1,2,3-프로페인트라이일 옥타데칸산염

Tristearin

HCID 11146CAS 555-43-1

기본 정보

표준 SMILES
CCCCCCCCCCCCCCCCCC(=O)OCC(COC(=O)CCCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCCC
InChIKey
DCXXMTOCNZCJGO-UHFFFAOYSA-N
분자식
C57H110O6
평균 분자량
891.5 g/mol
단동위원소 질량
890.83024124

개요

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.

이름 및 식별자

우선 이름
Tristearin
IUPAC
2,3-di(octadecanoyloxy)propyl octadecanoate
현지명
1,2,3-프로페인트라이일 옥타데칸산염
영어명
Glycerol tristearate
분자식
C57H110O6
분자량
891.48

이름 및 동의어

TRISTEARIN555-43-1Glycerol tristearateGlyceryl tristearateTrioctadecanoinTRISTEAROYLGLYCEROLStearic triglycerideStearin, tri-Spezialfett 118Stearoyl triglycerideDynasan 1182,3-di(octadecanoyloxy)propyl octadecanoate
이름 더 보기
1,2,3-프로페인트라이일옥타데칸산염1,2,3-프로페인트라이일옥타데칸산염트라이스테아린STEARINGTShydrogenatedoilHydrogenated tallowGlycerintristearat
Stearic acid triglycerin esterStearic acid triglycerideGlycerol, trioctadecanoateOctadecanoic acid, 1,2,3-propanetriyl esterP6OCJ2551RDTXSID8047503CHEBI:45956209-097-6

데이터베이스 식별자

CAS
555-43-1
PubChem CID
11146
DTXSID
DTXSID8047503
ChEBI
CHEBI:45956
UNII
P6OCJ2551R
EC Number
209-097-6
Nikkaji
J6.468H

물성

구조 계산 물성

XLogP
25.2
극성 표면적
78.9 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
6
회전 가능 결합 수
56
무거운 원자 수
63

실험 및 물리화학적 성질

Chemical ClassesOther Classes -> Stearates
Lipids · 2건

Lipids -> Unambiguous Lipids

Lipids -> Glycerolipids [GL] -> Triradylglycerols [GL03] -> Triacylglycerols [GL0301]

Polymers · 2건

Plastics -> N.a.

Plastics -> Other functions -> Processing agent

Cosmetics · 2건

Cosmetic ingredients (Tristearin) -> CIR (Cosmetic Ingredient Review)

Solvent; Skin conditioning; Emollient; Refatting; Viscosity controlling

LogPlog Kow = 24 /Estimated/
OdorOdorless

물리화학적 성질

녹는점
72 · 72-75 °C
끓는 점
260 °C · 260 °C
밀도
480 · d480 0.862
굴절률
80 · nD80 1.4385
인화점
327 °C · 327 °C
저장 조건
-20 °C · -20°C

화학적 성질

off-white to cream powder

안전 및 규제

GHS 분류

GHS Classification · 3건

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.

유해성 정보

Regulatory Information · 4건

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

Other Safety InformationIMAP assessments - Octadecanoic acid, 1,2,3-propanetriyl ester: Human health tier I assessment
Hazards SummaryNegative results in 14-day feeding studies of rats up to 20 g/kg; [HSDB] May cause irritation; [MSDSonline] See STEARATES.
EPA Safer ChemicalChemical: Glycerol tristearatate
Hazard Classes and CategoriesNot Classified

안전 및 보호

Cleanup MethodsAEROBIC: 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).
Disposal Methods · 1건

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.

독성 정보

Environmental Fate · 3건

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).

Toxicity SummarySafe in the present practices of use and concentration. Ingredient, concentration, and use information are available in documents discoverable at https://cir-reports.cir-safety.org
Soil Adsorption/Mobility · 1건

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.

Natural Pollution SourcesTristearin is present in many animal and vegetable fats including cacao oil, butter, and tallow(1).
Human Toxicity Excerpts · 2건

/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 · 1건

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).

안전 데이터

wgk
-
tsca
TSCA listed
HS 번호
29159000
safety_code
24/25
기존화학 물질
KE-26406
스토리지 클래스
11 - Combustible Solids

화학 및 산업

약리 정보

Metabolism/MetabolitesHydrolysis of /Tristearin/ by hepatic triacylglycerol lipase in plasma from ICR mice has been demonstrated in vitro.
Absorption, Distribution and Excretion · 4건

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.

Cellular LocationsExtracellular
Metabolite PathwaysDe Novo Triacylglycerol Biosynthesis TG(18:0/18:0/18:0)

용도 및 제조

Uses · 6건

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 · 2건

(1979) No Data

(1981) No Data

U.S. Imports · 2건

(1979) No Data

(1981) No Data

U.S. Production · 3건

2023: 75,000 - <500,000 lb

(1979) NOT PRODUCED COMMERCIALLY IN U.S.

(1981) NOT PRODUCED COMMERCIALLY IN U.S.

Consumer UsesAnti-caking agent
Industry UsesAnti-caking agent
응용 분야 · 2건

개요Glyceryl 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.

용도Present in animal and vegetable fats.

공급사50 곳

北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
南通鲁尔化工有限公司18012215199 · [email protected]
추가 설명 · 1건

정의ChEBI: 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.

관련 반응

9건

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