9,10-Dihydroxystearic Acid
(Synonyms: 9,10-二羟硬脂酸；9,10-二羟基十八酸) 目录号 : GC45753An oxidation product of oleic acid
Cas No.:120-87-6
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
9,10-Dihydroxystearic acid is an oxidation product of oleic acid that can be formed from oleic acid in HepG2 cells.[1] It activates peroxisome proliferator-activated receptor α (PPARα) in CV-1 cells when used at concentrations ranging from 50 to 100 μM.[2] 9,10-Dihydroxystearic acid (4% in the diet) decreases blood glucose levels, increases insulin sensitivity, and decreases body weight in high-fat diet-fed KKAy diabetic mice.
Reference:
[1]. Jing, H.-J., Zhang, Y.-H., Wang, J., et al. Conversion of oleic acid to 9,10-dihydroxystearic acid in human hepatic cancer HepG2 cells. Junyi Jinxiu Xueyuan Xuebao 31(6), 597-599 (2010).
[2]. Yu, X., Zhang, Y., Liu, Y., et al. Effects of 9,10-dihydroxysteatic acid on glucose metabolism in KKAy mice. Wei Sheng Yan Jiu 39(4), 423-425 (2010).
| Cas No. | 120-87-6 | SDF | |
| 别名 | 9,10-二羟硬脂酸；9,10-二羟基十八酸 | ||
| 化学名 | 9,10-dihydroxy-octadecanoic acid | ||
| Canonical SMILES | OC(CCCCCCCC(O)C(O)CCCCCCCC)=O | ||
| 分子式 | C18H36O4 | 分子量 | 316.5 |
| 溶解度 | DMF: 25mg/mL,DMSO: 10mg/mL,DMSO:PBS (pH 7.2) (1:5): 0.16mg/mL,Ethanol: 5mg/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。 |
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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 | 3.1596 mL | 15.7978 mL | 31.5956 mL |
| 5 mM | 0.6319 mL | 3.1596 mL | 6.3191 mL |
| 10 mM | 0.316 mL | 1.5798 mL | 3.1596 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。
pH-Responsive Liquid Marbles Based on Dihydroxystearic Acid
Langmuir 2022 May 10;38(18):5702-5707.PMID:35438998DOI:10.1021/acs.langmuir.2c00303.
Herein, we report pH-responsive liquid marbles stabilized by 9,10-Dihydroxystearic Acid (DHSA). The particle morphology and the pH-responsive behavior of the liquid marbles were investigated. The rolling time during the preparation of liquid marbles has a great influence on the thickness of powder adsorption and the stability of the marbles. Compared with the liquid marbles stabilized by other fatty acids (e.g., stearic acid and docosoic acid), the liquid marbles prepared by DHSA have a much higher mechanical robustness. The increase in the number of hydroxyl groups on the carbon chain of fatty acids improves the mechanical robustness of the liquid marbles. Such liquid marbles immediately disintegrated on the surface of an alkaline solution or after exposure to NH3 gas, which extends their applications in the NH3 sensor and chemical reactions.
omega-Hydroxylation of Z9-octadecenoic, Z9,10-epoxystearic and 9,10-dihydroxystearic acids by microsomal cytochrome P450 systems from Vicia sativa
Biochem Biophys Res Commun 1992 Apr 15;184(1):183-93.PMID:1567426DOI:10.1016/0006-291x(92)91176-q.
A microsomal fraction from etiolated Vicia sativa seedlings incubated aerobically with [1-14C]oleic acid (Z9-octadecenoic acid) or [1-14C]9,10-epoxystearic acid or [1-14C]9,10-Dihydroxystearic Acid catalyzed the NADPH-dependent formation of hydroxylated metabolites. The chemical structure of compounds formed from oleic, 9,10-epoxystearic or 9,10-dihydroxystearic acids was established by gas chromatography/mass spectra analysis to be 18-hydroxyoleic acid, 18-hydroxy-9,10-epoxystearic acid and 9,10,18-trihydroxystearic acid, respectively. The reactions required O2 and NADPH and were inhibited by carbon monoxide. As expected for monooxygenase reactions involving cytochrome P450, inhibition could be partially reversed by light and all three reactions were inhibited by antibodies raised against NADPH-cytochrome P450 reductase from Jerusalem artichoke. The omega-hydroxylation of the three substrates was enhanced in microsomes from clofibrate induced seedlings.
Synthesis of highly pure oxyphytosterols and (oxy)phytosterol esters. Part II. (Oxy)-sitosterol esters derived from oleic acid and from 9,10-Dihydroxystearic Acid [1]
Steroids 2008 Oct;73(11):1098-109.PMID:18533216DOI:10.1016/j.steroids.2008.04.010.
Several efficient synthetic routes giving readily access to (oxy)-sitosterol esters and (oxy)-cholesterol esters derived respectively from oleic acid and from 9,10-Dihydroxystearic Acid were developed for the first time. This approach allowed that sufficient amounts of the latter were available in order to carry out further biological studies.
Development, characterization and commercial application of palm based dihydroxystearic acid and its derivatives: an overview
J Oleo Sci 2011;60(5):237-65.PMID:21502724DOI:10.5650/jos.60.237.
Hydroxyl fatty acids and their derivatives are of high value due to their wide range of industrial application, including cosmetic, food, personal care and pharmaceutical products. Realizing the importance of hydroxyl fatty acids, and yet due to the absence of the conventional starting raw materials, Malaysia has developed 9,10-Dihydroxystearic Acid (9,10-DHSA) and its derivatives from locally abundant palm based oils. The aim of this article is to provide a general description of the works that have thus far being done on palm based 9,10-DHSA: starting from its conception and production from commercial grade palm based crude oleic acid via epoxidation and hydrolysis, purification through solvent crystallization and characterization through wet and analytical chemistry, moving on to developmental works done on producing its derivatives through blending, esterification, amidation and polymerization, and completing with applications of 9,10-DHSA and its derivatives, e.g. DHSA-stearates and DHSA-estolides, in commercial products such as soaps, deodorant sticks and shampoos. This article incorporates some of the patent filed technological knowhow on 9,10-DHSA and its derivatives, and will also point out some of the shortcomings in previously published documents and provide some recommendations for future research works in mitigating these shortcomings.
Lipase-catalyzed esterification of palm-based 9,10-Dihydroxystearic Acid and 1-octanol in hexane--a kinetic study
Biotechnol Lett 2004 Jan;26(1):11-4.PMID:15005144DOI:10.1023/b:bile.0000009452.73477.26.
The esterification of palm-based 9,10-Dihydroxystearic Acid (DHSA) and 1-octanol in hexane as catalyzed by lipase from Rhizomucor meihei (Lipozyme IM) followed Michaelis-Menten kinetics. The esterification reaction follows a Ping-Pong, Bi-Bi mechanism. The maximum rate was estimated to be 1 micromol min(-1) mg(-1) catalyst in hexane at 50 degrees C, and the Michaelis-Menten constants for DHSA and 1-octanol were 1.3 M and 0.7 M, respectively.