十二烷基苯磺酸 | 47221-31-8

• 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: 十二烷基苯磺酸
• 中文别名: 2-十二烷基苯磺酸
• 英文名称: dodecylbenzene-sulphonic acid
• 英文别名: 2-dodecylbenzenesulfonic acid；4-dodecylbenzenesulfonic acid；dodecylbenzene sulfonic acid；dodecylbenzenesulphonic acid；dodecylbenzenesulfonic acid；dodecybenzenesulfonic acid
• CAS: 47221-31-8
• 化学式: C₁₈H₃₀O₃S
• 分子量: 326.5
• InChiKey: WBIQQQGBSDOWNP-UHFFFAOYSA-N

物化性质

• 密度：
  1.052±0.06 g/cm3(Predicted)
• 物理描述：
  Dodecylbenzenesulfonic acid is a colorless liquid. It is soluble in water. It is corrosive to metals and tissue. It is used to make detergents.
• 颜色/状态：
  Light yellow to brown
• 沸点：
  > 440 °F = > 204.5 °C = > 477.7 deg K @ 1 atm
• 闪点：
  149 °C
• 腐蚀性：
  Dodecylbenzenesulfonic acid is corrosive to metals.
• 气味阈值：
  200 mg/l affected odor of water.

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  22
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  62.8
• 氢给体数：
  1
• 氢受体数：
  3

ADMET

毒理性

• 副作用

Dermatotoxin - 皮肤烧伤。

Dermatotoxin - Skin burns.

来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases

毒理性

• 相互作用

1,000 mg/l 的 0.1% 硬线性烷基苯磺酸（未定性）加上 100 mg N-甲基-N'-硝基-N-亚硝基胍给 15 只雄性查尔斯河大鼠连续灌胃 63 周后，在另一项研究中，给大鼠灌胃 1,000 mg/l 的 0.1% 软型线性烷基苯磺酸加上 100 mg N-甲基-N'-硝基-N-亚硝基胍连续灌胃 63 周/发生/未分化腺癌的发病率，由未分化的腺细胞组成，在实验组中观察到。在 6 例中发现了癌细胞淋巴侵犯，其中一例转移到了肠道淋巴结。由于表面活性剂的强烈渗透性质，胃癌的发生被增强了。对照组（10 只雄性）仅接受 100 mg/l 的 N-甲基-N'-硝基-N-亚硝基胍连续灌胃 63 周后，出现了分化良好的腺癌；没有发现淋巴侵犯或转移。/线性烷基苯磺酸/

1,000 mg/l of 0.1% hard linear alkylbenzenesulfonic acid (uncharacterized) plus 100 mg N-methyl-N'-nitro-N-nitrosoguanidine administered to 15 male Charles River rats for 63 weeks and in another study which administered 1,000 mg/l of 0.1% soft-type linear alkylbenzenesulfonic acid plus 100 mg N-methyl-N'-nitro-N-nitrosoquanidine for 63 weeks /incidences/ of undifferentiated adenocarcinoma, consisting of anaplastic glandular cells, were observed in the experimental groups. Lymphatic invasion of cancer cells was found in 6 cases, and one metastasized to intestinal lymph node. By virtue of the strong penetrating property of surfactants, gastric carcinogenesis was enhanced. Control rats (10 males) which received 100 mg/l of N-methyl-N'-nitro-N-nitrosoguanidine for 63 weeks revealed well differentiated adenocarcinomas; neither lymphatic invasion nor metastasis was found. /Linear alkylbenzenesulfonic acid/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 医疗监测

就业体检应进行以确保受雇人员没有呼吸器官疾病和皮肤过敏；...。/洗涤剂/

Employment medical examination should be carried out to ensure that persons employed are free from diseases of the respiratory organs and from skin allergies; ... . /Detergents/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 非人类毒性摘录

水蛭长时间暴露在4种洗涤剂（包括十二烷基苯磺酸）中，从孵化之日起就导致了它们生长和繁殖的显著变化。根据暴露的洗涤剂种类不同，水蛭的寿命减少了23-42%。贝壳生长发生了变化。贝壳的矿化减少了（20-40%）。繁殖力下降了30-74%。洗涤剂使水蛭产量下降。

A long-term exposure of Lymnaea stagnalis to 4 detergents /incl dodecylbenzenesulfonic acid/ from their day of hatching led to significant changes in their growth and reproduction. The longevity of the snails was reduced by 23-42% according to the product to which they were exposed. The shell growth was changed. The shell mineralization was reduced (20-40%). The fecundity was reduced by 30-74%. The Lymnaea yield was decr by detergents.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 非人类毒性摘录

一项关于0.9%线性烷基苯磺酸对ICR小鼠的致死性研究，经过9个月的喂养后，结果为阴性。没有观察到新植入体数量减少，或由于精子中的多染色体断裂导致的早期植入后或胚胎死亡。/线性烷基苯磺酸/

A dominant lethal study ... with ICR mice fed 0.9% linear alkylbenzenesulfonic acid for 9 months gave negative results. There was no decrease in the number of nascent implants or of early post-implantation or embryo deaths arising from multiple chromosomal breaks in spermatazoa. /Linear alkylbenzenesulfonic acid/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

直链烷基苯磺酸通过鱼的鳃和体表被吸收（鲤鱼），通过血液分布到各种组织和器官，运输到肝脏（对于金鱼和其他鱼类来说是胰腺），随后通过胆汁，随着粪便被排出体外。/直链烷基苯磺酸/

Linear alkylbenzenesulfonic acid is absorbed through the gills and body surface of fish (carp), distributed via blood to the various tissues and organs, transported to the hepatopancreas (liver for goldfish and others), and subsequently, via bile, eliminated with the feces. /Linear alkylbenzenesulfonic acid/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

(14)C-标记的十二烷基苯磺酸钠（DBS）... 以1.4 mg/kg的浓度每日通过饮食给予雄性大鼠，持续5周。... 从总共摄入的1.213 ± 0.08 mg/只DBS中，81.8%在给药期间被排出；其中52.4%通过粪便排出，29.4%通过尿液排出。在第35天的/研究/中，在所有分析的组织中检测到了低水平的(14)C-DBS衍生残留物。在仅用正常饮食1周后，发现排泄物中只有7.8%的标称储存量的(14)C。单次腹腔注射0.385 mg (14)C-DBS/大鼠，相当于2.26 ± 0.15 mg/kg体重，10天内总共排除了94.5%。在最初的24小时内排除了84.7%的剂量。所有(14)C-DBS的粪便和肾脏代谢物都...具有高度极性。/十二烷基苯磺酸钠/

(14)C-labeled sodium dodecylbenzenesufonate (DBS) ... administered daily in the diet at a concn of 1.4 mg/kg to male rats for 5 weeks. ... From a total uptake of 1.213 + or - 0.08 mg/animal of DBS, 81.8% was excreted during the dosing period; 52.4% in feces and 29.4% in urine. Low levels of (14)C-DBS-derived residues were detected in all tissues analyzed on day 35 of the /study/. Following 1 week on normal diet only 7.8% of the nominally stored amount of (14)C was found in the excreta. Single ip injection of 0.385 mg (14)C-DBS/rat 2.26 + or - 0.15 mg/kg body weight resulted in total elimination of 94.5% within 10 days. 84.7% of the dose was eliminated the first 24 hr. All (14)C-DBS fecal and renal metabolites were ... highly polar. /Sodium dodecylbenzenesulfonate/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

在单次口服/(35)S-标记/十二烷基苯磺酸钠后，大鼠通过尿液排出了剂量的64%，通过粪便排出了24%。另一项对恒河猴重复给予/(14)C-标记/烷基苯磺酸盐（平均分子量为349，是洗涤剂的主要成分）的类似研究表明，放射性物质并未在组织中积累。/含芳香环、硫的化合物/

After single oral dose of /(35)S-labeled/ sodium dodecylbenzenesulfonate, rats excreted 64% and 24% of the dose in urine and feces, respectively. A similar study of repeated doses of /(14)C-labeled/ alkylbenzenesulfonate (mean molecular wt 349, a major constituent of detergents) to rhesus monkeys has shown that radioactivity did not accumulate in the tissues. /Aromatic, sulfur-containing cmpd/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

(14)C烷基苯在蓝鳃太阳鱼(L. machrochirus)中的生物浓缩因子为35。该值明显小于预测的生物浓缩因子6300；这种差异归因于代谢。与洗衣粉中的表面活性剂线性烷基苯磺酸盐相比，烷基苯在组织分布和脱毒速率方面具有相似的模式，而已有研究表明线性烷基苯磺酸盐容易被代谢。

The bioconcentration factor for (14)C alkylbenzene in bluegill sunfish (L. machrochirus) was 35. The value was significantly smaller than the predicted bioconcentration factor of 6300; the discrepancy was ascribed to metabolism. Alkylbenzene had similar patterns of tissue distribution and depuration rates when compared to its sulfonated counterpart, linear alkylbenzene sulfonate, a surfactant in laundry detergents, which had been shown to be readily metabolized.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

在为期5周的时间内，每天通过饮食给雄性大鼠喂食浓度为1.4毫克/千克的(14)C标记十二烷基苯磺酸钠。从总共摄入的十二烷基苯磺酸钠（1.213 +/- 0.08毫克/动物）中，有81.8%在给药期间被排出；其中52.4%通过粪便排出，29.4%通过尿液排出。在实验的第35天，分析的所有组织中都检测到了低水平的(14)C十二烷基苯磺酸钠残留物。在恢复正常饮食1周后，仅发现排泄物中有7.8%的标称储存量的(14)C。单次腹腔注射0.385毫克(14)C十二烷基苯磺酸/大鼠（2.26 +/- 0.15毫克/千克体重）后，在10天内总共消除了94.5%。在最初的24小时内，有84.7%的剂量被排出。所有粪便和肾脏中的(14)C十二烷基苯磺酸衍生活动均由高度极性的代谢物组成。

(14)C labelled sodium dodecylbenzene sulfonate was administered daily in the diet at a concentration of 1.4 mg/kg to male rats for 5 weeks. From the total uptake (1.213 +/- 0.08 mg/animal) of sodium dodecylbenzene sulfonate, 81.8% was excreted during the dosing period; 52.4% in feces and 29.4% in urine. Low levels of (14)C sodium dodecylbenzene sulfonate derived residues were detected in all tissues analyzed on day 35 of the experiment. Following 1 week on normal diet only 7.8% of the nominally stored amount of (14)C was found in the excreta. Single ip application of 0.385 mg (14)C sodium dodecylbenzene/rat (2.26 +/- 0.15 mg/kg body weight) resulted in a total elimination of 94.5% within 10 days. 84.7% of the dose was eliminated in the first 24 hours. All fecal and renal (14)C sodium dodecylbenzene derived activity consisted of highly polar metabolites.

来源:Hazardous Substances Data Bank (HSDB)

反应信息

• 作为反应物：
  描述：

  十二烷基苯磺酸 生成 四(五氟苯基)-硼酸锂(1:1)
  参考文献：
  名称：

  COLORED COMPOSITION

  摘要：

  公开号：

  EP2957578B1
• 作为产物：
  描述：

  正十二烷基苯 在 硫酸 、 三氧化硫 作用下， 生成 十二烷基苯磺酸
  参考文献：
  名称：

  Distribution of para and ortho Isomers in Some Model Long Chain Alkylbenzenesulfonates

  摘要：

  DOI：

  10.1021/jo01060a050
• 作为试剂：
  描述：

  1-甲基吲哚 、 2-苯基-2-丙醇 在 十二烷基苯磺酸 作用下， 以 水 为溶剂， 反应 24.0h， 以95%的产率得到1-methyl-3-(2-phenylpropan-2-yl)-1H-indole
  参考文献：
  名称：

  表面活性剂型布朗斯台德酸催化水中酒精的脱水亲核取代。

  摘要：

  已经开发出使用十二烷基苯磺酸（DBSA）作为水中的表面活性剂型布朗斯台德酸催化剂，用多种以碳原子和杂原子为中心的亲核试剂对苯甲醇进行脱水亲核取代的方案。该反应系统可以应用于水中1-羟基糖的立体选择性C-糖基化。[反应：请参见文字]。

  DOI：

  10.1021/ol062813j

文献信息

• [EN] NOVEL ANTIVIRAL COMPOUNDS<br/>[FR] NOUVEAUX COMPOSÉS ANTIVIRAUX
  申请人：UNIV LEUVEN KATH

  公开号：WO2014170368A1

  公开（公告）日：2014-10-23

  The present invention relates to a series of novel compounds and derivatives thereof, methods to prevent or treat viral infections by using the novel compounds, processes for their preparation, their use to treat or prevent viral infections and their use to manufacture a medicine to treat or prevent viral infections, preferably infections with viruses belonging to the family of the Togaviridae and more preferably infections with chikungunya virus (CHIKV).

  本发明涉及一系列新化合物及其衍生物，利用这些新化合物预防或治疗病毒感染的方法，以及它们的制备过程，用于治疗或预防病毒感染以及用于制造治疗或预防病毒感染的药物，最好是用于治疗属于Togaviridae家族的病毒，更好地是用于治疗寨卡病毒感染。
• [EN] INSECTICIDAL TRIAZINONE DERIVATIVES<br/>[FR] DÉRIVÉS DE TRIAZINONE INSECTICIDES
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：WO2013079350A1

  公开（公告）日：2013-06-06

  Compounds of the formula (I) or (I'), wherein the substituents are as defined in claim 1, are useful as pesticides.

  式(I)或(I')的化合物，其中取代基如权利要求1所定义的那样，可用作杀虫剂。
• [EN] QUINAZOLINE DERIVATIVES, COMPOSITIONS, AND USES RELATED THERETO<br/>[FR] DÉRIVÉS DE QUINAZOLINE, COMPOSITIONS ET UTILISATIONS ASSOCIÉES
  申请人：UNIV EMORY

  公开号：WO2013181135A1

  公开（公告）日：2013-12-05

  The disclosure relates to quinazoline derivatives, compositions, and methods related thereto. In certain embodiments, the disclosure relates to inhibitors of NADPH-oxidases (Nox enzymes) and/or myeloperoxidase.

  该披露涉及喹唑啉衍生物、组合物以及相关方法。在某些实施例中，该披露涉及NADPH-氧化酶（Nox酶）和/或髓过氧化物酶的抑制剂。
• Immunosuppressive effects of pteridine derivatives
  申请人：——

  公开号：US20030236255A1

  公开（公告）日：2003-12-25

  Novel poly-substituted pteridinediones (lumazines), and mono- or polysubstituted 2-thiolumazines, 4-thiolumazines or 2,4-dithiolumazines, having disclosed substituents in positions 1, 3, 6 and 7 of the pteridine ring, and pharmaceutically acceptable salts thereof, are useful as biologically active ingredients in preparing pharmaceutical compositions especially for the treatment or prevention of a CNS disorder, a cell proliferative disorder, a viral infection, an immune or auto-immune disorder or a transplant rejection. Combinations of the pteridine derivatives of the invention with an immunosuppressant or immunomodulator drug, an antineoplastic drug or an antiviral agent, providing potential synergistic effects, are also disclosed.

  新型多取代的喹啉二酮（卢马嗪），以及单取代或多取代的2-硫代卢马嗪，4-硫代卢马嗪或2,4-二硫代卢马嗪，在喹啉环的1、3、6和7位上具有已披露的取代基，并且其药学上可接受的盐，在制备药物组合物中作为生物活性成分特别用于治疗或预防中枢神经系统疾病、细胞增殖障碍、病毒感染、免疫或自身免疫障碍或移植排斥。本发明的喹啉衍生物与免疫抑制剂或免疫调节剂药物、抗肿瘤药物或抗病毒药物的组合，提供潜在的协同效应。
• SYNTHESIS OF R-GLUCOSIDES, SUGAR ALCOHOLS, REDUCED SUGAR ALCOHOLS, AND FURAN DERIVATIVES OF REDUCED SUGAR ALCOHOLS
  申请人：Archer Daniels Midland Company

  公开号：US20170121258A1

  公开（公告）日：2017-05-04

  Disclosed herein are methods for synthesizing 1,2,5,6-hexanetetrol (HTO), 1,6 hexanediol (HDO) and other reduced polyols from C5 and C6 sugar alcohols or R glycosides. The methods include contacting the sugar alcohol or R-glycoside with a copper catalyst, most desirably a Raney copper catalyst with hydrogen for a time, temperature and pressure sufficient to form reduced polyols having 2 to 3 fewer hydoxy groups than the starting material. When the starting compound is a C6 sugar alcohol such as sorbitol or R-glycoside of a C6 sugar such as methyl glucoside, the predominant product is HTO. The same catalyst can be used to further reduce the HTO to HDO.

  本文披露了一种从C5和C6糖醇或R-糖苷合成1,2,5,6-己烷四醇（HTO）、1,6-己二醇（HDO）和其他还原多元醇的方法。该方法包括将糖醇或R-糖苷与铜催化剂接触，最理想的是与氢气一起在足够的时间、温度和压力下形成具有比起始物质少2到3个羟基的还原多元醇。当起始化合物是C6糖醇，如山梨醇或C6糖的R-糖苷，主要产物是HTO。同一催化剂可用于进一步将HTO还原为HDO。

表征谱图