Grundinformationen
- Standard-SMILES
CCCCCCCCCCCCCCCCCC(=O)OCC(COC(=O)CCCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCCC- InChIKey
DCXXMTOCNZCJGO-UHFFFAOYSA-N- Summenformel
- C57H110O6
- Durchschnittliche Molmasse
- 891,5 g/mol
- Monoisotopische Masse
- 890,83024124
Überblick
Tristearoylglycerol is a triglyceride that is glycerol in which all three hydroxy groups have been formally esterified with stearic acid. It has a role as a plant metabolite and a Caenorhabditis elegans metabolite. It is functionally related to an octadecanoic acid.
Namen und Bezeichner
- Bevorzugter Name
- Tristearin
- IUPAC
- 2,3-di(octadecanoyloxy)propyl octadecanoate
- Lokaler Name
- Glycerintristearat
- Englischer Name
- Glycerol tristearate
- Summenformel
- C57H110O6
- Molmasse
- 891.48
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
555-43-1- PubChem CID
- 11146
- DTXSID
DTXSID8047503- ChEBI
CHEBI:45956- UNII
- P6OCJ2551R
- EC Number
- 209-097-6
- Nikkaji
- J6.468H
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 25,2
- Polarare Oberfläche (TPSA)
- 78,9 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 6
- Frei drehbare Bindungen
- 56
- Schwere Atome
- 63
- Formalladung
- 0
- Komplexität
- 886
Experimentelle und physikochemische Eigenschaften
Lipids
Lipids -> Unambiguous Lipids
Lipids -> Glycerolipids [GL] -> Triradylglycerols [GL03] -> Triacylglycerols [GL0301]
Polymers
Plastics -> N.a.
Plastics -> Other functions -> Processing agent
Cosmetics
Cosmetic ingredients (Tristearin) -> CIR (Cosmetic Ingredient Review)
Solvent; Skin conditioning; Emollient; Refatting; Viscosity controlling
Color/Form
White powder
Colorless crystals or powder
Solubility
Insoluble in water. Soluble in chloroform, carbon disulfide
Insoluble in ethanol; very soluble in acetone, benzene
Soluble in hot alcohol; almost insoluble in cold alcohol, ether, petroleum ether
Physikochemische Eigenschaften
- Schmelzpunkt
- 72 · 72-75 °C
- Siedepunkt
- 260 °C · 260 °C
- Dichte
- 480 · d480 0.862
- Brechungsindex
- 80 · nD80 1.4385
- Flammpunkt
- 327 °C · 327 °C
- storage temp.
- -20 °C · -20°C
- Löslichkeit
- Chloroform (Slightly), Ethyl Acetate (Slightly, Heated)
- Aggregatzustand
- Solid
- Farbe
- White to Off-White
- Geruch (Odor)
- odorless, tasteless
- Biologische Quelle
- synthetic
- Merck
- 14 · 14,9756
- BRN
- 1718456 · 1718456
- Henry's Law Constant
- 7 · 7.0×10-3 mol/(m3Pa) at 25℃, HSDB (2015)
- Dielectric constant
- 2.3 · 2.3(Ambient)
- Kosmetik-Inhaltsstoffe Funktionen
- SKIN CONDITIONINGVISCOSITY CONTROLLING
- InChIKey
- DCXXMTOCNZCJGO-UHFFFAOYSA-N
- SMILES
- CCCCCCCCCCCCCCCCCC(=O)OCC(COC(=O)CCCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCCC
- LogP
- 24.672 · 24.672 (est)
- CAS Datenbank
- 555 · 555-43-1(CAS DataBase Reference)
- NIST chemische Informationen
- Tristearin(555-43-1)
- EPA chemische Informationen
- Tristearin (555-43-1)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
This chemical does not meet GHS hazard criteria for 100% (198 of 198) of all reports.
Not Classified
Aggregated GHS information provided per 198 reports by companies from 1 notifications to the ECHA C&L Inventory.
Gefahrenhinweise
Regulatory Information
Chemical: Octadecanoic acid, 1,2,3-propanetriyl ester
Octadecanoic acid, 1,1',1''-(1,2,3-propanetriyl) ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Octadecanoic acid, 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)
Status: Active Update: 24-03-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/12757
Glycerol tristearate: Does not have an individual approval but may be used under an appropriate group standard
Sicherheit und Schutzausrüstung
Disposal Methods
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.
Toxikologische Informationen
Environmental Fate
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).
Soil Adsorption/Mobility
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.
Human Toxicity Excerpts
/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
Artificial Pollution Sources
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).
Environmental Bioconcentration
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).
Volatilization from Water/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).
Non-Human Toxicity Excerpts
/LABORATORY ANIMALS: Acute Exposure/ The acute oral toxicity of Tristearin was evaluated using ten Sprague-Dawley rats (males and females; weights =150 to 300 g). None of the animals died during the 14-day period after dosing. The LD50 was >20.0 g/kg. At necropsy, none of the animals had gross lesions.
/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ The short-term oral toxicity of ... tristearin, and triolein was evaluated using four groups of ten weanling rats, respectively. Each glyceryl ester was administered orally at a concentration of 25% in the diet for a period of 10 weeks. Equal gains in body weight were reported for all groups tested. No lesions were found at necropsy or microscopic examinations that were attributable to administration of test diets.
/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ Five weanling albino rats were fed 5% Tristearin in the diet daily for 37 days. Another group of five rats was fed a control diet (no tristearin). The animals ranged in weight from 62 to 66 g. Growth rates for the two groups were identical. At necropsy, no abnormalities were found that were related to the administration of tristearin. No significant differences in organ weight were found between the two groups.
/GENOTOXICITY/ The mutagenicity of ... triolein, and tristearin was evaluated using S. typhimurium strains TA1535, TA100, TA1537, TA1538, and TA98, with and without metabolic activation... At a test concentration of 4 mg per plate, ... tristearin (in DMSO) were not mutagenic, with or without metabolic activation, in any of the strains tested. The same was true for Triolein at a test concentration of 1 mg per plate. The test concentrations of 1 mg/plate and 4mg/plate represented the greatest doses tested due to limits of solubility, which did not allow testing at concentrations great enough to cause lethality. Based on the results of this test, triolein, and tristearin were not mutagenic.
For more Non-Human Toxicity Excerpts (Complete) data for TRISTEARIN (6 total), please visit the HSDB record page.
Environmental Abiotic Degradation
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).
Probable Routes of Human Exposure
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)
Sicherheitsdaten
- wgk
- -
- tsca
- TSCA listed
- hs_code
- 29159000
- safety_code
- 24/25
- Speicherklasse
- 11 - Combustible Solids
- Giftige Stoffe Daten
- 555-43-1(Hazardous Substances Data)
Chemie und Industrie
Pharmakologische Informationen
Absorption, Distribution and Excretion
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.
Verwendung und Herstellung
Uses
CIR ingredient: Tristearin
Found in various animal and vegetable fats; [Merck Index] Used in textile sizes, candles, soaps, adhesive pastes, and metal polishes; Also used for water-proofing paper, for leather stuffing, as a food additive (crystallization accelerator in chocolate), and as a lubricant in cosmetics; [HSDB]
Pulp and Paper Processing [Category: Industry]
In textile sizes. Formerly in making candles.
Soap; candies; adhesive pastes; metal polishes; water-proofing paper; leather stuffing; manufacture of stearic acid.
Food additive (crystallization accelerator in chocolate).
U.S. Exports
(1979) No Data
(1981) No Data
U.S. Imports
(1979) No Data
(1981) No Data
U.S. Production
2023: 75,000 - <500,000 lb
(1979) NOT PRODUCED COMMERCIALLY IN U.S.
(1981) NOT PRODUCED COMMERCIALLY IN U.S.
Methods of 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.
Use Classification
EPA Safer Chemical Functional Use Classes -> Solvents
Safer Chemical Classes -> Green circle - The chemical has been verified to be of low concern
Plastics -> Polymer Type -> N.a.
Cosmetics -> Solvent; Skin conditioning; Emollient; Refatting; Viscosity controlling
Plastics -> Other functions -> Processing agent
General Manufacturing Information
Plastics Material and Resin Manufacturing
Octadecanoic acid, 1,1',1''-(1,2,3-propanetriyl) ester: ACTIVE
Anwendungen
BeschreibungGlyceryl tristearate is prepared by reacting glycerin with stearic acid in the presence of a suitable catalyst such as aluminum oxide. It also occurs in many animal and vegetable fats such as tallow and cocoa butter. It is a white, microfine crystalline powder. It is soluble in hot alcohol, benzene and chloroform, very slightly soluble in cold alcohol, in ether and in petroleum ether, and insoluble in water.
VerwendenPresent in animal and vegetable fats.
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
Nachgelagerte Produkte
Anbieter50 Anbieter
Ergänzende Hinweise
DefinitionChEBI: Tristearoylglycerol is a triglyceride that is glycerol in which all three hydroxy groups have been formally esterified with stearic acid. It has a role as a plant metabolite and a Caenorhabditis elegans metabolite. It derives from an octadecanoic acid.
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