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ACA (1-(1-Adamantylcarbonyl)proline) is supplied by Rexar as a chemical reference material for analytical chemistry, compound identification and laboratory-based comparison workflows. This material is intended exclusively for controlled research environments requiring verified chemical identity, structural confirmation and consistent reference-grade specifications.
ACA (CAS 35084-48-1) is available directly through the Rexar webshop and supplied in sealed laboratory packaging for distribution within the EU. Each batch is clearly labeled for internal traceability and analytical reference purposes.
ACA | CAS 35084-48-1 | Molecular formula: C14H21NO3 | Molecular weight: 251.32 g/mol.
ACA consists of a proline-derived pyrrolidine ring substituted with an adamantylcarbonyl moiety. The adamantane cage structure is a rigid tricyclic hydrocarbon framework known for its steric bulk and conformational stability.
The presence of the adamantane group introduces hydrophobic character and steric shielding, while the proline-derived carboxylic acid contributes polar functionality. This combination produces a molecule with amphiphilic characteristics that may influence chromatographic and solubility behavior.
The amide bond linking the adamantylcarbonyl group to the proline scaffold provides structural rigidity and defined conformational geometry.
ACA contains a chiral center derived from the proline moiety. Stereochemical configuration may influence chromatographic behavior when analyzed using chiral stationary phases.
The adamantane framework itself is conformationally locked, contributing to predictable NMR spectral characteristics and reduced conformational flexibility compared to linear alkyl substituents.
The carbonyl group introduces a localized electron-withdrawing effect, while the carboxylic acid group may participate in hydrogen bonding interactions in both solution and solid state.
These electronic characteristics influence UV absorption, IR stretching frequencies and NMR chemical shifts.
In IR spectroscopy, characteristic bands corresponding to the carbonyl (C=O) stretching vibration and carboxylic acid O–H stretching are typically observed.
In proton NMR spectroscopy, adamantane protons generate distinct multiplet patterns due to the symmetrical cage structure. The pyrrolidine ring and carboxylic acid proton appear in characteristic regions depending on solvent conditions.
ACA typically demonstrates moderate retention in reversed-phase HPLC systems due to its mixed hydrophobic and polar character.
Mobile phase composition, pH and column chemistry may influence separation performance during analytical method development.
Under electrospray ionization conditions, ACA typically forms a protonated molecular ion. Fragmentation pathways may involve cleavage at the amide linkage or within the adamantane substituent.
These fragmentation characteristics support structural confirmation during LC-MS analysis.
ACA is typically observed as a crystalline solid. Intermolecular hydrogen bonding between carboxylic acid groups may influence crystal packing.
Solid-state characterization may include melting point determination, XRPD analysis and thermal profiling using DSC.
Predicted physicochemical data sourced from external chemical databases and computational modeling tools.
Solubility may vary depending on pH and solvent system used during analytical procedures.
Safety classification based on predicted data from external chemical safety databases.
Additional chemical and predicted safety information can be consulted via an external database: ACA on ChemicalBook .
What is the CAS number of ACA?
The CAS number of ACA is CAS 35084-48-1.
Does ACA contain an adamantane cage structure?
Yes. The molecule includes a rigid adamantane-derived moiety contributing steric bulk and hydrophobic character.
In which form is ACA supplied?
This product is supplied as a white to off-white crystalline powder in sealed laboratory packaging.
Is this product intended for human or animal use?
No. This material is supplied exclusively as a laboratory reference compound.
Is ACA available for shipment within the EU?
Yes. Orders are supplied through the Rexar webshop in sealed laboratory packaging.
The adamantane moiety present in ACA represents a rigid tricyclic cage hydrocarbon system. Adamantane derivatives are characterized by exceptional conformational stability due to their diamond-like carbon framework. This structural rigidity reduces internal rotational freedom and contributes to well-defined spectroscopic signatures.
The bulky cage structure introduces significant steric shielding around the amide linkage, potentially influencing intermolecular interactions and chromatographic retention. Compared to linear alkyl chains, the adamantane substituent provides enhanced three-dimensional volume and spatial orientation.
ACA contains both a carboxylic acid group and an amide linkage capable of participating in hydrogen bonding. In solution, hydrogen bonding interactions may influence solubility and retention behavior. In the solid state, carboxylic acid groups may form dimeric hydrogen-bonded pairs, contributing to crystal lattice stabilization.
These interactions can affect melting behavior and powder morphology.
The pyrrolidine ring derived from proline exhibits defined conformational preferences. Ring puckering and restricted rotation around the amide bond may influence NMR coupling constants and chemical shift patterns.
Computational modeling and conformational analysis may be applied to evaluate energetically favored geometries.
The predicted pKa of approximately 3.7 corresponds to the carboxylic acid functionality. Under neutral or slightly basic conditions, partial deprotonation may occur, affecting solubility and chromatographic response.
Ionization state plays a role in reversed-phase HPLC retention, particularly when mobile phase pH is adjusted.
Although ACA lacks an extended aromatic conjugated system, the carbonyl functional groups contribute to UV absorption in lower wavelength regions. IR spectra typically display strong C=O stretching bands corresponding to both amide and carboxylic acid groups.
Hydrogen-bonded O–H stretching vibrations may broaden under certain conditions.
The adamantane cage produces characteristic aliphatic carbon signals in 13C NMR spectra, typically appearing in clustered regions due to structural symmetry. The carbonyl carbons appear downfield and are clearly distinguishable.
Proton NMR spectra show multiplet patterns associated with the cage hydrogens and ring methylene groups, providing structural confirmation.
Under electrospray ionization, ACA generally forms a protonated molecular ion [M+H]+. Fragmentation may occur via cleavage of the amide bond or through partial fragmentation of the adamantane cage.
Characteristic fragment ions assist in confirming molecular identity in LC-MS workflows.
Thermal profiling using differential scanning calorimetry (DSC) may reveal melting transitions or decomposition onset temperatures. The rigid cage structure may contribute to relatively sharp phase transitions compared to flexible aliphatic derivatives.
Thermogravimetric analysis (TGA) may be used to assess mass loss upon heating.
Within the class of adamantane-substituted amino acid derivatives, ACA is distinguished by its specific proline scaffold and carbonyl linkage. Comparative profiling against other adamantane-based compounds may reveal differences in polarity, solubility and retention time.
For laboratory reference use, compound identity may be confirmed through a combination of analytical techniques including HPLC retention time comparison, NMR spectral matching, IR fingerprint analysis and mass spectrometric verification.
Multi-technique validation enhances confidence in structural assignment and batch consistency.
Does the adamantane group influence chromatographic retention?
Yes. The hydrophobic cage structure increases retention in reversed-phase systems.
Can ACA form hydrogen-bonded dimers in the solid state?
Yes. The carboxylic acid functionality may participate in dimer formation.
Is ACA structurally rigid?
Yes. The adamantane cage and amide linkage contribute to conformational stability.
Disclaimer:
This product is intended for laboratory research use only. It is not intended for human or animal consumption, nor for medical, diagnostic, or therapeutic applications.
| Intended use: | Laboratory research and analytical reference purposes only |
| Application area: | Analytical chemistry, reference comparison and method development |
| End user: | Professional users in controlled research environments |
| Regulatory classification: | Chemical reference material |
