122-32-7CCCCCCCC/C=C\CCCCCCCC(=O)OCC(COC(=O)CCCCCCC/C=C\CCCCCCCC)OC(=O)CCCCCCC/C=C\CCCCCCCCPHYFQTYBJUILEZ-IUPFWZBJSA-NTriolein is a triglyceride formed by esterification of the three hydroxy groups of glycerol with oleic acid. Triolein is one of the two components of Lorenzo's oil. It has a role as a plant metabolite and a Caenorhabditis elegans metabolite. It is functionally related to an oleic acid.
122-32-7DTXSID3026988CHEMBL2110597、CHEMBL4297656CHEBI:53753Cosmetic ingredients (Triolein) -> CIR (Cosmetic Ingredient Review)
Skin conditioning; Solvent; Viscosity controlling; Emollient; Refatting
Agrochemicals -> Pesticide active substances
Active substance -> EU Pesticides database: Not approved
Colorless to yellowish, oily liquid
POLYMORPHIC
This chemical does not meet GHS hazard criteria for 100% (291 of 291) of all reports.
Not Classified
Aggregated GHS information provided per 291 reports by companies from 1 notifications to the ECHA C&L Inventory.
Chemical: 9-Octadecenoic acid, 1,2,3-propanetriyl ester, (Z)-
9-Octadecenoic acid (9Z)-, 1,1',1''-(1,2,3-propanetriyl) ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 9-Octadecenoic acid (9Z)-, 1,1',1''-(1,2,3-propanetriyl) ester are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
2007/442
Status: Active Update: 09-03-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/5426
9-Octadecenoic acid (9Z)-, 1,2,3-propanetriyl ester: Does not have an individual approval but may be used under an appropriate group standard
In the small intestine, most triglycerides are split into monoglycerides, free fatty acids, and glycerol, which are absorbed by the intestinal mucosa. [HSDB] High-dose feeding of rats causes liver changes; [RTECS] May cause irritation; [MSDSonline]
Triolein (major skin lipid) was irradiated with 300-nm ultraviolet (UV) light, and the conditions for exposure approximated those at the skin surface exposed to sunlight. Using gas chromatography, the irradiated samples were analyzed for the presence of acrolein, formaldehyde, and acetaldehyde. The maximum amount of acrolein (1.05 nmol/mg Triolein) was formed after 6 hours of irradiation. Maximum amounts of formaldehyde (6 nmol/mg Triolein) and acetaldehyde (2.71 nmol/mg Triolein) were formed after 12 hours of irradiation.
Hydrolysis of /Triolein/ by hepatic triacylglycerol lipase in plasma from ICR mice has been demonstrated in vitro.
The metabolism of triolein in vitro was evaluated using isolated perfusion of a rat liver in tandem with an isolated rat hind-end. This permitted the study of lipid transfer between the two. In the absence of added triolein, a net removal of free fatty acids was demonstrated in both tissue beds when fatty acid gradients across tissue beds were measured. Following the addition of 100 mg of triolein (as [(3)H]-glycerol-[(14)C]triolein) to either reservoir in the system, an appreciable net production of free fatty acid was noted for the hind-end gradient at 30 minutes. This hind-end free fatty acid efflux amounted to more than one third of the catabolism of triolein.
In experimental studies, embolization of the cerebral hemisphere with triolein emulsion has revealed reversible magnetic resonance imaging (MRI) findings in the subacute stage. /The aim of this study was/ to investigate the changes in the major metabolites, by proton magnetic resonance spectroscopy (MRS), in a cerebral fat embolism induced by a triolein emulsion.The internal carotid arteries of 19 cats were injected with a triolein emulsion, and multivoxel MRS was performed 30 min, 1 day, and 7 days later. In the control group, six cats were injected with normal saline. The MR spectra were evaluated for N-acetyl aspartate (NAA), creatine (Cr), and choline (Cho), along with the presence of lipid and lactate. Semiquantitative analyses of NAA/Cr, Cho/Cr, NAA/Cho, and lipid/Cr ratios compared the median values of the ipsilateral metabolite ratios with those of the contralateral side and in the control group for each point in time.The NAA/Cr, Cho/Cr, and NAA/Cho ratios in the ipsilateral cerebral hemisphere of the embolized group after 30 min, 1 day, and 7days were not significantly different from the contralateral hemisphere of the embolized and control groups (P>0.05). The lipid/Cr ratio in the ipsilateral cerebral hemisphere of the embolized group was significantly higher when compared with the control group (P=0.012 at 30 min, P=0.001 on day 1, and P=0.018 on day 7). Cerebral fat embolism induced by a triolein emulsion resulted in no significant change in the major metabolites of the brain in the acute stage, except for an elevated lipid/Cr ratio, which suggests the absence of any significant hypoxic-ischemic changes in the lesions embolized using a fat emulsion.
Wird geladen…
Insoluble in water
Soluble in chloroform, ether, carbon tetrachloride and slightly soluble in alcohol.
237 °C at 18 atm
Boiling Point at 760 mm Hg = 554 °C /Estimated via extrapolation/
-4 °C
-32 °C
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.
IM administration of tetracycline hydrochloride 250 mg/kg /to rats/ significantly decreased the intestinal absorption of intragastrically administration triolein.
The oral administration of 2 g neomycin/kg, twice daily, reduced in rats the in vivo intestinal absorption of (14)C-labeled triolein.
The purpose of this study is to evaluate the effect of dexamethasone on the damaged blood-ocular barrier caused by triolein emulsion, using contrast-enhanced MR imaging. An emulsion of 0.1-mL triolein in 20 mL of saline was infused into the carotid arteries of 32 cats, 12 cats were placed in the treatment group and 18 cats were placed in the Control group. Thirty minutes after the infusion of triolein emulsion, a set of orbital pre- and post-contrast T1-weighted MR images (T1WIs) were obtained. Infusion of 10 mg/kg dexamethasone into the ipsilateral carotid artery of each of the cats in the treatment group cats and 20 mL saline in each of the cats in the control group was given. A second set of pre- and post-contrast orbital T1WIs were obtained three hours following triolein emulsion infusion. Qualitative analysis was performed for the the anterior chamber (AC), the posterior chamber (PC), and in the vitreous humor of the ipsilateral and contralateral eyes. The signal intensity ratios of the ipsilateral eye over the contralateral eye were quantitatively evaluated in the three ocular chambers on the first and second set of T1WIs, and were then statistically compared. Qualitatively, the AC, the PC or the vitreous did not show immediate contrast enhancement on the first and the second set of post-contrast T1WIs. However, the AC and the PC showed delayed contrast enhancement for both groups of cats on the second pre-contrast T1WIs. No enhancement or minimally delayed enhancement was seen for the vitreous humor. Quantitatively, the signal intensity ratios in the PC of the treatment group of cats were statistically lower than the ratios of the control group of cats for the second set of T1WIs (p = 0.037). The AC and vitreous showed no statistically significant difference between the feline treatment group and control group (p > 0.05). Contrast-enhanced MR images revealed increased vascular permeability in the PC of the eye after infusion of triolein emulsion. Dexamethasone seems to decrease the breakdown of the blood-aqueous barrier in the PC.
Fat embolization (FE) is an often overlooked and poorly understood complication of skeletal trauma and some orthopedic procedures. Fat embolism can lead to major pulmonary damage associated with fat embolism syndrome (FES). A model of FE in unanesthetized rats, using intravenous injection of the neutral fat triolein, was used to study the potential therapeutic effect on lung histopathology of altering the production of, or response to, endogenous angiotensin (Ang) II. Either captopril, an Ang I converting enzyme inhibitor, or losartan, an Ang II type 1 receptor blocker, was injected 1 hour after FE by triolein injection. After euthanasia at 48 hours, histopathologic evaluation was used to compare the drug-treated animals with control animals that received only triolein. Histology of the lungs of rats treated only with triolein revealed severe, diffuse pathology. Alveolar septa showed severe, diffuse inflammation. Bronchial lumina showed severe mucosal epithelial loss. The media of the pulmonary small arteries and arterioles was thicker, and the lumen patency was reduced 60% to 70%. Trichrome staining confirmed the abundant presence of collagen in the media and adventitia, as well as collagen infiltrating the bronchial musculature. Both captopril and losartan treatments reduced the inflammatory, vasoconstrictor, and profibrotic effects present at 48 hr (p<0.001). With treatment, the vascular lumen remained patent, and the fat droplets were reduced in size and number. There was a reduction in the number of infiltrating leukocytes, macrophages, myofibroblasts, and eosinophils, along with a significant decrease in hemorrhage and collagen deposition (p<0.001). Pathologic changes in bronchial epithelium were also diminished. The results suggest that the use of drugs that act on the renin-Ang system might provide an effective and targeted therapy for fat embolism syndrome.
For more Interactions (Complete) data for TRIOLEIN (6 total), please visit the HSDB record page.
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1X10+10(SRC), determined from a structure estimation method(2), indicates that triolein is expected to be immobile in soil(SRC). Volatilization of triolein from moist soil surfaces may be an important fate process(SRC) given an estimated Henry's Law constant of 9.6X10-4 atm-cu m/mole(SRC), using a fragment constant estimation method(2). However, volatilization from soil is expected to be attenuated by adsorption. Triolein is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure range of 5X10-5 mm Hg(3) to 1.1X10-9 mm Hg(SRC), determined from a fragment constant method(2). 14C-Labeled triolein biodegraded to CO2 at a rate of 63.5% to 84% over 140 days in a sewage sludge amended soil(4), suggesting that biodegradation may occur in the soil environment(SRC).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1X10+10(SRC), determined from a structure estimation method(2), indicates that triolein is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 9.6X10-4 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 11 hours and 13 days, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 5.1X10+5 years(SRC) if adsorption is considered(4). A base-catalyzed second-order hydrolysis rate constant of 0.15 L/mole-sec(SRC) was estimated using a structure estimation method(5); this corresponds to half-lives of 1.5 years and 55 days at pH values of 7 and 8, respectively(5). According to a classification scheme(6),an estimated BCF of 3.2(SRC), from an estimated log Kow of 23(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). In respirometry tests using an inoculum developed from activated sludge from a local municipal wastewater treatment plant, triolein had a biodegradation rate constant of 0.0025 per hour(7) which corresponds to a half-life of 11.6 days(SRC).
ATMOSPHERIC FATE: Triolein, which is liquid at room temperatures, has vapor pressure estimates that vary by several orders of magnitude at 25 °C(SRC); a vapor pressure of 1.1X10-9 mm Hg can be estimated(SRC) from a fragment constant method(1) while a vapor pressure of 5X10-5 mm Hg at 25 °C(2) can be determined from limited measured data and estimates at much higher temperatures and extrapolation(SRC). According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(3), triolein may exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase triolein is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 1.7 hours(SRC), calculated from its rate constant of 2.32X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(1). Vapor-phase triolein is also degraded in the atmosphere by reaction with ozone(SRC); the half-life for this reaction in air is estimated to be 0.7 hours(SRC), calculated from its rate constant of 3.9X10-16 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(1). Particulate-phase triolein may be removed from the air by wet or dry deposition(SRC).
Using a structure estimation method based on molecular connectivity indices(1), the Koc for triolein can be estimated to be 1X10+10(SRC). According to a classification scheme(2), this estimated Koc value suggests that triolein is expected to be immobile in soil.
/CASE REPORTS/ Functional deficiency of lipoprotein lipase (LPL) was found in a patient with severe hypertriglyceridemia. The patient was 39-year-old man with a plasma triglyceride level of 2032 mg/dL, and suffered from recurrent pancreatitis. His post heparin plasma LPL mass was almost normal, but the LPL activity was remarkably decreased. Gene analysis showed that homozygote missense mutation (204 Asp (GAC)-Glu (GAG)) exists in exon 5 of LPL gene. The patient LPL purified from post heparin plasma scarcely hydrolyzed VLDL-triglyceride and also triolein emulsified with Triton X-100 or phosphatidylcholine. When phosphatidylethenolamine, phosphatidylserine and cardiolipin were used as an emulsifier for triolein, triolein-hydrolyzing activity of the patient's LPL was observed and was much higher than that of wild-type LPL. Mutant LPL gene (Asp204-Glu) was made by site-direct mutagenesis and was transfected to COS-1 cell. The expressed LPL (Asp204-Glu) also showed the same properties. These results suggested that the LPL (Asp204-Glu) is a functional deficiency, and the activity could be recovered by using acidic phospholipids as an emulsifier.
AEROBIC: C14-labeled triolein, added at 100 mg/kg of soil, resulted in 63.5% of theoretical CO2 evolution in 151 days using a sewage sludge amended soil inoculum at 5g dry weight and 60% maximum water holding capacity(1). At a concentration of 750 mg/kg of soil, C14-labeled triolein resulted in 84% of theoretical CO2 in 146 days(1). In respirometry tests using a master culture inoculum developed from activated sludge from a local municipal wastewater treatment plant and 30-day incubation period, triolein had a biodegradation rate constant of 0.0025 per hour(2) which corresponds to a half-life of 11.6 days(SRC).
An estimated BCF of 3 was calculated in fish for triolein(SRC), using an estimated log Kow of 23.3(1) and a regression-derived equation(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).
The estimated Henry's Law constant for triolein is 9.6X10-4 atm-cu m/mole(SRC) determined using a fragment constant estimation method(1). This Henry's Law constant indicates that triolein is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 11 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 13 days(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 5.1X10+5 years if adsorption is considered(3). Triolein is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure range of 5X10-5 mm Hg(4) to 1.1X10-9 mm Hg(SRC), determined from a fragment constant method(1).
Effects of protopanaxdiol (PDG) and protopanaxatriol (PTG) types of ginsenosides isolated from the leaves of American ginseng on porcine pancreatic lipase activity were determined in vitro. PDG inhibited the pancreatic lipase activity in a dose-dependent manner at the concentrations of 0.25-1 mg/mL. It inhibited hydrolysis of about 83.2% of triolein at about 1 mg/mL of PDG. However, PTG showed no inhibitory activity. Therefore, anti-obesity activity of PDG was evaluated in mice fed a high-fat diet. The results demonstrated that PDG was effective in preventing and healing obesity, fatty liver and hypertriglyceridemia in mice fed with a high-fat diet.
In the small intestine, most triglycerides are split into monoglycerides, free fatty acids, and glycerol, which are absorbed by the intestinal mucosa. Within the epithelial cells, resynthesized triglycerides collect into globules along with cholesterol and phospholipids and are encased in a protein coat as chylomicrons. Chylomicrons are transported in the lymph to the thoracic duct and eventually to the venous system. The chylomicrons are removed from the blood as they pass through the capillaries of adipose tissue. Fat is stored in adipose cells until it is transported to other tissues as free fatty acids which are used for cellular energy or incorporated into cell membranes.
When (14)C-labeled long-chain triglycerides are administered intravenously, 25% to 30% of the radiolabel is found in the liver within 30 to 60 minutes, with less than 5% remaining after 24 hours. Lesser amounts of radiolabel are found in the spleen and lungs. After 24 hours, nearly 50% of the radiolabel has been expired in carbon dioxide, with 1% of the carbon label remaining in the brown fat. The concentration of radioactivity in the epididymal fat is less than half that of the brown fat.
Rats were fed an emulsion diet (via stomach tube) consisting of 95 parts triolein (Glycerol Trioleate) and 5 parts glycerol 1- (14)C-trioleate. The percentage of administered glycerol 1- (14)C-trioleate that was identified in the lymph in 24 hours was 88%. In an earlier study four male rats (weights 250 g) were dosed orally with [1-(14)C]triolein. The percentage of radioactivity that was absorbed in 24 hours ranged from 57% to 92% (mean =78.2%). The percentage of absorbed activity that was recovered in the lymph fat from the thoracic duct ranged from 51% to 83% (mean =65.5%).
After a single dose of [1- (14)C]triolein was administered intravenously into fasted rats, a high rate of uptake was noted within the first hour in the following organs: liver, myocardium, gastric mucosa, and diaphragm. However, after 24 hours, radioactivity in these tissues had decreased markedly. A similar pattern of distribution was noted in mice; however, large amounts of radioactivity were also noted in the brown fat, white adipose tissue, and spleen, even after 24 hours.
For more Absorption, Distribution and Excretion (Complete) data for TRIOLEIN (7 total), please visit the HSDB record page.
CIR ingredient: Triolein
A major component of oils and fats, e.g., olive oil; [Merck Index] Used as lubricant (e.g. for cosmetics, drugs, and textiles), emulsifier (e.g. for water/oil mixtures), intermediate for radioactive iodine derivatives, and plasticizer; Used in sweet almond oil for medicines and cosmetics; [HSDB]
Textiles (Fiber & Fabric Manufacturing) [Category: Industry]
Textile lubricants
Lubricant, eg, for cosmetics, drugs
Emulsifier, eg, for water/oil mixtures
(1979) No Data
(1981) No Data
(1979) No Data
(1981) No Data
2023: 100,000 - <250,000 lb
(1979) PROBABLY GREATER THAN 4.54X10+6 GRAMS
(1981) PROBABLY GREATER THAN 6.81X10+6 GRAMS
9-Octadecenoic acid (9Z)-, 1,2,3-propanetriyl ester is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).
Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#5450]
Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: 9-Octadecenoic acid (9Z)-, 1,1',1''-(1,2,3-propanetriyl) ester. Aggregated National Production Volume: 500,000 to < 1 million pounds.
Preparation by esterification of oleic acid.
It is the predominating constituent in expressed almond oil, in lard oil, & in many of the more fluid animal oils & those of vegetable origin. It is separated & purified by cold expression, the other constituents being retained by their lack of fluidity at low temp.
The triglyceride of oleic acid, occurring in most fats and oils. It constitutes 70-80% of olive oil
Reaction of refined oil, eg, olive oil, with glycerol followed by fractional distillation; reaction of oleic acid with glycerol; separation & purification from fats & oils as liquid phase by cold expression.
EPA Safer Chemical Functional Use Classes -> Solvents
Safer Chemical Classes -> Green circle - The chemical has been verified to be of low concern
Cosmetics -> Skin conditioning; Solvent; Viscosity controlling; Emollient; Refatting
Petroleum Lubricating Oil and Grease Manufacturing
9-Octadecenoic acid (9Z)-, 1,1',1''-(1,2,3-propanetriyl) ester: ACTIVE
Stable water-in-oil emulsions (with a high water content) for cosmetics are prepared by dissolving the neutral oil & 5-50% lecithin emulsifier at less than or equal to 70 °C, cooling to 0-12 °C, & adding water to a concentration of 50-83%. The neutral oil can be a glycerol, such as glyceryl trioleate, or propylene glycol ester of a carbon 8-12 fatty acid or isopropyl myristate.
One of the chief constituents of nondrying oils and fats.
Beschreibung1,2,3-Trioleoyl glycerol is a triacylglycerol that contains oleic acid (Item Nos. 90260 | 24659) at the sn-1, sn-2, and sn-3 positions. It inhibits oxidized LDL-induced decreases in cell viability and superoxide dismutase (SOD) and glutathione peroxidase (GPX) activities and increases in apoptosis in endothelial cells when used at a concentration of 10 μM. 1,2,3-Trioleoyl glycerol has been found in sunflower, corn, and extra virgin olive oils. It has been used as a standard for the quantification of triacylglycerols in extra virgin olive oil by high temperature gas chromatography-(ionic trap)mass spectrometry (HTGC-(IT)MS). 1,2,3-Trioleoyl glycerol is a major component of Lorenzo''s oil.
VerwendenGlycerol trioleate can be used as an emulsifier, also as creams, lotions and lipsticks matrix. Used as textile finishing agent in textile industry, also used as additive in pigment grind. In pharm industry, used as ointment, emulsifiable paste, suppository, lotion, emulsifier in air agent, stabilizing agent, lubricating agent, antifoaming agents. In food industry, it has the function as emulsify, disperse, defoaming, blister, antistaling of starch and control fat agglutination, usually used as agent in candy, ice cream, cookie and bread. When used in beverage, could avoid ester to float, and avoid protein to sink, therefore to improve stability. When used in bread, cookie , could improve organization structure, increase volume, antistaling, prolong warranty validity.
DefinitionChEBI: A triglyceride formed by esterification of the three hydroxy groups of glycerol with oleic acid. Triolein is one of the two components of Lorenzo's oil.