Oleic Anhydride
(Synonyms: 油酸酐) 目录号 : GC44499
A fatty acid anhydride
Cas No.:24909-72-6
Sample solution is provided at 25 µL, 10mM.
;)
,-1-7$$$37316672.jpg');)
;)
;)
$$$36806353.jpg');)
;33(7)%EF%BC%9A546-561$$$37156877.jpg');)
;)
;)
;)
%201124-1138.$$$35908550.jpg');)
%20766-780.$$$37100057.jpg');)
%20418-432.$$$36893736.jpg');)
%EF%BC%9A-240-255.$$$35108512.jpg');)
533-545$$$36543525.jpg');)
%201-13.$$$36600053.jpg');)
;)
Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Oleic anhydride is a fatty acid anhydride that inhibits sphingosine-induced phosphorylation of p32 in Jurkat T cells when used at concentrations ranging from 30 to 100 μM. It has been used in the synthesis of various phospholipids and triglycerides.
| Cas No. | 24909-72-6 | SDF | |
| 别名 | 油酸酐 | ||
| Canonical SMILES | CCCCCCCC/C=C\CCCCCCCC(OC(CCCCCCC/C=C\CCCCCCCC)=O)=O | ||
| 分子式 | C36H66O3 | 分子量 | 546.9 |
| 溶解度 | DMF: miscible,DMSO: miscible,Ethanol: 100 mg/ml,Ethanol:PBS(pH 7.2) (1:1): 0.5 mg/ml | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
||
| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
 |
1 mg | 5 mg | 10 mg |
| 1 mM | 1.8285 mL | 9.1424 mL | 18.2849 mL |
| 5 mM | 0.3657 mL | 1.8285 mL | 3.657 mL |
| 10 mM | 0.1828 mL | 0.9142 mL | 1.8285 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Enzyme-Assisted Synthesis of High-Purity, Chain-Deuterated 1-Palmitoyl-2-oleoyl- sn-glycero-3-phosphocholine
ACS Omega 2020 Aug 26;5(35):22395-22401.PMID:32923797DOI:10.1021/acsomega.0c02823.
1-Palmitoyl-d 31-2-oleoyl-d 32-sn-glycero-3-phosphocholine (POPC-d 63) with the palmitoyl and oleoyl chains deuterium-labeled was produced in three steps from 1-palmitoyl-2-hydroxy-sn-glycero-3-phosphocholine, deuterated palmitic acid, and deuterated Oleic Anhydride. Esterification at the sn-2 position was achieved under standard chemical conditions, using DMAP to catalyze the reaction between the 2-lysolipid and oleic anhydride-d 64. Complete regioselective sn-1 acyl substitution was achieved in two steps using operationally simple, enzyme-catalyzed regioselective hydrolysis and esterification to substitute the sn-1 chain for a perdeuterated analogue. This method provides chain-deuterated POPC with high chemical purity (>96%) and complete regiopurity, useful for a variety of experimental techniques. This chemoenzymatic semisynthetic approach is a general, modular method of producing highly pure, mixed-acyl phospholipids, where the advantages of both chemical synthesis (efficiency, high yields) and biocatalytic synthesis (specificity, nontoxicity) are realized.
Metabolism and motility in prebiotic structures
Philos Trans R Soc Lond B Biol Sci 2011 Oct 27;366(1580):2885-93.PMID:21930579DOI:10.1098/rstb.2011.0141.
Easily accessible, primitive chemical structures produced by self-assembly of hydrophobic substances into oil droplets may result in self-moving agents able to sense their environment and move to avoid equilibrium. These structures would constitute very primitive examples of life on the Earth, even more primitive than simple bilayer vesicle structures. A few examples of simple chemical systems are presented that self-organize to produce oil droplets capable of movement, environment remodelling and primitive chemotaxis. These chemical agents are powered by an internal chemical reaction based on the hydrolysis of an Oleic Anhydride precursor or on the hydrolysis of hydrogen cyanide (HCN) polymer, a plausible prebiotic chemistry. Results are presented on both the behaviour of such droplets and the surface-active properties of HCN polymer products. Such motile agents would be capable of finding resources while escaping equilibrium and sustaining themselves through an internal metabolism, thus providing a working chemical model for a possible origin of life.
Chain-length-dependent autocatalytic hydrolysis of fatty acid anhydrides in polyethylene glycol
J Phys Chem B 2014 Mar 27;118(12):3461-8.PMID:24588328DOI:10.1021/jp4125233.
Autocatalytic hydrolysis of fatty acid anhydrides induced by the spontaneously formed vesicles has been studied for years. However, whether the reaction autocatalyzed by vesicles formed in diluted solutions applies also to macromolecular crowded conditions remains unknown. The aim of this study is to characterize hydrolysis behavior of fatty acid anhydrides and formation of vesicles in crowded media. Inert macromolecular crowding agents such as polyethylene glycol (PEG) and Dextran were used to probe the impact of external crowding on the autocatalytic hydrolysis of fatty acid anhydrides with varied hydrophobic chain length. Under stringent conditions of crowding, hydrolysis rates of octanoic anhydride, nonanoic anhydride, and decanoic anhydride were found to decrease, but the rates of lauric anhydride and Oleic Anhydride increased. These results suggest that the effect of the crowding agent on the hydrolysis of fatty acid anhydrides was chain-length-dependent. Characterization of the size and polydispersity of vesicles formed from hydrolyzed fatty acid anhydrides in crowding revealed that long-chain fatty acids formed monodisperse vesicles easier at lower concentrations of PEG. Measurement of the critical aggregation concentration of ionized fatty acid in the presence of PEG showed that crowding media promoted vesicle formation from long-chain fatty acids but inhibited those from fatty acids with fewer carbon atoms. Further investigation of the diffusion property of ionized fatty acids in crowding agents suggested that PEG might create more hydrophobic areas for long-chain fatty acids anhydrides, which subsequently promoted the unreacted anhydride in the aqueous phase to be solubilized in the formed vesicles. This research provides information for understanding the autocatalytic reaction accompanied by self-producing aggregates and the behavior of fatty acids in crowding media.
Synthesis of single- and double-13C-labeled cholesterol oleate
Chem Phys Lipids 1988 Sep;48(1-2):147-51.PMID:3208413DOI:10.1016/0009-3084(88)90143-0.
Cholesterol oleate with the 13C-label in oleic acid at the carbonyl and/or in the sterol ring at position 4 was synthesized by two methods: (1) cholesterol was condensed with Oleic Anhydride, prepared from [1-13C] oleic acid, in the presence of dimethylaminopyridine (DMAP) in anhydrous chloroform at room temperature for 4--5 h; (2) cholesterol or 13C-enriched cholesterol at position 4 were reacted with 90% [1-13C]-oleic acid in the presence of dicyclohexylcarbodiimide (DCC) and DMAP at room temperature in anhydrous chloroform for 1.25 h. The single-13C and double-13C-labeled cholesterol oleate were obtained in 90% yields after purification by silicic acid column chromatography. Their purity was assessed by thin-layer chromatography (TLC), high-performance liquid chromatography (HPLC) and 13C-NMR spectroscopy. Tritium-labeled cholesterol oleate was also synthesized by method 1 using the fatty acid anhydride.
Enzymatic RNA replication in self-reproducing vesicles: an approach to a minimal cell
Biochem Biophys Res Commun 1995 Feb 6;207(1):250-7.PMID:7531971DOI:10.1006/bbrc.1995.1180.
The replication of a RNA template catalyzed by Q beta replicase was obtained in oleic acid/oleate vesicles simultaneously with the self-reproduction of the vesicles themselves. This was accomplished by entrapping the enzyme Q beta replicase, the RNA template, and the ribonucleotides ATP, CTP, GTP, and UTP inside the vesicles. The water-insoluble Oleic Anhydride was then added externally. It binds to the vesicle bilayer where it is catalytically hydrolyzed yielding the carboxylate surfactant in situ, which then brings about growth and reproduction of the vesicles themselves. This experiment is presented as a first approach to a synthetic minimal cell, in which the reproduction of the membrane and the replication of the internalized RNA molecules proceed simultaneously.