Putreanine - ≥95% , CAS No.25887-39-2

CAS: 25887-39-2 Cat. No.: P1029747 Formula: C₇H₁₆N₂O₂ Peso molecolare: 160.210

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: C(CCNCCC(=O)O)CN
• IUPAC Name: 3-(4-aminobutylamino)propanoic acid
• InChIKey: BTSHXVLJDRJCMM-UHFFFAOYSA-N
• INCHI: 1S/C7H16N2O2/c8-4-1-2-5-9-6-3-7(10)11/h9H,1-6,8H2,(H,10,11)
• Peso molecolare: 160.210

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 Beta amino acids and derivatives

• 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
• Direct Parent: Beta amino acids and derivatives
• Alternative Parents: Amino acids Monocarboxylic acids and derivatives Dialkylamines Carboxylic acids Organopnictogen compounds Organic oxides Monoalkylamines Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Beta amino acid or derivatives - Amino acid - Carboxylic acid - Secondary aliphatic amine - Monocarboxylic acid or derivatives - Secondary amine - Carbonyl group - Primary amine - Organooxygen compound - Organonitrogen compound - Organic nitrogen compound - Primary aliphatic amine - Amine - Hydrocarbon derivative - Organic oxygen compound - Organic oxide - Organopnictogen compound - Aliphatic acyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as beta amino acids and derivatives. These are amino acids having a (-NH2) group attached to the beta carbon 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: 160.210 g/mol
• XLogP3: -3.200
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 160.121 Da
• Monoisotopic Mass: 160.121 Da
• Topological Polar Surface Area: 75.400 Ų
• Heavy Atom Count: 11
• Formal Charge: 0
• Complexity: 107.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• 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 validated or vendor-recommended application protocols are provided for this item beyond the general note: For research use only.

General guidance for handling highly polar amino alcohols (not item-specific):

• Preparation of stock solutions: if structure permits, prepare aqueous or aqueous-alcohol stocks (e.g., water, PBS, or ethanol/water) at known molarity; filter (0.22 µm) if used in biochemical assays.
• pH adjustment: dissolve the free base under slight acidification (e.g., dilute HCl) to form a soluble ammonium salt; neutralize as required in the workflow.
• Analytical QC: verify identity/purity by NMR (1H, 13C), HRMS, and, if chiral centers existed, chiral HPLC (not typically needed for linear amino alcohols without stereocenters). KF for water content when relevant.

Please consult the CoA/SDS for SKU-specific details such as exact solubility, salt form, and any stabilizers before establishing protocols.

Biological Roles

General biochemistry context (not specific to SKU P1029747):

• Origin: “Putreanine” is used in the literature to denote an amino alcohol generated in the catabolism of the polyamine putrescine. In several microbes and plants, putrescine is transaminated to 4‑aminobutanal, which can be further reduced to an amino alcohol (often described as putreanine) or oxidized to γ‑aminobutyric acid (GABA).
• Pathway linkages: Polyamine turnover intersects with nitrogen metabolism and stress responses. Amino alcohol intermediates may be transient metabolites or shuttled into pathways that form osmolytes or cell wall constituents.
• Chemical biology utility: Labeled putreanine analogs (e.g., 13C/15N) can be used to trace flux through polyamine degradation, and amino alcohol functionality enables conjugation to probes, resins, or fluorophores via either the amine or the alcohol.
• Physicochemical behavior: Protonation of the amine at physiological pH promotes aqueous solubility and potential uptake through polyamine transporters in some organisms; the hydroxyl group can participate in enzymatic transformations (e.g., phosphorylation, oxidation) in model systems.

Caveats:

• Exact metabolite identity and abundance depend strongly on species and growth conditions; some organisms may not accumulate a discrete “putreanine” pool.
• The above roles are literature-based background and are not product specifications. For experiments requiring defined stereochemistry, chain length, or salt state, verify the exact structure and purity of SKU P1029747 via CoA/SDS.

All uses are for research purposes only; no clinical or diagnostic claims are made.

Buffer Applications

This product is not typically used as a classical buffering agent. Primary aliphatic amino alcohols can exhibit limited buffering capacity around the pKa of their conjugate acid (literature pKa for simple primary aliphatic ammonium ions is commonly ~9–10), but they lack the well-defined, narrow buffering ranges and low UV background associated with standard buffers (e.g., Tris, HEPES).

If a temporary pH hold near alkaline conditions is needed in a synthetic or biochemical step, dedicated buffers are recommended. For reproducible pH control, select established systems:

• Tris (pKa 8.1 at 25 °C) for pH 7–9.
• CAPS (pKa 10.4) for pH 9.7–11.1.
• Bicine/CHES for pH 8–10 range.

For SKU P1029747, no buffer specifications, recipes, or validated buffer applications are provided. Refer to the CoA/SDS if any salt form or additional buffering-relevant data are supplied.

Green Alternatives

Context: Without confirmed structure and properties for SKU P1029747, specific substitution guidance must be conservative. The following are general considerations for amino alcohol reagents used as linkers or auxiliaries.

Potential greener choices (general):

• Bio-based amino alcohols (e.g., ethanolamine, serinol derivatives) can sometimes substitute as linkers where precise chain length is not critical, offering improved availability and established safety profiles.
• Use of water or bio‑ethanol as solvents when compatible with the chemistry can reduce reliance on dipolar aprotics (DMF, NMP). Employ water-tolerant coupling systems (e.g., EDC•HCl/NHS) where possible.
• Catalysis and protecting-group minimization: consider direct amidation protocols (e.g., catalytic boric acid or enzymatic acylations) to avoid stoichiometric activators and chlorinated reagents.

Tradeoffs to evaluate:

• Functionality spacing: replacing a specific amino alcohol with a shorter/longer homolog can alter biological or materials performance (binding distance, cationic density).
• Process mass intensity: greener solvents may require longer reaction times or give lower conversions, offsetting benefits.
• Purification: aqueous workups are greener but may complicate isolation of highly polar amino alcohol derivatives; ion-exchange resins can help recover product while minimizing solvent use.

Recommendation: Confirm the exact identity and role of SKU P1029747 in your workflow. Where feasible, benchmark greener solvents (water, ethanol, 2-MeTHF) and catalytic/solvent-free methods against your existing protocol, while maintaining the required performance specifications.

Pharmaceutical Uses

Item-specific regulatory/formulation status: Not specified for this item; refer to CoA/Spec Sheet. This product is supplied strictly for research use only.

General, non-clinical context for amino alcohols (literature; not item-specific):

• Role as intermediates: amino alcohols are common intermediates for synthesizing cationic lipids, ionizable headgroups, and prodrugs (via carbamate/amide linkages). Their bifunctionality enables modular assembly of delivery materials or excipient prototypes in medicinal chemistry workflows.
• Salt formation: conversion to pharmaceutically acceptable salts (e.g., hydrochloride, sulfate) can tune solubility and processability during early formulation screening; however, such forms must be explicitly specified for any particular lot.
• Analytical aspects: due to UV transparency above ~210–220 nm in many cases, detection in HPLC may require derivatization (e.g., with OPA or FMOC) or charged aerosol detection.

Caveats:

• No pharmacopeial monograph is implied or claimed for SKU P1029747.
• No therapeutic, diagnostic, or clinical claims are made. Any use in process development or excipient prototyping must remain within a research/lab context and comply with institutional and regulatory guidelines.

Physical Properties

Item-specific values

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
• Density, melting/boiling point, refractive index, UV cutoff, water content, residual solvents, peroxide content: Not specified for this item; refer to CoA/Spec Sheet.

Literature/general expectations for small aliphatic amino alcohols (not item specifications):

• State: often low-melting solids or low-viscosity liquids; frequently hygroscopic.
• Solubility: typically fully miscible with water and polar organic solvents (methanol, ethanol); limited solubility in nonpolar hydrocarbons.
• Acid–base: primary amines are basic (conjugate-acid pKa typically ~9–10 for aliphatic primary amines, literature); protonation greatly increases water solubility.
• Hydrogen bonding: both donor and acceptor capabilities; strong interactions with protic solvents.

Practical notes (general):

• Hygroscopicity and CO2 uptake are common for small aliphatic amines; containers should be kept tightly closed to prevent concentration drift or salt formation on exposure to air.
• Water content can influence reactivity in coupling or protection steps; Karl Fischer or loss-on-drying may be warranted when moisture-sensitive transformations are planned.

Caution: None of the above literature values are specifications for SKU P1029747. For experimental design, confirm exact physical constants and state for this product via the CoA/SDS.

Quality and Grades

Item-specific quality details

• Grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
• Stabilizers/inhibitors: Not specified for this item; refer to CoA/Spec Sheet.
• UV cutoff/low-UV suitability: Not specified for this item; refer to CoA/Spec Sheet.

Guidance on interpreting grades (general, not item-specific):

• Research grade: suitable for most synthetic/biochemical experiments; may not include full trace-metal analysis.
• Analytical/HPLC grade: tighter limits on nonvolatile residue and low UV background—preferred for detection-limited chromatography.
• Bio/biochemical grade: controlled bioburden/endotoxin; relevant for enzymology or cell-free systems (still research-use only).

Practical quality considerations for amino alcohols (general):

• Water content can drift due to hygroscopicity; check KF before moisture-sensitive steps.
• Amine value/titration can diagnose degradation (e.g., salt formation, oxidation to amides rarely under storage).
• If provided as a salt (e.g., hydrochloride), note the free-base content and neutralization protocol before use.

For SKU P1029747, consult the CoA for:

• Assay (%), residual solvents, water content, and any stabilizers.
• If applicable, titration method for assay (acidimetric vs. chromatographic) and trace-metal profile when relevant to catalysis or bioassays.

Reaction and Applications

Manufacturer-stated applications: None provided beyond “For research use only.”

Literature/general applications of putreanine-type amino alcohols (not item-specific):

• Bifunctional building block: primary amine and primary alcohol enable orthogonal derivatization (e.g., amide formation at N; ester/ether formation at O). Useful as a linker between carboxylates and activated halides.
• Polyamine pathway probes: amino alcohol analogs of putrescine can serve as biochemical tools to interrogate polyamine transport or catabolism in microbes and plants (enzyme substrate studies, isotope labeling).
• Surface/cationic headgroup installation: quaternization of the amine yields ammonium species for surfactants, lipidoids, or ion-exchange ligands; the alcohol enables tethering to polymers or silica.
• Protecting-group chemistry: N-Boc or N-Cbz protection allows selective O-functionalization; conversely, O‑silylation permits selective N‑acylation/alkylation.

Practical tips (general):

• Maintain anhydrous conditions for moisture-sensitive couplings (e.g., carbodiimide-mediated O-acylation, peptide-type couplings to form amide derivatives).
• Control protonation state: free-base form required for nucleophilic substitutions; acid salts increase stability/handling but reduce nucleophilicity.
• For selective functionalization, consider temporary masking (Boc/Cbz at N; TBDMS/TBDPS at O) and chemoselective activation (tosylates/mesylates at O for intramolecular cyclizations).

Note: The above are general literature uses for amino alcohols and may or may not apply to the exact form of SKU P1029747. Verify structure and salt state on the CoA before planning syntheses.

Reaction Conditions

The following are general, literature-based conditions for transforming small aliphatic amino alcohols and are not specifications for SKU P1029747.

• N‑Acylation (amide formation):

  • Solvent: DCM, DMF, or MeCN.
  • Reagents: acid chlorides/anhydrides with base (DIPEA, TEA) or EDC•HCl/HOBt for carboxylic acids.
  • Temperature: 0–25 °C typically; 1–16 h.
  • Notes: protect the alcohol if O‑acylation competes; monitor by LC/MS.

• Carbamate (urethane) formation:

  • Solvent: DCM, THF, MeCN.
  • Reagents: Boc2O (for N‑Boc) or CDI + alcohol component for O‑carbonate.
  • Temperature: 0–25 °C; 2–6 h.

• O‑Sulfonylation (to form leaving group):

  • Solvent: DCM or THF.
  • Reagents: MsCl/TsCl, base (TEA, pyridine), 0–25 °C.
  • Followed by intramolecular SN to cyclize (heating in DMF, 60–100 °C) as chain length permits.

• Reductive alkylation at N:

  • Solvent: MeOH/EtOH or MeCN.
  • Reagents: aldehyde/ketone + NaBH3CN or NaBH(OAc)3; pH-controlled (AcOH buffer).
  • Temperature: 0–25 °C; 2–12 h.

• Quaternization:

  • Solvent: MeCN, acetone, or neat.
  • Reagents: alkyl halide (e.g., MeI) at 25–60 °C; 2–24 h.

Workup/purification tips:

• Neutralize carefully and partition based on protonation state (acidify to move ammonium to aqueous; basify for free-base extraction).
• For highly polar products, consider ion-exchange resins or reverse-phase chromatography. Dry thoroughly to remove residual water that can impact downstream steps.

Safety and Handling

Item-specific hazard details

• GHS classification, signal word, hazard statements, and pictograms: Not specified for this item; refer to SDS.
• Storage conditions (from Product Data): Store at room temperature.

General safety information for small aliphatic amino alcohols (literature; not product-specific):

• Hazards: can be irritating to skin, eyes, and respiratory tract; liquid or concentrated solutions may cause burns upon prolonged contact depending on basicity.
• PPE: chemical-resistant gloves (e.g., nitrile), lab coat, splash goggles. Use in a fume hood to avoid inhalation of vapors/aerosols.
• Incompatibilities: strong oxidizers (risk of exotherm), acylating/alkylating agents (react vigorously), isocyanates, acid chlorides, and carbonyl-activating reagents; strong acids/bases can cause exothermic neutralization.
• First aid (overview; defer to SDS): rinse eyes/skin with water for ≥15 minutes; remove contaminated clothing; if inhaled, move to fresh air; if ingested, do not induce vomiting; seek medical attention in all cases of exposure.
• Spill response: absorb with inert material; avoid neutralizing spills with strong acids/bases without containment because of heat evolution; ventilate area.
• Fire safety: many amino alcohols are combustible liquids/solids; use CO2, dry chemical, or alcohol-resistant foam. Combustion may release nitrogen oxides.

Always consult the official SDS for SKU P1029747 for authoritative hazard classification, exposure limits, and emergency measures.

Solvent Selection

Item-specific solvent data: Not specified for this item; refer to CoA/Spec Sheet.

General guidance for small aliphatic amino alcohols (literature-based, not item specifications):

• Polarity: highly polar; typically miscible with water, methanol, ethanol; soluble in DMSO.
• Extraction/partitioning: exist partially/fully protonated near neutral pH; liquid–liquid extraction often requires basification to liberate the free base for organic partitioning (e.g., into EtOAc or MTBE). Conversely, acidify to transfer to aqueous phase as ammonium salt.
• Drying: aqueous solutions can be lyophilized or dried over mild desiccants; avoid strong dehydrating agents that form salts or esters.

When to choose versus alternatives:

• Use water or aqueous alcohols when handling protonated forms or for biochemistry workflows.
• Use polar aprotic solvents (DMF, DMSO, MeCN) for coupling/protection chemistry where hydrogen-bonding competition should be moderated.
• Avoid nonpolar solvents unless converted to less polar derivatives (e.g., carbamates, amides) or used as salts with phase-transfer.

Small comparison (general):

• Water: best for protonated forms; green and safe.
• MeOH/EtOH: good solvency; compatible with many derivatizations; flammable.
• DMSO/DMF: dissolve at high concentrations; facilitate coupling; consider workup and toxicity profiles.

Note: Confirm the exact salt state and solubility for SKU P1029747 on the CoA before final solvent selection.

Storage and Reconstitution

Item-specific storage (from Product Data):

• Storage conditions: Room temperature.
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.

General guidance for amino alcohol reagents (not item-specific):

• Container: store tightly sealed in chemically compatible bottles to minimize moisture and CO2 uptake; consider desiccant packs for long-term storage.
• Light/air sensitivity: most simple amino alcohols are air-stable; avoid prolonged exposure to strong light/heat to prevent discoloration or byproduct formation.
• Stability as salts: hydrochloride or other mineral-acid salts can enhance stability and handling but reduce nucleophilicity; liberate free base immediately before use if required.

Reconstitution (if supplied as a solid or viscous oil):

• Solvents: water, methanol, ethanol, or DMSO are commonly effective for amino alcohols. For this specific SKU, solubility is Not specified—determine empirically on a small scale or consult the CoA.
• Filtration: use 0.22 µm for sterile or particulate-sensitive workflows.
• Aliquoting: prepare single-use aliquots to avoid repeated exposure to ambient moisture.

Always defer to the product’s CoA/SDS for definitive guidance on storage limits, shelf life, and any reconstitution instructions specific to SKU P1029747.

Structure and Identity

Item-specific (from Product Data)

• Product name: Putreanine (SKU: P1029747)
• CAS: 25887-39-2
• InChIKey: 34076 (as provided; format appears non-standard — verify against CoA/SDS)
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.

Context and literature notes (clearly non-spec):

• In the biochemical literature, the term “putreanine” is commonly used to describe an amino alcohol derived from the polyamine putrescine via transamination/reduction (e.g., a 4‑aminobutanol scaffold). Exact structure and salt form can vary across sources. For CAS 25887-39-2, consult the supplier’s CoA/SDS to confirm the definitive structure and any counterions.
• Typical functional-group motif for putreanine-type compounds: a primary amine and a primary alcohol separated by a short aliphatic chain (amino alcohol). These confer bifunctional reactivity (nucleophilic N and O sites) and high hydrophilicity.

2D structural description (general for amino alcohols; literature-based):

• Linear aliphatic chain bearing a terminal hydroxyl group (–CH2OH) and a terminal primary amino group (–CH2NH2); no rings; no stereocenters.

Important: Do not use the above literature description as a specification for SKU P1029747. For this catalog item, definitive identifiers (exact structure, formula, MW, salt state) are Not specified and must be verified on the CoA/Spec Sheet.

Synthetic Utility

General synthetic value for putreanine-type amino alcohols (not item-specific):

• Functional handles: primary amine and primary alcohol provide orthogonal points of attachment. Typical transformations include:
  • N‑acylation (amides, carbamates, ureas) using acid chlorides/anhydrides or CDI/carbodiimide systems.
  • O‑acylation/alkylation (esters, ethers) after selective N protection (Boc, Cbz) or O‑silylation (TBDMS) for the complementary selectivity.
  • Intramolecular cyclizations after O‑sulfonylation (Ms/Ts) to form azacycles (e.g., morpholine, pyrrolidine derivatives) depending on chain length.
  • Quaternization to generate ammonium salts for phase-transfer catalysis or surfactant-like materials.
• Linker chemistry: serves as a spacer between carboxylates and electrophiles; the alcohol can be activated (e.g., as a carbonate) to couple with nucleophiles while preserving the amine (protected).
• Retrosynthetic flexibility: accessible derivatizations allow rapid entry to libraries of cationic or zwitterionic motifs for materials chemistry and chemical biology probes.

Practical considerations:

• Control chemoselectivity by protection: Boc on N generally survives O‑acylation; TBDMS on O survives many N‑acylations.
• Protonation state: conduct nucleophilic substitutions with the free base (adjust pH or liberate from the salt in situ with base); isolate derivatives as stable salts for storage.
• Purification: polar compounds benefit from ion-exchange chromatography or reverse-phase methods; derive to neutral carbamates/urethanes to enhance chromatographic behavior when needed.

Target Specificity

Not applicable. SKU P1029747 (Putreanine) is a small-molecule reagent and does not have antigen/epitope targets, clone designations, or species reactivity. No item-specific targeting information is provided in the Product Data.