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glyceryl tributyrate

Chemical Structure

General Material Information

Preferred name glyceryl tributyrate
Trivial Name Tributyrin
Short Description tributyrin
Formula C15 H26 O6
CAS Number 60-01-5
FEMA Number 2223
Flavis Number 9.211
ECHA Number 200-451-5
FDA UNII S05LZ624MF
Nikkaji Number J4.798H
Beilstein Number 1714746
MDL MFCD00009392
COE Number 747
xLogP3-AA 2.40 (est)
Bio Activity Summary External link
NMR Predictor External link
JECFA Food Flavoring 922 tributyrin
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 60-01-5 ; GLYCEROL TRIBUTYRATE
Synonyms
  • butanoic acid 1,2,3-propane triyl ester
  • butanoic acid 1,2,3-propanetriyl ester
  • butanoic acid, 1,2,3-propanetriyl ester
  • butyric acid 2-butyryloxy-1-butyryloxymethyl-ethyl ester
  • butyric acid triester with glycerin
  • butyrin
  • butyryl triglyceride
  • 1,3-di(butanoyloxy)propan-2-yl butanoate
  • glycerin tributyrate
  • glycerol tributanoate
  • glycerol tributyrate
  • glycerol tributyrin
  • propane-1,2,3-triyl tributanoate
  • 1,2,3-propanetriyl tributanoate
  • 1,2,3-propanetriyl tributyrate
  • tri-N-butyrin
  • tributyrin
  • tributyrl glyceride
  • 1,2,3-tributyrylglycerol
  • 1,3-di(butanoyloxy)propan-2-yl butanoate
  • Butyrin, tri-
  • Tributyroin
  • Tributin
  • Tributyryl glyceride
  • Glyceroltributyrin
  • Tributyrylglycerol
  • Glyceryl tributanoate
  • NSC 661583
  • Tributanoin
  • 2,3-Di(butanoyloxy)propyl butanoate
  • Propane-1,2,3-triyl tributyrate

US / EU / FDA / JECFA / FEMA / Scholar / Patents

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Literature & References

1,3-di(butanoyloxy)propan-2-yl butanoate
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:60-01-5
Pubchem (cid):6050
Pubchem (sid):134972768
Publications by PubMed
Production and characterization of a tributyrin esterase from Lactobacillus plantarum suitable for cheese lipolysis.
A novel esterase gene cloned from a metagenomic library from neritic sediments of the South China Sea.
Purification and characterization of a pregastric esterase from a hygienized kid rennet paste.
Purification and partial characterization of psychrotrophic Serratia marcescens lipase.
Comparative proteome profiling of bovine and human Staphylococcus epidermidis strains for screening specifically expressed virulence and adaptation proteins.
Preparation of low calorie structured lipids catalyzed by 1,5,7-triazabicyclo[4.4.0]dec-5-ene(TBD)-functionalized mesoporous SBA-15 silica in a heterogeneous manner.
The chemopreventive activity of the histone deacetylase inhibitor tributyrin in colon carcinogenesis involves the induction of apoptosis and reduction of DNA damage.
Dietary supplementation with tributyrin alleviates intestinal injury in piglets challenged with intrarectal administration of acetic acid.
Transcriptomic responses provide a new mechanistic basis for the chemopreventive effects of folic acid and tributyrin in rat liver carcinogenesis.
Encapsulation of mixtures of tuna oil, tributyrin and resveratrol in a spray dried powder formulation.
Isolation and biochemical characterization of Bacillus pumilus lipases from the Antarctic.
The chemopreventive activity of the butyric acid prodrug tributyrin in experimental rat hepatocarcinogenesis is associated with p53 acetylation and activation of the p53 apoptotic signaling pathway.
Lipolysis within single culture and co-culture biofilms of dairy origin.
Molecular cloning of a novel bioH gene from an environmental metagenome encoding a carboxylesterase with exceptional tolerance to organic solvents.
Anticarcinogenic actions of tributyrin, a butyric acid prodrug.
Biotechnological and safety characterization of Enterococcus lactis, a recently described species of dairy origin.
[Gene cloning, expression and characterization of two cold-adapted lipases from Penicillium sp. XMZ-9].
Cloning, sequencing, and characterization of lipase genes from a polyhydroxyalkanoate (PHA)-synthesizing Pseudomonas resinovorans.
Tributyrin attenuates obesity-associated inflammation and insulin resistance in high-fat-fed mice.
Characterization of lipases from Staphylococcus aureus and Staphylococcus epidermidis isolated from human facial sebaceous skin.
Enzymatically catalyzed synthesis of low-calorie structured lipid in a solvent-free system: optimization by response surface methodology.
Butyrate delivered by butyrylated starch increases distal colonic epithelial apoptosis in carcinogen-treated rats.
Expression of active recombinant human gastric lipase in Nicotiana benthamiana using the CPMV-HT transient expression system.
Construction of the yeast whole-cell Rhizopus oryzae lipase biocatalyst with high activity.
Changes in psychrotrophic microbial populations during milk creaming to produce Grana Trentino cheese.
Site-specific saturation mutagenesis on residues 132 and 450 of Candida rugosa LIP2 enhances catalytic efficiency and alters substrate specificity in various chain lengths of triglycerides and esters.
Preparation of a whole-cell biocatalyst of Aspergillus niger lipase and its practical properties.
Design of nano-laminated coatings to control bioavailability of lipophilic food components.
SOA genes encode proteins controlling lipase expression in response to triacylglycerol utilization in the yeast Yarrowia lipolytica.
Emulsion-based delivery systems for tributyrin, a potential colon cancer preventative agent.
Development of an indirect method for measuring porcine pancreatic lipase in human duodenal fluid.
Quantitative determination of alpha-tocopherol distribution in a tributyrin/Brij 30/water model food emulsion.
Characterization and selection of autochthonous lactic acid bacteria isolated from traditional Iberian dry-fermented salchichón and chorizo sausages.
Importance of the residue Asp 290 on chain length selectivity and catalytic efficiency of recombinant Staphylococcus simulans lipase expressed in E. coli.
Characterization of new biosurfactant produced by Klebsiella sp. Y6-1 isolated from waste soybean oil.
Altering the substrate specificity of Candida rugosa LIP4 by engineering the substrate-binding sites.
Supplementary biochemical tests useful for the differentiation of oxidase positive staphylococci.
Phospholipid-based microemulsions suitable for use in foods.
Lipolytic activity and radial daily growth rate changes during incubation of thermomyces lanuginosus on natural and synthetic fatty substrates.
Technological properties of Enterococcus faecium isolated from ewe's milk and cheese with importance for flavour development.
Kinetic studies of lycopene isomerization in a tributyrin model system at gastric pH.
Screening of Korean medicinal plants for lipase inhibitory activity.
Purification and characterization of a pregastric esterase from a hygienized kid rennet paste.
Degradation of African locust bean oil by Bacillus subtilis and Bacillus pumilus isolated from soumbala, a fermented African locust bean condiment.
Purification and partial characterization of psychrotrophic Serratia marcescens lipase.
Esterolytic and lipolytic activities of lactic acid bacteria isolated from ewe's milk and cheese.
Enzymes from isolates of Pseudomonas fluorescens involved in food spoilage.
Early weaning of calves using feedstuffs. A rationalization based on inhibition of lipolysis.
Influence of solvent absorption on the migration of Irganox 1076 from LDPE.
[Quantitative occurrence of lipolytic and proteolytic enzymes in food of animal origin].
Taxonomical and technological characteristics of Saccharomyces spp. associated with blue veined cheese.
Fatty acid steryl, stanyl, and steroid esters by esterification and transesterification in vacuo using Candida rugosa lipase as catalyst.
Presence and changes in populations of yeasts on raw and processed poultry products stored at refrigeration temperature.
Biochemical properties of Streptococcus macedonicus strains isolated from Greek Kasseri cheese.
Cloning, characterization, controlled overexpression, and inactivation of the major tributyrin esterase gene of Lactococcus lactis.
The effects of environmental conditions on the lipolytic activity of strains of Penicillium roqueforti.
Regulation of intestinal peptidases by nutrients in human fetuses and children.
Butyric acid and tributyrin induce apoptosis in human hepatic tumour cells.
Initiation of growth arrest and apoptosis of MCF-7 mammary carcinoma cells by tributyrin, a triglyceride analogue of the short-chain fatty acid butyrate, is associated with mitochondrial activity.
Isolation and characterization of a tributyrin esterase from Lactobacillus plantarum 2739.
Method for the rapid quantitative detection of lipolytic activity among food fermenting microorganisms.
Optimized enzymatic synthesis of geranyl butyrate with lipase AY from Candida rugosa.
Regulation of food intake by metabolic fuels in white-crowned sparrows.
Proteolytic and lipolytic activities of Micrococcus roseus (65), Halomonas elongata (16) and Vibrio sp. (168) isolated from Danish bacon curing brines.
Lipolytic activity and degradation of rapeseed oil and rapeseed by spoilage fungi.
Study of surface yeast flora of Roquefort cheese.
The effect of triacylglycerol chain length on food intake in domestic fowl.
Various dietary fibers have different effects on lipase-catalyzed hydrolysis of tributyrin in vitro.
Factors affecting growth and lipase production by meat lactobacilli strains and Brochothrix thermosphacta.
[Lipolytic activity from milk isolated strains of the species Thermoactinomyces vulgaris, Tsiklinsky 1899 (author's transl)].
Simple media containing stabilized tributyrin for demonstrating lipolytic bacteria in foods and soils.
Assay for lipolytic and proteolytic activity using marine substrates.
Publications by J-Stage
A Novel Alkaline Esterase from Sporosarcina sp. nov. Strain eSP04 Catalyzing the Hydrolysis of a Wide Variety of Aryl-carboxylic Acid Esters

Other Information

(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
FDA Substances Added to Food (formerly EAFUS):View
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C13870
HMDB (The Human Metabolome Database):HMDB31094
FooDB:FDB003099
Export Tariff Code:2917.19.7050
FDA Listing of Food Additive Status:View
ChemSpider:View
Wikipedia:View
Formulations/Preparations:
•purity: not less than 99% of c15h26o6. •grades: technical; fcc.

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 302.36743164062
Specific gravity @ 20 °C
Pounds per Gallon 8.606 to 8.631
Refractive Index 1.435 to 1.438 @ 20 °C
Boiling Point 287 to 288°C @ 760 mm Hg
Acid Value 5 max KOH/g
Vapor Pressure 0.001 mmHg @ 25 °C
Flash Point TCC Value 173.89 °C TCC
logP (o/w) 2.951 est
Solubility
alcohol Yes
ether Yes
water, 133 mg/L @ 37 °C (exp) Yes
water No

Organoleptic Properties

Odor Type: Cheesy
cheesy, waxy, creamy, fatty, acidic
General comment At 100.00 %. cheese waxy creamy fatty
Mosciano, Gerard P&F 24, No. 2, 49, (1999) Cheese, waxy, fatty, acidic
Flavor Type: Bitter
bitter, waxy, fatty, cheesy, buttery
Mosciano, Gerard P&F 24, No. 2, 49, (1999) At 30.00 ppm. Bitter, waxy, fatty, cheese and butter nuances

Potential Uses

Applications
Flavoring purposes Butterscotch, Caramel, Cheese

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
None - None found.
S 02 - Keep out of the reach of children.
S 24/25 - Avoid contact with skin and eyes.
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Pictogram
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-rat LD50 3200 mg/kg
Kodak Company Reports. Vol. 21MAY1971

oral-mouse LD50 12800 mg/kg
Kodak Company Reports. Vol. 21MAY1971

intravenous-mouse LD50 320 mg/kg
BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Acta Physiologica Scandinavica. Vol. 40, Pg. 338, 1957.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
inhalation-rat LC > 75 ppm/6H
Kodak Company Reports. Vol. 21MAY1971

Safety in use information

Category:
flavoring agents and adjuvants
Recommendation for glyceryl tributyrate usage levels up to:
not for fragrance use.
Maximised Survey-derived Daily Intakes (MSDI-EU): 27.00 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA): 2.00 (μg/capita/day)
Structure Class: I
Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS).
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library
publication number: 3
Click here to view publication 3
average usual ppmaverage maximum ppm
baked goods: -290.00000
beverages(nonalcoholic): -0.10000
beverages(alcoholic): --
breakfast cereal: --
cheese: --
chewing gum: --
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: 2.0000050.00000
fish products: --
frozen dairy: -0.04000
fruit ices: -0.04000
gelatins / puddings: -0.36000
granulated sugar: --
gravies: --
hard candy: 0.330001000.00000
imitation dairy: --
instant coffee / tea: --
jams / jellies: --
meat products: --
milk products: --
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: --
snack foods: --
soft candy: --
soups: --
sugar substitutes: --
sweet sauces: --

Safety references

European Food Safety Athority(EFSA):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies...

European Food Safety Authority (EFSA) reference(s):

Flavouring Group Evaluation 64 (FGE.64): Consideration of aliphatic acyclic diols, triols, and related substances evaluated by JECFA (57th meeting) structurally related to aliphatic primary and secondary saturated and unsaturated alcohols, aldehydes, acetals, carboxylic acids and esters containing an additional oxygenated functional group and lactones from chemical groups 9, 13 and 30 evaluated by EFSA in FGE.10Rev1 (EFSA, 2008ab)
View page or View pdf

EPI System: View
ClinicalTrials.gov:search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):60-01-5
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :6050
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:1
1,3-di(butanoyloxy)propan-2-yl butanoate
Chemidplus:0000060015
RTECS:ET7350000 for cas# 60-01-5