12-hydroxy Stearic Acid
(Synonyms: 12-羟基硬脂酸) 目录号 : GC49310
A hydroxy fatty acid
Cas No.:106-14-9
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
12-hydroxy Stearic acid is a hydroxy fatty acid produced by the hydrogenation of ricinoleic acid .1 It is a low molecular weight gelator that self-assembles to form organogels.2 Administration of paclitaxel in 12-hydroxy stearic acid-containing gel nanocarriers enhances tumor growth suppression in an H22 murine hepatocellular carcinoma model.3 Formulations containing 12-hydroxy stearic acid have been used in cosmetic products as emollients.
1.Fameau, A.-L., and Rogers, M.A.The curious case of 12-hydroxystearic acid — the Dr. Jekyll & Mr. Hyde of molecular gelatorsCurr. Opin. Colloid Interface Sci.4568-82(2020) 2.Burkhardt, M., Noirez, L., and Gradzielski, M.Organogels based on 12-hydroxy stearic acid as a leitmotif: Dependence of gelation properties on chemical modificationsJ. Colloid Interface Sci.466369-376(2016) 3.He, W., Lv, Y., Zhao, Y., et al.Core-shell structured gel-nanocarriers for sustained drug release and enhanced antitumor effectInt. J. Pharm.484(1-2)163-171(2015)
| Cas No. | 106-14-9 | SDF | |
| 别名 | 12-羟基硬脂酸 | ||
| Canonical SMILES | CCCCCCC(O)CCCCCCCCCCC(O)=O | ||
| 分子式 | C18H36O3 | 分子量 | 300.5 |
| 溶解度 | DMF: 10 mg/ml,DMSO: 10 mg/ml,Ethanol: 10 mg/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 | 3.3278 mL | 16.6389 mL | 33.2779 mL |
| 5 mM | 0.6656 mL | 3.3278 mL | 6.6556 mL |
| 10 mM | 0.3328 mL | 1.6639 mL | 3.3278 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。
Organogels based on 12-hydroxy Stearic Acid as a leitmotif: Dependence of gelation properties on chemical modifications
J Colloid Interface Sci 2016 Mar 15;466:369-76.PMID:26752432DOI:10.1016/j.jcis.2015.12.025.
Various compounds based on the structural leitmotif of 12-hydroxy Stearic Acid (HSA) were studied with respect to their ability to form organogels. They were modified by ethoxylation in order to avoid the acid group of HSA, which is unwanted for many of the applications of organogels. In this paper, it is shown that the rheological performance of organogels depends strongly on the extent of ethoxylation, exhibiting an optimum at intermediate degrees of ethoxylation. Furthermore, we reveal that the ability for gelation as well as the mechanical properties are substantially reduced by the presence of stearic acid (SA) in the original reaction mixture, which is a typical contamination of HSA. This is quantified by the amount of gelator required for gelation and the elastic moduli observed for the gels. At the same time the mesoscopic structure, as probed by small-angle neutron scattering (SANS), is almost unchanged for different degrees of ethoxylation or the addition of SA--and similarly thick fibres are observed, while the viscoelastic parameters evolve. Accordingly the elastic efficiency of the individual structural units is responsible for the observed changes in the gelation properties. These findings are relevant for the application of such low molecular weight organogelators in practical formulations, as one can optimise the rheological properties of organogelators by appropriately choosing the degree of ethoxylation.
Docosahexaenoic Acid Esters of Hydroxy Fatty Acid Is a Novel Activator of NRF2
Int J Mol Sci 2021 Jul 15;22(14):7598.PMID:34299218DOI:10.3390/ijms22147598.
Fatty acid esters of hydroxy fatty acids (FAHFAs) are a new class of endogenous lipids with interesting physiological functions in mammals. Despite their structural diversity and links with nuclear factor erythroid 2-related factor 2 (NRF2) biosynthesis, FAHFAs are less explored as NRF2 activators. Herein, we examined for the first time the synthetic docosahexaenoic acid esters of 12-hydroxy Stearic Acid (12-DHAHSA) or oleic acid (12-DHAHOA) against NRF2 activation in cultured human hepatoma-derived cells (C3A). The effect of DHA-derived FAHFAs on lipid metabolism was explored by the nontargeted lipidomic analysis using liquid chromatography-mass spectrometry. Furthermore, their action on lipid droplet (LD) oxidation was investigated by the fluorescence imaging technique. The DHA-derived FAHFAs showed less cytotoxicity compared to their native fatty acids and activated the NRF2 in a dose-dependent pattern. Treatment of 12-DHAHOA with C3A cells upregulated the cellular triacylglycerol levels by 17-fold compared to the untreated group. Fluorescence imaging analysis also revealed the suppression of the degree of LDs oxidation upon treatment with 12-DHAHSA. Overall, these results suggest that DHA-derived FAHFAs as novel and potent activators of NRF2 with plausible antioxidant function.
Discovery of Eicosapentaenoic Acid Esters of Hydroxy Fatty Acids as Potent Nrf2 Activators
Antioxidants (Basel) 2020 May 8;9(5):397.PMID:32397146DOI:10.3390/antiox9050397.
Branched fatty acid esters of hydroxy fatty acids (FAHFAs) are a recently discovered class of biologically active lipids with anti-inflammatory and anti-diabetic properties. Despite the possible link between endogenous FAHFA levels and nuclear factor erythroid 2-related factor 2 (Nrf2), their possible function as antioxidants and the mechanisms involved in this are unknown. Here, we investigate FAHFAs' plausible antioxidant potential with reference to their effect on the Nrf2 levels, oxidative stress, and lipid droplet oxidation in human hepatocytes (C3A). Six authentic FAHFAs were chemically synthesized and performed activity-based screening by reporter gene assay. Among them, eicosapentaenoic acid (EPA) esterified 12-hydroxy Stearic Acid (12-HSA) and 12-hydroxy oleic acid (12-HOA) FAHFAs showed less cytotoxicity compared to their free fatty acids and potent activators of Nrf2. To define their mode of action, relative levels of nuclear Nrf2 were determined, which found a higher amount of Nrf2 in nucleus of cells treated with 12-EPAHSA compared to the control. Furthermore, 12-EPAHSA increased the expression of Nrf2-dependent antioxidant enzyme genes (NQO1, GCLM, GCLC, SOD-1, and HO-1). Fluorescence imaging analysis of linoleic-acid-induced lipid droplets (LDs) in C3A cells treated with 12-EPAHSA revealed the strong inhibition of small-size LD oxidation. These results suggest that EPA-derived FAHFAs as a new class of lipids with less cytotoxicity, and strong Nrf2 activators with plausible antioxidant effects via the induction of cytoprotective proteins against oxidative stress, induced cellular damage.
Structuring of sunflower oil by stearic acid derivatives: Experimental and molecular modelling studies
Food Chem 2020 Sep 15;324:126801.PMID:32353654DOI:10.1016/j.foodchem.2020.126801.
Structuring of vegetable oils has potential application in food, pharmaceutical and cosmetic products. In this study, structuring effects of stearic acid derivatives on sunflower seed oil were systematically investigated by experimental and molecular simulation methods. Stearic acid (SA), 12-hydroxy Stearic Acid (HSA) and 2-hydroxyethyl stearate (HES) were able to structure sunflower seed oil, among which the structuring ability of HES was reported for the first time. The oleogel formed with HSA exhibited good mechanical properties (such as hardness, fracturability, adhesiveness, chewiness and storage modulus), which coincided with its highest solid fat content and degree of crystallinity. Oleogels containing SA and HES showed similar mechanical properties. Both the molecular dynamics (MD) simulation and independent gradient model (IGM) confirmed that the HSA dimer possessed the strongest interaction during the self-assembly process while the dimers of HES and SA had similar interactions, which could explain their structuring performance.
Injectable Pasty Biodegradable Polyesters Derived from Castor Oil and Hydroxyl-Acid Lactones
J Pharmacol Exp Ther 2019 Sep;370(3):736-741.PMID:31092539DOI:10.1124/jpet.119.259077.
Pasty polymers offer a platform for injectable implants for drug delivery. A library of biodegradable pasty polymers was synthesized by bulk ring-opening polymerization of lactide, glycolide, trimethylene carbonate, or caprolactone using castor oil or 12-hydroxy Stearic Acid as hydroxyl initiators and stannous octoate as the catalyst. Some of the polymers behaved as Newtonian liquids. Pasty polymers of poly(caprolactone) and poly(trimethylene carbonate) were stable under physiologic conditions for over 1 month in vitro, whereas polymers of poly(lactic-co-glycolic acid) degraded within 10 days. These pasty polymers offer a platform for pasty injectable biodegradable carriers for drugs and fillers. SIGNIFICANCE STATEMENT: New injectable pasty, in situ forming drug delivery systems are described and are advantageous due to their ease of administration, tunable viscosity, and biodegradability. Polyesters based on lactide, glycolide, trimethylene carbonate, and caprolactone, which are commonly used as absorbable implants and drug carriers, were conjugated onto natural hydroxyl fatty acids. These polymers have potential use as wrinkle fillers and drug carriers.