α-hydroxymyristic acid | 67253-09-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: α-hydroxymyristic acid
• 英文别名: (S)-α-hydroxymyristic acid；alpha-Hydroxy myristic acid；(2S)-2-hydroxytetradecanoic acid
• CAS: 67253-09-2
• 化学式: C₁₄H₂₈O₃
• 分子量: 244.375
• InChiKey: JYZJYKOZGGEXSX-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  17
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  肉豆蔻酸 在 cytochrome P₄₅₀ peroxygenase CYP₁₅₂N₁ ferric form 作用下， 以 aq. phosphate buffer 为溶剂， 反应 0.02h， 以91%的产率得到
  参考文献：
  名称：

  由细胞色素P450过氧化酶催化的脂肪酸的α-氧化脱羧反应，产生较短的烷基链脂肪酸†

  摘要：

  属于CYP152家族的细胞色素P450过氧化酶使用H 2 O 2催化脂肪酸的氧化。CYP152N1从隔离微小杆菌属菌。AT1b在生理H 2 O 2浓度下专门催化肉豆蔻酸的α-选择性羟基化。但是，通过增加H 2 O 2（1-10 mM）的浓度，由肉豆蔻酸产生了一系列短链烷基脂肪酸，例如十三烷酸。由肉豆蔻酸得到的十三烷酸的收率达到17％。一个18O标记的氧化剂研究表明CYP152N1催化α-羟基肉豆蔻酸的过氧化反应形成α-酮麦芽酸，然后H 2 O 2自发分解生成十三烷酸。CYP152N1的晶体结构分析显示，它与其他CYP152家族酶（例如CYP152A1和CYP152B1）具有高度相似性。CYP152N1中容纳的α-羟基肉豆蔻酸的MD模拟提出了α-羟基肉豆蔻酸可能用于脱羧反应的预氧化构象。

  DOI：

  10.1039/c7cy02263h

文献信息

• Acylated glycerides useful in low calorie fat-containing food compositions
  申请人：THE PROCTER & GAMBLE COMPANY

  公开号：EP0184259A2

  公开（公告）日：1986-06-11

  alpha-Acylated glycerides having the formula: wherein each R' is a C10-C14 alkyl group and wherein each R2 is a C14-C16 aliphatic group are disclosed. These alpha-acylated glycerides are useful as non-digestible fats in low calorie fat-containing food compositions.

  本发明公开了具有以下式子的α-酰化甘油酯：其中每个 R' 是一个 C10-C14 烷基，每个 R2 是一个 C14-C16 脂肪族基团。 这些α-酰化甘油酯可用作含低热量脂肪的食品组合物中的非消化脂肪。
• Use of aldehydes formulated with nanoparticles and/or nanoemulsions to enhance disease resistance of plants to liberibacters
  申请人：UNIVERSITY OF FLORIDA RESEARCH FOUNDATION, INC.

  公开号：US10772326B2

  公开（公告）日：2020-09-15

  Methods and compositions based upon natural phenolic aromatic aldehydes (ex: cinnamaldehyde, benzaldehyde) are provided, which find use as curing agents for systemic bacterial infections of living plants, in particular against Gram negative bacteria and more particularly species of Liberibacter, including Ca. Liberibacter asiaticus. The curing agent compositions described are used synergistically with other antimicrobial compounds, such as those that plants manufacture or release as a result of biotic or abiotic stresses, including the application of the subject aldehydes, certain proteins, whether produced by recombinant methods or not, nanoparticles, nanoemulsions, or by natural essential oils such as carvacrol or allicin. The aromatic aldehydes have high volatility and exhibit phytotoxicity when applied above certain amounts. Systemic infections and infestations of a variety of plant parts can be treated, including those of leaves and roots. Methods of applying the compositions for agriculture use are disclosed.

  提供了基于天然酚类芳香醛（例如：肉桂醛、苯甲醛）的方法和组合物，可用作活体植物系统性细菌感染的固化剂，特别是针对革兰氏阴性细菌，尤其是自由杆菌的种类，包括Ca.asiaticus）。所述固化剂组合物可与其他抗微生物化合物协同使用，例如植物在生物或非生物胁迫下制造或释放的化合物，包括应用所述醛类、某些蛋白质（无论是否通过重组方法生产）、纳米颗粒、纳米乳液或天然精油（如香芹酚或大蒜素）。芳香醛具有高挥发性，施用超过一定量时会产生植物毒性。可以治疗多种植物部位的系统感染和侵染，包括叶片和根部的感染和侵染。此外，还公开了用于农业用途的组合物的施用方法。
• Topical compositions of urea and ammonium lactate
  申请人：Arkin Moshe

  公开号：US20050037040A1

  公开（公告）日：2005-02-17

  Pharmaceutical, cosmetic and cosmeceutical compositions for topical application, containing, as active ingredients, urea and/or derivatives thereof and alpha-hydroxy acid and/or an ammonium salt thereof, such as ammonium lactate, processes of manufacturing same and use of same in the treatment of medical and cosmetic skin and scalp conditions.

  用于局部应用的药物、化妆品和药妆组合物，作为活性成分，含有尿素和/或其衍生物以及α-羟基酸和/或其铵盐，如乳酸铵，其生产工艺以及在治疗医疗和美容皮肤和头皮疾病中的用途。
• Glycolipids and analogues thereof as antigens for NK T cells
  申请人：Tsuji Moriya

  公开号：US20060211856A1

  公开（公告）日：2006-09-21

  This invention relates to immunogenic compounds which may serve as ligands for NKT (natural killer T) cells and to methods of use thereof in modulating immune responses.

  本发明涉及可作为 NKT（自然杀伤 T）细胞配体的免疫原性化合物及其用于调节免疫反应的方法。
• Crystal Structure of H2O2-dependent Cytochrome P450SPα with Its Bound Fatty Acid Substrate
  作者：Takashi Fujishiro、Osami Shoji、Shingo Nagano、Hiroshi Sugimoto、Yoshitsugu Shiro、Yoshihito Watanabe

  DOI：10.1074/jbc.m111.245225

  日期：2011.8

  Cytochrome P450(SP alpha) (CYP152B1) isolated from Sphingomonas paucimobilis is the first P450 to be classified as a H2O2-dependent P450. P450(SP alpha) hydroxylates fatty acids with high alpha-regioselectivity. Herein we report the crystal structure of P450(SP alpha) with palmitic acid as a substrate at a resolution of 1.65 angstrom. The structure revealed that the C-alpha of the bound palmitic acid in one of the alternative conformations is 4.5 angstrom from the heme iron. This conformation explains the highly selective alpha-hydroxylation of fatty acid observed in P450(SP alpha). Mutations at the active site and the F-G loop of P450(SP alpha) did not impair its regioselectivity. The crystal structures of mutants (L78F and F288G) revealed that the location of the bound palmitic acid was essentially the same as that in the WT, although amino acids at the active site were replaced with the corresponding amino acids of cytochrome P450(BS alpha) (CYP152A1), which shows beta-regioselectivity. This implies that the high regioselectivity of P450(SP alpha) is caused by the orientation of the hydrophobic channel, which is more perpendicular to the heme plane than that of P450(BS alpha)