IdentificationPhysical DataSpectraRoute of Synthesis (ROS)Safety and HazardsOther Data
Identification
Product NameEthyl (R)-3-hydroxybutyrateIUPAC Nameethyl (3R)-3-hydroxybutanoateMolecular StructureCAS Registry Number 24915-95-5MDL NumberMFCD00075386SynonymsEthyl (R)-3-hydroxybutyrate24915-95-5ethyl (3R)-3-hydroxybutanoateEthyl (R)-(-)-3-hydroxybutyrateEthyl (R)-3-hydroxybutanoate(R)-ETHYL 3-HYDROXYBUTANOATEMFCD00075386(R)-3-Hydroxybutyric acid ethyl ester(R)-3-hydroxy-butyric acid ethyl ester(R)-(-)-3-Hydroxybutyric Acid Ethyl EsterButanoic acid, 3-hydroxy-, ethyl ester, (3R)-(R)-(-)-3-HYDROXY-N-BUTYRIC ACID ETHYL ESTERethyl (R)-3-oxobutanoateEthyl(R)-3-hydroxybutyrateSCHEMBL434191ethyl (3R)-3-hydroxybutyrate(3R)-ethyl 3-hydroxybutanoateethyl (R)-beta-hydroxybutanoateEthyl R-(-)-3-hydroxybutyrateCHEBI:28707DTXSID20331464(R)-Ethyl(-)-3-hydroxybutyrateethyl (R)-(-)3-hydroxybutanoate(R)-Ethyl (-)-3-hydroxybutyrateCS-D1461HY-Y1131SC1027AKOS005146360AKOS015855502AC-5700GS-3059(R)-3-hydroxybutanoic acid ethyl esterEthyl (R)-(-)-3-hydroxybutyrate, 98%H1029C03499EN300-209122J-015729Q27103848Molecular FormulaC6H12O3Molecular Weight132.16InChIInChI=1S/C6H12O3/c1-3-9-6(8)4-5(2)7/h5,7H,3-4H2,1-2H3/t5-/m1/s1InChI KeyOMSUIQOIVADKIM-RXMQYKEDSA-NIsomeric SMILESCCOC(=O)C(C)O
Patent InformationPatent IDTitlePublication DateUS2022/110905Efficient anti-bacterial hydroxy acid ester oligomer2022US2021/94900SYNTHESIS OF 3-HYDROXYBUTYRYL 3-HYDROXYBUTYRATE AND RELATED COMPOUNDS2021KR2019/26747Beta - hydroxy butyrate and butanediol compositions and methods of using method-chain fatty acid ester and methods of using2019US2015/210665ORGANOCATALYTIC PROCESS FOR ASYMMETRIC SYNTHESIS OF DECANOLIDES2015
Physical Data
AppearanceWhite or off-white powder
Boiling Point, °CPressure (Boiling Point), Torr66885 - 89287.1 - 87.72681 - 832084 - 852086 - 86.5227412
Description (Association (MCS))Temperature (Association (MCS)), °CPartner (Association (MCS))Further physical properties of the adsorbed molecule.32.85Ni32(3-picoline)6(1,2-propanediol)12(H2O)11
Spectra
Description (NMR Spectroscopy)Nucleus (NMR Spectroscopy)Solvents (NMR Spectroscopy)Frequency (NMR Spectroscopy), MHzChemical shifts, Spectrum1Hchloroform-d1Chemical shifts1Hchloroform-d1Chemical shifts, Spectrum13Cchloroform-d1101Chemical shifts, Spectrum1Hdimethylsulfoxide-d6400Chemical shifts1Hchloroform-d1400Chemical shifts13Cchloroform-d1100Chemical shifts, Spectrum1Hchloroform-d1400
Description (IR Spectroscopy)Solvent (IR Spectroscopy)BandsBandsneat liquidATR (attenuated total reflectance), BandsBandschloroformBandschloroformBandschloroform
Route of Synthesis (ROS)
Route of Synthesis (ROS) of EthylR-3-hydroxybutyrate CAS 24915-95-5
ConditionsYieldWith lithium aluminium tetrahydride In diethyl ether for 1h; Ambient temperature;86%With lithium aluminium tetrahydride In diethyl ether at 0℃; for 0.5h;85.6%Stage #1: Ethyl (R)-3-hydroxybutanoate With lithium aluminium tetrahydride In diethyl ether at 0 - 20℃; for 3h; Inert atmosphere;Stage #2: With water In diethyl etherExperimental Procedure5.2. General procedure for the synthesis of 1,3-diols from β-hydroxyestersGeneral procedure: This method was adapted from the literature.14 To a suspension of LiAlH4 (7.6 mmol, 1 equiv) in dry diethyl ether (6 mL) was added a solution of β-hydroxyester (7.6 mmol, 1 equiv) in dry diethyl ether (5 mL) at 0 °C. The mixture was stirred for 3 h at room temperature and then quenched with distilled water (1 mL). After 10 mn, a 30% NaOH solution (1.5 mL) was added followed by 1 mL of distilled water. The reaction mixture was passed through a Celite pad. The filtrate was dried over MgSO4, concentrated under vacuum and purified by column chromatography if necessary (silica gel, cyclohexane/ethyl acetate 20/80) to afford the desired diol.81%
Safety and Hazards
Pictogram(s)SignalWarningGHS Hazard StatementsH227 (50%): Combustible liquid H315 (100%): Causes skin irritation H319 (100%): Causes serious eye irritation H335 (100%): May cause respiratory irritation H413 (50%): May cause long lasting harmful effects to aquatic life Precautionary Statement CodesP210, P261, P264, P264+P265, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P370+P378, P403, P403+P233, P405, and P501(The corresponding statement to each P-code can be found at the GHS Classification page.)
Other Data
TransportationUnder room temperature away from lightHS CodeStorageUnder room temperature away from lightShelf Life1 yearMarket Price
DruglikenessLipinski rules componentMolecular Weight132.159logP0.245HBA3HBD1Matching Lipinski Rules4Veber rules componentPolar Surface Area (PSA)46.53Rotatable Bond (RotB)4Matching Veber Rules2
Use PatternEthylR-3-hydroxybutyrate CAS 24915-95-5 is a versatile multidentate ligand commonly used as a metal chelating agent. Its strong chelation properties make it ideal for various applications involving metal ion analysis and testing. In spectrophotometric methods, it is used to determine the concentrations of metals such as iron, copper, cobalt, and chromium. For iron and manganese, it plays a crucial role in iodometric titrations, providing reliable measurements. Furthermore, this compound is applied in the rapid determination of calcium in bones and teeth, aiding in biological and medical studies. Its utility extends to complexometric titrations, where it is used for the precise measurement of thorium and sulfates. Overall, trans-1,2-Cyclohexanediaminetetraacetic acid monohydrate is an essential reagent in various fields, including analytical chemistry, biology, and environmental science, due to its ability to form stable complexes with a wide range of metal ions, ensuring accuracy and precision in quantitative analysis. https://www.chemwhat.com/ethyl-r-3-hydroxybutyrate-cas-24915-95-5/
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