2-十八烯酸单甘油酯 - CAS号 3443-84-3

物化性质

熔点：

23-23.5 °C
沸点：

485.4±35.0 °C(Predicted)
密度：

0.9963 g/cm3
闪点：

113 °C
溶解度：

氯仿（微溶）、乙酸乙酯（微溶）
物理描述：

Solid

计算性质

辛醇/水分配系数(LogP)：

6.3
重原子数：

25
可旋转键数：

19
环数：

0.0
sp3杂化的碳原子比例：

0.86
拓扑面积：

66.8
氢给体数：

2
氢受体数：

4

安全信息

WGK Germany：

3
储存条件：

-20°C密封避光保存

SDS

SDS：c58920798aff5e9932fca62b45b29b1f

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制备方法与用途

生物活性
2-Oleoylglycerol 是饮食中天然存在的脂质。这种物质是 GPR119 激动剂，在瞬时转染的 COS-7 细胞中激活 hGPR119 的 EC50 值为 2.5 μM，并且在体内能够刺激胰高血糖素样肽 1 (GLP-1) 分泌。
靶点
IC50: 2.5 μM (hGPR119) (in COS-7 cells)

上下游信息

上游原料

中文名称	英文名称	CAS号	化学式	分子量
——	2,3-di-O-oleoyl-sn-glycerol	33735-55-6	C₃₉H₇₂O₅	620.998
1,2-二油酰基-sn-甘油	1,2-dioleoyl-sn-glycerol	24529-88-2	C₃₉H₇₂O₅	620.998
——	1,2-dioleoylglycerol	2442-61-7	C₃₉H₇₂O₅	620.998
甘油三油酸酯	trioleoylglycerol	122-32-7	C₅₇H₁₀₄O₆	885.449
——	1,3-dibutyroyl-2-oleoylglycerol	——	C₂₉H₅₂O₆	496.728
——	1-monooleoyl glycerol	111-03-5	C₂₁H₄₀O₄	356.546
——	2-α-Linolenoyloxy-1,3-bis-oleoyloxy-propan	95576-93-5	C₅₇H₁₀₀O₆	881.417
——	glycidyl oleate	5431-33-4	C₂₁H₃₈O₃	338.531
油酸甲酯	Methyl oleate	112-62-9	C₁₉H₃₆O₂	296.494

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	2-oleoyl-1-steraoylglycerol	21059-30-3	C₃₉H₇₄O₅	623.014
——	1-O-palmitoyl-2-O-oleoyl glycerol	3123-73-7	C₃₇H₇₀O₅	594.96
1,2-二油酰基-sn-甘油	1,2-dioleoyl-sn-glycerol	24529-88-2	C₃₉H₇₂O₅	620.998
——	1-O-palmitoyl-2-[(9z)-octadenoyl]-glycerol	29541-66-0	C₃₇H₇₀O₅	594.96
1-硬脂酰-2-油酰基-Sn-甘油	sn-1-O-stearoyl-2-O-oleoyl glycerol	53702-48-0	C₃₉H₇₄O₅	623.014
——	1,2-dioleoylglycerol	2442-61-7	C₃₉H₇₂O₅	620.998
——	1,3-di-O-acetyl-2-O-oleoylglycerol	55401-63-3	C₂₅H₄₄O₆	440.621
——	1-palmitoyl-2-oleoyl-3-stearoylglycerol	2190-27-4	C₅₅H₁₀₄O₆	861.427
——	1,3-dicapryloyl-2-oleyl-glycerol	——	C₃₇H₆₈O₆	608.943
1,3-二硬脂酰-2-油酰基甘油	1,3-distearoyl-2-oleoylglycerol	2846-04-0	C₅₇H₁₀₈O₆	889.481

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反应信息

作为反应物：

描述：

2-十八烯酸单甘油酯以正己烷为溶剂，反应 24.0h，生成 1-monooleoyl glycerol

参考文献：

名称：

脂肪酸去饱和对2-单酰基甘油自发酰基迁移的影响

摘要：

AbstractThe effect of desaturation from the C9 to the C15 carbon of 2‐monoacylglycerol (2‐MAG) fatty acids on spontaneous acyl migration is described. Three 2‐MAG species, 2‐monooleoylglycerol (C18:1 cis‐Δ9), 2‐monolinoleoylglycerol (C18:2 cis‐Δ9,12), and 2‐monolinolenoylglycerol (C18:3 cis‐Δ9,12,15) were synthesized by lipase‐catalyzed ethanolysis of their respective triacylglycerols and isolated in >60 % yield and at 2‐MAG purities of >95 % relative to 1‐monoacylglycerol (1‐MAG). 1H‐NMR spectroscopy was used to monitor the spontaneous acyl migration of the 2‐MAG species over a temperature range from 20 to 80 °C. The relative energies of activation calculated from the Arrhenius relationships of the 2‐MAG acyl migration rate constants were 73.3, 68.0, and 72.9 kJ mol−1 for the three 2‐MAG species, respectively. Density functional calculations performed using the B3LYP functional at the 6‐31+G* basis set on the three ketal ring intermediate of the three 2‐MAG species followed a similar trend with a lack of relative energetic preference associated with the degree of desaturation. The kinetically determined relative activation energies were approximately twofold higher than the theoretical relative Gibbs free energies of the intermediates, suggesting that other factors influence acyl migration. In general, increasing desaturation after the C9 carbon of 2‐MAG fatty acids had no appreciable effect on acyl migration rates.

DOI：

10.1007/s11746-012-2113-z
作为产物：

描述：

甘油三油酸酯在 lipase from Rhizopus oryzae 、乙醇、水作用下，以正庚烷为溶剂，反应 6.0h，以76%的产率得到2-十八烯酸单甘油酯

参考文献：

名称：

Effective and highly selective lipase-mediated synthesis of 2-monoolein and 1,2-diolein in a two-phase system

摘要：

DOI：

10.1016/j.molcatb.2014.11.014

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文献信息

[EN] MODULATORS OF CELLULAR ADHESION<br/>[FR] MODULATEURS DE L'ADHESION CELLULAIRE

申请人：SUNESIS PHARMACEUTICALS INC

公开号：WO2005044817A1

公开（公告）日：2005-05-19

The present invention provides compounds having formula (I): and pharmaceutically acceptable derivatives thereof, wherein R1-R4, n, p, A, B, D, E, L and AR1 are as described generally and in classes and subclasses herein, and additionally provides pharmaceutical compositions thereof, and methods for the use thereof for the treatment of disorders mediated by the CD11/CD18 family of cellular adhesion molecules (e.g., LFA-1).

本发明提供具有以下式（I）的化合物及其药学上可接受的衍生物，其中R1-R4、n、p、A、B、D、E、L和AR1如本文中一般描述的那样，并且另外提供这些药物组合物以及用于治疗由CD11/CD18细胞粘附分子家族介导的疾病（例如LFA-1）的使用方法。
[EN] SUBSTITUTED AROMATIC COMPOUNDS AND RELATED METHOD FOR THE TREATMENT OF FIBROSIS<br/>[FR] COMPOSÉS AROMATIQUES SUBSTITUÉS ET PROCÉDÉ ASSOCIÉ POUR LE TRAITEMENT DE LA FIBROSE

申请人：PROMETIC BIOSCIENCES INC

公开号：WO2014138906A1

公开（公告）日：2014-09-18

The present invention relates to compounds of: or a pharmaceutically acceptable salt thereof, wherein A is C5 alkyl, C6 alkyl, C5 alkenyl, C6 alkenyl, C(0)-(CH2)n-CH3 or CH(OH)-(CH2)n-CH3 wherein n is 3 or 4; R1 is H, F or OH; R2 is C5 alkyl, C6 alkyl, C5 alkenyl, C6 alkenyl, C(0)-(CH2)n-CH3 or CH(OH)-(CH2)n-CH3 wherein n is 3 or 4; R3 is H, F, OH or CH2Ph; R4 is H, F or OH; Q is 1 ) (CH2)mC(0)OH wherein m is 1 or 2, 2) CH(CH3)C(0)OH, 3) C(CH3)2C(0)OH, 4) CH(F)-C(0)OH, 5) CF2-C(0)OH, or 6) C(0)-C(0)OH; and compositions comprising the same and the method using the same for the prevention or treatment of various fibrotic diseases and conditions in subjects, including pulmonary fibrosis, liver fibrosis, skin fibrosis, renal fibrosis, pancreas fibrosis, systemic sclerosis, cardiac fibrosis or macular degeneration.

本发明涉及以下化合物的制备：或其药用盐，其中A为C5烷基、C6烷基、C5烯基、C6烯基、C(0)-(CH2)n-CH3或CH(OH)-(CH2)n-CH3，其中n为3或4；R1为H、F或OH；R2为C5烷基、C6烷基、C5烯基、C6烯基、C(0)-(CH2)n-CH3或CH(OH)-(CH2)n-CH3，其中n为3或4；R3为H、F、OH或CH2Ph；R4为H、F或OH；Q为1）（CH2）mC(0)OH，其中m为1或2，2）CH(CH3)C(0)OH，3）C(CH3)2C(0)OH，4）CH(F)-C(0)OH，5）CF2-C(0)OH，或6）C(0)-C(0)OH；以及包含该化合物的组合物和使用该化合物预防或治疗受试者各种纤维化疾病和状况的方法，包括肺纤维化、肝纤维化、皮肤纤维化、肾纤维化、胰腺纤维化、系统性硬化病、心肌纤维化或黄斑变性。
[EN] MIGRASTATIN ANALOG COMPOSITIONS AND USES THEREOF<br/>[FR] COMPOSITIONS DE SUBSTANCES ANALOGUES A LA MIGRASTATINE ET LEURS UTILISATIONS

申请人：CORNELL RES FOUNDATION INC

公开号：WO2004087672A1

公开（公告）日：2004-10-14

In one aspect, the present invention provides pharmaceutical compositions comprising a therapeutically effective amount of a compound of general formula (I), wherein R1-R6, Ra-RC, Q, Y1, Y2 and n are as defined herein, whereby the composition is formulated for administration to a subject at a dosage between about 0.1 mg/kg to about 50 mg/kg of body weight. In another aspect, the present invention provides a method for treating breast tumor metastasis in a subject comprising administering to a subject in need thereof a therapeutically effective amount of the inventive composition described directly above and a pharmaceutically acceptable carrier, adjuvant or vehicle.

在一方面，本发明提供了包含式(I)化合物的治疗有效量的药物组合物，其中R1-R6，Ra-RC，Q，Y1，Y2和n如本文所述定义，该组合物为用于向受试者给药而配制成，剂量为约0.1 mg/kg至约50 mg/kg体重。在另一方面，本发明提供了一种治疗受试者乳腺癌转移的方法，包括向需要治疗的受试者给药治疗有效量的上述创新组合物以及药用可接受载体、佐剂或车辆。
Dioxanes and uses thereof

申请人：——

公开号：US20040072849A1

公开（公告）日：2004-04-15

In recognition of the need to develop novel therapeutic agents and efficient methods for the synthesis thereof, the present invention provides novel compounds of general formula (I): 1 and pharmaceutically acceptable derivatives thereof, wherein R 1 , R 2 , R 3 , n, X and Y are as defined herein. The present invention also provides pharmaceutical compositions comprising a compound of formula (I) and a pharmaceutically acceptable carrier. The present invention further provides compounds capable of inhibiting histone deacetylatase activity and methods for treating disorders regulated by histone deacetylase activity (e.g., cancer and protozoal infections) comprising administering a therapeutically effective amount of a compound of formula (I) to a subject in need thereof. The present invention additionally provides methods for modulating the glucose-sensitive subset of genes downstream of Ure2p. The present invention also provides methods for preparing compounds of the invention.

鉴于需要开发新型治疗剂和有效的合成方法，本发明提供了一般式(I)的新化合物： 1 及其药学上可接受的衍生物，其中R 1 ，R 2 ，R 3 ，n，X和Y如本文所定义。本发明还提供了包含一种式(I)化合物和药学上可接受的载体的药物组合物。本发明还提供了能够抑制组蛋白去乙酰化酶活性的化合物以及治疗由组蛋白去乙酰化酶活性调节的疾病的方法（例如，癌症和原虫感染），包括向需要的受体施用一种式(I)化合物的治疗有效量。本发明还提供了调节Ure2p下游葡萄糖敏感基因子集的方法。本发明还提供了制备本发明化合物的方法。
Isomigrastatin Analogs In The Treatment Of Cancer

申请人：Danishefsky Samuel J.

公开号：US20090054488A1

公开（公告）日：2009-02-26

The present invention provides compounds having formula (I): (I) wherein n, R 1 -R 5 , R a -R b , Q, Y 1 and Y 2 are as defined herein; and additionally provides methods for the synthesis thereof, compositions thereof, and methods for the use thereof in the treatment of various disorders including cancer, metastasis and disorders involving increased angiogenesis.

本发明提供具有以下式（I）的化合物：（I）其中n，R1-R5，Ra-Rb，Q，Y1和Y2如本文所定义；此外还提供了其合成方法、组合物以及在治疗包括癌症、转移和涉及增加血管生成的各种疾病中使用的方法。

2-十八烯酸单甘油酯 | 3443-84-3

分子结构分类