12-甲基十三烷酸 | 2724-57-4

• 物质功能分类: 分析化学 - 食品安全 - 脂肪酸、脂肪酸甲酯
• 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: 12-甲基十三烷酸
• 中文别名: 12-甲基十三酸
• 英文名称: isomyristic acid
• 英文别名: 12-methyltridecanoic acid；12-Methyltridecansaeure
• CAS: 2724-57-4
• 化学式: C₁₄H₂₈O₂
• mdl: MFCD00083433
• 分子量: 228.375
• InChiKey: YYVJAABUJYRQJO-UHFFFAOYSA-N

物化性质

• 熔点：
  53.3-53.6 °C
• 沸点：
  320.89°C (estimate)
• 密度：
  0.8577 (rough estimate)
• 溶解度：
  可溶于DMSO
• 物理描述：
  Solid
• 保留指数：
  2657
• 稳定性/保质期：
  存在于烟叶中。

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  16
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.928
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2915900090
• 储存条件：
  2-8°C

制备方法与用途

合成制备方法

1. 烟草：18。

反应信息

• 作为反应物：
  描述：

  12-甲基十三烷酸 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以90%的产率得到12-甲基-十三醇
  参考文献：
  名称：

  Biotechnological Production of Methyl-Branched Aldehydes

  摘要：

  A number of methyl-branched aldehydes impart interesting flavor impressions, and especially 12-methyltridecanal is a highly sought after flavoring compound for savory foods. Its smell is reminiscent of cooked meat and tallow. For the biotechnological production of 12-methyltridecanal, the literature was screened for fungi forming iso-fatty acids. Suitable organisms were identified and successfully grown in submerged cultures. The culture medium was optimized to increase the yields of branched fatty acids. A recombinant carboxylic acid reductase was used to reduce 12-methyltridecanoic acid to 12-methyltridecanal. The efficiency of whole-cell catalysis was compared to that of the purified enzyme preparation. After lipase catalyzed hydrolysis of the fungal lipid extracts, the released fatty acids were converted to the corresponding aldehydes, including 12-methyltridecanal and 12-methyltetradecanal.

  DOI：

  10.1021/acs.jafc.6b04793
• 作为产物：
  描述：

  magnesium,2-methylbutane,bromide 在 乙醚 、 三溴化磷 作用下， 生成 12-甲基十三烷酸
  参考文献：
  名称：

  Fordyce; Johnson, Journal of the American Chemical Society, 1933, vol. 55, p. 3371

  摘要：

  DOI：

文献信息

• Convergent Synthesis of Calcium-Dependent Antibiotic CDA3a and Analogues with Improved Antibacterial Activity via Late-Stage Serine Ligation
  作者：Delin Chen、Kathy Hiu Laam Po、Pilar Blasco、Sheng Chen、Xuechen Li

  DOI：10.1021/acs.orglett.0c01544

  日期：2020.6.19

  A convergent synthesis via the late-stage serine ligation of naturally occurring calcium-dependent antibiotic CDA3a and its analogues has been developed, which allowed us to readily synthesize the analogues with the variation on the lipid tail. Some analogues were found to show 100–500-fold higher antimicrobial activity than the natural compound CDA3a against drug resistant bacteria. This study will

  已经开发了通过后期丝氨酸连接天然存在的钙依赖性抗生素CDA3a及其类似物的聚合合成方法，这使我们能够容易地合成具有脂质尾巴变异的类似物。发现某些类似物对天然抗药性细菌的抗菌活性比天然化合物CDA3a高100-500倍。这项研究将增进我们对CDA3a的了解，并为进一步开发提供有价值的抗菌先导候选物。
• Process for preparing polyol esters
  申请人：Adamzik Michael

  公开号：US20110087045A1

  公开（公告）日：2011-04-14

  The present invention relates to a process for preparing polyol esters by reacting polyols with linear or branched aliphatic monocarboxylic acids having 3 to 20 carbon atoms by partial recycling of the aliphatic monocarboxylic acid removed into the esterification reaction or into subsequent esterification batches.

  本发明涉及一种通过将多元醇与具有3至20个碳原子的线性或支链脂肪族一元羧酸反应，通过将从酯化反应中去除的脂肪族一元羧酸部分回收到酯化反应或随后的酯化批次中制备聚醇酯的方法。
• PROCESS FOR PREPARING POLYOL ESTERS
  申请人：Frey Guido D.

  公开号：US20120190883A1

  公开（公告）日：2012-07-26

  The present invention relates to a process for preparing polyol esters by reacting polyols with linear or branched aliphatic monocarbocxylic acids having 3 to 20 carbon atoms, the reaction taking place in the presence of a Lewis acid comprising at least one element from groups 4 to 14 of the Periodic Table of the Elements as catalyst, and in the presence of an adsorbent, the reaction product being subjected subsequently to a steam treatment.

  本发明涉及一种通过将多元醇与具有3至20个碳原子的直链或支链脂肪族单羧酸反应制备聚醇酯的方法，其中反应在存在作为催化剂的周期表元素4至14族中至少一个元素的路易斯酸和吸附剂的情况下进行，并且随后将反应产物进行蒸汽处理。
• Structure-antitumor Activity Relationship of Semi-synthetic Spicamycin Derivatives.
  作者：TERUYUKI SAKAI、HIROYUKI KAWAI、MASARU KAMISHOHARA、ATSUO ODAGAWA、AKASHI SUZUKI、TAKESHI UCHIDA、TOMIKO KAWASAKI、TAKASHI TSURUO、NOBORU OTAKE

  DOI：10.7164/antibiotics.48.1467

  日期：——

  New derivatives of spicamycin modified at the fatty acid moieties of the molecule were synthesized and their structure-activity relationships were examined. The antitumor activity was greatly influenced by modification of the fatty acid moieties to tetradecadienoyl or dodecadienoyl analogues exhibiting better antitumor activity against COL-1 human colon cancer xenograft than SPM VIII.

  新合成了一系列在分子脂肪酸部分进行了修饰的斯匹卡霉素衍生物，并研究了它们的构效关系。通过对脂肪酸部分进行修饰，将其转化为十四碳二烯酸或十二碳二烯酸类似物，这些衍生物对COL-1人结肠癌异种移植模型的抗肿瘤活性显著优于SPM VIII。
• Method for Producing Polyol Esters
  申请人：OXEA GmbH

  公开号：US20150344400A1

  公开（公告）日：2015-12-03

  A process for preparing polyol esters by reacting polyols with linear or branched aliphatic monocarboxylic acids having 3 to 20 carbon atoms, is characterized in that a mixture of the starting compounds is allowed to react in the presence of a Lewis acid containing at least one element of groups 4 to 14 of the periodic table of the elements as a catalyst and in the presence of an adsorbent with removal of the water formed, and then the crude ester obtained is aftertreated by adding a further adsorbent which is an acidic activated carbon having a pH of 1 to 6.5.

  通过将具有3至20个碳原子的线性或支链脂肪族一元羧酸与多元醇反应来制备聚醇酯的方法，其特征在于允许起始化合物的混合物在含有周期表元素4至14族中至少一个元素的路易斯酸存在下反应，并在吸附剂的存在下去除生成的水，然后通过添加具有pH值为1至6.5的酸性活性碳的进一步吸附剂对得到的粗酯进行后处理。