2,3-dihydroxypropyl (9Z,12Z,15Z)-9,12,15-octadecatrienoate | 18465-99-1

• 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: 2,3-dihydroxypropyl (9Z,12Z,15Z)-9,12,15-octadecatrienoate
• 英文别名: 1-linolenoylglycerol；glyceryl linolenate；(Z,Z,Z)-9,12,15-octadecatrienoic acid 2,3-dihydroxypropyl ester；1-O-(9Z,12Z,15Z-octadecatrienoyl)glycerol；monolinolenin；9,12,15-octadecatrienoic acid, 2,3-dihydroxypropyl ester, (Z,Z,Z)-；1-Monolinolenin；1-Monolinolenoyl-rac-glycerol；2,3-dihydroxypropyl (9Z,12Z,15Z)-octadeca-9,12,15-trienoate
• CAS: 18465-99-1
• 化学式: C₂₁H₃₆O₄
• 分子量: 352.514
• InChiKey: GGJRAQULURVTAJ-PDBXOOCHSA-N

物化性质

• 熔点：
  284 °C
• 沸点：
  484.8±45.0 °C(Predicted)
• 密度：
  0.9834 g/cm3
• LogP：
  5.512 (est)
• 保留指数：
  2161

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  25
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2916190090

反应信息

• 作为反应物：
  描述：

  2,3-dihydroxypropyl (9Z,12Z,15Z)-9,12,15-octadecatrienoate 在 溴 、 Petroleum ether 作用下， 生成 9,10,12,13,15,16-hexabromo-octadecanoic acid-(2,3-dihydroxy-propyl ester)
  参考文献：
  名称：

  Daubert; Baldwin, Journal of the American Chemical Society, 1944, vol. 66, p. 998

  摘要：

  DOI：
• 作为产物：
  描述：

  Γ-十八碳三烯酸 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 32.0h， 生成 2,3-dihydroxypropyl (9Z,12Z,15Z)-9,12,15-octadecatrienoate
  参考文献：
  名称：

  Biochemical characterization of the PHARC-associated serine hydrolase ABHD12 reveals its preference for very-long-chain lipids

  摘要：

  Polyneuropathy, hearing loss, ataxia, retinitis pigmentosa, and cataract (PHARC) is a rare genetic human neurological disorder caused by null mutations to the Abhd12 gene, which encodes the integral membrane serine hydrolase enzyme ABHD12. Although the role that ABHD12 plays in PHARC is understood, the thorough biochemical characterization of ABHD12 is lacking. Here, we report the facile synthesis of mono-1-(fatty)acyl-glycerol lipids of varying chain lengths and unsaturation and use this lipid substrate library to biochemically characterize recombinant mammalian ABHD12. The substrate profiling study for ABHD12 suggested that this enzyme requires glycosylation for optimal activity and that it has a strong preference for very-long-chain lipid substrates. We further validated this substrate profile against brain membrane lysates generated from WT and ABHD12 knockout mice. Finally, using cellular organelle fractionation and immunofluorescence assays, we show that mammalian ABHD12 is enriched on the endoplasmic reticulum membrane, where most of the very-long-chain fatty acids are biosynthesized in cells. Taken together, our findings provide a biochemical explanation for why very-long-chain lipids (such as lysophosphatidylserine lipids) accumulate in the brains of ABHD12 knockout mice, which is a murine model of PHARC.

  DOI：

  10.1074/jbc.ra118.005640

文献信息

• .gamma.-Aminobutyric acid esters. 2. Synthesis, brain uptake, and pharmacological properties of lipid esters of .gamma.-aminobutyric acid
  作者：James N. Jacob、Victor E. Shashoua、Alexander Campbell、Ross J. Baldessarini

  DOI：10.1021/jm00379a019

  日期：1985.1

  than that of free GABA. The results indicate that there is little or no blood-brain barrier for the GABA ester molecules at doses up to 0.36 mmol/kg. Both ester compounds, but neither free GABA nor the lipid components delivered systemically, demonstrated central nervous system depressant properties by inhibiting the general motor activity of mice. Brain tissue has esterase activity which can release

  合成了两种由U-14C标记和未标记的γ-氨基丁酸（GABA）制成的脂质酯，以测试类似于脂质双层膜正常成分的天然脂质类似物可以穿透血脑屏障并将外源GABA转运至大脑。1-亚油酰基-2,3-双（4-氨基丁酰基）丙烷-1,2,3-三醇和1,2-二亚油酰基-3-（4-氨基丁酰基）丙烷-1,2,3-三醇的吸收相对于肝脏，小鼠大脑的自由度分别比游离GABA高75倍和127倍。结果表明，剂量高达0.36 mmol / kg时，GABA酯分子几乎没有血脑屏障。既有酯化合物，也没有游离GABA或脂质成分，都是系统性递送的 通过抑制小鼠的一般运动活动，证明具有中枢神经系统抑制作用。脑组织具有酯酶活性，可以从这些化合物释放GABA。这表明这些化合物作为“前药”在中枢神经系统中释放GABA。
• Site-Specific Deuteration of Polyunsaturated Alkenes
  作者：A. V. Smarun、M. Petković、M. S. Shchepinov、D. Vidović

  DOI：10.1021/acs.joc.7b02169

  日期：2017.12.15

  and expensive syntheses. In this report, we disclose a very efficient catalytic protocol for site-specific deuteration of PUFAs and analogous poly-alkenes under exceptional kinetic control. Deuterium oxide (D2O) has been identified not only as a deuterium source but also as a crucial component in the overall reaction mechanism responsible for averting the formation of thermodynamically favored side-products

  药物和生物学相关分子的选择性氘化在制药行业中变得越来越重要。多不饱和脂肪酸（PUFA）在其双烯丙基位点的位点选择性同位素增强已被认为是防止这些分子氧化损伤的一种独特方法，这种氧化损伤与神经元和视网膜疾病，动脉粥样硬化和衰老有关。用于制备位点选择性氘代PUFA的典型方法需要相当长，费力且昂贵的合成。在这份报告中，我们公开了非常有效的催化方案，用于在特殊动力学控制下对PUFA和类似聚烯烃进行位点特异性氘化。氧化氘（D 2O）不仅被认为是氘源，而且在整个反应机制中也起着至关重要的作用，该机制负责避免形成热力学上有利的副产物。
• [EN] NOVEL ANTIMICROBIAL PEPTIDES AND THEIR APPLICATION<br/>[FR] NOUVEAUX PEPTIDES ANTIMICROBIENS ET LEUR APPLICATION
  申请人：INFINITEC ACTIVOS S L

  公开号：WO2015135896A1

  公开（公告）日：2015-09-17

  The present invention relates to a compound of formula (I) and to compositions comprising said compound, as well as the use of said compound and/or said compositions to prevent fungal and/or bacterial growth.

  本发明涉及式(I)的化合物，以及包含该化合物的组合物，以及使用该化合物和/或所述组合物来防止真菌和/或细菌生长。
• [EN] COMPOUNDS USEFUL FOR THE TREATMENT AND/OR CARE OF THE SKIN, HAIR, NAILS AND/OR MUCOUS MEMBRANES<br/>[FR] COMPOSÉS UTILES DANS LE TRAITEMENT ET/OU LE SOIN DE LA PEAU, DES CHEVEUX, DES ONGLES ET/OU DES MUQUEUSES
  申请人：LUBRIZOL ADVANCED MAT INC

  公开号：WO2018071640A1

  公开（公告）日：2018-04-19

  The invention relates to a peptide of formula (I) R1-Wm-Xn-AA1-AA2-AA3-Yp-Zq-R2, cosmetic or pharmaceutical compositions comprising same and its use, for example, in the reduction of lipid accumulation in the skin, the treatment of cellulite and/or the treatment of the symptoms of skin aging.

  该发明涉及一种肽，其化学式为(I) R1-Wm-Xn-AA1-AA2-AA3-Yp-Zq-R2，包括相同肽的化妆品或药用组合物以及其用途，例如在减少皮肤脂质积聚、治疗橘皮组织和/或治疗皮肤老化症状中的应用。
• UV ABSORBER FORMULATIONS
  申请人：Acker Stephanie

  公开号：US20100111884A1

  公开（公告）日：2010-05-06

  Disclosed is a UV filter composition comprising (a) an organic UV absorber of formula (1), wherein R 1 and R 2 , independently of one another, are C 3 -C 18 alkyl; C 2 -C 18 alkenyl; a radical of the formula —CH 2 —CH(OH)—CH 2 —O-T 1 ; or R 1 and R 2 are a radical of the formula (4a); R 7 is a direct bond; a straight-chain or branched C 1 -C 4 alkylene radical or a radical of the formula (I) or (II); R 8 , R 9 and R 10 , independently of one another, are C 1 -C 18 alkyl; C 1 -C 18 alkoxy or a radical of the formula (III); R 11 is C 1 -C 5 alkyl; m 1 is a number from 1 to 4; p 1 is 0; or a number from 1 to 5; A 1 is a radical of the formula (1b), (1c) or (1d); R 3 is hydrogen; C 1 -C 10 alkyl; —(CH 2 CHR 5 —O)n 1 -T 2 ; or —CH 2 —CH(—OH)—CH 2 —O-T 2 ; R 4 is hydrogen; M; C 1 -C 5 alkyl; or —(CH 2 )m 2 —O-T 3 ; R 5 is hydrogen; or methyl; T 1 , T 2 and T 3 independently from each other are hydrogen; or C 1 -C 18 alkyl; Q 1 is C 1 -C 18 alkyl, M is a metal cation; m 2 is 1 to 4; and n 1 is 1-16, (b) dimethyl capramide, (c) a cosmetically acceptable carrier; and water.

  本发明公开了一种紫外线过滤组合物，包括（a）式（1）的有机紫外线吸收剂，其中R1和R2独立地是C3-C18烷基；C2-C18烯基；式—CH2—CH（OH）—CH2—O-T1的基团；或者R1和R2是式（4a）的基团；R7是直链或支链C1-C4烷基、式（I）或（II）的基团；R8、R9和R10独立地是C1-C18烷基、C1-C18烷氧基或式（III）的基团；R11是C1-C5烷基；m1是1至4的数字；p1是0或1至5的数字；A1是式（1b）、（1c）或（1d）的基团；R3是氢、C1-C10烷基、式—（CH2CHR5—O）n1-T2或式—CH2—CH（—OH）—CH2—O-T2；R4是氢、M、C1-C5烷基或式—（CH2）m2—O-T3；R5是氢或甲基；T1、T2和T3互相独立地是氢或C1-C18烷基；Q1是C1-C18烷基，M是金属阳离子；m2是1至4的数字；n1是1-16，（b）二甲基辛酰胺，（c）化妆品可接受载体；和水。