3-羟基壬酸 | 33796-87-1

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物 - 无环羧酸
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 中文名称: 3-羟基壬酸
• 中文别名: (R)-3-羟基壬酸
• 英文名称: (R)-3-hydroxynonanoic acid
• 英文别名: 3-hydroxynonanoic acid；(R)-3-hydroxy-nonanoic acid；rechtsdrehende β-Oxy-pelargonsaeure；(R)-3-Hydroxy-nonansaeure；D-3-Hydroxy-pelargonsaeure；D-3-Hydroxy-nonansaeure；(3R)-3-hydroxynonanoic acid
• CAS: 33796-87-1
• 化学式: C₉H₁₈O₃
• 分子量: 174.24
• InChiKey: XBUXARJOYUQNTC-MRVPVSSYSA-N

物化性质

• LogP：
  1.519 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2918199090

反应信息

• 作为反应物：
  描述：

  3-羟基壬酸 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 4.0h， 生成 (R)-(-)-1,3-壬烷二醇
  参考文献：
  名称：

  Application of microbial enantiofacially selective hydrolysis in natural product synthesis

  摘要：

  Pichinia farinosa IAM 4682 mediated enantiofacially selective hydrolysis worked efficiently (65-70% yield) on the interface-bioreactor in a reproducible manner, which established the product, (R)-2-benzylcyclohexanone (84-87%e.e.), to be the starting material for the synthesis of optically active natural products. Methyl (R)3-hydroxy-12- methyltridecanoate. a constituent of lipopolysaccharide, and (R)-1,3-nonanediol, a secretion of cucumber fly, were synthesized via this common intermediate, of which the optically active secondary alcohol moiety was derived from the above chiral ketone by Baeyer-Villiger oxidation. Final products were enantiomerically enriched to 94-95% e.e., by the lipase-mediated enantioselective transesterification which could remove the minor enantiomer as the corresponding acetate.

  DOI：

  10.1016/s0957-4166(00)86269-2
• 作为产物：
  描述：

  蓖麻油酸 在 臭氧 作用下， 生成 3-羟基壬酸
  参考文献：
  名称：

  Matthes; Kuerschner, Archiv der Pharmazie, 1931, p. 92,104

  摘要：

  DOI：

文献信息

• ESTERS AND AMIDES AS PLA2 INHIBITORS
  申请人：——

  公开号：US20020019416A1

  公开（公告）日：2002-02-14

  1 The present invention relates to a novel fatty acid derivative of formula (I), wherein R 1 is acyl group; R 2 is acyl(lower)alkyl; R 3 is hydrogen, aryl(lower)alkyl, etc.; R 4 is acyl(lower)alkyl; and X is —O—, —NH— or formula (II) [wherein R 5 is lower alkyl, etc.]; and a pharmaceutically acceptable salt thereof, which is useful as a medicament; the processes for the preparation of said fatty acid derivative or a salt thereof; a pharmaceutical composition comprising said fatty acid derivative or a pharmaceutically acceptable salt thereof; etc.

  本发明涉及一种新颖的脂肪酸衍生物，其化学式为（I），其中R1是酰基；R2是酰基（较低）烷基；R3是氢，芳基（较低）烷基等；R4是酰基（较低）烷基；X为—O—，—NH—或化学式（II）[其中R5为较低烷基等]；及其药学上可接受的盐，可用作药物；制备所述脂肪酸衍生物或其盐的方法；包含所述脂肪酸衍生物或其药学上可接受的盐的药物组合物等。
• Process for producing optically active 3-halogenocarboxylic acid ester and 3-azidocarboxylic acid ester
  申请人：——

  公开号：US20030225301A1

  公开（公告）日：2003-12-04

  A process for producing an optically active 3-azide-carboxylic acid ester by reacting an optically active 3-hydroxycarboxylic acid ester and a thionyl halide in the presence of a basic substance in an organic solvent to produce an optically active 3-halogenocarboxylic acid ester which is then reacted with an azide salt represented by the formula: MN 3 (wherein M is an alkaline metal) in water or a mixture of water and a water soluble organic solvent.

  通过在有机溶剂中，在碱性物质存在下，将光学活性的3-羟基羧酸酯和硫酰卤在一起反应，产生光学活性的3-卤代羧酸酯，然后将其与由公式表示的偶氮盐（其中M是碱性金属）在水或水和水溶性有机溶剂的混合物中反应，从而生产光学活性的3-偶氮基羧酸酯的方法。
• Chemical Synthesis of a Glycolipid Library by a Solid-Phase Strategy Allows Elucidation of the Structural Specificity of Immunostimulation by Rhamnolipids
  作者：Jörg Bauer、Klaus Brandenburg、Ulrich Zähringer、Jörg Rademann

  DOI：10.1002/chem.200600482

  日期：2006.9.18

  variations in the carbohydrate part, the lipid components, and the stereochemistry of the 3-hydroxy fatty acids was designed and synthesized. The enantioselective synthesis of the 3-hydroxy fatty acid building blocks was achieved by employing asymmetric hydrogenation of 3-oxo fatty acids. Glycolipids were prepared by this approach without any intermediary isolation steps, mostly in excellent yields. Final

  描述了通过疏水辅助开关相（HASP）合成的糖脂文库的首次合成。HASP合成可在溶液相步骤和与附着在疏水性二氧化硅载体上的分子进行的固相支持反应之间灵活切换。设计并合成了衍生自先导化合物1-a强免疫刺激鼠李糖脂的糖脂库-碳水化合物部分，脂质成分和3-羟基脂肪酸的立体化学存在差异。通过使用3-氧代脂肪酸的不对称氢化来实现3-羟基脂肪酸结构单元的对映选择性合成。糖脂是通过这种方法制备的，无需任何中间分离步骤，大部分收率都很高。通过酶促酯裂解完成对羧酸的最终脱保护。通过测定细胞因子肿瘤坏死因子α（TNFα）向培养基中的分泌，测试所有制备的鼠李糖脂对人单核细胞的免疫刺激特性。观察到的鼠李糖脂的构效关系表明了一种特定的，基于识别的作用方式，鼠李糖脂的结构变化很小，从而在低微摩尔浓度下对鼠李糖脂的免疫刺激活性产生了强烈影响。
• METHOD OF OXIDATIVE MOLECULAR CLEAVAGE OF A FATTY COMPOUND
  申请人：Godard Anaïs

  公开号：US20140371487A1

  公开（公告）日：2014-12-18

  A method of oxidative molecular cleavage of a fatty compound, includes: —forming a liquid composition, referred to as a fatty composition, consisting of at least one aliphatic carboxylic acid, the fatty composition including the fatty compound; characterised in that it then involves: —adding, to the fatty composition, a solution of at least one quaternary ammonium salt in water capable of forming an emulsion from the fatty compound and water, then; —adding, to the emulsion, a liquid solution of at least one tungstophosphoric acid in a composition including hydrogen peroxide (H 2 O 2 ), in such a way as to form, in situ in the emulsion, a quantity of a phase-transfer catalyst, formed from tungstophosphoric acid and at least one quaternary ammonium from the quaternary ammonium salt(s), and to allow the oxidative molecular cleavage of the fatty compound.

  一种氧化分子裂解脂肪化合物的方法，包括：形成一种液体组合物，称为脂肪组合物，由至少一种脂肪族羧酸组成，脂肪组合物包括脂肪化合物；其特征在于随后涉及：向脂肪组合物中添加至少一种季铵盐在水中的溶液，能够从脂肪化合物和水中形成乳液，然后；向乳液中添加至少一种钨磷酸的液体溶液在包括过氧化氢（H2O2）的组合物中，以便在乳液中原位形成一定量的相转移催化剂，由钨磷酸和至少一种季铵盐（从季铵盐）形成，并允许对脂肪化合物进行氧化分子裂解。
• Simultaneous Enzyme/Whole-Cell Biotransformation of C18 Ricinoleic Acid into (<i>R</i> )-3-Hydroxynonanoic Acid, 9-Hydroxynonanoic Acid, and 1,9-Nonanedioic Acid
  作者：Hee-Jeong Cha、Eun-Ji Seo、Ji-Won Song、Hye-Jin Jo、Akula Ravi Kumar、Jin-Byung Park

  DOI：10.1002/adsc.201701029

  日期：2018.2.15

  produced from ricinoleic acid ((9Z,12R)‐12‐hydroxyoctadec‐9‐enoic acid) by a fatty acid double bond hydratase, into (R)‐3‐hydroxynonanoic acid, 9‐hydroxynonanoic acid, and 1,9‐nonanedioic acid with a high conversion yield of ca. 70%. The biotransformation was driven by enzyme/whole‐cell biocatalysts, consisting of the esterase of Pseudomonas fluorescens and the recombinant Escherichia coli expressing the

  已经研究了可再生长链脂肪酸到工业上相关的C9羧酸的区域特异性氧基官能化。一个例子是由脂肪酸双键水合酶将蓖麻油酸（（9 Z，12 R）-12-羟基十八碳9-9烯酸）生产的10,12-二羟基十八碳烯酸生物催化转化为（R）- 3-羟基壬酸，9-羟基壬酸和1,9-壬二酸，转化率高。70％。生物转化是由酶/全细胞生物催化剂驱动的，该酶由荧光假单胞菌的酯酶和表达黄斑微球菌仲醇脱氢酶的重组大肠杆菌组成。，恶臭假单胞菌KT2440的Baeyer-Villiger单加氧酶和不动杆菌属的伯醇/醛脱氢酶。NCIMB9871。在20 U / g具有不溶性反应物的干细胞中，高转化率和高产物形成速率表明，各种（多羟基）脂肪酸可通过同时进行的酶/整个细胞生物转化而转化为多功能产品。这项研究将有助于疏水物质的基于酶的功能化。