Serinol-d , CAS No.2708287-37-8

CAS: 2708287-37-8 Cat. No.: S1450755 Fórmula: C₃H₄D₅NO₂ Peso molecular: 96.14

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Descripción general

Serinol-d 5 is the deuterium labeled Serino.

Specifications

Condiciones de almacenamiento de almacenamiento

Store at -20°C

Enviado en

Ice chest + Ice pads

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Nombres e identificadores

• Peso molecular: 96.14

Application Protocols

No vendor-validated biological assay protocols are provided for this item.

• General example (analytical, literature-style) for LC–MS internal standard:
  • Prepare a 1 mg/mL primary stock in 50:50 water–methanol. For minimal H/D exchange at OH/NH, prepare in dry MeCN or DMSO and dilute immediately before injection.
  • Spike calibration standards and QC samples at a fixed concentration (e.g., 50–200 ng/mL) across the calibration range of the unlabeled analyte.
  • Use reversed-phase LC with volatile buffers (e.g., 5–10 mM ammonium formate, pH 3–4). Monitor MRM transitions offset by the mass difference corresponding to the isotopic label.
  • Assess matrix effects by post-extraction addition; verify co-elution and parallel response factors.

These are illustrative guidelines only. For SKU S1450755, any tested applications, recommended dilutions, or controls are Not specified for this item; refer to CoA/Spec Sheet.

Biological Roles

Contextual (literature) note: Serinol (2-amino-1,3-propanediol) is an amino alcohol structurally related to backbones found in sphingoid bases and glycerol derivatives, though it is not itself a primary metabolite in most organisms.

• Potential research contexts (general):

  • Metabolic analog studies: serinol derivatives can serve as simplified analogs to probe enzymatic recognition of amino alcohol motifs in lipid-processing enzymes (e.g., kinases, acyltransferases) in vitro.
  • Labeling/trace studies: deuterated serinol can be used to assess incorporation, turnover, or exchange phenomena in biochemical systems containing amino alcohols, provided no H/D exchange occurs at the positions tracked.
  • Protein modification chemistry: as a nucleophilic scaffold, serinol can form carbamates/urethanes and be appended to biomolecules or polymers for conjugation experiments.

• Spectral/analytical utility:

  • Internal standard in targeted bioanalytical quantification of serinol or related analytes via LC–MS/MS; isotope dilution corrects for matrix effects and ion suppression.

Important limitations:

• No medical or clinical use is implied; material is intended for research use only (per product data).
• Exact biological behavior depends strongly on charge state, derivatization, and isotopic labeling pattern, which are Not specified for this item; refer to CoA/Spec Sheet for definitive details if needed for your assay design.

Buffer Applications

This product is not typically used as a primary buffering agent. While amino alcohols can exhibit buffering capacity around the pKa of the conjugate acid of the amine, serinol is generally employed as a building block or analytical standard rather than a buffer.

• General notes (literature):

  • The protonated amine in amino alcohols often has a pKa in the ~9–10 range, conferring limited buffering capacity near basic pH. However, dedicated buffers (e.g., Tris, HEPES, AMPD) are preferred for reproducibility and well-characterized temperature coefficients.
  • When used in biochemical assays, the presence of multiple hydrogen-bond donors/acceptors can influence protein interactions; this is usually avoided for buffer selection to minimize confounding effects.

• Practical advice:

  • If a buffer with amino alcohol character is desired, choose established systems (e.g., Tris, Bis–Tris, AMPD) with known Good’s buffer properties and published recipes.
  • For LC–MS sample prep using this material as an internal standard, volatile buffers (ammonium formate/acetate, pH ~3–6) are commonly used; avoid strong bases/acids if preservation of exchangeable deuterium is required.

Conclusion: For pH control, select a dedicated buffer. Use Serinol-d primarily as an isotopic standard or synthetic handle.

Green Alternatives

Green chemistry considerations for handling and transforming amino-diols and their deuterated analogs focus on solvent choice, protection strategies, and minimizing hazardous reagents.

• Solvent choices (general):

  • Prefer water/ethanol for benign processing when isotopic integrity at OH/NH is not required. If exchange must be avoided, use lower-toxicity aprotic solvents such as dimethyl carbonate (DMC) or propylene carbonate where compatible.
  • Avoid chlorinated solvents when possible; replace DCM with ethyl acetate, 2-MeTHF, or CPME for extractions and some protection steps.

• Reagent alternatives:

  • Carbonate formation: use organic carbonates (e.g., triphosgene alternatives such as CDI or green carbonate donors) instead of phosgene-derived reagents.
  • Oxidations: prefer TEMPO/bleach or oxygen-mediated catalytic systems over chromium(VI) oxidants; Swern/DMP are effective but consider waste impact.

• Energy/resource efficiency:

  • Conduct protection/derivatization under solvent-minimized or solvent-free conditions when practicable (e.g., ball milling silylations or acylations) to reduce waste.
  • Employ continuous-flow microreactors for hazardous acylations, enabling better heat/mass transfer and reduced solvent volumes.

• Comparison (general, literature):

  • DCM vs 2-MeTHF: 2-MeTHF offers lower toxicity and is bio-based; however, its water content and peroxide formation risk must be managed; polarity differences can affect protection selectivity.
  • DMF/DMSO vs propylene carbonate: propylene carbonate is greener but more viscous and may complicate workup; compatibility with carbodiimide couplings can be limited.

Note: Select green alternatives consistent with maintaining deuterium labeling for SKU S1450755, particularly avoiding unnecessary protic media if exchangeable D must be preserved.

Pharmaceutical Uses

No therapeutic claims are made. For research and development contexts only.

• Typical roles for deuterated small molecules in pharma R&D (general):

  • Internal standards for bioanalytical LC–MS quantitation of amino alcohols in DMPK and biomarker studies; isotopic co-elution improves quantitative accuracy.
  • Reference materials in method validation (specificity, accuracy, precision, linearity, stability) per ICH and FDA bioanalytical guidance.
  • Chemical intermediate/building block to prepare labeled derivatives for in vitro mechanistic assays (e.g., metabolism, covalent tagging, PROTAC-like linker exploration when derivatized).

• Excipients/formulation: Amino alcohols can act as co-solvents or pH-modifying agents in some formulations; however, deuterated variants are rarely used as excipients due to cost and analytical purpose. Any such use would require appropriate pharmacopeial qualification, which is Not specified for this item; refer to CoA/Spec Sheet.

• Compliance/documentation:

  • For regulated workflows, ensure traceability: batch-specific CoA with isotopic enrichment, impurity profile, and storage/stability data; retain SDS and shipping records (temperature logs if cold-chain critical).

Note: SKU S1450755 is designated For research use only (per product data) and is not intended for human or veterinary use.

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.

• Literature/general values for the non-deuterated parent (serinol; for context only):

  • Typical melting point (literature): ~89–93 °C for the free base; forms hygroscopic solids and various salt forms depending on protonation.
  • Solubility: highly soluble in water and polar protic solvents (literature); miscible with methanol/ethanol; limited solubility in nonpolar solvents.
  • pKa (conjugate acid of the amine): commonly reported in the ~9–10 range (literature), influenced by temperature/ionic strength.
  • LogP: strongly negative to near 0 (very hydrophilic; literature estimates), reflecting multiple hydrogen-bond donors/acceptors.

• Isotopic effects (general): Deuteration minimally affects bulk physical properties (mp/bp/solubility) but can slightly shift vibrational spectra (IR, NMR) and, rarely, phase behavior. Any exact property shift depends on labeling extent/positions.

• Spectroscopy (general guidance):

  • 1H NMR signals corresponding to deuterated positions are attenuated/absent; 2H NMR can confirm incorporation.
  • IR C–D stretches appear near 2100–2200 cm⁻¹ (literature), distinguishable from C–H stretches (~2850–3000 cm⁻¹).

Important: Do not treat the above as specifications. For SKU S1450755, definitive physical data are Not specified for this item; refer to CoA/Spec Sheet.

Quality and Grades

• Item-specific quality information

  • Grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
  • Stabilizers/additives: Not specified for this item; refer to CoA/Spec Sheet.

• Guidance for deuterated small molecules (general):

  • Isotopic enrichment: For quantitative applications (e.g., LC–MS internal standards), enrichment level and labeling homogeneity are critical. Confirm %D at each labeled position on the CoA; minor protium back-exchange can occur on heteroatom-bound hydrogens (OH/NH) and should be disclosed or stabilized by derivatization where relevant.
  • Chemical purity vs. isotopic purity: Distinct metrics. Chemical purity refers to organic impurities/inorganic residues; isotopic purity refers to the ratio of deuterated to non-deuterated isotopologues. Both should be evaluated for your method’s tolerance.
  • Chromatography grade considerations: For LC–MS workflows, low UV background and minimal nonvolatile residues are desirable; if not specified as LC–MS grade, pre-cleanup or additional purification may be warranted for trace analysis.

• Suggested verification steps on receipt (best practices):

  • Record 1H/2H NMR to confirm labeling pattern and check for exchangeable sites (run in dry, nonprotic solvents if assessing C–D incorporation).
  • Acquire HRMS to verify exact mass consistent with the stated isotopologue.
  • If using as a reference standard, establish a calibration curve with gravimetrically prepared solutions and assess matrix effects.

Please consult the CoA/Spec Sheet for the exact grade, purity, and isotopic enrichment of SKU S1450755.

Reaction and Applications

Deuterated serinol is primarily useful as an isotopically labeled reagent/standard, while the amino-diol functionality enables diverse derivatizations.

• Applications (general/literature):

  • Stable-isotope internal standard for quantitative LC–MS/MS of serinol or related amino alcohols; improves accuracy via isotope-dilution calibration.
  • Mechanistic probes: tracing hydrogen transfer, exchange, or kinetic isotope effects in transformations involving amino alcohols, imine/oxazolidine formation, and oxidation.
  • Derivatization handle: 1,3-diol permits selective mono-/di-acylation, carbonate/oxazolidinone formation; the amine can be protected (Boc, Cbz, Fmoc) to control chemoselectivity.

• Representative chemistries (general):

  • Protection: Boc protection with Boc2O/TEA in DCM or DMF; Fmoc with Fmoc-Cl/Na2CO3 aq-organic biphasic; Cbz with Cbz-Cl.
  • Diol functionalization: formation of cyclic carbonates (e.g., with phosgene equivalents or CDI); selective silylation (TBDMS-Cl, imidazole) for regioselective transformations.
  • Oxazolidine formation: condensation with aldehydes/ketones under Dean–Stark or molecular sieves; useful for temporary protection and stereocontrol in certain syntheses.
  • Oxidation: TEMPO/bleach or Dess–Martin for alcohol oxidation (with appropriate amine protection); note potential isotope scrambling only at exchangeable sites.

• Practical tips:

  • Minimize exposure to protic media when preservation of D at exchangeable positions (OH/NH) is critical. Carbon-bound deuterium is typically robust under neutral conditions.
  • For MS workflows, match the analyte’s derivatization state (e.g., dansylation, carbamate formation) to ensure co-elution and similar ionization efficiency.

All examples above are general guidance; tailor to the specific isotopic pattern of SKU S1450755.

Reaction Conditions

The following are general literature-style conditions for transformations of amino-diols like serinol; optimize for your substrate and labeling pattern.

• Amine protection (Boc):

  • Typical: Boc2O (1.1–1.5 eq), TEA or NaHCO3, DCM or MeCN, 0–25 °C, 1–4 h. Monitor by TLC/LC–MS. Work up by aqueous quench and extract.

• Selective silylation of primary OH:

  • TBDMS-Cl (1.1–1.5 eq), imidazole (2 eq), DMF, 0–25 °C, 2–6 h. Secondary OH remains largely unprotected under kinetic conditions; adjust stoichiometry for di-silylation if needed.

• Oxazolidine formation (temporary protection):

  • Aldehyde (1–1.5 eq) with catalytic p-TsOH, toluene, Dean–Stark or 3 Å molecular sieves, reflux 2–6 h; hydrolyze with dilute aq. acid at rt.

• Carbonate formation (diol to cyclic carbonate):

  • Using triphosgene or CDI equivalents in DCM/MeCN with base (Et3N, DBU), 0–25 °C. Safer alternatives include organic carbonate donors under catalytic conditions.

• Oxidation of secondary alcohol (with protected amine):

  • TEMPO (5–10 mol%), NaOCl (1.5 eq), pH 8–9 buffer, 0–5 °C to rt; or Dess–Martin periodinane in DCM, 0–25 °C. Avoid protic acidic media if preserving exchangeable D.

• LC–MS internal standard use:

  • Prepare stock at 0.5–1.0 mg/mL in water:MeOH (1:1) or MeCN:water with 0.1% FA; store aliquots at −20 °C. Validate stability and H/D retention by periodic re-analysis.

Note: Conditions are generic; for SKU S1450755, item-specific stability/reactivity data are Not specified for this item; refer to CoA/Spec Sheet.

Safety and Handling

• Authoritative source: Always consult the product’s SDS for definitive hazard, first-aid, and disposal guidance.

• Item-specific hazard data

  • Signal word: Not specified for this item; refer to SDS.
  • H-statements: Not specified for this item; refer to SDS.
  • GHS classification/pictograms: Not specified for this item; refer to SDS.

• General safety profile for amino-diols (literature/good practice):

  • Hazards: May cause skin/eye irritation; dust or aerosols can irritate the respiratory tract. Amino alcohols can be corrosive at high concentrations or elevated temperatures. Avoid inhalation and prolonged contact.
  • PPE: lab coat, safety glasses or chemical splash goggles, and appropriate chemically resistant gloves (e.g., nitrile). Use in a fume hood when weighing or when heating/handling volatile forms or solutions that could aerosolize.
  • Incompatibilities: Strong oxidizers; acyl halides/anhydrides (vigorous acylation); isocyanates; strong acids/bases may cause exothermic neutralization/condensation. For solid amino alcohols, avoid contact with reactive carbonyl compounds unless intended (can form imines/oxazolidines upon dehydration).
  • First aid (overview): eye/skin contact—rinse with water for ≥15 minutes; remove contaminated clothing. Inhalation—move to fresh air; seek medical attention if symptoms persist. Ingestion—rinse mouth; do not induce vomiting; seek medical advice.
  • Fire safety: Combustible organic solid; use CO2, dry chemical, or foam. Thermal decomposition may release nitrogen oxides and carbon oxides.

• Waste disposal: Collect aqueous/organic solutions in appropriate organic waste streams per institutional and local regulations.

Storage per product data: Store at −20 °C. Shipments are sent in an ice chest with ice pads to maintain low temperature.

Solvent Selection

Serinol derivatives are highly polar, hydrogen-bonding amino-diols. Solvent strategy largely depends on whether the amine is protected and on intended application.

• General polarity/miscibility (literature):

  • Highly soluble in water and polar protic solvents (methanol, ethanol). Solubility in DMSO is typically excellent; DMF also suitable for coupling protocols.
  • Poorly soluble in nonpolar solvents unless transformed into less polar derivatives (e.g., protected amine and/or acylated diols).

• Choosing a solvent (use-case driven):

  • Analytical/internal standard (LC–MS): Prepare stock in water, 50:50 water–methanol, or water–acetonitrile with 0.1% formic acid/base as required by the method. Avoid protic solvents if you must prevent H/D exchange at OH/NH.
  • Protection/coupling chemistry: Dry DMF, DCM/DMF mixtures, or MeCN are common, often with amine protection (Boc/Fmoc) before selective diol derivatization.
  • Crystallization: Zwitterionic amino alcohols often crystallize from alcohol–ether or alcohol–ester mixtures; salts (e.g., hydrochloride) may require aqueous alcohol systems.

• Comparison notes (general):

  • Water vs MeOH: water maximizes solubility but promotes H/D exchange at OH/NH; dry MeOH is convenient but may still exchange. For isotopic integrity at carbon-bound D, exchange is negligible; at OH/NH, consider using dry aprotic solvents (DMSO-d6, DMF) for handling/analysis.

Always confirm actual solubility and exchange behavior for SKU S1450755 experimentally, as item-specific data are not provided.

Storage and Reconstitution

• Storage (item-specific): Store at −20 °C (per product data). Maintain dry, tightly closed conditions to limit moisture uptake and potential H/D exchange at OH/NH sites.

• Shipping (item-specific): Shipped in an ice chest with ice pads to preserve low temperature.

• Reconstitution (general guidance):

  • For analytical stocks, dissolve in a suitable solvent such as water, methanol, acetonitrile, or DMSO depending on the intended application. If preservation of exchangeable deuterium is critical, favor dry aprotic solvents (e.g., anhydrous MeCN or DMSO) and minimize exposure to protic media.
  • Prepare concentrated stocks (e.g., 1–10 mg/mL), filter if necessary (0.22 µm PTFE for organic solutions), and aliquot to minimize freeze–thaw cycles.

• Stability considerations (general):

  • Store aliquots at −20 °C, protected from light and moisture. Allow vials to equilibrate to room temperature in a desiccator before opening to prevent condensation.
  • Monitor isotopic integrity over time by LC–MS or 1H/2H NMR, especially if stored in protic solvents.

• Shelf life: Not specified for this item; refer to CoA/Spec Sheet.

• Research use note: For research use only (per product data).

Structure and Identity

Brief overview: Serinol-d denotes a deuterium-labeled serinol (2-amino-1,3-propanediol) isotopologue. Exact labeling pattern (position and %D) is not specified in the item data.

• Item-specific identifiers

  • CAS: 2708287-37-8 (as provided)
  • Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.

• Structural features (general, literature):

  • Parent scaffold: serinol = HO–CH2–CH(OH)–CH2–NH2 (an amino alcohol bearing a 1,3-diol and a primary amine).
  • Functional groups: primary alcohol (C1), secondary alcohol (C2), primary amine (C3) on a propane backbone.
  • Protonation: typically exists as a zwitterion or protonated amine under neutral to mildly acidic conditions due to the basic amine and hydrogen-bonding diols.
  • Isotopic labeling: the suffix “-d” indicates replacement of one or more hydrogens by deuterium; without a specification (e.g., -d2, -d4, position-specific), the exact isotopologue cannot be inferred.

• 2D description (general): a three-carbon chain with hydroxyls at C1 and C2; the terminal carbon bears a primary amine. Deuterium atoms, when present, substitute for specific hydrogens on carbon and/or heteroatom-bound positions depending on the labeled synthesis route.

Note: For precise isotopic enrichment and structural identifiers of SKU S1450755, consult the product CoA/Specification Sheet.

Synthetic Utility

Serinol-d combines a primary amine with a 1,3-diol, offering rich chemoselectivity; deuterium labeling adds value for mechanistic and analytical studies.

• Functional group reactivity (general):

  • Amine: acylation (amides, carbamates), sulfonylation (sulfonamides), alkylation; requires protection to direct selectivity.
  • 1,3-Diol: selective mono-/di-protection (silyl, acyl, carbonate); intramolecular cyclization to oxazolidines/oxazolidinones with carbonyl reagents.
  • Oxidation/Reduction: alcohol oxidation to carbonyls (with amine protection); reductive amination on derived carbonyls expands diversity.

• Strategic uses:

  • Chiral auxiliaries/ligand scaffolds: after further functionalization, serinol frameworks appear in oxazoline/oxazolidine ligands.
  • Polymer chemistry: diol enables incorporation into polycarbonates/polyurethanes; deuteration can facilitate spectroscopic tracking within materials.
  • Isotope mapping: position-specific D permits KIE studies and mapping of hydrogen transfers in catalytic cycles.

• Protecting group logic:

  • Protect amine first (Boc/Fmoc/Cbz) to allow diol manipulation without undesired acylation; regioselective protection of the primary vs secondary OH via sterics or by using silyl groups of differential lability (TBDMS vs TMS).
  • Temporary formation of oxazolidines with aldehydes affords selective transformation at C1 or C2, later hydrolyzed under mild acid.

• Caution for isotopes:

  • Avoid conditions that scramble deuterium at exchangeable positions (strong acids/bases, prolonged protic media, metal-catalyzed H/D exchange) if isotopic integrity is essential.

Target Specificity

Not applicable. This product is a small-molecule reagent (deuterated serinol), not an antibody or affinity reagent. No antigen/epitope or species reactivity applies.