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Glycerintributyrat
GLYCERYL TRIBUTYRATE · GLYCEROL TRIBUTYRATE · FEMA 2223 · BUTYRIN · C4:0 · Glycerol tributanoate · C15H26O6 · Tributyroin
Identifikatoren & physikalische Daten
| CAS No. | 60-01-5 |
|---|---|
| Summenformel | C15H26O6 |
| Durchschnittliche Molmasse | 302,36 g/mol |
| Monoisotopische Masse | 302,17293855 g/mol |
| SMILES | CCCC(=O)OCC(COC(=O)CCC)OC(=O)CCC |
| InChIKey | UYXTWWCETRIEDR-UHFFFAOYSA-N |
| PubChem CID | 6050 |
| ChEMBL | CHEMBL118722 |
| ChEBI | CHEBI:35020 |
| EC No. | 200-451-5 |
| DTXSID | DTXSID4052267 |
| Lokaler Name | Glycerintributyrat |
Chemische & physikalische Eigenschaften
| XLogP | 2,4 |
|---|---|
| Polarare Oberfläche (TPSA) | 78,9 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 6 |
| Frei drehbare Bindungen | 14 |
| Schwere Atome | 21 |
| Formalladung | 0 |
| Komplexität | 304 |
| Arzneimittel | Pharmaceuticals -> Listed in ZINC15 |
| SpringerMaterials Properties | Boiling point |
| LogP (Verteilungskoeffizient) | log Kow = 2.54 |
| Geruch | FRUITY, BUTTERY |
| Geschmack | Bitter taste |
| Lebensmittelzusatzstoffe | FLAVORING AGENT OR ADJUVANT, SOLVENT OR VEHICLE -> FDA Substance added to food |
| Dichte | 1.032 at 20 °C1.034-1.0371.0335 |
| Aromastoffe | EU Flavoring substances |
| Color/Form | COLORLESSOily liquid |
| Löslichkeit | SOL IN ACETONE, BENZENEVery soluble in alcohol and etherIn water, 133 mg/L at 37 °C0.133 mg/mL at 37 °Cinsoluble in watersoluble in organic solvents, oilsmiscible (in ethanol)H2O: insolubleNot miscible in water. |
| Flammpunkt | 356 °F180 °C (Open cup)345 °F |
| Siedepunkt | 307 °C308 °C305 °C |
| Schmelzpunkt | -75 °C |
| Brechungsindex | n20/D 1.435(lit.) |
| FEMA | 2223 | (TRI-)BUTYRIN |
| Lagerbedingungen | Store at RT. |
| Aggregatzustand | Liquid |
| Farbe | Clear colorless to yellow |
| Geruch | at 100.00 %. cheese waxy creamy fatty |
| Geruchsart | cheesy |
| Biologische Quelle | synthetic |
| JECFA Number | 922 |
| Merck | 14,9620 |
| BRN | 1714746 |
| Henry-Konstante | 1.0×103 mol/(m3Pa) at 25℃, HSDB (2015) |
| Stabilität | Stable. Incompatible with strong oxidizing agents. |
| Hauptanwendungen | food and beverages |
| InChI | 1S/C15H26O6/c1-4-7-13(16)19-10-12(21-15(18)9-6-3)11-20-14(17)8-5-2/h12H,4-11H2,1-3H3 |
| InChIKey | UYXTWWCETRIEDR-UHFFFAOYSA-N |
| SMILES | CCCC(=O)OCC(COC(=O)CCC)OC(=O)CCC |
| LogP (Verteilungskoeffizient) | 2.95 |
| CAS Datenbank | 60-01-5(CAS DataBase Reference) |
| EPA chemische Informationen | Tributyrin (60-01-5) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 100% (119 of 119) of all reports.Not ClassifiedAggregated GHS information provided per 119 reports by companies from 1 notifications to the ECHA C&L Inventory. |
|---|---|
| Regulatorische Informationen | Chemical: Butanoic acid, 1,2,3-propanetriyl esterCommission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)Butanoic acid, 1,2,3-propanetriyl ester: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | IMAP assessments - Butanoic acid, 1,2,3-propanetriyl ester: Human health tier I assessment |
| FDA-Anforderungen | Substance added directly to human food affirmed as generally recognized as safe (GRAS).Synthetic flavoring substances and adjuvants /for animal drugs, feeds, and related products/ that are generally recognized as safe for their intended use, within the meaning of section 409 of the Act. Tributyrin is included on this list. |
| Flammable Limits | Lower flammable limit: 0.5% (by volume) @ 406 °F (208 °C) |
| NFPA Hazard Classification | 0 - Materials that, under emergency conditions, would offer no hazard beyond that of ordinary combustible materials.1 - Materials that must be preheated before ignition can occur. Materials require considerable preheating, under all ambient temperature conditions, before ignition and combustion can occur.0 - Materials that in themselves are normally stable, even under fire conditions. |
| Hazard Classes and Categories | Not Classified |
| Reinigungsverfahren | AEROBIC: Tributyrin is oxidized by activated sludge with a measured oxygen uptake of 300 mg/L in 7 days(1). Activated sludge at a concn of 2,500 mg/L, was exposed to tributyrin using a Warburg constant temperature respirometeroxygen uptake was used to determine amount of degradation of the tributyrin(1). Nocardia erythropolis, which readily degrades several phthalate esters, has been shown to be twice as active against tributyrin(2). |
| Entsorgungsverfahren | 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 qualitypotential migration in soil or watereffects on animal, aquatic, and plant lifeand conformance with environmental and public health regulations. |
| Wechselwirkungen | Effect of feeding tributyrin on toxicity of diisopropylfluorophosphate (DFP) in mice. After 36 hr of tributyrin feeding the DFP toxicity is 1.7 time normal & after 14 days of feeding it is only 1.15 times normal. . |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 570(SRC), determined from a log Kow of 2.54(2) and a regression-derived equation(3), indicates that tributyrin is expected to have low mobility in soil(SRC). Volatilization of tributyrin from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 9.6X10-9 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Tributyrin is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 0.0013 mm Hg(SRC), determined from a fragment constant method(5). Tributyrin is biodegraded by activated sludge with a measured oxygen uptake of 300 mg/L in 7 days(6), indicating that biodegradation may be an important fate process in soil(SRC).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 570(SRC), determined from a log Kow of 2.54(2) and a regression-derived equation(3), indicates that tributyrin is 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 9.6X10-9 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 50(SRC), from an estimated log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Tributyrin is biodegraded by activated sludge with a measured oxygen uptake of 300 mg/L in 7 days(7), indicating that biodegradation may be an important fate process in water(SRC).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), tributyrin, which has an estimated vapor pressure of 0.0013 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase tributyrin 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 1.2 days(SRC), calculated from its rate constant of 1.3X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Tributyrin does not contain chromophores that absorb at wavelengths >290 nm and therefore would not be expected to be susceptible to direct photolysis by sunlight(SRC). |
| Ökotoxizitätsauszüge | /AQUATIC SPECIES/ Tributyrin did not inhibit amylase activity in /carp/ fingerling but did in adults. |
| Soil Adsorption/Mobility | The Koc of tributyrin is estimated as 570 (SRC), using a log Kow of 2.54(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that tributyrin is expected to have low mobility in soil. |
| Human Toxicity Excerpts | /HUMAN EXPOSURE STUDIES/ ... We treated 13 patients with escalating doses of tributyrin from 50 to 400 mg/kg/day. Doses were administered p.o. after an overnight fast, once daily for 3 weeks, followed by a 1-week rest. Intrapatient dose escalation occurred after two courses without toxicity greater than grade 2. The time course of butyrate in plasma was assessed on days 1 and 15 and after any dose escalation. Grade 3 toxicities consisted of nausea, vomiting, and myalgia. Grades 1 and 2 toxicities included diarrhea, headache, abdominal cramping, nausea, anemia, constipation, azotemia, lightheadedness, fatigue, rash, alopecia, odor, dysphoria, and clumsiness. There was no consistent increase in hemoglobin F with tributyrin treatment. |
| Artificial Pollution Sources | Tributyrin's production and use as a plasticizer and flavoring agent(1) may result in its release to the environment through various waste streams(SRC). |
| Environmental Biodegradation | AEROBIC: Tributyrin is oxidized by activated sludge with a measured oxygen uptake of 300 mg/L in 7 days(1). Activated sludge at a concn of 2,500 mg/L, was exposed to tributyrin using a Warburg constant temperature respirometeroxygen uptake was used to determine amount of degradation of the tributyrin(1). Nocardia erythropolis, which readily degrades several phthalate esters, has been shown to be twice as active against tributyrin(2). |
| Environmental Bioconcentration | An estimated BCF of 50 was calculated for tributyrin(SRC), using a log Kow of 2.54(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate(SRC), provided the compound is not metabolized by the organism(SRP). |
| Volatilization from Water/Soil | The Henry's Law constant for tributyrin is estimated as 9.6X10-9 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that tributyrin is expected to be essentially nonvolatile from water surfaces(2). Tributyrin's Henry's Law constant indicates that volatilization from moist soil surfaces will not occur(SRC). Tributyrin is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 0.0013 mm Hg(SRC), determined from a fragment constant method(3). |
| Non-Human Toxicity Excerpts | /LABORATORY ANIMALS: Acute Exposure/ Inhalation of 78 ppm for 6 hr caused temporary hyperpnea in the rat, but no fatalities or other symptoms were observed./LABORATORY ANIMALS: Acute Exposure/ Feeding mice a diet containing 12% tributyrin increased the butyrylcholinesterase activity to about 2.4 times normal & reduced the acetylcholinesterase activity to about 0.55 times normal. These changes intervene between 3rd & 9th day of regimen./LABORATORY ANIMALS: Acute Exposure/ ... In Experiment 1, glucose was decreased by intraruminal administration of 84 or 168 g of tributyrin /in goat/. Tributyrin caused transient hyperglycemia immediately after administration. beta-Hydroxybutyrate was increased in a dose-dependent manner by tributyrin, caused large increases of insulin in plasma. In Experiment 2, 84 g of tributyrin administered intraruminally decreased glucose/LABORATORY ANIMALS: Acute Exposure/ ...We administered tributyrin (500 mL), tributyrin (500 mL) plus magnesium propionate (400 g), tributyrin (500 mL) plus sodium propionate (400 g), or tributyrin (500 mL) plus 1,2-propanediol (400 mL) as a single dose into rumens of lactating cows and then measured in blood the plasma concentrations of glucose, acetoacetate, 3-hydroxybutyrate, free fatty acids, and insulin as a function of time. Tributyrin administration caused hypoglycemia and hyperketonemia similar to the ketotic condition in less than 3 hr and was a negative correlation of --.88 between glucose and ketone concentrations in blood plasma. Administration of either magnesium propionate, sodium propionate, or 1,2-propanediol could counteract the hypoglycemia and hyperketonemia induced by tributyrin administration without significantly changing the insulin response.For more Non-Human Toxicity Excerpts (Complete) data for TRIBUTYRIN (10 total), please visit the HSDB record page. |
| Environmental Abiotic Degradation | The rate constant for the vapor-phase reaction of tributyrin with photochemically-produced hydroxyl radicals has been estimated as 1.3X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 1.2 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). A base-catalyzed second-order hydrolysis rate constant of 3.2X10-1 L/mole-sec(SRC) was estimated using a structure estimation method(2)this corresponds to half-lives of 250 and 25 days at pH values of 7 and 8, respectively(2). Tributyrin does not contain chromophores that absorb at wavelengths >290 nm and therefore would not be expected to be susceptible to direct photolysis by sunlight(SRC). |
| Probable Routes of Human Exposure | Occupational exposure to tributyrin may occur through inhalation and dermal contact with this compound at workplaces where tributyrin is produced or used. (SRC) |
| Wassergefährdungsklasse (WGK) | 1 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29171900 |
| RTECS-Nr. | ET7350000 |
| Sicherheitshinweise (S) | 24/25 |
| Lagerklasse | 10 - Combustible liquids |
| Gefahrstoffdaten | 60-01-5(Hazardous Substances Data) |
Anwendungen & Verwendung
Beschreibung
Tributyrin (C15H26O6), also known as butyrin or glyceryl tributyrate, is the triester of glycerin and butyric acid. It is prepared by esterifcation of glycerin with excess butyric acid. Glycerol tributyrate has a characteristic odor and a bitter taste.
Verwenden
Tributyrin is a flavoring agent that is the triester of glycerin and butyric acid. it is prepared by esterification of glycerin with excess butyric acid. it is used in the following foods: baked goods; alcoholic beverages; nonalcoholic beverages; fats and oils; frozen dairy des- serts and mixes; gelatins, puddings and fillings; and soft candy. it is also termed butyrin and glyceryl tributyrate.
Herstellung & Synthese
synthetische
Prepared by esterifcation of glycerol with excess butyric acid.