Tristearin
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Tristearin
structure -
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CAS No:
555-43-1
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Formula:
C57H110O6
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Chemical Name:
Tristearin
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Synonyms:
Octadecanoic acid,1,1′,1′′-(1,2,3-propanetriyl) ester;Stearin,tri-;Octadecanoic acid,1,2,3-propanetriyl ester;Glyceryl tristearate;Tristearin;Glycerol tristearate;Stearic acid triglyceride;Stearic acid triglycerin ester;Trioctadecanoin;Stearic triglyceride;Glycerol trioctadecanoate;Stearoyl triglyceride;Spezialfett 118;Dynasan 118;Glycowax S 932;Hardened Oil;Tristearoylglycerol;Edenor NHTl;Glycerine tristearate;Rikemal VT;Glycerin tristearate;SSS;Triglyceride StStSt;Prisorine 2041;Loxiol EP 218;Edenor NHTi;Glyceryl trioctadecanoate;Daiwax STG;Glycolube TS;Coatex 21;Rikemal VT 50;Triglyceride SSS;Tegin BL 150V;Pationic 919;Ligalub GT;Radia 7512;A 3D;Esteride G-S;PPM 17000;Dynasan D118;1,2,3-Propanetriyltris(octadecanoate);2,3-Di(octadecanoyloxy)propyl octadecanoate;41755-77-5;160170-82-1;606967-51-5
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CAS No:
Description
Tristearin is a tristearate of glycerol, one of the components of animal fat, and a natural oil with a chemical formula of C57H110O6. It is a colorless, tasteless, odorless crystal or powder, insoluble in water, ether and ligroin, and soluble in ethanol, chloroform, and carbon disulfide. It can be hydrolyzed into stearic acid and glycerol in acid or alkaline solution, and react with sodium hydroxide to obtain sodium stearate. Its density is 0.862g/cm3, melting point is 71-73℃, boiling point is 260°C at 760 mmHg, and flash point is 327°C. Tristearin is mainly used in food, soap making, and the preparation of stearic acid.
Tristearin Basic Attributes
891.48000
891.48
209-097-6
P6OCJ2551R
DTXSID8047503
White powder|Colorless crystals or powder
2915709000
Characteristics
78.90000
25.2
DryPowder; PelletsLargeCrystals
0.8559 g/cm3 @ Temp: 90 °C
55 °C
260ºC
327ºC
1.4477 (25ºC)
Soluble in hot alcohol; almost insoluble in cold alcohol, ether, petroleum ether
-20ºC
5.4X10-17 mm Hg at 25 deg C /Estimated/
Odorless
Tasteless
Henry's Law constant = 1.4X10-3 atm-cu m/mole at 25 °C /Estimated/
On heating above 55 °C it solidifies and melts again at 72 °C.|Hydroxyl radical reaction rate constant = 7.2X10-11 cu cm/molec-sec at 25 °C /Estimated/
Safety Information
NONH for all modes of transport
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S24/25
Stable under normal temperatures and pressures.
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.
AEROBIC: Tristearin, at a concentration of 0.05 mg/L, degraded 24% of its theoretical CO2 yield in 5 days using an activated sludge inoculum(1).
Toxicity
Tristearin is present in many animal and vegetable fats including cacao oil, butter, and tallow(1).
Tristearin's production and use in soap, candles, adhesive paste, metal polish, water proofing, textile sizes and leather stuffing(1) may result in its release to the environment through various waste streams(SRC). Tristearin is present in many animal and vegetable fats including cacao oil, butter, and tallow(2).
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 tristearin is expected to be immobile in soil(SRC). Volatilization of tristearin from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.4X10-3 atm-cu m/mole(SRC), using a fragment constant estimation method(3). However, volatilization from moist soil surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. Tristearin is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 5.5X10-17 mm Hg(SRC), determined from a fragment constant method(4). Tristearin has been shown to biodegrade 24% within 5 days in activated sludge(5), indicating that biodegradation may be an important environmental fate process in soil(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 tristearin 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 1.4X10-3 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Estimated volatilization half-lives for a model river and model lake are 5.2 hours and 13 days, respectively. 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 4.8X10+5 years if adsorption is considered(5). A base-catalyzed second-order hydrolysis rate constant of 0.15 L/mole-sec(SRC) was estimated using a structure estimation method(6); this corresponds to half-lives of 1.5years and 55 days at pH values of 7 and 8, respectively(6). According to a classification scheme(7), a BCF in fish of <10(8), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Tristearin has been shown to biodegrade 24% within 5 days in activated sludge(8), indicating that biodegradation may be 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), tristearin, which has an estimated vapor pressure of 5.4X10-17 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 tristearin may be removed from the air by wet and dry deposition(SRC). 14C-labeled tristearin was degraded (9.9%) after being subject to light at 290 nm for 17 hours(3), indicating the potential for direct photolysis(SRC).
A base-catalyzed second-order hydrolysis rate constant of 0.15 L/mole-sec(SRC) was estimated using a structure estimation method(1); this corresponds to half-lives of 1.5 years and 55 days at pH values of 7 and 8, respectively(1). 14C labeled tristearin was degraded 9.9% after being subject to light at 290 nm for 17 hours(2). This shows some degradation may occur by UV light despite the lack of chromophores that absorb in that range(SRC).
A BCF of <10 was measured in fish(1). According to a classification scheme(2) this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC), provided the compound is not altered physically or chemically once released into the environment(SRP).
Using a structure estimation method based on molecular connectivity indices(1), the Koc for tristearin can be estimated to be 1X10+10(SRC). According to a classification scheme(2), this estimated Koc value suggests that tristearin is expected to be immobile in soil.
The Henry's Law constant for tristearin is estimated as 1.4X10-3 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that tristearin 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 5.2 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 4.8X10+5 years if adsorption is considered(3). Tristearin's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC), however when soil adsorption is considered volatilization from moist soil surfaces seems unlikely. Tristearin is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 5.4X10-17 mm Hg(SRC), determined from a fragment constant method(4).
Occupational exposure to tristearin may occur through inhalation of dust and dermal contact with this compound at workplaces where tristearin is produced or used. The general population may be exposed to tristearin via dermal contact with consumer products containing this compound. (SRC)
Drug Information
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 14C-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.|The absorption of [1- 14C]tristearin was evaluated using groups consisting of six to seven male Wistar rats (weights =200 to 250 g). The rats were prepared either with an external bile fistula or a sham operation (control group), and then allowed to recover for 6 to 12 hours. Weighed doses of [1- 14C]tristearin were fed in a pellet of bran. Doses of 25, 50, 100, and 200 mg were administered to four groups, respectively. The rats were killed after 16 hours and lipid from the stomach, small gut, and colon (with feces) was extracted. Absorption was expressed as the percentage of the dose that had left the stomach. Only rats in which 80% or more of the dose had left the stomach were used. Tristearin absorption was classified as poor at all administered doses. Significantly lower absorption of tristearin was noted only in the 200 mg dose group ( p <.02, n=6)|Feeding expt with (14)C-labelled tristearin indicated that ruminal bacteria actively hydrogenated, degraded, and synthesized fatty acids. Stearic acid seemed to be absorbed from small intestine at slower rate than other fatty acids.
Hydrolysis of /Tristearin/ by hepatic triacylglycerol lipase in plasma from ICR mice has been demonstrated in vitro.
Basic treatment: Establish a patent airway. 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 normal saline 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 ... . /Poison A and B/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/
/HUMAN EXPOSURE STUDIES/ The skin irritation and sensitization potential of an eye defining pencil containing 1.68%Tristearin was evaluated in a 6-week study using 160 subjects (mainly females). Seven subjects withdrew from the study for reasons unrelated to administration of the test substance, reducing the test population to 153 subjects. The repeated-insult patch test (RIPT) protocol used was a modification of the Draize-Shelanski RIPT procedure. The undiluted test substance was applied liberally (under occlusive patches) to the scapular back three times per week for a total of nine applications. After a 2-week non-treatment period, two consecutive occlusive challenge patches containing the test substance were applied to a different site on the scapular back. Reactions were not observed in any of the subjects during the induction or challenge phase. It was concluded that the eye defining pencil did not induce irritant contact dermatitis or allergic contact dermatitis.|/HUMAN EXPOSURE STUDIES/ ... Tristearin at 1.68%, in commercial products were also negative in repeated-insult patch tests. Tristearin at 0.32% in a commercial product induced transient, mild to moderate, ocular irritation after instillation into the eyes of human subjects
glyceryl tristearate
Tristearin Use and Manufacturing
Prepared from stearic acid and glycerol in the prresence of Al2O3.|Reaction of stearic acid with glycerol; separation from solid fats, eg, tallow, as solid phase by expression under controlled conditions.
In textile sizing, formerly in making candles.Glyceryl Tristearate is a formulation aid, lubricant, and release agent, prepared by reacting stearic acid with glycerol in the presence of a suitable catalyst. The additive is used as a crystallization accelerator in cocoa products; a formulation aid in confections; a formulation in fats and oils; and a winterization and fractionation aid in fat and oil processing.
100,000 - 500,000 lb|(1979) NOT PRODUCED COMMERCIALLY IN U.S.|(1981) NOT PRODUCED COMMERCIALLY IN U.S.
Grade: Technical, also graded as to source.
Construction|Octadecanoic acid, 1,1',1''-(1,2,3-propanetriyl) ester: ACTIVE
FATTY ACIDS SUCROSE ESTERS INCL TRISTEARIN WERE SEPARATED BY THIN LAYER CHROMATOGRAPHY.
Lipids -> Glycerolipids [GL] -> Triradylglycerols [GL03] -> Triacylglycerols [GL0301]|Cosmetics -> Emollient; Refatting; Skin conditioning; Solvent; Viscosity controlling
Computed Properties
Molecular Weight:891.5
XLogP3:25.2
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:56
Exact Mass:890.83024122
Monoisotopic Mass:890.83024122
Topological Polar Surface Area:78.9
Heavy Atom Count:63
Complexity:886
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Drug Function and Efficacy
This product is a broad-spectrum antifungal drug that has antibacterial effects on a variety of fungi, especially Candida albicans, and also has antibacterial effects on certain Gram-positive bacteria. Its mechanism of action is to inhibit the synthesis of fungal cell membranes and affect their metabolic processes.
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