Butanoic acid, 3-hydroxy-, -, ethyl ester

YEAST REDUCTION OF ETHYL ACETOACETATE (S)-(+)-ETHYL 3-HYDR0XYBUTAN0ATE (Butanoic acid, 3-hydroxy-, ethyl ester, ( ))... 

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)... 

The mixture of (2S,3S,5S)-2-(2,6-dimethylphenoxyacetyl)amino-3-hydroxy-5-amino-l,6-diphenylhexane (100 g, 0.22 mol), 2S-(l-tetrahydro-pyrimid-2-onyl)-3-methyl butanoic acid methyl ester (44.8 g, 0.22 mol) and 750 ml DMF was cooled in an ice/water bath. N-Hydroxybenzotriazole (90.9 g, 0.67 mol), l-ethyl-3-[3-dimethylaminopropyl]carbodiimide (86 g, 0.45 mol) and triethylamine (62.5 ml, 0.45 mol) were added and the ice bath was removed, allowing the reaction mixture to stir with warming to room temperature for 5 hours. The mixture was diluted with 1000 ml of IPAC and quenched with 1000 ml of water. The mixture was shaken and separated, the aq. layer was extracted IPAC, the organics were washed with 10% HCI, solution of NaHC03 with 100 ml hexanes, then washed 500 ml water, and brine, dried over MgS04, filtered and concentrated to provide. (2S,3S,5S)-2-(2,6-dimethylphenoxyacetyl)amino-3-hydroxy-5-(2S-(l-tetrahydro-pyrimid-2-onyl)-3-methylbutanoyl)amino-l,6-diphenylhexane as a white foam. 

Chemical Name Butanoic acid, 2-methyl-, (lS,3R,7S,8S,8aR)-l,2,3,7,8,8a-hexahydro-3,7-dimethyl-8-(2-((2R,4R)-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl)-l-naphthalenyl ester, (2S)-... 

Benzenedicarboxylic acid, bis [2-(1,1-d i methylethyl )-6-[[3-( 1,1 -d imethy lethy I )-2-hydroxy-5-methylphenyl] methyl]-4-methylphenyl] ester Bis r2,4-bis (1,1-dimethylethyl)-6-methylphenyll ethyl ester, phosphorous acid Bis [3,3-bis (4-hydroxy-3-t-butylphenyl) butanoic acid], glycol 3,9-Bis [2-(3-(3-t-butyl-4-hydroxy-5-methylphenyl) propionyloxyM, 1 -dimethylethyl]-2,4,8,10-tetraoxaspiro (5.5) undecane 1,2-Bis (3,5-di-t-butyl-4-hydroxyhydrocinnamoyl) hydrazine... 

Important components of hard cheeses (Gouda type) include some carboxylic acid esters (ethyl butanoate, ethyl hexanoate), as well as carboxylic acids (acetic, butyric, isobutyric, valeric, isovaleric, 2-methylbutyric and caproic acids). Cheeses manufactured using bacteria of the genus Propionibacterium (such as Emmental and Gruyere) contain propionic acid and other lower fatty acids, methyl thioacetate, some oxocarboxylic acids, various alcohols, esters (such as ethyl butanoate), lactones (such as 8-decalactone), amines and other basic compounds (also skatole in addition to aliphatic amines), alkylpyrazines (e.g. 2-sec-butyl-3-methoxypyrazine), 4-hydroxy-2,5-dimethyl-2H-furan-3-one (furaneol), 2-ethyl-4-hydroxy-5-methyl-2H-furan-3-one (homofuraneol) and a range of other compounds. 

Some workers avoid delay. Pai)adium-on-carbon was used effectively for the reductive amination of ethyl 2-oxo-4-phenyl butanoate with L-alanyl-L-proline in a synthesis of the antihyperlensive, enalapril maleate. SchifTs base formation and reduction were carried out in a single step as Schiff bases of a-amino acids and esters are known to be susceptible to racemization. To a solution of 4,54 g ethyl 2-oxO 4-phenylbutanoate and 1.86 g L-alanyl-L-proline was added 16 g 4A molecular sieve and 1.0 g 10% Pd-on-C The mixture was hydrogenated for 15 hr at room temperature and 40 psig H2. Excess a-keto ester was required as reduction to the a-hydroxy ester was a serious side reaction. The yield was 77% with a diastereomeric ratio of 62 38 (SSS RSS)((55). 

In another investigation, the volatile compounds were isolated [19] using a Porapack Q trap by vacuum for 2 h and were then eluted with hexane. The esters were the chemical class of compounds that predominated in the samples among 21 volatile compounds detected. Ethyl butanoate, ethyl 2-methylbutano-ate, 1-butanol, ethyl hexanoate, 3-hydroxy-2-butanone, ethyl octanoate, acetic acid, linalool, palmitic acid, and oleic acid were identified in cupuacu pulp by solid-phase extracton [15]. 

These terpene notes are supported by (Z)-3-hexenol, (E)-2-hexenal, (E)-2-hexenol with their fresh, green character. Gamma- and delta-lactones (4-decanolide, 5-decan-olide, 4-dodecanolide, 5-dodecanolide-(Z)-7-decen-5-olide) impart the sweet, creamy, buttery, peach and apricot character. 2,5-Dimethyl-4-hydroxy-furan-3(2H)-one and 2,5-dimethyl-4-methoxy-furan-3(2H)-one are responsible for the sweet creamy fruity body. A bouquet of esters imparts the overall fruity character (mainly esters of ethyl-, (Z)-3-hexenyl and butyl alcohol with acetic-, butanoic-, 2-butenoic, 3-hydroxybutanoic- and hexanoic acid). 

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