Cholesteryl Nervonate
(Synonyms: C24:1-CE, 24:1 Cholesterol ester) 目录号 : GC49726
A cholesterol ester
Cas No.:60758-73-8
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Cholesteryl nervonate is a cholesterol ester composed of cholesterol and nervonic acid .1 It has been found in human meibum. Cholesteryl nervonate has been used in the generation of liposomes.2
1.Butovich, I.A.Cholesteryl esters as a depot for very long chain fatty acids in human meibumJ. Lipid. Res.50(3)501-513(2009) 2.Miyazaki, Y., Hara-Hotta, H., Matsuama, T., et al.Hemolysis of phosphatidylcholine-containing erythrocytes by serratamic acid from Serratia marcescensInt. J. Biochem.25(7)1033-1038(1992)
| Cas No. | 60758-73-8 | SDF | Download SDF |
| 别名 | C24:1-CE, 24:1 Cholesterol ester | ||
| Canonical SMILES | C[C@]12C(C[C@@H](OC(CCCCCCCCCCCCC/C=C\CCCCCCCC)=O)CC2)=CC[C@]3([H])[C@]1([H])CC[C@@]4(C)[C@@]3([H])CC[C@@]4([C@@H](CCCC(C)C)C)[H] | ||
| 分子式 | C51H90O2 | 分子量 | 735.3 |
| 溶解度 | Chloroform: 50mg/mL | 储存条件 | -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。 |
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| 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 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 1.36 mL | 6.7999 mL | 13.5999 mL |
| 5 mM | 0.272 mL | 1.36 mL | 2.72 mL |
| 10 mM | 0.136 mL | 0.68 mL | 1.36 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。
Conformation and packing of unsaturated chains in crystals of Cholesteryl Nervonate at 123 K
J Lipid Res 1984 Aug;25(8):851-6.PMID:6548506doi
At 123 K, cholesterol cis-15-tetracosenoate (Cholesteryl Nervonate, C51H90O2) is monoclinic, space group P2(1) with a = 12.948(5), b = 8.805(5), c = 42.98(5) A, beta = 105.93(3) degrees, [lambda(CuK alpha) = 1.5418 A], having two independent molecules (A) and (B) in the unit cell. The crystal structure at 123 K has been determined from 6329 reflections with sin theta/lambda less than 0.54 A-1, of which 1990 gave I greater than 2 sigma(I). Structure refinement by Fourier methods and block diagonal least squares gave R = 0.232 for all reflections, R = 0.135 for those with I greater than 2 sigma(I). The crystal structure consists of layers in which there is close packing of cholesteryl groups and the proximal segments of the ester chains. This layer structure occurs also in cholesteryl palmitoleate and the alkanoate esters C9 through C12. Because the nervonate chains are longer, they become aligned in the interface region between layers, but without a regular subcell structure being established. The nervonate (A)-chain is almost extended, while the (B)-chain has two bends, one in the saturated region. Both chains have complex dislocations at the cis-double bond.
Analysis of Comparison of Human Meibomian Lipid Films and Mixtures with Cholesteryl Esters In Vitro Films using High Resolution Color Microscopy
Invest Ophthalmol Vis Sci 2012 Jul 10;53(8):4710-9.PMID:22695957DOI:10.1167/iovs.12-10022.
Purpose: The lipid layer of the tears has been studied in vivo using high resolution color microscopy (HRCM). The purpose of these experiments was to gain further insight into the structure of the lipid layer by applying HRCM to in vitro meibomian lipid films. Methods: Films of human meibomian lipids, Cholesteryl Nervonate, cholesteryl palmitate, or their mixtures, were spread on a Langmuir trough. Changes to the films were monitored using HRCM as the films were compressed to different surface pressures. The penetration of albumin into a meibomian lipid film also was studied. Results: Small amounts of meibomian lipids at low pressures formed very thin films estimated to be 5.2 nm thick. Compression caused spots to appear in the films. At higher concentrations, micro lenses were a feature of the film. Cholesteryl Nervonate formed a multilayered oil slick that did not change with surface pressure. Cholesteryl palmitate formed a stiff film that collapsed at high compression. Mixtures of Cholesteryl Nervonate and meibomian lipids showed that they mixed to increase surface pressures above that of the individual components. HRCM also allowed albumin to be seen penetrating the meibomian lipid film. Conclusions: HRCM combined with in vitro surface pressure measurements using a Langmuir trough is useful for modeling meibomian lipid films. The films often resemble the appearance of the lipid layer of in vivo films. The data indicate that the lipid layer might be modeled best as a duplex film containing an array of liquid crystals.
Physical properties of cholesteryl esters having 20 carbons or more
Biochim Biophys Acta 1981 Apr 23;664(1):98-107.PMID:7236700DOI:10.1016/0005-2760(81)90032-1.
By polarizing microscopy and differential scanning calorimetry we observed that the relative stability of the smectic and cholesteric mesophases of cholesteryl esters of acyl chain length of 20 carbons or more depends on the length of the acyl chain and its degree of unsaturation. Significantly, the addition of a single double bond to the acyl chain of a fully saturated cholesteryl ester which exhibits no mesophases (e.g., cholesteryl behenate (C22:0) and cholesteryl lignocerate (C24:0) yields an ester which displays an unusually stable smectic mesophase, bot no cholesteric mesophase. In fact, increasing unsaturation was found to have a destabilizing effect on the cholesteric phase. Similarly, a decrease in thermal stability of the cholesteric mesophase was observed with increasing thermal stability of the smectic mesophase increased in the same series. X-ray scattering data are presented on the smectic mesophase of cholesteryl erucate (C22:1) and Cholesteryl Nervonate (C24:1). Significant differences in molecular packing of these two monounsaturated omega = 9 cholesteryl esters in the crystalline state are demonstrated by preliminary X-ray scattering experiments.
Coulometric detection in high-performance liquid chromatographic analysis of cholesteryl ester hydroperoxides
Free Radic Biol Med 1996;20(3):365-71.PMID:8720907DOI:10.1016/0891-5849(96)02062-x.
A highly sensitive and simple method for the determination of cholesteryl ester hydroperoxides (ChE-OOH) was developed using high-performance liquid chromatography (HPLC) with coulometric electrochemical detection. The lowest detectable level by this technique was 2 pmol for cholesteryl linoleate hydroperoxides at the signal-to-noise ratio of 3. This method was applied to the determination of ChE-OOH presumably present in human plasma. Although ChE-OOH could not be detected, the ChE-OOH level in the fluid was estimated to be less than 27 nM. It was found that the extraction efficiency of an internal standard, Cholesteryl Nervonate, was decreased by lowering its amount spiked to the plasma. The concentration of ChE-OOH in human plasma and plasma lipoprotein, which were peroxidized with a radical initiator in vitro, could be determined by use of this standard. HPLC-coulometric technique is, therefore, useful to measure the peroxidation of plasma lipids in vitro.
Temperature-dependent molecular motions of cholesterol esters: a carbon-13 nuclear magnetic resonance study
Biochemistry 1982 Dec 21;21(26):6857-67.PMID:7159569DOI:10.1021/bi00269a036.
Carbon-13 NMR spectroscopy at 50.3 MHz has been used to study four long-chain cholesterol esters with a double bond in the omega-9 position: cholesteryl oleate, C18:1, omega-9; cholesteryl linoleate, C18:2, omega-6,9; cholesteryl erucate, C22:1, omega-9; Cholesteryl Nervonate, C24:1, omega-9. The linoleate and oleate esters exhibit two metastable liquid-crystalline phases (cholesteric and smectic), whereas the longer chain esters form a stable smectic phase but no cholesteric phase [Ginsburg, G. S., & Small, D. M. (1981) Biochim. Biophys. Acta 664, 98-107]. Line widths (nu 1/2), spin--lattice relaxation times (T1), and nuclear Overhauser enhancements (NOE) were measured for all well-resolved resonances from ring and fatty acyl (FA) carbons at different temperatures in the isotropic liquid of each ester. T1 and NOE values of FA resonances were constant between the FA-2 carbon and olefinic region of each acyl chain and increased markedly for carbons near the chain terminus. FA carbon motions are thus restricted and/or highly correlated in the region between the ring and the olefinic carbons, suggesting that strong interactions occur between cholesterol ester molecules in this region of the FA chain. These results also suggest that the FA chains are approximately extended in the isotropic liquid. Steroid ring methine C-6 and C-3 nu 1/2's increased differentially on cooling to the liquid leads to liquid crystal transition temperature (Tm) of each ester, indicative of increasingly anisotropic ring rotations. The rotational anisotropy was quantitated by using a prolate ellipsoid model for the cholesterol ester molecule for which two correlation times (corresponding to rotations about the long and short molecular axes) were calculated from the C-3 and C-6 nu 1/2 values. The C-3/C-6 nu 1/2 ratio was directly proportional to the anisotropy of the ring motions as measured by the ratio of the two correlation times. At any given temperature relative to Tm, the C-3 and C-6 nu 1/2's and the C-3/C-6 nu 1/2 ratios were larger for cholesterol esters which have a cholesteric phase than for esters which have no cholesteric phase, showing that steroid ring motions were more restricted and more anisotropic prior to the formation of a cholesteric phase. Cholesteryl erucate and Cholesteryl Nervonate have longer regions of FA chain interactions which result in greater chain cooperativity, apparently preventing the preordering of steroid rings to the degree necessary for formation of a cholesteric phase. Thus, these esters form the smectic phase directly from the isotropic liquid. These results are applied to the cholesterol ester transition in plasma low-density lipoproteins.