12-Hydroxystearic acid

300.477

300.48

227-283-5

2385

DTXSID8026725

Crystals from alcohol

2918199090

57.53000

6.03

DryPowder; OtherSolid; PelletsLargeCrystals

0.9±0.1 g/cm3

82 °C

436.3±18.0 °C at 760 mmHg

231.8±17.7 °C

1.468

In water, 0.424 mg/L at 25 deg C (est)

-20ºC

1.94X10-8 mm Hg at 25 deg C (est)

Henry's Law constant = 1.41X10-9 atm-cu m/mol at 25 °C (est)

pKa = 4.75 (est)

A C18 straight chain fatty acid with an -OH group attached to the carbon chain; combustible

NONH for all modes of transport

3

R36/37/38

S22-S24/25

WI3850000

Xi: Irritant;

P264, P280, P305+P351+P338, P33, P313

H319

SRP: Criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 422 companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H319 (92.31%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]|P264, P280, P305+P351+P338, and P337+P313|Aggregated GHS information provided by 60 companies from 4 notifications to the ECHA C&L Inventory.

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.

12-Hydroxyoctadecanoic acid's production and use in skin, hair and cosmetic products(1) and in lithium greases and chemical intermediates(2) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 900(SRC), determined from a structure estimation method(2), indicates that 12-hydroxyoctadecanoic acid is expected to have low mobility in soil(SRC). The pKa of 12-hydroxyoctadecanoic acid is 4.75(3), indicating that this compound will almost entirely exist in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization from moist soil is not expected because the acid exists as an anion and anions do not volatilize(SRC). 12-Hydroxyoctadecanoic acid is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.94X10-8 mm Hg at 25 °C(SRC), determined from a fragment constant method(5). 12-Hydroxyoctadecanoic acid degraded 93% of theoretical BOD using activated sludge in the Japanese MITI test(6), suggesting that biodegradation is an important environmental fate process in soil(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 900(SRC), determined from a structure estimation method(2), indicates that 12-hydroxyoctadecanoic acid is expected to adsorb to suspended solids and sediment(SRC). An estimated pKa of 4.75(3) indicates 12-hydroxyoctadecanoic acid will exist almost entirely in the anion form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process(SRC). According to a classification scheme(4), an estimated BCF of 56(SRC), from an estimated log Kow of 6.41(5) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is moderate, provided the compound is not metabolized by the organism(SRC). 12-Hydroxyoctadecanoic acid degraded 93% of theoretical BOD using activated sludge in the Japanese MITI test(6), suggesting that biodegradation is an important environmental fate process in water(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 12-hydroxyoctadecanoic acid, which has an estimated vapor pressure of 1.94X10-8 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase 12-hydroxyoctadecanoic acid may be removed from the air by wet or dry deposition(SRC). 12-Hydroxyoctadecanoic acid does not contain chromophores that absorb at wavelengths >290 nm(3), and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

12-Hydroxyoctadecanoic acid is not expected to undergo hydrolysis in the environment due to its lack of functional groups that hydrolyze under environmental conditions(1). 12-Hydroxyoctadecanoic acid does not contain chromophores that absorb at wavelengths >290 nm(1), and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

An estimated BCF of 56 was calculated in fish for 12-hydroxyoctadecanoic acid(SRC), using an estimated log Kow of 6.41(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate(SRC), provided the compound is not metabolized by the organism(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of 12-hydroxyoctadecanoic acid can be estimated to be 900(SRC). According to a classification scheme(2), this estimated Koc value suggests that 12-hydroxyoctadecanoic acid is expected to have low mobility in soil. The estimated pKa of 12-hydroxyoctadecanoic acid is 4.75(3), indicating that this compound will almost entirely exist in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4).

An estimated pKa of 4.75(1) indicates 12-hydroxyoctadecanoic acid will exist almost entirely in the anion form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process(SRC). Volatilization from moist soil is not expected because the acid exists as an anion and anions do not volatilize(SRC). 12-Hydroxyoctadecanoic acid is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.94X10-8 mm Hg(SRC), determined from a fragment constant method(2).

According to the 2006 TSCA Inventory Update Report, the number of persons reasonably likely to be exposed in the industrial manufacturing, processing, and use of 12-hydroxyoctadecanoic acid is 1-99; the data may be greatly underestimated(1).|NIOSH (NOES Survey 1981-1983) has statistically estimated that 52,609 workers (4,374 of these were female) were potentially exposed to 12-hydroxyoctadecanoic acid in the US(1). Occupational exposure to 12-hydroxyoctadecanoic acid may occur through dermal contact with this compound at workplaces where 12-hydroxyoctadecanoic acid is produced or used. Use data indicate that the general population may be exposed to 12-hydroxyoctadecanoic acid via dermal contact, primarily when using hair, skin and cosmetic products that contain this compound(SRC).

/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.

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.

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

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.

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

/HUMAN EXPOSURE STUDIES/ The skin irritation potential of four antiperspirant prototype formulations ... containing 7% hydroxystearic acid was evaluated using 35 healthy adult volunteers between the ages of 8 and 65 years old (33 females; 2 males). The four formulations were applied to the back of each subject (in vertical rows over the scapulae areas) in occlusive and semiocclusive patch tests. Prior to patch application, test sites on the back were wiped with a pad containing 70% isopropyl alcohol. Each formulation was applied to a patch by wiping the antiperspirant stick across the patch approximately five times. The quantity of test material applied per patch application (occlusive and semiocclusive) was in the range of 0.05 to 0.1 g. The semiocclusive patches were applied to the left side of the back three times, each for 48 hours (total of three 48-hour applications per test site). Occlusive patches were applied to the right side of the back (total of three 24-hours applications per test site). Both semiocclusive and occlusive patches were reinforced with strips of tape. Following patch removal, subjects were instructed to rinse the test sites with warm water. Patches were also removed by laboratory personnel, and were not reapplied to anysite that was assigned a score of 2 or greater. Test sites were evaluated for skin irritation within 24 hours after patch removal according to the following scale: 0 (no visible erythema) to 3 (severe erythema, very intense redness). Reactions to semiocclusive patches were scored on days 4, 7, and 10; occlusive patch test reactions were scored on days 4, 6, and 8. ... Semioccluded patches produced reactions in as many as nine of the subjects, whereas occluded patches produced reactions in as many as 17 individuals. Only two reactions were noted in the semioccluded patch controls and only one in the occluded patch controls. Although the formulations reportedly contained the same concentration of Hydroxystearic Acid, there were small differences in the numbers of individuals reacting to each.|/CASE REPORTS/ A 34-year-old male experienced severe allergic contact dermatitis from 12-hydroxystearic acid in a lip balm and from hydrogenated castor oil in an underarm deodorant. He also had a positive patch-test reaction to bis-diglyceryl polyacyladipate-2, which is present in the implicated lip balm and which itself contains 12-hydroxystearic acid. He was also incidentally found to have contact allergy to ricinoleic acid and castor oil. Ricinoleic acid is the principal fatty acid in castor oil, whereas 12-hydroxystearic acid is the principal fatty acid in hydrogenated castor oil. These two fatty acids are each 18-carbon 12-hydroxylated fatty acids, differing only in degree of saturation. The lack of patch-test reactivity to the analogous nonhydroxylated fatty acids, stearic acid (C18:0), and oleic acid (C18:1) indicates that 12-hydroxylation was required for allergenicity in this patient. In addition, serial dilution testing demonstrated that saturation of the hydroxylated C18 fatty acid enhanced its allergenicity.

12-hydroxy stearic acid

Oil and gas drilling, extraction, and support activities|Octadecanoic acid, 12-hydroxy-: ACTIVE|Octadecanoic acid, 12-hydroxy-, homopolymer: ACTIVE|XU - indicates a substance exempt from reporting under the Chemical Data Reporting Rule, (40 CFR 711).|Cosmetic oil bases are prepared with 12-hydroxystearic acid oligoesters which are produced by esterification of 12-hydroxystearic acid.|The synthesis of four sugar-based surfactants derived from glucose and (R)-12-hydroxystearic acid is described. The surfactants have a hydroxy group in the hydrophobic part, which is either free or acylated using acetyl chloride, hexanoyl chloride, or myristoyl chloride. Three of the synthesized surfactants are water-soluble and are evaluated with respect to their critical micelle concentrations and hemolytic activities. The fourth surfactant has limited water solubility and is not further included in the study. The investigated surfactants are all hemolytic close to their respective critical micelle concentration indicating that their use in parenteral formulations may be limited. Nevertheless, surfactants having the proposed structure appear as promising alternatives to existing solubilizing agents for pharmaceutical applications.

8-, 9-, 10-, & 12-HYDROXYSTEARIC ACID (AS METHYL ESTERS) WERE SEPARATED BY 2-DIMENSIONAL THIN-LAYER CHROMATOGRAPHY.

EPA Safer Chemical Functional Use Classes -> Surfactants|Safer Chemical Classes -> Green circle - The chemical has been verified to be of low concern|Fatty Acyls [FA] -> Octadecanoids [FA02] -> Other Octadecanoids [FA0200]|Cosmetics -> Cleansing; Emulsifying; Surfactant