isostearyl dichlorophosphate | 111415-22-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: isostearyl dichlorophosphate
• 英文别名: [2-(1,3,3-trimethyl-n-butyl)-5,7,7-trimethyl-n-octyl] dichlorophosphate；[2-(1,3,3-Trimethyl-n-butyl)-5,7,7-trimethyl-n-octyl]dichlorophosphate；5-(dichlorophosphoryloxymethyl)-2,2,4,8,10,10-hexamethylundecane
• CAS: 111415-22-6
• 化学式: C₁₈H₃₇Cl₂O₂P
• 分子量: 387.37
• InChiKey: AJHONUHPARXGII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  23
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  isostearyl dichlorophosphate 、 5,6-O-isopropylidene-L-ascorbic acid 生成 isostearyl 2-O-L-ascorbyl phosphate
  参考文献：
  名称：

  Inhibitory Effects of a Novel Ascorbic Derivative, Disodium Isostearyl 2-O-L-Ascorbyl Phosphate on Melanogenesis

  摘要：

  我们研究了一种新型两亲性抗坏血酸衍生物异硬脂酰2-O-<小>L-抗坏血酸磷酸二钠（VCP-IS-2Na）对培养的人类黑色素瘤细胞、正常人类黑色素细胞和三维培养的人类皮肤模型中黑色素生成的抑制作用。用 300 μM浓度的 VCP-IS-2Na 处理的黑色素瘤细胞和用 100 μM浓度的 VCP-IS-2Na 处理的黑色素细胞的黑色素合成分别减少到未处理细胞的 23% 和 52%，但细胞活力未受影响。VCP-IS-2Na 还能显著抑制黑色素瘤细胞和黑色素细胞的细胞酪氨酸酶活性。通过对色素沉着的宏观和微观观察以及黑色素的定量测量，评估了人体皮肤模型中黑色素的合成情况。用 1.0% VCP-IS-2Na 处理人体皮肤模型不会抑制细胞的活力，而黑色素的合成却减少到对照组的 21%。相比之下，<小>L抗坏血酸（VC）和 VCP-Na 似乎并不抑制黑色素的合成和细胞酪氨酸酶的活性。这些结果表明，VCP-IS-2Na 可能是一种有效的皮肤美白剂，我们期待着 VCP-IS-2Na 在化妆品行业中的应用。

  DOI：

  10.1248/cpb.56.292
• 作为产物：
  描述：

  2-(4,4-二甲基戊烷-2-基)-5,7,7-三甲基-辛烷-1-醇 在 三乙胺 、 三氯氧磷 作用下， 以 甲苯 为溶剂， 反应 12.0h， 生成 isostearyl dichlorophosphate
  参考文献：
  名称：

  ASCORBIC ACID DERIVATIVES AND SKIN-WHITENING COSMETICS

  摘要：

  公开号：

  EP1666484B1

文献信息

• Permeation and Metabolism of a Novel Ascorbic Acid Derivative, Disodium Isostearyl 2-O-&lt;i&gt;L&lt;/i&gt;-Ascorbyl Phosphate, in Human Living Skin Equivalent Models
  作者：H. Shibayama、M. Hisama、S. Matsuda、M. Ohtsuki

  DOI：10.1159/000139128

  日期：——

  A novel amphiphilic vitamin C (VC) derivative, disodium isostearyl 2-O-<i>L</i>-ascorbyl phosphate (VCP-IS-2Na), which possesses a C₁₈ alkyl chain attached to a stable ascorbate derivative, sodium <i>L</i>-ascorbic acid 2-phosphate (VCP-Na), was evaluated as a topical prodrug of VC with transdermal activity in human living skin equivalent (LSE) models. The permeation assay used was EPI-606X in the Franz-type diffusion cell system. VCP-IS-2Na exhibited much better permeability than VC and VCP-Na. The accumulation assays applied were EPI-200X and LSE-high by the dynamic system. The increased skin accumulation of VCP-IS-2Na was superior to that of VCP-Na and VC. VCP-IS-2Na that is susceptible to enzymatic hydrolysis by esterase and/or phosphatase released VC in the skin. Measurement of the metabolites that permeated and accumulated from the skin model suggested that VCP-IS-2Na was mainly metabolized via VCP-Na to VC in EPI-606X and EPI-200X, while it was mainly metabolized directly to VC in TESTSKIN LSE-high. Thus, these characteristics indicate that the novel VC derivative, VCP-IS-2Na, may be advantageous as a readily available source of VC for skin care applications.

  一种新型两性维生素C（VC）衍生物，二钠异硬脂基2-O- L -抗坏血酸磷酸酯（VCP-IS-2Na），其具有连接到稳定抗坏血酸衍生物的C 18 烷基链，即钠 L -抗坏血酸2-磷酸酯（VCP-Na），在人类活体皮肤等效模型中评估为VC的局部前药，并具有透皮活性。渗透实验采用EPI-606X在弗兰茨型扩散池系统中。VCP-IS-2Na的渗透性远远优于VC和VCP-Na。应用的积累实验是EPI-200X和LSE-high通过动态系统。VCP-IS-2Na在皮肤中的积累增加优于VCP-Na和VC。易受酯酶和/或磷酸酶水解的VCP-IS-2Na在皮肤中释放VC。从皮肤模型中渗透和积累的代谢物的测量表明，在EPI-606X和EPI-200X中，VCP-IS-2Na主要通过VCP-Na代谢为VC，而在TESTSKIN LSE-high中主要直接代谢为VC。因此，这些特性表明，这种新型VC衍生物VCP-IS-2Na可能作为皮肤护理应用的易得VC来源具有优势。
• Ascorbic acid derivatives and skin-whitening cosmetics
  申请人：Shibayama Hiroharu

  公开号：US20060264407A1

  公开（公告）日：2006-11-23

  It is an object to provide an L-ascorbic acid derivative which can keep the L-ascorbic acid stable to heat and light and thus has a long shelf life, which is high in permeability into the skin, which can be quickly hydrolyzed by phosphatase, an enzyme that is ubiquitous in vivo, and which exhibits physiological activities that are inherent to L-ascorbic acid and beneficial to health, a method for producing such an L-ascorbic acid derivative, and a skin-whitening cosmetic material. There is provided an ascorbic acid derivative comprising an L-ascorbic acid-2-phosphate ester or a salt thereof wherein the phosphate ester has a branched alkyl group, the L-ascorbic acid-2-phosphate ester being of formula [13]. The ascorbic acid derivative is produced by a method comprising reacting a branched alkanol with phosphorus oxychloride to synthesize monoalkyldichlorophosphate or dialkylmonochlorophosphate, reacting the thus obtained substance with 5,6-O-isopropylidene-L-ascorbic acid obtained by reacting L-ascorbic acid with acetone, and subjecting the thus obtained substance to acid hydrolysis. There is also provided a cosmetic material containing such an ascorbic acid derivative by 0.05 to 80 percent by weight. (wherein each of R 1 and R 2 is a hydrogen (H) atom or an alkyl group having branches and including 3 to 30 carbon atoms, but not both of R 1 and R 2 are hydrogen (H) atoms)

  本发明旨在提供一种L-抗坏血酸衍生物，该衍生物可以使L-抗坏血酸在热和光下保持稳定性，因此具有长时间的保质期，其渗透性高，可以快速被磷酸酶水解，磷酸酶是普遍存在于体内的酶，并且具有固有于L-抗坏血酸的生理活性和有益于健康的功效，以及生产这种L-抗坏血酸衍生物的方法和美白皮肤的化妆品材料。提供一种抗坏血酸衍生物，包括L-抗坏血酸-2-磷酸酯或其盐，其中磷酸酯具有支链烷基，L-抗坏血酸-2-磷酸酯的化学式为[13]。通过将支链醇与氧化氯磷反应合成单烷基二氯磷酸酯或双烷基单氯磷酸酯，将所得物质与通过将L-抗坏血酸与丙酮反应得到的5,6-O-异丙基-L-抗坏血酸反应，并将所得物质进行酸水解制备出该抗坏血酸衍生物。还提供了一种化妆品材料，其中包含0.05至80重量百分比的抗坏血酸衍生物。（其中R1和R2中的每一个是氢（H）原子或具有分支的烷基，包括3至30个碳原子，但R1和R2中不同时存在氢（H）原子）
• Sensors and sensor arrays of conducting and insulating composites and methods of use thereof
  申请人：Lewis S. Nathan

  公开号：US20050263394A1

  公开（公告）日：2005-12-01

  The present invention provides a class of sensors prepared from at least a first material having a positive temperature coefficient of resistance and a second non-conductive or insulating material compositionally different than the first material that show an increase sensitivity detection limit for polar and non-polar analytes. The sensors have applications in the detection of analytes in the environment, associated with diseases and microorganisms.

  本发明提供了一类至少由具有正电阻温度系数的第一种材料和成分不同于第一种材料的第二种非导电或绝缘材料制备而成的传感器，这些传感器对极性和非极性分析物的灵敏度检测限均有所提高。这些传感器可用于检测环境中与疾病和微生物有关的分析物。
• Sensor arrays for detecting analytes in fluids
  申请人：Lewis S. Nathan

  公开号：US20060034731A1

  公开（公告）日：2006-02-16

  The disclosure provides methods, apparatuses and expert systems for detecting analytes in fluids. The apparatuses include a chemical sensor comprising first and second conductive elements (e.g. electrical leads) electrically coupled to and separated by a sensing area comprising a chemically sensitive resistor which provides an electrical path between the conductive elements.

  本公开提供了用于检测流体中分析物的方法、装置和专家系统。这些装置包括一个化学传感器，该传感器由第一和第二导电元件（如导线）组成，这两个导电元件电耦合到一个传感区域并被该传感区域隔开，该传感区域由一个化学敏感电阻器组成，该电阻器在导电元件之间提供一条电通路。
• US6387329B1
  申请人：——

  公开号：US6387329B1

  公开（公告）日：2002-05-14