The efficiency of 12-Hydroxystearic acid (12HSA) and its derivatives as gelling agents and their use as lubricants have been the subject of substantial research [1].

Absorption, Distribution and Excretion
The distribution and metabolism of 12-hydroxystearic Acid were evaluated using 90 young male albino rats (Slonaker substrain of Wistar strain; weights = 43 to 83 g). The rats were divided into groups of six and fed the following diets over a period of 16 weeks: 20% corn oil (control diet); 1 % hydrogenated castor oil and 19% corn oil; and 10% hydrogenated castor oil and 10% corn oil. Laboratory chow accounted for 80% of each diet. The fatty acid composition of hydrogenated castor oil that was added to the diet was as follows: 86.5% 12-hydroxystearic acid, 10.3% nonoxygenated acids, and 3.2% 12-ketostearic acid. Therefore, the actual dietary concentrations of 12-hydroxystearic acid that were fed to experimental animals were 0.87% (in 1% hydrogenated castor oil diet) and 8.7% (in 10% hydrogenated castor oil diet). At 8 weeks after the initiation of feeding, half of the groups were fed a corn oil diet for the remainder of the 16-week study. ... Lipids were extracted from adipose tissue samples and carcasses (three rats on each diet) after 8, 12, and 16 weeks The number of rats on each experimental diet that were alive at 4, 8, 12, and 16 weeks was 33, 30, 12, and 6 rats, respectively. The number of control rats that were alive at 4, 8, 12, and 16 weeks was 15, 15, 12, and 6, respectively. ... 12-Hydroxystearic acid was deposited in abdominal fat, as well as other body lipids, along with its metabolites (hydroxypalmitic acid, hydroxymyristic acid, and hydroxylauric acid). The percent composition of hydrogenated castor oil-derived hydroxy fatty acids in rat lipids was 81% 12-hydroxystearic acid, 17% 10-hydroxypalmitic acid, 1.6% 8-hydroxymyristic acid, and 0.4% 6-hydroxylauric acid. The greatest content of hydroxy acids in lipids was 4.4% in abdominal fat obtained from rats after four weeks of feeding of the 8.7% 12-hydroxystearic acid diet. This concentration decreased during the following weeks, and, at 16 weeks, was less than 2% (approximately the same concentration that was detected in carcass lipids). Hydroxy acids (as % of dry carcass weight) increased during weeks 8 to 16 in rats on both diets, 0.87% and 8.7% 12-hydroxystearic acid. After the diet for half of the experimental rats was changed to corn oil (control diet) at 8 weeks, the tissue content of hydroxy fatty acids decreased rapidly.
When 12-hydroxystearate was added to the diet of one dog (weight not stated) in the amount of 2.2 g/day, 12-hydroxystearic acid accounted for 46% of the total fecal fatty acids. When the amount added to the diet was increased to 8.8 g/day, 12-hydroxystearic acid accounted for 60.2% of the total fecal fatty acids.
12-Hydroxystearic acid fed to normal dogs, steatorrhea was not produced & absorption in amt similar to that of unsubstituted stearic acid was observed.

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Metabolism / Metabolites
10-Hydroxypalmitic acid & 8-hydroxymyristic acid were characterized as metabolites of 12-hydroxystearic acid.

Interactions
A low molecular mass gelator can form soft solids in a variety of organic liquids and vegetable oils. These soft solids are generally called organogels. ...This study /examined organogel prepared/ using 12-hydroxystearic acid (12-HSA) as a gelator for soybean oil and investigated its characteristics as a controlled release formulation for lipophilic compounds. The release rate of ibuprofen, a model lipophilic compound, from organogel decreased with the increase of 12-HSA concentration in the formulation; however, the difference in the concentration of 12-HSA in the formulation did not affect the diffusivity of ibuprofen in the organogel. The erosion constant of organogel in the intestinal tract was examined by using simulated gastric fluid and intestinal fluid. Regardless of 12-HSA concentration in the formulation, organogel is very stable in the simulated gastric fluid. On the other hand, the erosion constant of organogel in the simulated intestinal fluid increased with the decreasing concentration of 12-HSA. Therefore, it is speculated that the difference in the release rate of ibuprofen among organogels with various concentrations of 12-HSA was mainly caused by the difference in the erosion rate. To characterize the organogel effect in vivo, ibuprofen was orally administered to rats in an aqueous suspension or organogel. Ibuprofen concentration in plasma rapidly increased after administration with an aqueous suspension, whereas organogel suppressed the rapid absorption. In conclusion, organogel is clearly useful as an oral controlled release formulation for lipophilic compounds.

[1]. Aggregation of 12-Hydroxystearic Acid and Its Lithium Salt in Hexane: Molecular Dynamics Simulations. J Phys Chem B. 2016;120(29):7164-7173.

12-hydroxyoctadecanoic acid is a hydroxy fatty acid that is stearic acid bearing a hydroxy substituent at position 12. It has a role as a plant metabolite and a bacterial xenobiotic metabolite. It is a hydroxyoctadecanoic acid and a secondary alcohol. It is a conjugate acid of a 12-hydroxyoctadecanoate.
12-Hydroxyoctadecanoic acid has been reported in Bacillus cereus and Elaeagnus angustifolia with data available.
See also: Dipentaerythrityl tri-polyhydroxystearate (monomer of); Polyglyceryl-2 dipolyhydroxystearate (monomer of); Polyhydroxystearic acid (2300 MW) (monomer of) ... View More ...

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Mechanism of Action
In a study of primary and secondary lipid peroxidation products as modulators of DNA synthesis, murine Lewis carcinoma cells were treated with hydroxystearic acid at physiologic levels (50 and 100 uM). The test substance was dissolved in 90% ethanol and then added to the culture medium. DNA profiles obtained from flow cytometry analysis of cell cycle showed a time- and dose-dependent accumulation of cells in the G2-M phase compared to untreated exponentially growing cells. To determine if this effect was mediated by interaction of hydroxystearic acid with cyclin-dependent kinases-cyclin complexes, histone H1 kinase activity in C 108 cell crude extracts was measured. It was determined that hydroxystearic acid inhibited histone H1 kinase activity up to 95% of that noted for mitotic cells (synchronized control C108 cells).
12-Hydroxystearic acid (30 uM) also induced mitochondrial ATPase activity. ATPase activity was inhibited by rutamycin (blocks phosphorylation by ATP); this effect is expected for ATP-energized mitochondrial reactions. A small, but decided, mitochondrial volume change (swelling) was also induced by 30 pM 12-Hydroxystearic acid without the aid of ATP. This effect was inhibited by the respiratory inhibitor antimycin or dinitrophenol, but not by rutamycin; therefore, this effect was dependent on oxidative phosphorylation. 12-Hydroxystearic acid-induced mitochondrial swelling was enhanced when ATP was added to the reaction mixture. The investigators concluded that 12-Hydroxystearic acid interferes with the machinery of oxidative phosphorylation in rat liver mitochondria.

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Therapeutic Uses
/Experimental Therapy/ A low molecular mass gelator can form soft solids in a variety of organic liquids and vegetable oils. These soft solids are generally called organogels. ...This study /examined organogel prepared/ using 12-hydroxystearic acid (12-HSA) as a gelator for soybean oil and investigated its characteristics as a controlled release formulation for lipophilic compounds. ... Organogel is clearly useful as an oral controlled release formulation for lipophilic compounds.

C18H36O3

300.47664

300.266

106-14-9

12-Hydroxystearic acid-d5;2468637-39-8

7789

White to off-white solid powder

0.9±0.1 g/cm3

436.3±18.0 °C at 760 mmHg

80-81ºC

231.8±17.7 °C

0.0±2.4 mmHg at 25°C

1.468

6.03

2

3

16

21

229

0

ULQISTXYYBZJSJ-UHFFFAOYSA-N

InChI=1S/C18H36O3/c1-2-3-4-11-14-17(19)15-12-9-7-5-6-8-10-13-16-18(20)21/h17,19H,2-16H2,1H3,(H,20,21)

12-hydroxyoctadecanoic acid

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

DMSO : ~100 mg/mL (~332.80 mM)

Solubility in Formulation 1: ≥ 2.5 mg/mL (8.32 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

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 (Please use freshly prepared in vivo formulations for optimal results.)