赤式-9,10-二羟基十八烷酸 | 3639-32-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 赤式-9,10-二羟基十八烷酸
• 英文名称: erythro-9,10-dihydroxystearic acid
• 英文别名: (+/-)-erythro-9,10-Dihydroxy-octadecansaeure；(+/-)-erythro-9.10-Dihydroxy-stearinsaeure；erythro-9,10-dihydroxyoctadecanoic acid；9R,10S-dihydroxy-stearic acid；(9R,10S)-9,10-dihydroxyoctadecanoic acid
• CAS: 3639-32-5
• 化学式: C₁₈H₃₆O₄
• 分子量: 316.481
• InChiKey: VACHUYIREGFMSP-DLBZAZTESA-N

物化性质

• 熔点：
  90.0 °C

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  22
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  9,10-二羟基硬脂酸	Dihydroxystearic Acid	120-87-6	C18H36O4	316.481
  9,10-二羟基十八烷酸	threo-9,10-dihydroxyoctadecanoic acid	2391-05-1	C18H36O4	316.481
  9,10-二羟基十六烷酸	9,10-dihydroxy-hexadecanoic acid	29242-09-9	C16H32O4	288.428
  ——	(Z)-(9S,10R)-9,10-dihydroxyoctadec-12-enoic acid	125356-87-8	C18H34O4	314.466
  辛二酸	Suberic acid	505-48-6	C8H14O4	174.197
  反式-9,10-环氧十八烷酸	9,10-epoxystearic acid	2443-39-2	C18H34O3	298.466
  外消旋反式-9,10-环氧硬脂酸	trans-9,10-epoxystearic acid	13980-07-9	C18H34O3	298.466
  ——	10-hydroxy-9-oxo-octadecanoic acid	13985-42-7	C18H34O4	314.466
  ——	9-hydroxy-10-oxooctadecanoic acid	13985-41-6	C18H34O4	314.466
  ——	(Z)-9,10-epoxyoctadecanoic acid methyl ester	2566-91-8	C19H36O3	312.493
• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  9,10-二羟基十八烷酸	threo-9,10-dihydroxyoctadecanoic acid	2391-05-1	C18H36O4	316.481
  ——	(+/-)-erythro-Octadecan-1,9,10-triol	——	C18H38O3	302.498
  壬二酸	azelaic acid	123-99-9	C9H16O4	188.224
  壬酸	nonanoic acid	112-05-0	C9H18O2	158.241
  辛二酸	Suberic acid	505-48-6	C8H14O4	174.197
  辛酸	Octanoic acid	124-07-2	C8H16O2	144.214
  9-氧代壬酸	azelaic acid semialdehyde	2553-17-5	C9H16O3	172.224
  ——	cis-9,10-epoxystearic acid	24560-98-3	C18H34O3	298.466
  ——	10-hydroxy-9-oxo-octadecanoic acid	13985-42-7	C18H34O4	314.466
  ——	9-hydroxy-10-oxooctadecanoic acid	13985-41-6	C18H34O4	314.466

反应信息

• 作为反应物：
  描述：

  赤式-9,10-二羟基十八烷酸 在 氢氧化钾 作用下， 生成 9-ketoheptadecylic acid
  参考文献：
  名称：

  强碱中的有机反应-III：酮酸和羟基酸的裂变

  摘要：

  用合适的脂肪酸衍生物进行的研究澄清了醇和酮在浓碱中的许多反应。

  DOI：

  10.1016/0040-4020(60)80033-6
• 作为产物：
  描述：

  油酸甲酯 在 四氧化锇 、 N-甲基吗啉氧化物 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 、 丙酮 、 叔丁醇 为溶剂， 反应 36.0h， 生成 赤式-9,10-二羟基十八烷酸
  参考文献：
  名称：

  长链天然脂肪酸二羟基化衍生物胶凝能力的结构和溶解度参数相关性

  摘要：

  在不同距离尺度上建立结构-特性的相互关系是合理设计分子胶凝剂的重要挑战之一。在此，作为三种液体的胶凝剂，研究了源自三种天然分子（油酸，芥酸和蓖麻油酸）的一系列长链脂肪酸的二羟基化衍生物。关于组成哪种（或更少！）高效胶凝剂的结论是基于对各种热，结构，分子模型和流变学结果的分析得出的。凝胶剂在纯净固体或凝胶态下分子堆积方式与液体汉森溶解度数据之间的相关性得出以下结论：二醇立体化学，将两个羟基隔开的碳原子数，链烷烃的长度和链长是控制这些胶凝剂凝胶形成效率的最重要的结构参数。一些二醇胶凝剂的效率甚至比著名的出色胶凝剂更有效，R）-12-羟基硬脂酸; 其他人则更糟。沿着烷基链形成广泛的分子间氢键网络的能力似乎在促进纤维生长并因此而胶凝中起着关键作用。总而言之，结果证明了如何通过非常小的结构变化来调节凝胶的效率，并且还提出了如何利用其他结构修饰来产生有效的凝胶剂。

  DOI：

  10.1002/chem.201500096

文献信息

• Prilezhaev Dihydroxylation of Olefins in a Continuous Flow Process
  作者：Bas A. M. W. van den Broek、René Becker、Florian Kössl、Mariëlle M. E. Delville、Pieter J. Nieuwland、Kaspar Koch、Floris P. J. T. Rutjes

  DOI：10.1002/cssc.201100342

  日期：2012.2.13

  Epoxidation of both terminal and non‐terminal olefins with peroxy acids is a well‐established and powerful tool in a wide variety of chemical processes. In an additional step, the epoxide can be readily converted into the corresponding trans‐diol. Batch‐wise scale‐up, however, is often troublesome because of the thermal instability and explosive character of the peroxy acids involved. This article

  过氧酸将末端和非末端烯烃都进行环氧化，这在各种化学过程中都是公认的功能强大的工具。在另一个步骤中，环氧化物可以轻松转化为相应的反式二醇。但是，由于所涉及的过氧酸的热不稳定性和爆炸性，因此分批放大通常会很麻烦。本文介绍了一种连续流工艺的设计和半自动化优化，以及以本质安全的方式随后扩大到制备型生产量的方法。
• The use of thiophen as a chain-extender. Part IV. Synthetic dihydroxyacids
  作者：J. F. McGhie、W. A. Ross、D. H. Laney、J. M. Barker

  DOI：10.1039/j39680000001

  日期：——

  ecanoic, 5,6-dihydroxy-12-methyltetradecanoic, 5,6-dihydroxytetradecanedioic, 7,8-dihydroxyhexadecanedioic, and 9,10-dihydroxyoctadecanedioic acid by the desulphurisation of suitable substituted thiophens is described. The preparation of some derivatives of these acids is also described.

  4,5-二羟基十三烷酸，5,6-二羟基十四烷酸，9,10-二羟基十八烷酸，5,6-二羟基-12-甲基十三烷酸，5,6-二羟基-12-甲基十四烷酸，5,6-二羟基十四烷二酸，7,8的合成描述了通过合适的取代噻吩的脱硫而生成的-二羟基十六烷二酸和9，10-二羟基十八烷二酸。还描述了这些酸的一些衍生物的制备。
• The influence of pharmacy staff in non-prescription medicine sales
  作者：Lynne Emmerton、John Shaw

  DOI：10.1111/j.2042-7174.2002.tb00594.x

  日期：2011.2.22

  To monitor sales of non-prescription medicines from pharmacies in New Zealand, and report specifically on the involvement and influence of pharmacy staff.

  Purchasers of non-prescription medicines were interviewed in-store immediately following their purchase. A brief structured questionnaire was used to record current and previous medicine purchases, influences on first-time purchases and demographic descriptors. Non-intrusive observational data were collected where possible in the case of non-response.

  Data were collected in 12 pharmacies in New Zealand during winter 1999. Pharmacies were selected to approximate the population distribution, and had a range of sizes and practice settings. Interviews took place over five consecutive days in each pharmacy.

  The recorded purchases totalled 2,597 (69–397 per pharmacy), representing 71.2 per cent of observed medicine sales. Some two-thirds of all medicines had been purchased on a previous occasion. In two-thirds of sales, pharmacy assistants provided consultation with no pharmacist input. Two-thirds of purchases were for a pre-determined brand, and consultation occurred less frequently when these were self-selected from the shelf. Involvement by pharmacy staff was particularly noted when a change of brand occurred, when a desired brand was sought from staff, and when no particular brand was sought. For first-time purchases, the influence of pharmacy staff (62.2 per cent of all influences recorded) dominated that of family and friends (15.5 per cent).

  Pharmacy staff play an active role in non-prescription medicine sales, despite most purchases apparently being straightforward in nature. Guidelines for appropriate product selection and advice are particularly important when training pharmacy assistants.

  摘要 目标 监测新西兰药房非处方药品的销售情况，特别关注药房工作人员的参与和影响。 方法 在购买非处方药品后，立即在店内对购买者进行采访。使用简短的结构化问卷记录当前和以前的药品购买情况，首次购买的影响因素以及人口统计描述符。在无响应情况下，尽可能收集非侵入式的观察数据。 背景 1999年冬季，在新西兰的12家药房收集数据。选择药房以接近人口分布，并具有各种规模和实践设置。每家药房连续五天进行采访。 主要发现 记录的购买总数为2,597（每家药房69-397个），占观察到的药品销售的71.2％。大约三分之二的药品曾经被购买过。在三分之二的销售中，药房助理提供咨询，没有药剂师的参与。三分之二的购买是为预定品牌，当这些品牌从货架上自选时，咨询发生的频率较低。当更换品牌时，寻求员工提供所需品牌以及不寻求特定品牌时，特别注意药房工作人员的参与。对于首次购买，药房工作人员的影响（记录的所有影响中占62.2％）主导了家人和朋友的影响（占15.5％）。 结论 尽管大多数购买显然是简单的，但药房工作人员在非处方药销售中发挥着积极作用。在培训药房助理时，适当产品选择和建议的准则尤为重要。
• Insights into gold-catalyzed synthesis of azelaic acid
  作者：Anna Kulik、Andreas Martin、Marga-Martina Pohl、Christine Fischer、Angela Köckritz

  DOI：10.1039/c3gc41822g

  日期：——

  A novel green route for the synthesis of azelaic and pelargonic acid via aerobic gold-catalyzed cleavage of 9,10-dihydroxystearic acid (DSA) was investigated recently. In this study, the examination of the reaction mechanism is described. The results of the application of 18O-labeled molecular oxygen and sodium hydroxide as well as of diastereomeric pure erythro- and threo-DSA were discussed. Assumed

  最近研究了通过好氧金催化的9,10-二羟基硬脂酸（DSA）裂解合成壬二酸和壬酸的一种新的绿色途径。在这项研究中，描述了反应机理的检查。讨论了18 O标记的分子氧和氢氧化钠以及非对映体纯的赤型和苏型DSA的应用结果。假定合成了反应中间体，并使其经受与DSA相同的反应条件。作为从所得数据得出的结论，推测了氧化脱氢机理。另外，探索了在不同储存条件下使用的金催化剂的老化。
• Lower Extremity Blood Flow in Healthy Men: Effect of Smoking, Cholesterol, and Physical Activity — A Doppler Study
  作者：Lilja Petra Ásgeirsdóttir、Uggi Agnarsson、Guomundur S. Jónsson

  DOI：10.1177/000331970105200701

  日期：2001.7

  Tobacco smoking is one of the principal risk factors of peripheral arterial disease (PAD); choles terol level has a lesser impact. The effect of leisure-time physical activity (LTPA) has not been studied in depth. The aim of this study was to determine the relative effects of smoking, total cholesterol, and leisure-time physical activity on blood flow parameters in the lower extremi ties of healthy middle-aged men with no prior symptoms or diagnosis of PAD.

  The authors examined 130 men, aged 40-65 years, free of known arterial disease and hypertension. The men had either a total cholesterol concentration of <5.7 or > 7.0 mmol/L, and were either smokers or nonsmokers. LTPA was addressed by a questionnaire. Ankle-brachial index (ABI) was calculated and Doppler examination of the femoral artery was performed before and after an exercise test.

  Tobacco smoking related significantly to abnormal ABI and Doppler results (odds ratio [OR] 2.42) while the total cholesterol level did not. LTPA had a favorable effect (OR 0.51). Abnormal ABI response was greatest in smokers with high total cholesterol (p < 0.01).

  Tobacco smoking is a significant risk factor for abnormal ABI response and blood flow abnormalities in healthy men. Regular physical activity has a measurable protective effect. An abnormal ABI suggests early atherosclerosis and indicates risk factor assessment and physician intervention.

  吸烟是外周动脉疾病（PAD）的主要危险因素之一；胆固醇水平的影响较小。休闲时间的体育活动（LTPA）的影响尚未深入研究。本研究旨在确定吸烟、总胆固醇和休闲时间体育活动对未出现PAD症状或诊断的健康中年男性下肢血流参数的相对影响。 作者研究了130名40-65岁的男性，他们没有已知的动脉疾病和高血压。这些男性的总胆固醇浓度要么小于5.7毫摩尔/升，要么大于7.0毫摩尔/升，他们要么吸烟要么不吸烟。通过问卷调查了休闲时间体育活动。计算了踝臂指数（ABI），并在运动测试前后对股动脉进行多普勒检查。 吸烟与ABI和多普勒结果异常显著相关（比值比[OR] 2.42），而总胆固醇水平则没有。LTPA具有有利影响（OR 0.51）。吸烟者中总胆固醇高的人ABI反应异常最严重（p <0.01）。 吸烟对健康男性的ABI反应异常和血流异常是一个重要的危险因素。定期的体育活动具有可测量的保护作用。异常的ABI表明早期动脉粥样硬化，并提示风险因素评估和医师干预。