L-alpha-Hydroxyisocaproic acid is an amino acid derivative featuring an alpha-hydroxy substituted isocaproic acid skeleton, placing a hydroxyl-bearing stereocenter at the alpha position relative to the carboxyl group and a branched aliphatic side chain consistent with an isoleucine-like carbon framework. The molecule contains a carboxylic acid functional group and an alpha-hydroxyl group, with the "L-alpha" designation indicating the specified stereochemical form at the alpha position while the side chain provides hydrophobic character and hydrogen-bonding capability through the hydroxyl. In biochemical and synthetic research, it is used as a defined hydroxy-functional building block or reference material for structure-property studies, and as a precursor in the preparation of more complex hydroxy-substituted carboxylic acid and peptide-related derivatives where controlled incorporation of an alpha-hydroxy motif is required.
CAT No: CP26351
CAS No:13748-90-8
Synonyms/Alias:L-Leucicacid;13748-90-8;(S)-2-hydroxy-4-methylpentanoicacid;(2S)-2-hydroxy-4-methylpentanoicacid;(S)-leucicacid;Hydroxyisocaproate;L-2-Hydroxy-4-methylvalericacid;L-Leucate;(S)-2-Hydroxy-4-methylvalericAcid;(S)-Leucate;L-a-Hydroxyisocaproate;hydroxy-isocaproicacid;L-2-Hydroxyisocaproate;L-alpha-HYDROXYISOCAPROICACID;(S)-(-)-2-Hydroxyisocaproicacid;(+)-a-Hydroxyisocaproate;L-alpha-Hydroxyisocaproate;(S)-2-Hydroxyisocaproate;L-a-Hydroxyisocaproicacid;(+)-2-Hydroxyisocaproate;L-2-hydroxyisocaproicacid;(+)-alpha-Hydroxyisocaproate;(+)-a-Hydroxyisocaproicacid;(S)-2-hydroxyisocaproicacid;(+)-2-hydroxyisocaproicacid
L-alpha-Hydroxyisocaproic acid is an α-hydroxy, α-substituted carboxylic acid derived from the isocaproic acid (leucine-like) carbon skeleton, featuring a stereogenic center at the α-position bearing both a hydroxyl and a carboxyl group. The molecule's hydroxyl enables hydrogen-bonding and can participate in esterification, ether formation, and oxidation-state adjustments, while the carboxylic acid supports salt formation and amide coupling chemistry. The chiral, hydroxy-bearing motif makes it a relevant stereochemical intermediate for constructing α-hydroxy acid derivatives and for preparing chiral building blocks used in peptide-adjacent syntheses and fine-chemical routes. The reactivity profile is dominated by carboxyl activation and controlled transformation of the secondary alcohol, enabling downstream conversion into protected forms or functionalized derivatives for synthetic and analytical workflows.
1. Chiral Building Block Synthesis
L-alpha-Hydroxyisocaproic acid is used in chiral synthesis programs where an α-hydroxy acid functionality is required as a stereodefined intermediate. The α-stereocenter and secondary alcohol allow conversion into esters, ethers, or oxidized carbonyl derivatives, while the carboxyl group can be activated for coupling or transformed into protected acid derivatives for stepwise sequence control. Stereochemical integrity can be maintained through appropriate protection of the hydroxyl during carboxyl activation and subsequent transformations. Downstream, the compound can serve as a feedstock for generating related chiral hydroxy acid intermediates used in synthetic organic chemistry and stereoselective route development.
2. Peptide Coupling Intermediate
L-alpha-Hydroxyisocaproic acid supports peptide-adjacent coupling strategies by providing a carboxyl group suitable for activation and a hydroxyl group that can be protected or derivatized to manage chemoselectivity. The α-hydroxy motif can be incorporated into peptide-like frameworks as an amino-acid analog precursor in methodologies that target α-hydroxy acid residues or hydroxy-containing linkers. Protecting-group strategies, such as hydroxyl protection prior to carboxyl activation, can help control side reactions during coupling chemistry and facilitate later deprotection to regenerate the free hydroxy functionality. The resulting hydroxy-containing fragments can be used to build stereodefined scaffolds for structure-activity relationship studies and chemical biology probes where hydroxy-mediated hydrogen bonding influences molecular recognition.
3. Derivatization For SAR Studies
L-alpha-Hydroxyisocaproic acid is applied in structure-activity relationship workflows that require systematic variation of α-hydroxy acid properties and functional-group presentation. The secondary alcohol can be oxidized, esterified, or converted into conformationally constrained derivatives, while the carboxyl group can be modified into amides or other carboxyl derivatives to tune polarity and ionization behavior. Chiral preservation at the α-center enables generation of stereochemically defined series suitable for comparing structure-dependent effects in binding assays or mechanistic studies. Downstream derivatives produced from this scaffold can feed combinatorial libraries of hydroxy acid analogs used to probe how stereochemistry and hydrogen-bonding capacity affect molecular interactions.
4. Analytical Reference Standards
L-alpha-Hydroxyisocaproic acid can be employed as a chiral reference material and analytical intermediate for quantification and method development involving α-hydroxy acid analytes. The presence of both a carboxylic acid and a secondary alcohol provides distinct derivatization handles for chromatographic or spectrometric workflows, including esterification or derivatization strategies that improve separation and detection. The stereodefined nature of the α-hydroxy center supports enantiomer-resolved analysis when paired with chiral stationary phases or stereospecific derivatization reagents. Downstream, the compound and its derivatives can function as standards for impurity profiling, metabolite identification studies, and process monitoring in chemical manufacturing contexts where hydroxy acid formation or transformation must be tracked.
5. Specialty Chemical Manufacturing
L-alpha-Hydroxyisocaproic acid is relevant to industrial fine-chemical synthesis routes that require chiral α-hydroxy acid intermediates for downstream functionalization. The carboxylic acid supports salt formation and activation chemistry, enabling conversion into intermediates that can be further processed into esters, amides, or polymerizable derivatives depending on the targeted end use. The secondary alcohol can be selectively protected during multi-step sequences to manage chemoselectivity, then unmasked to deliver the free hydroxy group for subsequent coupling or oxidation-state tuning. Downstream applications include preparation of functionalized hydroxy acid derivatives used as intermediates in specialty chemical production and as feedstocks for materials and formulation components where controlled polarity and hydrogen-bonding contribute to performance.
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