蛋白（SHBG）之间存在正相关，以及单甲基邻苯二甲酸盐（MMP）和MEP和MBP与黄体生成激素（LH）和自由睾酮的比例之间存在正相关。暴露于邻苯二甲酸盐与妊娠期的持续时间显著相关。根据一些研究，某些邻苯二甲酸盐的化学结构与前列腺素/血栓素、白细胞介素-1将邻苯二甲酸盐与诱导宫内炎症过程以及缩短妊娠期联系起来。

Phthalates are synthetic industrial compounds capable of disrupting the endocrine system. The phthalates have been the most common chemical compounds with the ability to disrupt the endocrine system. Phthalates, when acting in a critical period of the development of genital tract, lead to disturbances in the androgen-signaling pathway. Fetal testicular dysgenesis syndrome, otherwise known as the ”phthalate syndrome” in rodents, is a consequence of reduced level of fetal testosterone, insulin-like growth factor-3 (IGF-3) and follicule stimulating hormone (FSH). A negative correlation between levels in breast milk and free testosterone of babies was observed, while there was a positive correlation between mono-ethyl phthalate (MEP) and mono-butyl (MBP) with sex hormone bingind globuline (SHBG) and mono-metyl phthalate (MMP) and MEP and MBP with the ratio of lutenzing hormone (LH) and free testosterone. Exposure to phthalates is significantly associated with the duration of pregnancy. According to some studies, the chemical structure of some phthalates and prostaglandin/thromboxane, interleukin-1 connects the phthalates with induction of intrauterine inflammatory processes as well as shortening of pregnancy. (A15412)

来源:Toxin and Toxin Target Database (T3DB)

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

• 海关编码：
  2918990090

制备方法与用途

生物活性 Monoisobutyl phthalic acid 是一种邻苯二甲酸酯代谢物，存在于人的精液和胎粪中。

靶点

Human Endogenous Metabolite

体外研究 Monoisobutyl phthalic acid (Monoisobutyl phthalate) 是一种在人体内发现的邻苯二甲酸酯代谢物，存在于人类精液和胎粪中。

反应信息

• 作为反应物：
  描述：

  2-(异丁氧基羰基)苯甲酸 、 氯化亚砜 生成 2-methylpropyl 2-carbonochloridoylbenzoate
  参考文献：
  名称：

  BABIN, P.;DUNOGUES, J., TETRAHEDRON LETT., 1983, 24, N 30, 3071-3074

  摘要：

  DOI：
• 作为产物：
  描述：

  邻苯二甲酸二异丁酯 在 potassium hydroxide 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 10.0h， 以77%的产率得到2-(异丁氧基羰基)苯甲酸
  参考文献：
  名称：

  实用的大体积对称二酯选择性单水解

  摘要：

  我们先前报道的高效选择性单水解反应已应用于几种大体积对称双酯的单水解反应，包括二乙酯，二丙酯和二丁酯。与相应的二甲基酯相比，更大比例的极性非质子助溶剂，DMSO和KOH水溶液似乎有助于改善大体积二酯的反应性。该过程是温和且实用的，在简单条件下以高收率得到相应的半酯。

  DOI：

  10.1016/j.tetlet.2017.12.061

文献信息

• Practical selective monohydrolysis of bulky symmetric diesters: Comparing with sonochemistry
  作者：Jianjun Shi、Tian Zhao、Satomi Niwayama

  DOI：10.1016/j.tet.2018.09.051

  日期：2018.11

  The conditions of the practical selective monohydrolysis of symmetric diesters we previously reported have been modified and applied to selective monohydrolysis of bulky symmetric diesters. While ultrasound is generally considered effective for two-phase reactions, its effect actually turned out to be rather marginal. Instead, use of a larger proportion of a polar aprotic co-solvent, DMSO, and aqueous

  我们先前报道的对称二酯的实际选择性单水解的条件已被修改，并应用于大体积对称二酯的选择性单水解。虽然通常认为超声波对两相反应有效，但实际上其作用很小。相反，使用较大比例的极性非质子助溶剂，DMSO和KOH水溶液有助于提高反应速率并提高半酯的收率。反应简单，温和，实用，无需特殊装置。
• Palladium-Catalyzed Carboxylate-Assisted Ethoxycarboxylation of Aromatic Acids To Synthesize Monoethyl Phthalate Derivatives with Ethyl Bromodifluoroacetate
  作者：Na Tao、Jie Wang、Chunchen Yuan、Runsheng Zeng、Ying-Sheng Zhao

  DOI：10.1021/acs.orglett.9b03196

  日期：2019.11.1

  A novel and efficient approach for direct carbonation of aromatic acids with ethyl bromodifluoroacetate as the carbonyl source is reported. A broad range of substrates bearing various functional groups were tolerated, leading to monoalkyl phthalate derivatives in moderate to good yields.

  报道了一种新颖且有效的方法，以溴代二氟乙酸乙酯作为羰基源直接芳族酸碳酸化。容许带有各种官能团的多种底物，从而以中等至良好的产率产生邻苯二甲酸单烷基酯衍生物。
• 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。
• 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。
• Properties of a Newly Identified Esterase from Bacillus sp. K91 and Its Novel Function in Diisobutyl Phthalate Degradation
  作者：Junmei Ding、Chaofan Wang、Zhenrong Xie、Junjun Li、Yunjuan Yang、Yuelin Mu、Xianghua Tang、Bo Xu、Junpei Zhou、Zunxi Huang

  DOI：10.1371/journal.pone.0119216

  日期：——

  The widely used plasticizer phthalate esters (PAEs) have become a public concern because of their effects on environmental contamination and toxicity on mammals. However, the biodegradation of PAEs, especially diisobutyl phthalate (DiBP), remains poorly understood. In particular, genes involved in the hydrolysis of these compounds were not conclusively identified. In this study, the CarEW gene, which encodes an enzyme that is capable of hydrolyzing ρ-nitrophenyl esters of fatty acids, was cloned from a thermophilic bacterium Bacillus sp. K91 and heterologously expressed in Escherichia coli BL21 using the pEASY-E2 expression system. The enzyme showed a monomeric structure with a molecular mass of approximately 53.76 kDa and pI of 4.88. The enzyme exhibited maximal activity at pH 7.5 and 45°C, with ρ-NP butyrate as the best substrate. The enzyme was fairly stable within the pH range from 7.0 to 8.5. High-pressure liquid chromatography (HPLC) and electrospray ionization mass spectrometry (ESI-MS) were employed to detect the catabolic pathway of DiBP. Two intermediate products were identified, and a potential biodegradation pathway was proposed. Altogether, our findings present a novel DiBP degradation enzyme and indicate that the purified enzyme may be a promising candidate for DiBP detoxification and for environmental protection.

  广泛使用的增塑剂邻苯二甲酸酯（PAEs）因其对环境污染的影响和对哺乳动物的毒性而备受公众关注。然而，人们对 PAEs（尤其是邻苯二甲酸二异丁酯（DiBP））的生物降解仍然知之甚少。特别是，参与水解这些化合物的基因还没有被确定。本研究从嗜热芽孢杆菌 K91 中克隆了 CarEW 基因，该基因编码一种能够水解脂肪酸 ρ-硝基苯酯的酶，并利用 pEASY-E2 表达系统在大肠杆菌 BL21 中进行了异源表达。该酶呈单体结构，分子量约为 53.76 kDa，pI 为 4.88。该酶在 pH 7.5 和 45°C 时表现出最大活性，ρ-NP 丁酸盐是其最佳底物。该酶在 pH 值为 7.0 至 8.5 的范围内相当稳定。利用高压液相色谱法（HPLC）和电喷雾离子化质谱法（ESI-MS）检测了 DiBP 的分解途径。发现了两种中间产物，并提出了一种潜在的生物降解途径。总之，我们的研究结果提出了一种新型 DiBP 降解酶，并表明纯化的酶可能是一种很有前途的 DiBP 解毒和环境保护候选酶。