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60-01-5 | Propane-1,2,3-triyl tributyrate
CAS No: 60-01-5 Catalog No: AG0035IU MDL No:MFCD00009392
Product Description
Catalog Number:
AG0035IU
Chemical Name:
Propane-1,2,3-triyl tributyrate
CAS Number:
60-01-5
Molecular Formula:
C15H26O6
Molecular Weight:
302.3633
MDL Number:
MFCD00009392
IUPAC Name:
2,3-di(butanoyloxy)propyl butanoate
InChI:
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
InChI Key:
UYXTWWCETRIEDR-UHFFFAOYSA-N
SMILES:
CCCC(=O)OC(COC(=O)CCC)COC(=O)CCC
EC Number:
200-451-5
UNII:
S05LZ624MF
NSC Number:
661583
Properties
Complexity:
304
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
302.173g/mol
Formal Charge:
0
Heavy Atom Count:
21
Hydrogen Bond Acceptor Count:
6
Hydrogen Bond Donor Count:
0
Isotope Atom Count:
0
Molecular Weight:
302.367g/mol
Monoisotopic Mass:
302.173g/mol
Rotatable Bond Count:
14
Topological Polar Surface Area:
78.9A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
2.4
Literature
| Title | Journal |
|---|---|
| Adjuvant effect of short chain triacylglycerol tributyrin on a mouse contact hypersensitivity model. | Toxicology letters 20180301 |
| Chemopreventive effects of the dietary histone deacetylase inhibitor tributyrin alone or in combination with vitamin A during the promotion phase of rat hepatocarcinogenesis. | The Journal of nutritional biochemistry 20120801 |
| Tributyrin attenuates obesity-associated inflammation and insulin resistance in high-fat-fed mice. | American journal of physiology. Endocrinology and metabolism 20120715 |
| Modulation of histone deacetylase attenuates naloxone-precipitated opioid withdrawal syndrome. | Naunyn-Schmiedeberg's archives of pharmacology 20120601 |
| Dual function of tributyrin emulsion: solubilization and enhancement of anticancer effect of celecoxib. | International journal of pharmaceutics 20120530 |
| High-throughput screening method for lipases/esterases. | Methods in molecular biology (Clifton, N.J.) 20120101 |
| Purification, biochemical and kinetic properties of recombinant Staphylococcus aureus lipase. | Methods in molecular biology (Clifton, N.J.) 20120101 |
| Molecular modeling of lipase binding to a substrate-water interface. | Methods in molecular biology (Clifton, N.J.) 20120101 |
| Enzymatically catalyzed synthesis of low-calorie structured lipid in a solvent-free system: optimization by response surface methodology. | Journal of agricultural and food chemistry 20111214 |
| Suppressive effect of short-chain fatty acids on production of proinflammatory mediators by neutrophils. | The Journal of nutritional biochemistry 20110901 |
| Retinoic acid and tributyrin induce in-vitro radioiodine uptake and inhibition of cell proliferation in a poorly differentiated follicular thyroid carcinoma. | Nuclear medicine communications 20110701 |
| A new esterase, belonging to hormone-sensitive lipase family, cloned from Rheinheimera sp. isolated from industrial effluent. | Journal of microbiology and biotechnology 20110701 |
| Oral administration of tributyrin increases concentration of butyrate in the portal vein and prevents lipopolysaccharide-induced liver injury in rats. | Clinical nutrition (Edinburgh, Scotland) 20110401 |
| In vitro intestinal bioaccessibility of alkylglycerols versus triacylglycerols as vehicles of butyric acid. | Lipids 20110301 |
| Carica papaya lipase: a naturally immobilized enzyme with interesting biochemical properties. | Plant foods for human nutrition (Dordrecht, Netherlands) 20110301 |
| Preparation and evaluation of tributyrin emulsion as a potent anti-cancer agent against melanoma. | Drug delivery 20110201 |
| High-throughput insertion mutagenesis and functional screening in the entomopathogenic fungus Beauveria bassiana. | Journal of invertebrate pathology 20110201 |
| Identification of a putative triacylglycerol lipase from papaya latex by functional proteomics. | The FEBS journal 20110101 |
| Biochemical properties of pancreatic colipase from the common stingray Dasyatis pastinaca. | Lipids in health and disease 20110101 |
| Transesterification of triglycerides using nitrogen-functionalized carbon nanotubes. | ChemSusChem 20100222 |
| Reduction in postlaminectomy epidural adhesions in sheep using a fibrin sealant-based medicated adhesion barrier. | Journal of biomedical materials research. Part B, Applied biomaterials 20100201 |
| Genotypic and phenotypic variation among Staphylococcus saprophyticus from human and animal isolates. | BMC research notes 20100101 |
| Immunonutrition in patients undergoing major upper gastrointestinal surgery: a prospective double-blind randomised controlled study. | Scandinavian journal of surgery : SJS : official organ for the Finnish Surgical Society and the Scandinavian Surgical Society 20100101 |
| Identification and biochemical characterization of a GDSL-motif carboxylester hydrolase from Carica papaya latex. | Biochimica et biophysica acta 20091101 |
| Emulsion-based delivery systems for tributyrin, a potential colon cancer preventative agent. | Journal of agricultural and food chemistry 20091014 |
| Study of Thermomyces lanuginosa lipase in the presence of tributyrylglycerol and water. | Biophysical journal 20090617 |
| The exceptional activity of a phosphazenium hydroxide catalyst incorporated onto silica in the transesterification of tributyrin with methanol. | Chemical communications (Cambridge, England) 20090607 |
| Chemoprevention of rat hepatocarcinogenesis with histone deacetylase inhibitors: efficacy of tributyrin, a butyric acid prodrug. | International journal of cancer 20090601 |
| Mixed-substrate (glycerol tributyrate and fibrin) zymography for simultaneous detection of lipolytic and proteolytic enzymes on a single gel. | Electrophoresis 20090601 |
| [Determination of lipase activity by gas chromatography]. | Yao xue xue bao = Acta pharmaceutica Sinica 20090601 |
| Histone deacetylases modulate vascular smooth muscle cell migration induced by cyclic mechanical strain. | Journal of biomechanics 20090511 |
| Kinetic properties of dromedary pancreatic lipase: a comparative study on emulsified and monomolecular substrate. | Colloids and surfaces. B, Biointerfaces 20090501 |
| Multiple-layer substrate zymography for detection of several enzymes in a single sodium dodecyl sulfate gel. | Analytical biochemistry 20090301 |
| Chylomicrons promote intestinal absorption of lipopolysaccharides. | Journal of lipid research 20090101 |
| Arthrobacter sp. lipase immobilization for preparation of enantiopure masked beta-amino alcohols. | Bioorganic & medicinal chemistry 20090101 |
| Defect-mediated functionalization of carbon nanotubes as a route to design single-site basic heterogeneous catalysts for biomass conversion. | Angewandte Chemie (International ed. in English) 20090101 |
| Gene cloning and characterization of a novel esterase from activated sludge metagenome. | Microbial cell factories 20090101 |
| Isolation and physiological characterization of Bacillus clausii SKAL-16 isolated from wastewater. | Journal of microbiology and biotechnology 20081201 |
| Intestinal metabolism of weaned piglets fed a typical United States or European diet with or without supplementation of tributyrin and lactitol. | Journal of animal science 20081101 |
| [Cell surface display of Yarrowia lipolytica lipase Lip2 in Saccharomyces cerevisiae with a-agglutinin as carrier protein]. | Wei sheng wu xue bao = Acta microbiologica Sinica 20081101 |
| Solubilization of triglycerides in liquid crystals of nonionic surfactant. | Journal of colloid and interface science 20080901 |
| Evaluation of the pharmacokinetics of all-trans-retinoic acid (ATRA) in Wistar rats after intravenous administration of ATRA loaded into tributyrin submicron emulsion and its cellular activity on caco-2 and HepG2 cell lines. | Journal of pharmaceutical sciences 20080701 |
| Exploring the active site cavity of human pancreatic lipase. | Biochemical and biophysical research communications 20080606 |
| Butyrate and trichostatin A attenuate nuclear factor kappaB activation and tumor necrosis factor alpha secretion and increase prostaglandin E2 secretion in human peripheral blood mononuclear cells. | Nutrition research (New York, N.Y.) 20080501 |
| Quantitative determination of alpha-tocopherol distribution in a tributyrin/Brij 30/water model food emulsion. | Journal of colloid and interface science 20080401 |
| Purification and characterization of the first reptile pancreatic lipase: the turtle. | Pancreas 20080401 |
| A study of the growth of Pseudallescheria boydii isolates from sewage sludge and clinical sources on tributyrin, rapeseed oil, biodiesel oil and diesel oil. | Annals of agricultural and environmental medicine : AAEM 20080101 |
| Analysis of Yarrowia lipolytica extracellular lipase Lip2p glycosylation. | FEMS yeast research 20071201 |
| Isolation of lipase producing Bacillus sp. from olive mill wastewater and improving its enzyme activity. | Journal of hazardous materials 20071119 |
| Proteolytic cleavage of ostrich and turkey pancreatic lipases: production of an active N-terminal domain. | Pancreas 20071001 |
| Structure of a novel enzyme that catalyzes acyl transfer to alcohols in aqueous conditions. | Biochemistry 20070807 |
| Inhibition of histone deacetylase on ventricular remodeling in infarcted rats. | American journal of physiology. Heart and circulatory physiology 20070801 |
| Supplementary biochemical tests useful for the differentiation of oxidase positive staphylococci. | Systematic and applied microbiology 20070601 |
| Importance of the residue Asp 290 on chain length selectivity and catalytic efficiency of recombinant Staphylococcus simulans lipase expressed in E. coli. | Molecular biotechnology 20070501 |
| Scorpion digestive lipase: a member of a new invertebrate's lipase group presenting novel characteristics. | Biochimie 20070301 |
| Biochemical and structural comparative study between bird and mammal pancreatic colipases. | Journal of lipid research 20061201 |
| A sensitive assay for lipase using tetra sulfonatophenyl porphyrin. | Analytical biochemistry 20060915 |
| Biochemical characterization, cloning, and molecular modelling of chicken pancreatic lipase. | Archives of biochemistry and biophysics 20060715 |
| A double-blind, randomised, controlled trial to study the effects of an enteral feed supplemented with glutamine, arginine, and omega-3 fatty acid in predicted acute severe pancreatitis. | JOP : Journal of the pancreas 20060710 |
| A simple activity staining protocol for lipases and esterases. | Applied microbiology and biotechnology 20060501 |
| Val-407 and Ile-408 in the beta5'-loop of pancreatic lipase mediate lipase-colipase interactions in the presence of bile salt micelles. | The Journal of biological chemistry 20060324 |
| Technological properties of Enterococcus faecium isolated from ewe's milk and cheese with importance for flavour development. | Canadian journal of microbiology 20060301 |
| Evaluation of tributyrin lipid emulsion with affinity to low-density lipoprotein: pharmacokinetics in adult male Wistar rats and cellular activity on Caco-2 and HepG2 cell lines. | The Journal of pharmacology and experimental therapeutics 20060101 |
| Effects of interleukins 2 and 12 on TBT-induced alterations of MAP kinases p38 and p44/42 in human natural killer cells. | Journal of applied toxicology : JAT 20060101 |
| Substrate specificity and kinetic properties of enzymes belonging to the hormone-sensitive lipase family: comparison with non-lipolytic and lipolytic carboxylesterases. | Biochimica et biophysica acta 20051230 |
| Role of the lid hydrophobicity pattern in pancreatic lipase activity. | The Journal of biological chemistry 20051202 |
| Kinetic studies of lycopene isomerization in a tributyrin model system at gastric pH. | Journal of agricultural and food chemistry 20051116 |
| [Mechanism of differentiation and apoptosis in leukemia cells induced by tributyrin]. | Zhongguo shi yan xue ye xue za zhi 20051001 |
| Histone deacetylase inhibitors radiosensitize human melanoma cells by suppressing DNA repair activity. | Clinical cancer research : an official journal of the American Association for Cancer Research 20050701 |
| p21Waf1/Cip1 is a common target induced by short-chain fatty acid HDAC inhibitors (valproic acid, tributyrin and sodium butyrate) in neuroblastoma cells. | Oncology reports 20050601 |
| Mutations in the 'lid' region affect chain length specificity and thermostability of a Pseudomonas fragi lipase. | FEBS letters 20050425 |
| [A study of the Thermomyces lanuginosus lipolytic activity on tributyrin]. | Roczniki Panstwowego Zakladu Higieny 20050101 |
| Lipolytic activity and radial daily growth rate changes during incubation of thermomyces lanuginosus on natural and synthetic fatty substrates. | Roczniki Panstwowego Zakladu Higieny 20050101 |
| Screening for novel lipolytic enzymes from uncultured soil microorganisms. | Applied microbiology and biotechnology 20041101 |
| [Effects of tributyrin on SHI-1 leukemia cells in vitro]. | Zhonghua xue ye xue za zhi = Zhonghua xueyexue zazhi 20041101 |
| Preparation of tributyrin emulsion and characterization of the binding of the emulsion particles to low-density lipoprotein in vitro. | Journal of pharmaceutical sciences 20040701 |
| Genome-wide cloning and characterization of microbial esterases. | FEMS microbiology letters 20040401 |
| Sodium butyrate and tributyrin induce in vivo growth inhibition and apoptosis in human prostate cancer. | British journal of cancer 20040126 |
| [Effect of triester glycerol type of plasticizers on release of albumin from biodegradable polymer matrices]. | Ceska a Slovenska farmacie : casopis Ceske farmaceuticke spolecnosti a Slovenske farmaceuticke spolecnosti 20040101 |
| Determination of tributyrin and its metabolite butyrate in Wistar rat plasma samples by gas chromatography/mass spectrometry. | Rapid communications in mass spectrometry : RCM 20040101 |
| Ester synthesis in an aqueous environment by Streptococcus thermophilus and other dairy lactic acid bacteria. | Applied microbiology and biotechnology 20031101 |
| Structural insights into the lipase/esterase behavior in the Candida rugosa lipases family: crystal structure of the lipase 2 isoenzyme at 1.97A resolution. | Journal of molecular biology 20031003 |
| Sequence of the lid affects activity and specificity of Candida rugosa lipase isoenzymes. | Protein science : a publication of the Protein Society 20031001 |
| Production of a thermostable extracellular lipase by Kluyveromyces marxianus. | Biotechnology letters 20030901 |
| The amino acid sequences of the carboxyl termini of human and mouse hepatic lipase influence cell surface association. | Journal of lipid research 20030701 |
| Clinical and pharmacologic study of tributyrin: an oral butyrate prodrug. | Cancer chemotherapy and pharmacology 20030501 |
| Pancreatic lipase activity as influenced by unconjugated bile acids and pH, measured in vitro and in vivo. | The Journal of nutritional biochemistry 20030501 |
| Tributyrin inhibits human gastric cancer SGC-7901 cell growth by inducing apoptosis and DNA synthesis arrest. | World journal of gastroenterology 20030415 |
| Effects of temperature and pressure on Rhizomucor miehei lipase stability. | Journal of biotechnology 20030410 |
| The atypical lipase B from Candida antarctica is better adapted for organic media than the typical lipase from Thermomyces lanuginosa. | Biochimica et biophysica acta 20030321 |
| Degradation of African locust bean oil by Bacillus subtilis and Bacillus pumilus isolated from soumbala, a fermented African locust bean condiment. | Journal of applied microbiology 20030101 |
| Distribution of virulence genes in clinical and environmental isolates of Aeromonas spp. | Antonie van Leeuwenhoek 20030101 |
| Sample preparation for quantitation of tritium by accelerator mass spectrometry. | Analytical chemistry 20021215 |
| [Induction of cell differentiation and development of new anticancer drugs]. | Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan 20020801 |
| Tributyrin and lactitol synergistically enhanced the trophic status of the intestinal mucosa and reduced histamine levels in the gut of nursery pigs. | Journal of animal science 20020301 |
| Potentiating antitumor effects of a combination therapy with lovastatin and butyrate in the Lewis lung carcinoma model in mice. | International journal of cancer 20020220 |
| Early weaning of calves using feedstuffs. A rationalization based on inhibition of lipolysis. | Journal of agricultural and food chemistry 20020213 |
| Tributyrin-induced differentiation promotes apoptosis of LS 174T colon cancer cells in vitro. | International journal of oncology 20020101 |
| Potentiated antitumor effects of butyrate and actinomycin D in melanoma model in mice. | Oncology reports 20020101 |
| Purification and characterization of Lip2 and Lip3 isoenzymes from a Candida rugosa pilot-plant scale fed-batch fermentation. | Journal of biotechnology 20011130 |
| Improved enantioselectivity of a lipase by rational protein engineering. | Chembiochem : a European journal of chemical biology 20011001 |
| Tributyrin, an oral butyrate analogue, induces apoptosis through the activation of caspase-3. | Cancer letters 20010928 |
| Isolation and characterization of psychotrophic bacteria from oil-reservoir water and oil sands. | Applied microbiology and biotechnology 20010601 |
| 1,25-Dihydroxycholecalciferol enhances butyrate-induced p21(Waf1/Cip1) expression. | Biochemical and biophysical research communications 20010427 |
| Colipase residues Glu64 and Arg65 are essential for normal lipase-mediated fat digestion in the presence of bile salt micelles. | The Journal of biological chemistry 20010420 |
| Platelet-activating factor acetylhydrolases: broad substrate specificity and lipoprotein binding does not modulate the catalytic properties of the plasma enzyme. | Biochemistry 20010417 |
| Expression in Pichia pastoris of Candida antarctica lipase B and lipase B fused to a cellulose-binding domain. | Protein expression and purification 20010401 |
| Antitumor activity of tributyrin in murine melanoma model. | Cancer letters 20010326 |
| Purification and characterization of an extracellular lipase from Penicillium candidum. | Lipids 20010301 |
| Tributyrin, a butyrate precursor, impairs growth and induces apoptosis and differentiation in pancreatic cancer cells. | Anticancer research 20010101 |
| [Study on the differentiation and apoptosis of promyelocytic leukemia cells induced by tributyrin]. | Zhonghua xue ye xue za zhi = Zhonghua xueyexue zazhi 20000201 |
| Metabolic effects of intraruminal administration of 1,3-butanediol or tributyrin in lactating goats. | Journal of dairy science 19890801 |
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