3- Ethyl-2-hydroxybutyric acid

AS Gopalan, CJ Sih. Bifunctional chiral synthons via biochemical methods. 5. Preparation of (S)-ethyl hydrogen-3-hydroxyglutarate, key intermediate to (R)-4-amino-3-hydroxybutyric acid and L-carnitine. Tetrahedron Lett 25 5235-5238, 1984. 

Hydroxy-propionic acid 1,3-Propanediol, acrylamide, acrylic acid, acrylonitrile, ethyl-3-hydroxypropionic acid, L-alanine, L-serine, malonic acid, propiolactone, poly(3-HP), poly(3-hydroxybutyric acid-co-3-hydroxypropionic acid) Polymers, fine chemicals Cao et al., 1999 Werpy and Petersen, 2004 Zhang etal., 2004 Patel etal., 2006... 

Disposition in the Body. Readily absorbed after oral administration. The major metabolite is free bromide ion hydrolysis to an active metabolite, 2-bromo-2-ethylbutyramide, also occurs followed by oxidation to 2-bromo-2-ethyl-3-hydroxybutyramide other metabolites include 2-ethylbutyrylurea and 2-ethyl-2-hydroxybutyric acid. Carbromal is excreted in the urine mainly as bromide ion and partly as 2-ethyl-2-hydroxybutyric acid, with very little as unchanged drug. Peak bromide excretion is attained after about 48 hours. 

The cyanohydrin synthesis of a-hydroxy acids is very often carried out without isolation or purification of the cyanohydrins. The various techniques for the preparation of the cyanohydrins are discussed elsewhere (method 390). Hydrolysis to the a-hydroxy acids is usually effected by heating with concentrated hydrochloric acid. Excellent directions are given for mandelic acid (52% over-all from benzaldehyde), a-methyl-a-hydroxybutyric acid (65% from methyl ethyl ketone), and eighteen dialkyl- and alkylphenyl-glycolic acids (60-80%). Sodium hydroxide solution is used in the preparation of /S-hydroxypropionic acid from the /S-hydroxy nitrile (80%). ... 

C4H9N03 DL-4 amino-3-hydroxybutyric acid 924-49-2 22.50 1.0765 2 3996 C4H11NO N-ethyl-N-hydroxyethanamine 3710-84-7 -25.50 1.0697 2... 

C6H1202 1-ethylpropyl formate 58368-67-5 393.76 34.513 2 8555 C6H1203 2-ethyl-2-hydroxybutyric acid 3639-21-2 450.76 39.174 2... 

S) fi"-D-Galactometasaccharinic Acid.—Kiliani and Sanda reduced their parasaccharinic acid in the usual manner with hydriodic acid and red phosphorus. The product was a hexanoic lactone whose boiling point (217.5°) was precisely intermediate between that (220°) of the n-hexanoic 1,4-lactone obtained by a similar reduction of a -D-galactometasaccharinic acid and that (215°) reported for 2-ethylbutyro-l, 4-lactone. Kiliani, however, chose the latter structure for his lactone, since the corresponding acid, like DL-(2-ethyl-4-hydroxybutyric acid) and unlike either the enantiomor-... 

The hypothesis of the existence of the branched-chain parasaccharinic acid now depended solely on the identity of the reduction product, hydroxyhexanoic acid. To support his previous contention that the barium salt of this acid is, indeed, barium 2-ethyl-4-hydroxybutyrate, Kiliani also prepared the calcium salt and found that it, too, closely resembled the corresponding salt of 2-ethyl-4-hydroxybutyric acid. As emphasized by Kiliani, neither the reductions with hydriodic acid and red phosphorus nor the oxidations with nitric acid proceed in good yield to single products. Accordingly, Kihani remained firm in his conviction that his preparation, although it was apparently a mixture, nevertheless contained the branched-... 

R)-4-phenyl-2-hydroxybutyric acid ethyl ester is an important intermediate for the synthesis of the angiotensin-converting enzyme inhibitor benazepril [3] (see SCHEME 1). Its preparation via hydrogenation of the a-ketoester has been developed and scaled-up into a production process (10-2(X) kg scale, chemical yield >98%, ee 79-82%). One drawback of this process is the instability of the a-ketoester during distillation and storage. The hydrogenation of the a-ketoacid followed by esterification is an alternative route to the desired hydroxyester. 

Blends were prepared with cellulose or silk as soon as a common solvent was available [63, 69-71]. Recently, ionic liquids were used. The solvent l-ethyl-3-methyl-imidazolium acetate completely dissolves raw crustacean shells allowing to recover high purity chitin powder or films and fibres by direct spinning [72]. Films of poly(e-caprolactone) (PCL) blends with a-chitin and chitosan were produced. They are completely biodegradable and the crystallinity of PCL is suppressed in the blends due to hydrogen bond interaction between PCL and polysaccharides [73]. Blends were also realized with poly (3-hydroxybutyric acid) (PHB) and chitin or chitosan. They show faster biodegradation than the pure-state component polymers [74,75]. 

Synonyms Butanoic acid, 3-hydroxy-, ethyl ester Butyric acid, 3-hydroxy-, ethyl ester Ethyl 3-hydroxybutanoate Ethyl p-hydroxybutyrate Ethyl DL-3-hydroxybutyrate 3-Hydroxybutanoic acid ethyl ester DL-p-Hydroxy-n-butric acid ethyl ester 3-Hydroxybutyric acid ethyl ester DL-3-Hydroxybutyric acid ethyl ester Definition Ester commonly found in grapes and other berries Empirical C6H12O3 Formula CH3CH(0H)CH2C(0)0C2Hs Properties Colorless liq. fresh fruity grape flavor sol. 23 C > 100 mg/ml in water, DMSO, 95% ethanol, acetone sol. in alcohol m.w. 132.16 sp.gr. 1.017 b.p. 170 C flash pt. 64 C ref. index 1.4182(20 C)... 

Hydroxybutyric acid ethyl ester DL-3-Hydroxybutyric acid ethyl ester. See Ethyl 3-hydroxybutyrate... 

Hydroxybutyric acid, methyl ester, A1.22 Lactic acid, ethyl ester, A1.9 Cyclopentane-1,2,3-triol, A"22.10... 

Hydroxy-3-methylbutyric acid 2-Hydroxybutyric acid, methyl ester Lactic acid, ethyl ester A24.il A 1.22 A 1.9 2-Methylbutane-1,2-diol 2-Methylbutane-1,4-diol 2-Methylbutane-2,3-diol C5H12O3 A33.7 A27.20 A12.9... 

Lipase-catalyzed polymerization of oxyacid esters was reported. PPL catalyzed the polymerization of methyl 6-hydroxyhexanoate [89]. A polymer with a DP of up to 100 was synthesized by polymerization in hexane at 69 °C for more than 50 d. The PPL-catalyzed polymerization of methyl 5-hydroxypentanoate for 60 d produced a polymer with a DP of 29. Solvent effects were systematically investigated hydrophobic solvents such as hydrocarbons and diisopropyl ether were suitable for the enzymatic production of high-molecular-weight polymer. Various hydroxyesters, ethyl esters of 3- and 4-hydroxybutyric acids, 5- and 6-hydroxyhexanoic acids, 5-hydroxydodecanoic acid, and 15-hydroxypentadecanoic acid were polymerized by Pseudomonas sp. lipase at 45 °C to give the corresponding polyesters with molecular weights of several thousand [90]. 

---