DL-Carnitine is a zwitterionic amino acid derivative featuring a quaternary ammonium headgroup and a β-hydroxyamide side chain attached to a carbon framework that bears both amino and carboxyl functionalities in its native form. The molecule contains a positively charged trimethylammonium moiety, an alcohol-bearing β-hydroxyl group, and an amide carbonyl, with the "DL-" designation indicating a racemic mixture of stereoisomers at the chiral center(s) present in the carnitine backbone. DL-Carnitine is used in biochemical and analytical workflows as a chemically defined amino acid-like building block for studying carnitine-dependent chemical interactions, supporting isotopic labeling or method development, and serving as a substrate or reference material in assays that monitor carnitine-related transformations.
CAT No: CP05001
CAS No:496-93-5
Synonyms/Alias:Canaline;L-Canaline;496-93-5;(S)-2-Amino-4-(aminooxy)butanoicacid;O-Amino-L-homoserine;L-Homoserine,O-amino-;(2S)-2-amino-4-(aminooxy)butanoicacid;L-2-amino-4-(aminooxy)butyrate;L-2-amino-4-(aminooxy)butyricacid;L-a-amino-g-(aminooxy)-n-butyricacid;2-Amino-4-(aminooxy)butyricacid;L-CANALINEBASE;AC1L9B6J;SCHEMBL440859;CHEMBL1231652;CTK1D6980;HMDB12251;1-Amino-3-amino-oxybutyricacid;MolPort-019-904-731;ZINC1531042;ANW-63284;AKOS006274866;(2S)-2-amino-4-aminooxybutanoicacid;NE58530;(2S)-2-amino-4-aminooxy-butanoicacid
DL-Carnitine is a zwitterionic quaternary ammonium amino alcohol featuring a chiral carbon at the carnitine backbone and a hydroxyl-bearing side chain that can participate in hydrogen-bonding and salt formation. The molecule contains a trimethylammonium functionality and a carboxylate group, yielding strong polarity and water compatibility that influence extraction, ion-pairing, and chromatographic behavior. As a DL (racemic) amino acid derivative rather than a single enantiomer, it can be used to probe stereochemical effects in synthetic and analytical workflows where enantiopure carnitine is not required. The hydroxyl and carboxylate functionalities enable controlled derivatization, including esterification, salt formation, and conversion into protected or activated intermediates for downstream synthesis.
1. Chiral Analysis Standards
DL-Carnitine is applied in analytical research and method development where racemic reference material supports chiral HPLC, CE, or derivatization-based enantiomer detection strategies. The presence of both a carboxylate and a hydroxyl group enables formation of stable ion pairs and derivatized derivatives that can improve chromatographic resolution and detector response. The quaternary ammonium center provides strong ionic character, which can be exploited for reproducible retention behavior in ion-exchange and reversed-phase methods with appropriate additives. Racemic composition supports calibration and validation of stereoselective assays, including studies that compare derivatization reagents or chiral stationary phases for carnitine-like analytes. Downstream, the resulting analytical datasets can guide selection of enantiopure building blocks for stereospecific peptide, metabolite, or biochemical studies.
2. Chemical Manufacturing Intermediate
DL-Carnitine is used as a process chemistry intermediate in routes that require an amino alcohol scaffold bearing both carboxyl and hydroxyl functional groups for further functionalization. The carboxyl group can be converted into activated esters or amide-forming derivatives, while the alcohol can undergo etherification or oxidation-state adjustments depending on the target intermediate class. The permanently charged trimethylammonium moiety can influence phase behavior and workup design, making the compound relevant to manufacturing steps involving aqueous-organic partitioning and salt control. Racemic input can be suitable for non-stereospecific downstream transformations where the final product does not require a single enantiomer. The compound's structural features therefore support scalable preparation of carnitine-derived reagents for fine chemical synthesis and industrial intermediate generation.
3. Amino Alcohol Derivatization
DL-Carnitine is suitable for amino acid derivatization and synthetic organic chemistry programs that build functional derivatives from a chiral amino alcohol motif. The hydroxyl group enables formation of ethers, carbonate-like intermediates, and other oxygen-functional derivatives, while the carboxylate can be transformed into ester or amide linkers used for conjugation-ready intermediates. The zwitterionic nature supports controlled salt formation with acids or bases, which can be leveraged to tune solubility and reactivity in subsequent coupling chemistry. Although DL composition introduces stereochemical heterogeneity, derivatization steps can still produce well-defined downstream structures when stereochemistry is not the primary variable. Resulting carnitine-derived intermediates can serve as handles for attachment to polymers, small-molecule scaffolds, or analytical probes, extending amino acid chemistry into functional material and specialty chemical domains.
4. Bioconjugation and Labeling
DL-Carnitine can be employed in chemical biology workflows that require charged, hydroxyl-bearing biomolecule modification reagents or labeling intermediates. The carboxylate and hydroxyl functionalities can be converted into coupling partners that attach to amine-containing biomolecules or to surfaces via ester, amide, or linker-mediated strategies. The quaternary ammonium group provides strong ionic character, which can influence conjugate solubility, electrophoretic mobility, and interaction with ion-exchange materials during purification. Racemic starting material can be acceptable for labeling applications where the stereochemical identity of the carnitine moiety does not govern binding, while still enabling consistent linker chemistry. Downstream use can include generation of carnitine-tagged probes for biochemical assays, affinity materials, or analytical standards used to track carnitine-like chemistry in complex matrices.
5. Peptidomimetic Building Blocks
DL-Carnitine is used in peptidomimetic construction and molecular design efforts where an amino alcohol and carboxylate motif can be incorporated as a polarity-modulating element into peptide-like scaffolds. The functional groups can support amide bond formation at the carboxylate position and enable side-chain tethering strategies that mimic amino acid spacing and hydrogen-bonding patterns. The charged trimethylammonium center can be leveraged to tune overall cationic character of the designed scaffold, which can affect solubility and conformational preferences in peptide analogs. Racemic material may be selected for early-stage SAR studies or library synthesis where stereochemical resolution is deferred until later optimization steps. Resulting carnitine-containing analogs can function as research intermediates for structure-activity relationship studies, receptor-binding investigations, or enzyme-substrate analog design in applied peptide science.
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