86390-77-4 (2-乙酰基-1-油酰基-SN-丙三醇,1-Oleoyl-2-acetyl-sn-glycerol)

快速询单

结构式：

2-乙酰基-1-油酰基-SN-丙三醇MOL文件

CAS号：

86390-77-4

中文名称：

2-乙酰基-1-油酰基-SN-丙三醇

英文名称：

1-Oleoyl-2-acetyl-sn-glycerol

分子式：

C₂₃H₄₂O₅

分子量：

398.576588153839

简介：

1-Oleoyl-2-acetyl-sn glycerol是一种合成的，细胞渗透性二酰基甘油类似物。?1-Oleoyl-2-acetyl-sn glycerol激活钙依赖蛋白激酶C (PKC)，并诱导超氧化物的产生。

2-乙酰基-1-油酰基-SN-丙三醇(86390-77-4)名称与标识符

名称

中文别名：

1-油酰基-2-乙酰基-sn-丙三醇;2-乙酰基-1-油酰基-SN-丙三醇;1-(顺-9-油酰基)-2-乙酰基-sn-甘油;2-乙酰基-1-油酰基-sn-甘油;

英文别名：

9-Octadecenoic acid(9Z)-, (2S)-2-(acetyloxy)-3-hydroxypropyl ester;1-Oleoyl-2-acetyl-sn-glycerol;1-Oleoyl-2-acetyl-sn;(9Z)-9-Octadecenoic acid (2S)-2-(acetyloxy)-3-hydroxypropyl ester;OAG;1--(9Z-octadecenoyl)-2-acetoyl-sn-glycerol;2:0;DG(18:1(9Z);DG(18:1(9Z)/2:0/0:0);1--(9Z-octadecenoyl)-2-acetoyl-sn-glycerol; DG(18:1(9Z)/2:0/0:0); OAG;(2S)-2-(Acetyloxy)-3-hydroxypropyl (9Z)-9-octadecenoate (ACI);9-Octadecenoic acid (Z)-, 2-(acetyloxy)-3-hydroxypropyl ester, (S)- (ZCI);2-Acetyl-1-oleoyl-sn-glycerol;sn-1-Oleoyl-2-acetylglycerol;1-Oleoyl-2-acetyl-sn-glycerol (OAG);CHEMBL1591456;86390-77-4;(S)-2-Acetoxy-3-hydroxypropyl oleate;NCGC00161334-03;SR-01000946570-1;1-O-9Z-Octadecenoyl-2-O-acetyl-sn-glycerol;NCGC00161334-01;HMS1791G05;BP-29900;HY-131648;BSPBio_001403;Oleoylacetylglycerol;DA-59950;1-Olein-2-acetyl-sn-glycerol;HMS3649G05;AKOS027257477;9-Octadecenoic acid (Z)-, 2-(acetyloxy)-3-hydroxypropyl ester, (S)-;1-O-Octadecenoyl-2-O-acetylglycerol;BML2-F08;CS-0138170;SR-01000946570;IDI1_033873;1-(cis-9-Octadecenoyl)-2-acetyl-sn-glycerol;1-oleoyl-2-acetylglycerol;[(2S)-2-acetyloxy-3-hydroxypropyl] (Z)-octadec-9-enoate;SCHEMBL1002909;1-Oleoyl-2-acetyl-rac-glycerol;HMS3402G05;CHEBI:188094;MFCD00166985;HMS1989G05;HMS1361G05;1-oleoyl-2-acetyl-glycerol;9-Octadecenoic acid (9Z)-, (2S)-2-(acetyloxy)-3-hydroxypropyl ester;NCGC00161334-02;PD020881;oleyl acetyl glycerol;G90898;1-Oleoyl-2-acetyl-sn-glycerol - CAS 86390-77-4;1-Oleyl-2-acetylglycerol;

标识符

MDL：

MFCD00166985

InChIKey：

PWTCCMJTPHCGMS-YRBAHSOBSA-N

Inchi：

1S/C23H42O5/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23(26)27-20-22(19-24)28-21(2)25/h10-11,22,24H,3-9,12-20H2,1-2H3/b11-10-/t22-/m0/s1

SMILES：

[C@@H](CO)(OC(=O)C)COC(=O)CCCCCCC/C=C\CCCCCCCC

2-乙酰基-1-油酰基-SN-丙三醇(86390-77-4)物化性质

实验特性

LogP : 5.49110
PSA : 72.83000
折射率 : 1.471
沸点 : 490.0±15.0 °C at 760 mmHg
熔点 : No data available
蒸气压 : 0.0±2.8 mmHg at 25°C
闪点 : 152.3±13.9 °C
溶解度 : ethanol: 20 mg/mL
浓度 : 2 mg/mL (800100C-10mg)
5 mg/mL (800100C-25mg)
颜色与性状 : 无色粘性液体
稳定性 : Temperature Sensitive. This compound can rearrange to the 1,3-isomer in solution or during prolonged storage.
溶解性 : 乙醇: 20 mg/mL
密度 : 1.0±0.1 g/cm3

计算特性

精确分子量 : 398.30300
氢键供体数量 : 1
氢键受体数量 : 5
可旋转化学键数量 : 21
同位素质量 : 398.303
重原子数量 : 28
复杂度 : 406
同位素原子数量 : 0
确定原子立构中心数量 : 1
不确定原子立构中心数量 : 0
确定化学键立构中心数量 : 1
不确定化学键立构中心数量 : 0
共价键单元数量 : 1
疏水参数计算参考值（XlogP） : 6.9
互变异构体数量 : 无
表面电荷 : 0
拓扑分子极性表面积 : 72.8A^2

2-乙酰基-1-油酰基-SN-丙三醇(86390-77-4)安全信息

WGK Germany： 3
安全说明： H303+H313+H333
危险品运输编号： NONH for all modes of transport
危害声明：H303+H313+H333
警示性声明：P264+P280+P305+P351+P338+P337+P313
储存条件： −20°C
信号词： warning
FLUKA BRAND F CODES： 10-23

2-乙酰基-1-油酰基-SN-丙三醇(86390-77-4)推荐厂家更多厂家(15)

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2-乙酰基-1-油酰基-SN-丙三醇(86390-77-4)合成路线

合成路线：1 步

868368-11-0

_100%

86390-77-4

反应条件：

1.1 Reagents: Methanol , Pyridine Solvents: Tetrahydrofuran ; 2 h, rt

参考文献：

O-Silylated C3-halohydrins as a novel class of protected building blocks for total, regio- and stereocontrolled synthesis of glycerolipid frameworks

Stamatov, Stephan D.; et al, Organic & Biomolecular Chemistry, 2010, 8(2), 463-477

合成路线：1 步

868368-11-0

_100%

86390-77-4

反应条件：

1.1 Reagents: Pyridine Solvents: Methanol , Tetrahydrofuran ; 3 h, rt; 50 °C

参考文献：

Regioselective and stereospecific acylation across oxirane- and silyloxy systems as a novel strategy to the synthesis of enantiomerically pure mono-, di- and triglycerides

Stamatov, Stephan D.; et al, Organic & Biomolecular Chemistry, 2007, 5(23), 3787-3800

合成路线：1 步

868368-11-0

_100%

86390-77-4

反应条件：

1.1 Reagents: Pyridine Solvents: Methanol , Tetrahydrofuran ; 3 h, rt

参考文献：

A direct transformation of O-silyl groups into O-trichloroacetates. A novel synthetic approach to protein kinase C ligands: 1-oleoyl-2-acetyl- and 1-hexadecyl-2-acetyl-sn-glycerols

Stamatov, Stephan D.; et al, Tetrahedron Letters, 2005, 46(40), 6855-6859

合成路线：2 步

868368-09-6

4124-31-6

86390-77-4

反应条件：

1.1 Reagents: Triethylamine trihydrofluoride ; 2 h, 80 °C
2.1 Reagents: Pyridine Solvents: Methanol , Tetrahydrofuran ; 3 h, rt; 50 °C

参考文献：

Regioselective and stereospecific acylation across oxirane- and silyloxy systems as a novel strategy to the synthesis of enantiomerically pure mono-, di- and triglycerides

Stamatov, Stephan D.; et al, Organic & Biomolecular Chemistry, 2007, 5(23), 3787-3800

合成路线：2 步

868368-09-6

4124-31-6

86390-77-4

反应条件：

1.1 Reagents: Triethylamine trihydrofluoride ; 2 h, 80 °C
2.1 Reagents: Pyridine Solvents: Methanol , Tetrahydrofuran ; 3 h, rt

参考文献：

A direct transformation of O-silyl groups into O-trichloroacetates. A novel synthetic approach to protein kinase C ligands: 1-oleoyl-2-acetyl- and 1-hexadecyl-2-acetyl-sn-glycerols

Stamatov, Stephan D.; et al, Tetrahedron Letters, 2005, 46(40), 6855-6859

合成路线：2 步

868368-10-9

4124-31-6

86390-77-4

反应条件：

1.1 Reagents: Triethylamine trihydrofluoride ; 2 h, 80 °C
2.1 Reagents: Methanol , Pyridine Solvents: Tetrahydrofuran ; 2 h, rt

参考文献：

O-Silylated C3-halohydrins as a novel class of protected building blocks for total, regio- and stereocontrolled synthesis of glycerolipid frameworks

Stamatov, Stephan D.; et al, Organic & Biomolecular Chemistry, 2010, 8(2), 463-477

合成路线：2 步

868368-10-9

4124-31-6

86390-77-4

反应条件：

1.1 Reagents: Triethylamine trihydrofluoride ; 2 h, 80 °C
2.1 Reagents: Pyridine Solvents: Methanol , Tetrahydrofuran ; 3 h, rt

参考文献：

A direct transformation of O-silyl groups into O-trichloroacetates. A novel synthetic approach to protein kinase C ligands: 1-oleoyl-2-acetyl- and 1-hexadecyl-2-acetyl-sn-glycerols

Stamatov, Stephan D.; et al, Tetrahedron Letters, 2005, 46(40), 6855-6859

合成路线：3 步

1001440-52-3

75-36-5

86390-77-4

反应条件：

1.1 Reagents: Pyridine Solvents: Dichloromethane ; -20 °C; 2 h, rt
2.1 Reagents: Triethylamine trihydrofluoride ; 2 h, 80 °C
3.1 Reagents: Pyridine Solvents: Methanol , Tetrahydrofuran ; 3 h, rt; 50 °C

参考文献：

Regioselective and stereospecific acylation across oxirane- and silyloxy systems as a novel strategy to the synthesis of enantiomerically pure mono-, di- and triglycerides

Stamatov, Stephan D.; et al, Organic & Biomolecular Chemistry, 2007, 5(23), 3787-3800

合成路线：3 步

反应条件：

1.1 Solvents: Toluene ; 1.5 h, 80 °C
2.1 Reagents: Triethylamine trihydrofluoride ; 2 h, 80 °C
3.1 Reagents: Methanol , Pyridine Solvents: Tetrahydrofuran ; 2 h, rt

参考文献：

O-Silylated C3-halohydrins as a novel class of protected building blocks for total, regio- and stereocontrolled synthesis of glycerolipid frameworks

Stamatov, Stephan D.; et al, Organic & Biomolecular Chemistry, 2010, 8(2), 463-477

合成路线：4 步

849589-87-3

18162-48-6

86390-77-4

反应条件：

1.1 Reagents: Pyridine Solvents: Methanol , Dichloromethane , Pentane ; 0 °C; 20 min, rt
1.2 Reagents: Imidazole Solvents: Tetrahydrofuran ; 18 h, rt
2.1 Reagents: Pyridine Solvents: Dichloromethane ; -20 °C; 2 h, rt
3.1 Reagents: Triethylamine trihydrofluoride ; 2 h, 80 °C
4.1 Reagents: Pyridine Solvents: Methanol , Tetrahydrofuran ; 3 h, rt; 50 °C

参考文献：

Regioselective and stereospecific acylation across oxirane- and silyloxy systems as a novel strategy to the synthesis of enantiomerically pure mono-, di- and triglycerides

Stamatov, Stephan D.; et al, Organic & Biomolecular Chemistry, 2007, 5(23), 3787-3800

合成路线：4 步

193155-95-2

75-36-5

86390-77-4

反应条件：

1.1 Reagents: Trifluoroacetic acid , Tetrabutylammonium iodide Solvents: Chloroform ; 5 min, rt
1.2 5 min, rt
1.3 Reagents: Pyridine Solvents: Chloroform ; 1.5 h, rt
2.1 Solvents: Toluene ; 1.5 h, 80 °C
3.1 Reagents: Triethylamine trihydrofluoride ; 2 h, 80 °C
4.1 Reagents: Methanol , Pyridine Solvents: Tetrahydrofuran ; 2 h, rt

参考文献：

O-Silylated C3-halohydrins as a novel class of protected building blocks for total, regio- and stereocontrolled synthesis of glycerolipid frameworks

Stamatov, Stephan D.; et al, Organic & Biomolecular Chemistry, 2010, 8(2), 463-477

合成路线：5 步

849589-85-1

407-25-0

86390-77-4

反应条件：

1.1 Reagents: 1-Butanaminium, N,N,N-tributyl-, 2,2,2-trifluoroacetate (1:1) Solvents: Dichloromethane , Tetrahydrofuran ; 5 h, 80 °C
2.1 Reagents: Pyridine Solvents: Methanol , Dichloromethane , Pentane ; 0 °C; 20 min, rt
2.2 Reagents: Imidazole Solvents: Tetrahydrofuran ; 18 h, rt
3.1 Reagents: Pyridine Solvents: Dichloromethane ; -20 °C; 2 h, rt
4.1 Reagents: Triethylamine trihydrofluoride ; 2 h, 80 °C
5.1 Reagents: Pyridine Solvents: Methanol , Tetrahydrofuran ; 3 h, rt; 50 °C

参考文献：

Regioselective and stereospecific acylation across oxirane- and silyloxy systems as a novel strategy to the synthesis of enantiomerically pure mono-, di- and triglycerides

Stamatov, Stephan D.; et al, Organic & Biomolecular Chemistry, 2007, 5(23), 3787-3800

合成路线：5 步

849589-86-2

407-25-0

86390-77-4

反应条件：

参考文献：

Regioselective and stereospecific acylation across oxirane- and silyloxy systems as a novel strategy to the synthesis of enantiomerically pure mono-, di- and triglycerides

Stamatov, Stephan D.; et al, Organic & Biomolecular Chemistry, 2007, 5(23), 3787-3800