18667-97-5

Usage

Derived From

Butyric acid

Physical State

Clear, colorless liquid

Odor

Fruity

Solubility

Soluble in alcohol and ether; insoluble in water

Common Uses

Production of flavors and fragrances
Food additive for flavor enhancement
Potential applications in pharmaceuticals
Synthesis of other organic compounds

Upstream product

• 72-18-4 L-valine 
• 64-19-7 acetic acid 
• 503-74-2 3-methylbutyric acid 
• 75-36-5 acetyl chloride 
• 108-05-4 vinyl acetate 
• 4026-18-0 2-hydroxy-3-methylbutanoic acid 
• 17407-55-5 (S)-2-Hydroxy-3-methylbutanoic acid 
• 69798-62-5 2-acetoxy-3-methylbutanoic acid 
• 205880-35-9 (3R,6S)-6-isopropyl-3-(2-propenyl)morpholine-2,5-dione 
• 205880-31-5 (3RS,6S)-6-isopropyl-3-methoxymorpholine-2,5-dione 

Downstream Products

• 24347-63-5 methyl (S)-2-hydroxy-3-methylbutanoate 
• 3519-30-0 L-α-hydroxyisovaleric acid t-butyl ester 
• 849773-63-3 ARP101 
• 11042-59-4 neoantimycin 

Relevant academic research and scientific papers

Amber force field implementation, molecular modelling study, synthesis and MMP-1/MMP-2 inhibition profile of (R)- and (S)-N-hydroxy-2-(N-isopropoxybiphenyl-4-ylsulfonamido)-3-methylbutanamides

Ab initio calculations (B3LYP/Lanl2DZ level of theory) were performed in this study to determine all the structural and catalytic zinc parameters required in order to study MMPs and their complexes with hydroxamate inhibitors by means of the AMBER force f

First total synthesis of neoantimycin

The first total synthesis of neoantimycin (1), an unusual ring-extended antibiotic of the antimycin class, has been achieved, using intramolecular transesterification for construction of the 15-membered tetralactone core.

3-Aminoquinazolinones as chiral ligands in catalytic enantioselective diethylzinc and phenylacetylene addition to aldehydes

A series of readily known enantiomerically pure 3-aminoquinazolinones 1a-d were synthesised from easily accessible chiral pool α-hydroxy acids and α-amino acids in only four steps without any requirement of chromatography. These quinazolinones were examined as chiral ligands for catalytic enantioselective diethylzinc and phenylacetylene additions to aldehydes. For enantioselective alkylations, the effects of temperature, solvent, diethylzinc and ligand criteria were analysed, and the desired chiral alcohols were obtained in up to 86% ee. 3-Aminoquinazolinones 1a-d were also shown to be very useful ligands in enantioselective alkynylations of aldehydes. Based upon the optimised conditions, the corresponding propargylic alcohols were obtained in up to 94% ee.

Synthesis of new chiral ionic liquids from α-hydroxycarboxylic acids

New functionalized optically active N-methylimidazolium ionic liquids with an asymmetric center at the β-position to the imdazole ring were synthesized as bromide salts from optically active α-hydroxycarboxylic acids. The bromide anions were exchanged by carboxylate anions with Amberlite IRA 400 ionic exchange resin.

Zinc-catalyzed enantiospecific sp3-sp3 cross-coupling of α-hydroxy ester triflates with grignard reagents

(Chemical Equation Presented) Zinc chloride does the trick and efficiently catalyzes the enantiospecific cross-coupling of α-hydroxy ester triflates with Grignard reagents under mild conditions. Enantiopure α-hydroxy esters are directly available from the chiral pool or by diazotization of α-amino acids. Substantial variations in both reacting partners are tolerated making this methodology an attractive alternative to enolate alkylation featuring a reversal of polarity.

N-i-Propoxy-N-biphenylsulfonylaminobutylhydroxamic acids as potent and selective inhibitors of MMP-2 and MT1-MMP

Structural manipulation of the pharmacophoric model of type A selective MMP inhibitors (MMPi), obtained by the insertion of some alkyl substituents R 2 possessing an appropriate geometry, steric bulkiness and lipophilicity, is able to improve p

Synthesis of unsymmetrical 3,3′-biquinazoline-2,2′-diones by condensation of 3-aminoquinazolinones with benzoxazinones; fortuitous discovery, and further syntheses of 4-H-3-oxo-1,9a,10-triazaanthracen-9-ones

Condensation of 2-alkyl- or 2-aryl-3-aminoquinazolin-4-ones with benz[1,3]oxazin-4-ones gives the unsymmetrical 2,2′ disubstituted 3,3′ biquinazoline-4,4′-diones. The reaction is tolerant to a range of heteroatom and unsaturated functionality in the quina

A novel access to 2-aminofuranones via cyclization of functionalized γ-hydroxy-α,β-butenoates derived from N-hydroxybenzotriazole esters of α-hydroxy acids

The reaction between the N-hydroxybenzotriazole esters of substituted glycolic acids and alkyl cyanoacetates or malononitrile leads to the synthesis of γ-hydroxy-functionalized butenoates which are cyclized under mild conditions to the corresponding 2-amino-3,5-disubstituted-4-furanones. That the products are optically active is confirmed by measurements of their optical rotations. On the other hand, replacement of N-hydroxybenzotriazole by N-hydroxysuccinimide might lead to by-products depending on the functionalized glycolic acid used.

Synthesis and characterization of chiral N-O turns induced by α-aminoxy acids

Chiral α-aminoxy acids of various side chains were synthesized with high optical purity starting from chiral α-amino acids. The conformations of diamides 13a-e, 15, and 16 were probed by using NMR, FT-IR, and CD spectroscopic methods as well as X-ray crystallography. The right-handed turns with eight-membered-ring intramolecular hydrogen bonds between adjacent residues (called the N-O turns) were found to be preferred for D-aminoxy acid residues, and they were independent of the side chains. The rigid chiral N-O turns should have great potential in molecular design.

Synthesis of chiral α-acetoxy-N-acetylamides from chiral pyrimidylalkanols by the oxidative cleavage of pyrimidine ring

Acetates of chiral 5-pyrimidylalkanols are transformed into chiral α- acetoxy-N-acetylamides and α-acetoxyamides without racemization in high total yields by the oxidative cleavage of pyrimidine ring using ruthenium tetroxide.