트리에틸시트레이트

Triethyl Citrate

HCID 6506CAS 77-93-0

기본 정보

표준 SMILES
CCOC(=O)CC(O)(CC(=O)OCC)C(=O)OCC
InChIKey
DOOTYTYQINUNNV-UHFFFAOYSA-N
분자식
C12H20O7
평균 분자량
276.28 g/mol
단동위원소 질량
276.12090298

개요

Triethyl citrate is a carbonyl compound.

이름 및 식별자

우선 이름
Triethyl Citrate
IUPAC
triethyl 2-hydroxypropane-1,2,3-tricarboxylate
현지명
트리에틸시트레이트
영어명
Triethyl citrate
분자식
C12H20O7
분자량
276.28

이름 및 동의어

TRIETHYL CITRATE77-93-0Ethyl citrateCitroflex 2EudraflexHydragen CATCitric acid, triethyl ester1,2,3-Propanetricarboxylic acid, 2-hydroxy-, triethyl esterTriaethylcitratFEMA No. 3083Citroflex ecCitrofol ai
이름 더 보기
트라이에틸시트레이트트라이에틸시틀산염트리에틸시트레이트트리에틸시틀산염2-하이드록시-1,2,3-프로판트리카르복실산,트리에틸에스테르에틸시틀산트라이에틸시틀산염트라이에틸 시트레이트TECFEMA 3083citroflex2Crodamol TCHydagen C.A.Ttriethyl esterTriethylcitrat
Morflex tecCitric acid ethyl esterCitroflex c 2Triethylester kyseliny citronoveCitroflex sc 60Morflex c 2DTXSID0040701NSC-8907

데이터베이스 식별자

CAS
77-93-0
PubChem CID
6506
DTXSID
DTXSID0040701
ChEMBL
CHEMBL464988
ChEBI
CHEBI:168426
UNII
8Z96QXD6UM
EC Number
201-070-7、629-703-6
Nikkaji
J4.215C

물성

구조 계산 물성

XLogP
0.1
극성 표면적
99.1 Ų
수소 결합 공여자 수
1
수소 결합 수용자 수
7
회전 가능 결합 수
11
무거운 원자 수
19

실험 및 물리화학적 성질

Chemical Classes · 2건

Other Classes -> Other Organic Compounds

Waste-water effluent contaminant

Polymers · 2건

Plastics -> PUR; PVC (soft)

Plastics -> Plasticisers

Cosmetics · 2건

Cosmetic ingredients (Triethyl Citrate) -> CIR (Cosmetic Ingredient Review)

Solvent; Plasticiser; Antioxidant; Deodorant

SpringerMaterials PropertiesBoiling point
FragrancesFragrance Ingredient (Triethyl citrate) -> IFRA transparency List
OdorFruity odor

물리화학적 성질

녹는점
-55 °C · -55 °C
끓는 점
235 °C/150 · 235 °C/150 mmHg (lit.)
밀도
1.14 g/mL · 1.14 g/mL at 25 °C (lit.)
증기 밀도
9.7 · 9.7 (vs air)
Pour Point
-46 · -46
증기압
1 mm · 1 mm Hg ( 107 °C)

화학적 성질

Triethyl citrate is a clear, viscous, odorless, and practically colorless, hygroscopic liquid.

안전 및 규제

GHS 분류

GHS Classification · 6건

This chemical does not meet GHS hazard criteria for 96.4% (1942 of 2014) of all reports.

Not Classified

Aggregated GHS information provided per 2014 reports by companies from 5 notifications to the ECHA C&L Inventory.

Not Classified

Warning

H332: Harmful if inhaled [Warning Acute toxicity, inhalation]

유해성 정보

Regulatory Information · 4건

Chemical: 1,2,3-Propanetricarboxylic acid, 2-hydroxy-, triethyl ester

1,2,3-Propanetricarboxylic acid, 2-hydroxy-, 1,2,3-triethyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,2,3-Propanetricarboxylic acid, 2-hydroxy-, 1,2,3-triethyl 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: 01-12-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/14584

Ethyl citrate: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - 1,2,3-Propanetricarboxylic acid, 2-hydroxy-, triethyl ester: Human health tier I assessment
Fire HazardsCombustible.
Fire PotentialCombustible liquid when exposed to heat or flame.
Hazards Summary · 1건

Safe when used as a flavoring agent in food; [JECFA] Effects in lethal-dose studies include somnolence, ataxia, and convulsions; [RTECS] An eye and respiratory tract irritant; [ICSC] May cause irritation; Effects in high-dose animal studies include convulsions; [MSDSonline]

FDA Requirements · 2건

An ingredient whose use in food or food packaging is subject to a prior sanction or approval within the meaning of section 201(s)(4) of the Act is exempt from classification as a food additive. ... Substances classified as plasticizers, when migrating from food-packaging material shall include ... triethyl citrate.

Substance added directly to human food affirmed as generally recognized as safe (GRAS).

안전 및 보호

Fire FightingUse powder, carbon dioxide.
First Aid Measures · 4건

Fresh air, rest.

Remove contaminated clothes. Rinse skin with plenty of water or shower.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Give one or two glasses of water to drink.

Safe StorageWell closed.
Fire Fighting Procedures · 3건

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.

Advice for firefighters: Wear self contained breathing apparatus for fire fighting if necessary.

Use dry chemical, carbon dioxide.

Storage ConditionsKeep container tightly closed in a dry and well-ventilated place.
Cleanup Methods · 1건

Accidental release measures: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation.; Environmental precautions: Do not let product enter drains.; Methods and materials for containment and cleaning up: Soak up with inert absorbent material and dispose of as hazardous waste. Keep in suitable, closed containers for disposal.

독성 정보

Environmental Fate · 3건

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 20(SRC), determined from a structure estimation method(2), indicates that triethyl citrate is expected to have very high mobility in soil(SRC). Volatilization of triethyl citrate from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.8X10-9 atm-cu m/mole(SRC) based upon its vapor pressure, 6.87X10-4 mm Hg(3), and water solubility, 6.5X10+4 mg/L(5). Triethyl citrate is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). Biodegradation data in soil were not available(SRC, 2015). Based on data for acetyl tributyl citrate, a structural analog, triethyl citrate may be expected to biodegrade rapidly(SRC). Utilizing the Japanese MITI test acetyl tributyl citrate, present at 100 mg/L, reached 82% of its theoretical BOD in 4 weeks using an activated sludge inoculum at 30 mg/L(5) suggesting that biodegradation of triethyl citrate may be an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 20(SRC), determined from a structure estimation method(2), indicates that triethyl citrate is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 3.8X10-9 atm-cu m/mole(SRC) derived from its vapor pressure, 6.87X10-4 mm Hg(4), and water solubility, 6.5X10+4 mg/L(5). According to a classification scheme(6), an estimated BCF of 3(SRC), from an estimated log Kow of 0.33(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data in water were not available(SRC, 2015). Based on data for acetyl tributyl citrate, a structural analog, triethyl citrate may be expected to biodegrade rapidly(SRC). Utilizing the Japanese MITI test acetyl tributyl citrate, present at 100 mg/L, reached 82% of its theoretical BOD in 4 weeks using an activated sludge inoculum at 30 mg/L(7) suggesting that biodegradation of triethyl citrate 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), triethyl citrate, which has a vapor pressure of 6.87X10-4 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase triethyl citrate 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 4 days(SRC), calculated from its rate constant of 7.3X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Triethyl citrate does not contain chromophores that absorb at wavelengths >290 nm(4) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

Adverse EffectsNeurotoxin - Other CNS neurotoxin
Exposure RoutesThe substance can be absorbed into the body by inhalation of its aerosol and by ingestion.
Toxicity Summary · 2건

Safe 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

IDENTIFICATION AND USE: Triethyl citrate is a colorless, oily liquid with bitter taste. It is used as solvent and plasticizer for nitrocellulose and natural resins, softener, paint removers, agglutinant, perfume base, food additive (not over 0.25%) as an emulsifier and as a flavor-preserving agent. HUMAN EXPOSURE AND TOXICITY: Triethyl citrate 20% in petrolatum was not a primary irritant or sensitizer in human studies. ANIMAL STUDIES: Triethyl citrate, applied undiluted during epidermal induction, was a strong sensitizer in a guinea pig maximization test. Triethyl citrate 33.3% produced irritation in rabbit eyes. Intravenous administration of a 100 mg/kg bw dose of triethyl citrate to rabbits produced a marked increase in motor activity and respiration. A group of 20 mice given intraperitoneal doses of 350 mg/kg bw of triethyl citrate daily for 14 days had a slightly lower mean growth rate than control animals. No differences were seen in the two groups in erythrocyte and leucocyte blood cell count, clotting time and hemoglobin levels. Examination of the liver, lung and kidney tissues of two animals at necropsy revealed no pathological cellular changes. At doses ranging from 0.5 to 10 mg/kg b.w. triethyl citrate was nonteratogenic in the chicken embryo. Ames test using triethyl citrate (0.4%-1.6%) on Salmonella typhimurium TA1535, TA1537, TA1538 was negative with and without metabolic activation.

Signs and Symptoms · 3건

Cough.

Redness.

Vomiting.

Ongoing Test Status · 1건

EPA has released the first beta version (version 0.5) of the Interactive Chemical Safety for Sustainability (iCSS) Dashboard. The beta version of the iCSS Dashboard provides an interactive tool to explore rapid, automated (or in vitro high-throughput) chemical screening data generated by the Toxicity Forecaster (ToxCast) project and the federal Toxicity Testing in the 21st century (Tox21) collaboration. /The title compound was tested by ToxCast and/or Tox21 assays; Click on the "Chemical Explorer" button on the tool bar to see the data./[USEPA; ICSS Dashboard Application; Available from, as of April 22, 2015: http://actor.epa.gov/dashboard/]

규제 정보

FDA Requirements · 2건

An ingredient whose use in food or food packaging is subject to a prior sanction or approval within the meaning of section 201(s)(4) of the Act is exempt from classification as a food additive. ... Substances classified as plasticizers, when migrating from food-packaging material shall include ... triethyl citrate.

Substance added directly to human food affirmed as generally recognized as safe (GRAS).

FIFRA Requirements · 1건

Unless specifically excluded, residues resulting from the use of the following substance as either an inert or an active ingredient in a pesticide chemical formulation, including antimicrobial pesticide chemicals, is exempted from the requirement of a tolerance under FFDCA section 408, if such use is in accordance with good agricultural or manufacturing practices. Citric acid, triethyl ester is included on this list.

안전 데이터

wgk
1
tsca
TSCA listed
rtecs
GE8050000
독성
LD50 orally in Rabbit: > 3200 mg/kg LD50 dermal Rabbit > 5000 mg/kg
HS 번호
2918 15 00
risk_code
20

화학 및 산업

약리 정보

Mechanism of ActionThere was some evidence that type of effects produced may have resulted from binding of calcium by release of citrate ion with resultant hypocalcemia.
Metabolism/Metabolites · 4건

Triethyl citrate is hydrolyzed in vivo to citric acid and ethanol. Triethyl citrate appeared to be hydrolyzed at a slower rate with human serum compared to rat serum.

Samples of freshly collected rat or human serum were spiked with triethyl citrate and the disappearance of the triethyl citrate measured over a 4 hr period. Triethyl citrate was rapidly hydrolysed by rat serum (15 min), but hydrolysisoccurred at a much slower rate in human serum and was not complete at the end of the 4 hr test period.

Rat-, mouse- and human-liver homogenates as well as serum enzymes hydrolyse triethyl citrate to 1 mol citric acid and 3 mol ethanol/mol ester.

/Triethyl citrate/ is expected to be extensively metabolized by esterases and cytochrome P450 enzymes and break-down in the beta-oxidation or citric acid cycle or in cases subsequent glucuronidation. The substance is assumed to be excreted (if not metabolized completely in beta-oxidation and citric cycle) as metabolites (i.e. conjugates with glucuronic acid) via urine and to a lower extent via bile.

Absorption, Distribution and Excretion · 1건

In order to assess the toxicological behavior of triethyl citrate, the available experimental and predicted physico-chemical data have been evaluated. The substance is expected to be absorbed very well. The absorption of any metabolite of the substances of interest is fast and complete. Concerning the absorption after exposure via inhalation, as the chemical has a low vapor pressure, it is clear, that the substance is poorly available after inhalation. Given its lipophilicity (LogPow 1.17) - if absorbed - it is expected to be absorbed directly across the respiratory tract epithelium. The substance is expected to be also poorly absorbed following dermal exposure into the stratum corneum and to a certain extent into the epidermis, due to its molecular weight and its LogPow. In addition, the systemic toxicity via the skin is assumed to be low and this has been proven with the results of the acute dermal study with triethyl citrate, in which a LD50 of 5000 mg/kg bw has been obtained. Concerning the distribution in the body, triethyl citrate is expected to be mainly available in the circulatory system (due to its water solubility). The experimentally determined LogPow value, the water solubility and predicted behavior concerning absorption of the substance triethyl citrate do not indicate a potential for accumulation.

Cellular LocationsCytoplasm

용도 및 제조

Uses · 6건

CIR ingredient: Triethyl Citrate

Used as plasticizer (cellulose acetate, cellulose nitrate, vinyl acetate, natural resins, and hair fixative finishing sprays), softener, agglutinant, perfume base, food emulsifier, and flavor preserving agent; Also used in paint removers and for treatment of bloat in ruminants; [HSDB]

Dressing Hair [Category: Other]

Solvent and plasticizer for nitrocellulose and natural resins, softener, paint removers, agglutinant, perfume base, food additive (not over 0.25%).

MEDICATION (VET)

Used as a plasticizer and solvent for cellulose nitrate, cellulose acetate, and cellulose ethers. It can also be used as a plasticizer for PVC. It has been used as a solvent, in paint removers, in emulsifiers in food industry, and as a flavor-preserving agent.

U.S. Production · 4건

2023: 8,500,000 - <10,000,000 lb

(1975) PROBABLY GREATER THAN 4.54X10+5 GRAMS

Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: 1,2,3-Propanetricarboxylic acid, 2-hydroxy-, 1,2,3-triethyl ester. Aggregated National Production Volume: 1 to < 10 million pounds.

Non-confidential 2012 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: 1,2,3-Propanetricarboxylic acid, 2-hydroxy-, 1,2,3-triethyl ester. National Production Volume: 1,000,000 - 10,000,000 lb/yr.

Consumer UsesPlasticizer
Industry UsesSolvent
Methods of ManufacturingBy esterification of ethyl alcohol with citric acid.
Formulations/PreparationsGrades: Technical; refinded; Food Chemical Codex
응용 분야 · 3건

출처Reported found in Morello cherry, sour cherry and red currant. Also reported found in raw cabbage and white wine.

용도Triethyl Citrate is a sequestrant that is an oily liquid, slightly solu- ble in water. it is found in lemon drinks.

일반 설명Triethyl citrate is a safe direct food additive.

제조 방법

생산 방법Triethyl citrate is prepared by the esterification of citric acid and ethanol in the presence of a catalyst.

By esterification of ethyl alcohol with citric acid.

공급사50 곳

国药集团化学试剂有限公司86-21-63210123 · [email protected]
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]
山西锦洋药用辅料有限公司18234787927
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

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