lesquerolic acid | 5026-56-2

• 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: lesquerolic acid
• 英文别名: 14-Hydroxy-cis-11-eicosenoic acid；(Z)-14-hydroxyicos-11-enoic acid
• CAS: 5026-56-2
• 化学式: C₂₀H₃₈O₃
• 分子量: 326.52
• InChiKey: OONXYOAWMIVMCI-KAMYIIQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  23
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  lesquerolic acid 在 Sphingobacterium multivorum NRRL B-23212 、 Wallen fermentation medium 作用下， 以 水 为溶剂， 反应 48.0h， 以69.7 mg的产率得到14-oxo-cis-11-eicosenoic acid
  参考文献：
  名称：

  多重旋涡菌NRRL B-23212从来死酚酸生产14-氧-顺式-11-二十碳烯酸

  摘要：

  AbstractThe objective of this study was to explore the extent of microbial conversion of lesquerolic acid (14‐hydroxy‐cis‐11‐eicosenoic acid; LQA) by whole cell catalysis and to identify the newly converted products. Among compost isolates including NRRL strains B‐23212 (Sphingobacterium multivorum), B‐23213 (Acinetobacter sp.), B‐23257 (Enterobacter cloacae B), B‐23259 (Escherichia sp.) and B‐23260 (Pseudomonas aeruginosa) the S.multivorum strain was the only microorganism that converted LQA to produce a new product identified as 14‐oxo‐cis‐11‐eicosenoic acid by GC‐MS and NMR analyses. The conversion yield was 47.4% in 48 h at 200 rpm and 28°C in small shake flask experiments. In comparison, both Acinetobacter and Pseudomonas strains failed to convert LQA to major new products but used LQA apparently as an energy source during fermentation. For structural analysis, 6.88 g of 14‐oxo‐cis‐11‐eicosenoic acid was produced from converting 11 g LQA (a 62% yield) in 72 h at 200 rpm and 28 °C in Fernbach flasks using 18‐h‐old NRRL B‐23212 cultures and an improved medium that also contained EDTA and glycerol in lieu of glucose as carbon source. NRRL B‐23212 was further identified by 16S rRNA gene sequence analysis as a unique strain of S. multivorum. Therefore, S. multivorum NRRL B‐23212 possesses an enzymatic activity presumably a secondary alcohol dehydrogenase for converting LQA to produce 14‐oxo‐cis‐11‐eicosenoic acid, a first report that demonstrates the functional modification of LQA by whole cell catalysis.

  DOI：

  10.1007/s11746-007-1085-x

文献信息

• METHOD FOR THE SYNTHESIS OF OMEGA-AMINO-ALKANOIC ACIDS
  申请人：Dubois Jean-Luc

  公开号：US20100168453A1

  公开（公告）日：2010-07-01

  The invention relates to a method for the synthesis of amino acids/esters of general formula NH 2 —(CH 2 ) n —COOR in which n is an integer between 5 and 14, and R is either H or an alkyl radical including from 1 to 4 carbon atoms, from natural long-chain mono-unsaturated fatty acids or esters including at least 10 adjacent carbon atoms per molecule, said method comprising: first converting, if necessary, said natural long-chain fatty acid or ester into a monounsaturated fatty acid/ester of general formula R 1 —(CH 2 ) m —CH═CH—(CH 2 ) p —COOR in which R 1 is H, CH 3 or a COOR radical, m is an integer between 0 and 14 and p is an integer between 2 and 11, then submitting the latter to a crossed catalytic metathesis reaction with a compound of formula R 2 —CH═CH—R 3 in which R 2 is either H or CN and R 3 is CN or CH 2 NH 2 , provided that if R 2 is CN, R 3 can be only CN, and finally converting the resulting product of the general formula R 3 —CH═CH—(CH 2 ) p —COOR into an amino-acid, either by hydrogenation, or by hydrogenation of the triple terminal bond, or by amination of the double terminal bond.

  本发明涉及一种合成通式为NH2—(CH2)n—COOR的氨基酸/酯的方法，其中n为5至14之间的整数，R为H或包括1至4个碳原子的烷基基团，所述方法包括：首先，如果必要，将天然长链脂肪酸或酯转化为通式为R1—(CH2)m—CH═CH—(CH2)p—COOR的单不饱和脂肪酸/酯，其中R1为H，CH3或COOR基团，m为0至14之间的整数，p为2至11之间的整数；然后，将后者与通式为R2—CH═CH—R3的化合物进行交叉催化复分解反应，其中R2为H或CN，R3为CN或CH2NH2，如果R2为CN，则R3只能为CN；最后，将得到的通式为R3—CH═CH—(CH2)p—COOR的产品转化为氨基酸，可以通过氢化，或通过氢化末端的三键，或通过末端的双键的氨基化来实现。
• METHOD OF SYNTHESISING AMINO ACID BY METATHESIS, HYDROLYSIS, THEN HYDROGENATION
  申请人：ARKEMA FRANCE

  公开号：US20160002147A1

  公开（公告）日：2016-01-07

  A method of synthesising an amino acid from an unsaturated fatty compound I that includes at least the following steps: cross-metathesis with a short unsaturated compound II, one of compounds I or II comprising a nitrile function and the other of these compounds II or I an ester function, so as to obtain and recover at least one monounsaturated nitrile ester NEU; hydrolysis of the NEU in unsaturated acid nitrile NAU; hydrogenation of the NAU to saturated amino acid AA; and then purification of the AA, if applicable, in particular by crystallisation. Also, a polymer obtained by polymerisation using the amino acid synthesised according to the method.

  一种从不饱和脂肪化合物I合成氨基酸的方法，包括至少以下步骤：与短链不饱和化合物II进行交叉转化反应，其中化合物I或II中的一个包含腈基，而另一个化合物II或I包含酯基，以获得和回收至少一种单不饱和腈酯NEU；将NEU水解为不饱和酸腈NAU；将NAU加氢为饱和氨基酸AA；然后通过结晶等方法对AA进行纯化，如果需要的话。此外，通过使用根据该方法合成的氨基酸进行聚合得到的聚合物。
• COMBINED SYNTHESIS OF A NITRILE-ESTER/ACID AND OF A DIESTER/DIACID
  申请人：ARKEMA FRANCE

  公开号：US20160016894A1

  公开（公告）日：2016-01-21

  A method for the combined synthesis of a mono-unsaturated nitrile-ester(acid) and of a bi-functional carbonyl compound, wherein it includes a step including the cross metathesis mc1 of an unsaturated fatty acid/ester compound with an unsaturated nitrile compound, in which mc1 is performed with partial conversion such as to obtain and recover, separately, at least the following products: a mono-unsaturated nitrile-ester/acid and a symmetrical compound, diester or diacid respectively including a double bond located in the middle of the molecular chain of compound, and subsequently a step including the oxidation cleavage cp2 of the double bond of compound, such as to form a single type of carbonyl compound having formula R2-(CH2)n-COR′, in which R′ is H or OH, depending on the operating conditions selected for the oxidation cleavage cp2. Also, the production of monomers for the polymer industry.

  一种用于合成单不饱和腈酯（酸）和双官能羰基化合物的联合合成方法，其中包括一步骤，包括将不饱和脂肪酸/酯化合物与不饱和腈化合物进行交叉重排mc1的步骤，其中mc1是以部分转化进行的，以便分别获得和回收至少以下产品：单不饱和腈酯/酸和对称化合物，二酯或二酸，分别包括分子链中间位置的双键，并随后包括氧化裂解化合物的双键的步骤cp2，以形成具有化学式R2-(CH2)n-COR′的一种类型的羰基化合物，其中R′为H或OH，取决于选择用于氧化裂解cp2的操作条件。此外，用于聚合工业的单体的生产。
• Production of hydroxylated fatty acids in genetically modified plants
  申请人：——

  公开号：US20020104125A1

  公开（公告）日：2002-08-01

  This invention relates to plant fatty acyl hydroxylases. Methods to use conserved amino acid or nucleotide sequences to obtain plant fatty acyl hydroxylases are described. Also described is the use of cDNA clones encoding a plant hydroxylase to produce a family of hydroxylated fatty acids in transgenic plants.

  本发明涉及植物脂肪酰羟化酶。描述了利用保守氨基酸或核苷酸序列获得植物脂肪酰羟化酶的方法。还描述了利用编码植物羟化酶的 cDNA 克隆在转基因植物中产生羟化脂肪酸家族的方法。
• Separation of plant oil triglyceride mixtures by solid bed adsorption
  申请人：——

  公开号：US20040094477A1

  公开（公告）日：2004-05-20

  A solid bed adsorptive process for separating a seed oil into two substantially pure triglyceride functions. The process involves contacting a seed oil, such as castor oil, preferably as a concentrate, with an adsorbent in a bed, the adsorbent having a particle size greater than about 40 microns, and thereafter contacting the adsorbent with a desorbent material, preferably under minimal flow conditions, to obtain a raffinate output stream containing predominantly a second triglyceride and an extract output stream containing predominantly a first triglyceride. Purified fatty acid triglyceride esters obtainable from castor, vernonia, and lesquerella plant oils provide renewable, non-petroleum-based sources of chemical feedstocks.

  一种将种子油分离成两种基本纯的甘油三酯功能的固体床吸附工艺。该工艺包括将种子油（如蓖麻油，最好是浓缩物）与床中的吸附剂接触，吸附剂的粒径大于约 40 微米，然后将吸附剂与解吸材料接触，最好是在最小流量条件下接触，以获得主要含有第二甘油三酯的残渣输出流和主要含有第一甘油三酯的萃取输出流。可从蓖麻油、马齿笕油和lesquerella植物油中获得的纯化脂肪酸甘油三酯提供了可再生、非石油来源的化学原料。