Ureidovaleric acid - ≥95% , CAS No.55512-99-7

CAS: 55512-99-7 Cat. No.: U1035748 Formula: C₆H₁₂N₂O₃ Peso molecolare: 160.170 Numero EC: 157-009-9

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Specifiche e purezza

≥95%

Condizioni di conservazione di stoccaggio

Room temperature

Purezza

≥95%

Nomi e identificatori

• Sorrisi canonici: CCCC(C(=O)O)NC(=O)N
• IUPAC Name: 2-(carbamoylamino)pentanoic acid
• InChIKey: GMSQPJHLLWRMCW-UHFFFAOYSA-N
• INCHI: 1S/C6H12N2O3/c1-2-3-4(5(9)10)8-6(7)11/h4H,2-3H2,1H3,(H,9,10)(H3,7,8,11)
• Peso molecolare: 160.170

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Classe Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Level5 Amino acids and derivatives
          • Level6 Alpha amino acids and derivatives
            • Level7 N-carbamoyl-alpha amino acids and derivatives
              • Level8 N-carbamoyl-alpha amino acids

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Classe: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Amino acids and derivatives - Alpha amino acids and derivatives - N-carbamoyl-alpha amino acids and derivatives
• Direct Parent: N-carbamoyl-alpha amino acids
• Alternative Parents: Methyl-branched fatty acids Ureas Monocarboxylic acids and derivatives Carboxylic acids Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: N-carbamoyl-alpha-amino acid - Branched fatty acid - Methyl-branched fatty acid - Fatty acyl - Fatty acid - Carbonic acid derivative - Urea - Carboxylic acid - Monocarboxylic acid or derivatives - Organooxygen compound - Organonitrogen compound - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Carbonyl group - Organic oxide - Hydrocarbon derivative - Aliphatic acyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as n-carbamoyl-alpha amino acids. These are compounds containing an alpha amino acid which bears an carbamoyl group at its terminal nitrogen atom.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Proprietà chimiche e fisiche

• Peso molecolare: 160.170 g/mol
• XLogP3: -0.400
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 160.085 Da
• Monoisotopic Mass: 160.085 Da
• Topological Polar Surface Area: 92.400 Ų
• Heavy Atom Count: 11
• Formal Charge: 0
• Complexity: 158.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 1
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Application Protocols

No application protocols are specified for this item in the Product Data. As a small-molecule research chemical, typical workflows include:

• Preparing aqueous or DMSO stock solutions followed by dilution into assay media.
• Using standard organic synthesis protocols for esterification, amidation, or protection/deprotection as outlined under Reaction Conditions.

For any procedural details (concentrations, incubation times), develop method-specific SOPs and validate under your laboratory conditions.

Biological Roles

No specific biological role is provided in the Product Data for this item. The following perspective is general and intended for research-only contexts.

• Conceptual role (general)

  • Ureido-substituted ω-amino acids are useful chemical probes and reference standards in studies of non-enzymatic carbamoylation and urea-related chemistry in vitro. Their dual functionality provides handles for conjugation and immobilization in biochemical assays.

• Analytical relevance

  • Due to high polarity and multiple hydrogen-bonding sites, ureidovaleric acid can serve as a retention/ionization challenge compound in method development for HILIC, ion-pair LC, or capillary electrophoresis.

• Metabolism context (general)

  • Ureido groups are common in intermediates of pyrimidine catabolism and in carbamoyl transfer reactions; ureido–acids are often used as surrogates or standards when investigating such pathways in cell-free systems. Specific in vivo roles for ureidovaleric acid are not asserted here.

Research use only. Not for diagnostic or therapeutic use.

Buffer Applications

Ureidovaleric acid is not a standard buffering agent and does not constitute a defined buffer system with a well-characterized buffering range.

• Practical note
  • If present in buffered solutions, its acid–base behavior may contribute weakly near the carboxyl pKa, but it is not recommended as a primary buffer component.
  • For controlled pH, use established systems (e.g., phosphate, HEPES, Tris) and treat ureidovaleric acid as a solute of interest.

No item-specific pKa values or buffer recipes are provided; consult the CoA or measure empirically if buffer contributions must be quantified.

Green Alternatives

Green chemistry considerations focus on solvent choice and protection strategies rather than on replacing the molecule itself.

• Solvent selection (preferred greener options)

  • Water (pH-controlled) is the greenest primary solvent when feasible.
  • Bio-based or lower-toxicity polar solvents such as 2-MeTHF generally will not dissolve ureido acids well; consider ethanol/water mixtures as greener alternatives to DMF/DMSO when compatible.

• Process intensification

  • Employ aqueous coupling chemistry (e.g., EDC-mediated amidation in water or water/alcohol co-solvents) to reduce reliance on high-boiling dipolar aprotics.
  • Use catalytic, room-temperature esterifications (e.g., enzyme-catalyzed in greener solvents) where applicable.

• Comparison snapshot (general guidance)

  | Need | Conventional choice | Greener alternative | Trade-offs | |---|---|---|---| | High solubility for stock solutions | DMSO | Water or water/EtOH (pH-adjusted) | Possible stability limits; pH control required | | Amide coupling medium | DMF/NMP | Water, EtOH/water, 2-propanol/water | Solubility, rate, and reagent compatibility may vary | | Extraction | DCM/EtOAc | EtOAc, MTBE, CPME | Partitioning depends on pH and ionization |

• Waste minimization

  • Favor telescoped, aqueous operations and avoid unnecessary protection/deprotection cycles. Recover and reuse polar aprotic solvents where they are unavoidable.

No item-specific environmental metrics are provided; apply general green chemistry principles to your workflow.

Pharmaceutical Uses

No pharmaceutical or excipient designation is provided for this item in the Product Data.

• Research-only positioning

  • Supplied for research use only; not for human or veterinary use, and not for incorporation into clinical products.

• Formulation context (general laboratory)

  • As a highly polar small molecule, ureidovaleric acid may be dissolved in aqueous media for in vitro studies or used as a process intermediate/reference in analytical methods development. Any use in regulated formulations would require independent qualification and compliance review, which is outside the scope of this product.

There are no pharmacopeial monograph claims or GMP assurances stated for this catalog item.

Physical Properties

Item-specific specifications are not provided in the Product Data for this lot. The following points combine general expectations for ureido–carboxylic acids with literature information; do not treat as product specs.

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular formula / molecular weight: Not specified for this item; refer to CoA/Spec Sheet. (Literature: C6H12N2O3; ~160.17 g/mol.)
• State and polarity (general): Typically an off-white crystalline solid at ambient conditions; strongly polar and hydrogen-bonding due to one carboxyl and two urea N–H donors.
• Acid–base behavior (literature/general):
  • Carboxyl group pKa generally in the ~4–5 range for analogous ω-amino/ureido acids; secondary amide/ureido N–H groups are far less acidic and typically non-ionizing under neutral conditions.
  • Zwitterionic character possible near neutral pH depending on microenvironment and counterions.
• Solubility profile (general guidance):
  • Expected to be highly soluble in water and aqueous buffers at basic to neutral pH; solubility may decrease under strongly acidic conditions if extensive hydrogen-bonding leads to lattice stabilization.
  • Sparingly soluble to insoluble in nonpolar organic solvents; limited solubility in polar aprotics (DMSO, DMF) can be used for stock solutions when aqueous media are unsuitable.
• Thermal behavior (general): Ureido–acids often exhibit melting/decomposition at elevated temperatures with possible urea-related condensation; exact mp/bp not specified for this item.

Always consult the item’s CoA/Spec Sheet for definitive property values before designing processes or specifications.

Quality and Grades

• Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.

• General guidance on grades for small-molecule biochemicals

  • Research/biochemical grade emphasizes identity and typical organic impurities control suitable for discovery, analytical reference, or synthesis. UV–Vis transparency and trace-metals limits may or may not be specified depending on intended use.
  • If offered as HPLC or LC–MS grade in other contexts, this would imply stringent control of non-volatile residues and UV-absorbing impurities to support chromatographic applications. No such designation is provided here.

• Identity and impurity control (what to expect in a CoA)

  • Typical assays include NMR/IR identity confirmation, HPLC area % purity, loss on drying or water content (Karl Fischer), and residual solvents. Item-specific acceptance criteria are defined in the Spec Sheet; values are not provided here.

• Stabilizers/additives

  • None reported in Product Data. If stabilizers or counter-ions are relevant, they will be declared on the CoA.

• Fitness for purpose

  • This product is supplied for research use only. For regulated manufacturing, qualification against internal specifications and a formal quality agreement are recommended.

Always consult the item’s CoA/Spec Sheet for definitive specifications and test methods.

Reaction and Applications

With both a carboxylic acid and a ureido (carbamoyl) functionality, ureidovaleric acid is a versatile building block and reference standard.

• Representative research uses (general)

  • Biochemical standard: calibration/reference in studies of carbamoylated amino acid derivatives, urea metabolism, or nitrogen balance in chemical biology (non-clinical, research-only context).
  • Materials/synthesis: precursor to ω-amino acid derivatives (e.g., 5-aminovaleric acid) via selective ureido cleavage; intermediate toward polyamide-related monomers and heterocycles.

• Transformations enabled (literature/general)

  • Amide coupling at the carboxyl terminus to give ureido-functionalized amides/peptidomimetics.
  • Esterification (Fischer or Steglich) to access protected esters for downstream derivatization.
  • Selective deprotection/cleavage of the ureido group (acidic or basic hydrolysis) to unveil primary amines or to rearrange to urea-linked products.
  • Intramolecular cyclizations under dehydrating conditions can afford lactams or 2-pyrrolidone-type frameworks from ω-amino acid precursors after appropriate activation.

• Practical tips

  • Control pH during aqueous workups: the carboxylate form enhances water solubility; acidify to pH ~2–3 to extract into organics if needed (general practice for carboxylic acids).
  • In coupling reactions, standard peptide reagents (EDC/HOBt, HATU, DIC/DMAP) are applicable. Protecting strategies may be required to avoid undesired reaction at the ureido N–H.
  • For analytical methods, LC–MS with aqueous mobile phases containing volatile buffers (e.g., ammonium formate) supports good ionization of polar ureido acids.

These are general/literature practices; adapt to your substrate and consult primary references.

Reaction Conditions

No item-specific reaction conditions are provided. The following are general starting points for transformations involving ureido–carboxylic acids; verify and optimize for your substrate.

• Amide coupling at the carboxyl terminus (general)

  • Solvent: DMF, DCM, or water/DMF mixtures; for greener options, EtOH/water can work with EDC.
  • Reagents: EDC·HCl (1.1–1.5 eq) with HOBt/HOAt or Oxyma; or HATU (1.1 eq) with DIPEA (2–3 eq).
  • Temperature/time: 0–25 °C, 1–16 h. Monitor by LC–MS/HPLC.

• Esterification (Steglich-type)

  • Solvent: DCM or THF.
  • Reagents: DCC (1.1 eq) and catalytic DMAP (0.1 eq) with ROH (excess).
  • Temperature: 0–25 °C; 2–12 h. Filter DCU byproduct, purify by chromatography or recrystallization.

• Ureido group manipulations (general)

  • Hydrolysis/deprotection: Aqueous acid or base at elevated temperature can cleave carbamoyl linkages; conditions must be tuned to avoid over-degradation (e.g., 1–2 M HCl, 60–80 °C; or 1–2 M NaOH, 40–60 °C). Confirm by LC–MS.
  • N-acylation: With acyl chlorides/anhydrides under basic conditions (e.g., DIPEA, pyridine) in DMF or DCM at 0–25 °C.

• Workup considerations

  • Exploit pH-switching: extract neutral/esterified products into EtOAc after acidification; recover acids by basification and back-extraction.
  • Due to high polarity, reversed-phase chromatography or ion-exchange may be advantageous for purification.

All parameters above are literature-style guidance, not specifications; adjust for scale and safety.

Safety and Handling

• GHS and hazard classification

  • Signal Word: Not specified for this item; refer to SDS.
  • H-Statements: Not specified for this item; refer to SDS.
  • GHS Classification and Pictograms: Not specified for this item; refer to SDS.

• Anticipated hazards (general for ureido–carboxylic acids)

  • Low volatility, low flammability solid; may cause eye/skin irritation or GI discomfort if ingested. Dust may irritate respiratory tract.
  • Not known as a strong sensitizer; avoid unnecessary exposure until SDS is reviewed.

• PPE and engineering controls

  • Wear lab coat, safety glasses, and appropriate disposable gloves (e.g., nitrile). Handle powders in a fume hood or with local exhaust to minimize dust.
  • Avoid inhalation of dust and contact with eyes and skin. Wash thoroughly after handling.

• Incompatibilities and stability (general)

  • Avoid strong oxidizers and strong bases/acids at elevated temperature that can promote hydrolysis or condensation of the ureido group.
  • Hygroscopic uptake is possible for polar acids; keep container tightly closed to prevent caking.

• First-aid overview (consult SDS for details)

  • Eyes: Rinse with water for several minutes; remove contact lenses; seek medical attention if irritation persists.
  • Skin: Wash with soap and water; remove contaminated clothing.
  • Inhalation: Move to fresh air; seek medical attention if symptoms occur.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical advice.

Defer to the product’s SDS for authoritative hazard information and emergency guidance.

Solvent Selection

Ureidovaleric acid is a highly polar, hydrogen-bonding bifunctional compound. Solvent choice is driven by the need to dissolve both the carboxylate and the ureido moieties.

• Polarity class and miscibility (general)

  • Polar protic media: Water and aqueous buffers are generally the most effective, especially at mildly basic pH (to form the carboxylate). Alcohols (MeOH/EtOH) may dissolve limited amounts.
  • Polar aprotic media: DMSO and DMF provide good solubilization for stock solutions when water is unsuitable; acetonitrile is typically less effective.
  • Nonpolar media: Hexanes/toluene are inappropriate due to poor solubility.

• Practical selection tips

  • For biochemical assays: Prepare concentrated stocks in water or aqueous buffer (pH 7.5–9) or in DMSO, then dilute into the working medium. Filter if particulates persist.
  • For synthetic steps (e.g., coupling/esterification): Use DMF, DMSO, NMP, or aqueous-organic biphasic systems with phase-transfer bases if necessary.
  • To crystallize/purify: Anti-solvent strategies (e.g., water/EtOH or water/acetone combinations) can be effective; adjust pH to reduce ionization before crystallization.

• Small comparison (general guidance)

  • Water (pH-adjusted): maximal solubility and green profile; may require buffering to control hydrolysis.
  • DMSO: excellent solvency; high boiling point can complicate removal.
  • DMF: strong solvency; consider toxicity and removal strategies.

Note: No item-specific solubility numbers are provided; verify solubility empirically under your conditions.

Storage and Reconstitution

• Storage conditions (from Product Data)

  • Store at room temperature. Keep container tightly closed in a dry, well-ventilated place.

• Shipping

  • Shipped In: Not specified for this item; refer to CoA/Spec Sheet.

• Stability considerations (general)

  • Protect from prolonged exposure to moisture to prevent caking and from elevated temperatures that may promote ureido condensation or hydrolysis.
  • For long-term storage, a desiccated environment and protection from light are prudent, although no light sensitivity is specified.

• Reconstitution and solution handling (general guidance)

  • Aqueous stocks: Dissolve in water or buffer; mild basification (e.g., to pH 7.5–9) can aid dissolution. Filter-sterilize if needed for analytical work.
  • Organic stocks: DMSO or DMF can be used when water is unsuitable. Prepare fresh or aliquot and store at 2–8 °C to limit hydrolysis; avoid repeated freeze–thaw cycles.
  • Working solutions: Use promptly. Assess stability by LC–MS/HPLC in your matrix, as item-specific solution stability data are not provided.

• Research Use Note

  • For research use only.

For definitive shelf-life and solution stability, consult the product’s CoA/Spec Sheet and SDS.

Structure and Identity

Ureidovaleric acid is a bifunctional, carbamoylated ω-amino–carboxylic acid (a ureido-substituted pentanoic acid) useful as a polar building block and metabolite standard.

• Item-specific identifiers (from Product Data)

  • SKU: U1035748
  • Product Name: Ureidovaleric acid
  • CAS: 55512-99-7
  • PubChem CID: 286268
  • InChIKey: 106080
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Structure description (general chemistry/literature)

  • Preferred IUPAC-style description: 5-(ureido)pentanoic acid; equivalently N-carbamoyl-5-aminovaleric acid.
  • Functional groups: terminal carboxylic acid (–CO2H) and an internal ureido (–NH–CO–NH2) moiety attached at C-5 relative to the acid terminus.
  • Connectivity in words: a five-carbon aliphatic chain bearing a carboxylic acid at one end and a secondary carbamoyl urea substituent on the terminal methylene at the opposite end (HOOC–(CH2)4–NH–CO–NH2).
  • Stereochemistry: achiral; no stereocenters.

• Calculated/literature identifiers (informational; not item specifications)

  • Typical molecular formula (literature): C6H12N2O3
  • Typical molecular weight (literature): ~160.17 g/mol
  • Typical SMILES (literature): NC(=O)NCCCC(=O)O

Notes

• The above “literature” values are provided for context and are not item-specific specifications. Always verify against the item’s CoA/Spec Sheet before use in regulated workflows.

Synthetic Utility

The combination of a terminal carboxylic acid and an internal ureido unit makes ureidovaleric acid a versatile synthon for nitrogen-rich scaffolds and polar conjugates.

• Functional group handles

  • Carboxyl group: amenable to esterification, amidation, Curtius/Schmidt-type activation (via suitable derivatives), and coupling into peptidomimetics.
  • Ureido moiety: can engage in H-bonding, serve as a masked diamine equivalent, or be selectively modified (e.g., N-acylation, alkylation under activation) while generally resisting many nucleophiles under mild conditions.

• Retrosynthetic value

  • Serves as an ω-amino acid equivalent where the terminal amine is present as a ureido carbamoyl; deprotection/hydrolysis strategies can regenerate primary amines or transform into urea-linked conjugates.

• Example synthetic directions (literature/general)

  • Convert to protected esters (e.g., methyl/benzyl esters) to enable non-aqueous transformations; later deprotect under standard conditions (saponification/hydrogenolysis).
  • Couple at the carboxylate with HATU/EDC to append the ureido-bearing side chain to peptides or small-molecule cores, leveraging the ureido group for additional H-bonding interactions in target recognition studies.
  • Cyclization strategies from ω-amino acid frameworks (after appropriate activation or deprotection) give access to lactams and 2-pyrrolidone derivatives.

These utilities are general; optimize protecting groups and conditions to avoid undesired reaction at ureido N–H sites.

Target Specificity

Not applicable — this product is a small-molecule chemical, not an affinity reagent or biological targeting agent. No antigen/epitope or species reactivity information applies.