D-Talitol-1-C , CAS No.D1452511

CAS: D1452511 Cat. No.: D1452511 Summenformel: C₅₁₃CH₁₄O₆ Molekulargewicht: 183.16

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Übersicht

D-Talitol-1- 13 C is the 13 C labeled D-Talitol.

Specifications

Storage

Store at -20°C

Verschickt in

Ice chest + Ice pads

Dieses Produkt erfordert Kühlkettenversand. Grundversand und andere Economy-Optionen sind nicht verfügbar.

Namen und Kennungen

• Molekulargewicht: 183.16

Application Protocols

Not applicable in the sense of assay‑validated immunotechniques.

• No tested applications (e.g., WB, IHC, IF, FC) or recommended dilutions are provided for this small‑molecule reagent.

General laboratory usage examples (literature/general)

• Preparation of stock solutions: Dissolve in ultrapure water to desired concentration (e.g., 0.5–2.0 M for osmolyte studies). Filter sterilize (0.22 µm) if using in biological assays. Record exact concentration gravimetrically due to high viscosity at elevated concentrations.
• Derivatization for analysis: For GC‑MS quantitation, prepare per‑O‑TMS derivatives using BSTFA/TMCS as per standard carbohydrate protocols; include an internal standard alditol of distinct retention time.
• HPAEC‑PAD: Use a CarboPac column with NaOH/NaOAc gradients; inject standards spanning anticipated concentration range to establish response factors.

Note

• These are general procedures for hexitol polyols and are not validated for this specific SKU. Optimize conditions for your system and consult method‑specific literature.

Biological Roles

General biochemistry (literature/general; not product‑specific, not medical)

• Class: Sugar alcohol (alditol). While sorbitol and mannitol are prominent polyols in biology, D‑talitol is a less common diastereomer but shares physicochemical properties (high hydrophilicity, osmotic activity).
• Metabolic context: In the polyol pathway, aldoses are reduced to alditols by aldose reductases; the reverse oxidation by polyol dehydrogenases is stereoselective and organism‑dependent. Specific catabolism of D‑talitol may occur in select microbes with corresponding dehydrogenases, yielding D‑talose or downstream metabolites via oxidation/isomerization.
• Osmoregulation: Polyols act as compatible solutes/osmoprotectants in various organisms, stabilizing proteins and membranes by preferential exclusion and water-structuring effects.
• Macromolecular interactions: Multiple hydroxyls participate in dense hydrogen‑bond networks with proteins and nucleic acids, often stabilizing folded states and reducing aggregation.
• Analytical use: In labeled form (if present; not specified here), position‑specific 13C/14C alditols are used to trace carbon flow in carbohydrate metabolism, to probe enzyme mechanisms, and to calibrate NMR/MS responses.

Caveats

• Biological activities and uptake strongly depend on transporter specificity and enzyme recognition for a given stereoisomer. Do not generalize data from sorbitol/mannitol directly to D‑talitol without experimental confirmation.
• All uses are for research and laboratory investigations only; not intended for food, feed, or clinical applications.

Buffer Applications

Applicability

• D‑Talitol‑1‑C is not a buffering agent. However, as a neutral polyol it can be incorporated into aqueous buffers as an osmolyte or protein‑stabilizing cosolute.

Practical guidance (literature/general)

• Concentration ranges: 0.1–1.0 M are typical for osmotic stress studies; 1–10% w/v commonly used to enhance protein stability during storage. Verify solubility and viscosity constraints at your target temperature.
• Compatibility: Generally compatible with common buffers (phosphate, Tris, HEPES) across pH 6–8. Avoid strong oxidants in the buffer. Presence of borate will complex with vicinal diols and can alter effective free concentration.
• Filtration/sterilization: Prepare solutions in ultrapure water, adjust buffer components, then sterile filter (0.22 µm). Polyols are heat stable but may caramelize or dehydrate at elevated temperatures in the dry state; solution autoclaving is typically acceptable if needed, but confirm stability for your system.
• Analytical considerations: High refractive index and conductivity impacts may influence certain detectors or electrophoretic separations; include appropriate blanks.

Notes

• Item‑specific buffer recipes and validated concentrations are not provided. Optimize empirically for your target biomolecule and consult the CoA/SDS for any constraints relevant to this SKU.

Green Alternatives

Context

• D‑Talitol‑1‑C is a substrate/reagent rather than a process solvent. Green‑chemistry considerations mainly pertain to solvent choice and protection strategies during its derivatization.

Greener choices for processing polyols (literature/general)

• Solvent selection: Favor water or water/ethanol systems where feasible. Replace DMF/DMSO with glycerol, ethylene glycol, or deep eutectic solvents (DES) for certain transformations (e.g., acetalizations, biocatalysis), acknowledging viscosity and workup tradeoffs.
• Protection chemistry: Use acetone (low toxicity, recyclable) over chlorinated solvents for acetonide formation; catalytic acids in solvent‑free or solvent‑reduced protocols are reported.
• Oxidations: Prefer catalytic TEMPO/bleach in water or electrochemical oxidations over stoichiometric chromium or manganese reagents. Oxygen/air with alcohol dehydrogenase catalysts affords benign byproducts.
• Workup/waste: Employ aqueous biphasic separations and minimize derivatization steps via site‑selective catalysis to reduce solvent/waste footprint.

Comparison (typical options)

• Aqueous media: Greenest option; excellent compatibility with polyols; may need salting‑out or membrane techniques for isolation.
• Alcohols (EtOH): Renewable feedstock; good solvency; flammable.
• Dipolar aprotics (DMF/DMSO): High solvency but poor EHS profiles; consider minimizing use or replacing with safer alternatives.

Note

• No item‑specific EHS metrics are provided. Apply institutional green‑chemistry guidelines (e.g., CHEM21, PMI metrics) to your chosen route.

Pharmaceutical Uses

Scope

• No pharmacopeial grade, compendial status, or excipient designation is specified for this item. The content below reflects general, nonclinical roles of polyols in formulation science.

General formulation roles of hexitol polyols (literature/general)

• Stabilizers/tonicity agents: Sugar alcohols are widely used to adjust osmolality and stabilize proteins or peptides during lyophilization and liquid storage via preferential hydration.
• Bulking agents/cryoprotectants: In lyophilized cakes, polyols provide matrix structure and protect against freeze–thaw stress; mannitol is archetypal, while other hexitols can exhibit different crystallization tendencies.
• Taste masking/sweetness: Polyols provide nonreducing sweetness—relevant for oral solid/liquid prototypes (research only), though D‑talitol’s sensory profile is not widely documented relative to sorbitol/mannitol.
• Compatibility: Nonreducing nature reduces Maillard reactions compared with reducing sugars; however, residual carbonyl impurities can still react with amines—quality control is essential.

Caveats

• This SKU is designated for research use only; not intended for human or veterinary use, APIs, or GMP manufacture.
• If pharmaceutical development is envisioned, verify grade, residual solvents, metals, endotoxin/bioburden, and polymorphism/solid‑state behavior—none are specified for this item.

Physical Properties

Item-specific specifications

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Any numeric specifications (mp, bp, density, water content, metals, UV cutoff): Not specified for this item; refer to CoA/Spec Sheet.

Literature/general properties for D-talitol and related hexitols (for guidance only; not product specs)

• Phase/form: Typically a white, crystalline or microcrystalline solid; many hexitols are hygroscopic to mildly hygroscopic.
• Melting point: Polyols of the hexitol family commonly exhibit high melting points (often >140 °C), some with decomposition on melting (literature; exact value for D-talitol depends on polymorph and hydration).
• Boiling point: Not practically observed at ambient pressure due to decomposition; nonvolatile solid (literature).
• Solubility: Very high in water; increasing solubility in polar protic solvents (methanol, ethanol) and polar aprotic solvents capable of hydrogen bonding (DMSO, DMF). Poorly soluble in nonpolar hydrocarbons and chlorinated solvents (literature).
• LogP: Strongly negative/very hydrophilic due to six hydroxyl groups (literature/estimated behavior).
• pKa: Multiple alcohol OH groups with typical pKa ~14–16 (very weakly acidic; literature general for aliphatic alcohols).
• Refractive index: Not applicable to solids; solutions follow typical additive behavior (literature).
• Hygroscopicity: Many hexitols can absorb moisture; handle quickly in ambient air if accurate masses are critical (literature practical note).

Notes

• Use these literature descriptors for planning only. For exact numerical values and acceptance criteria for this SKU, consult the item’s 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.

Interpretation and guidance (general)

• Polyols intended for biochemical or isotopic studies are often offered in research grade, high-purity (>95–98%), or specialized grades (e.g., isotopically enriched at a defined carbon). The product name “D‑Talitol‑1‑C” may suggest position‑specific carbon labeling in some contexts; however, no isotopic information is specified for this item. Verify any labeling (e.g., 1‑13C) on the CoA before use in tracer experiments.
• Analytical expectations: QA typically includes identity by 1H/13C NMR, purity by qNMR or HPLC, water by KF, and residual solvent limits. For chiral polyols, optical rotation or chiral HPLC may be used to confirm D‑configuration (general practice; not product‑specific).
• UV background: Polyols have minimal UV absorbance above ~210 nm; if HPLC detection requires UV, derivatization may be necessary. HPAEC‑PAD or RI detectors are typical for carbohydrates.
• Metals and inorganic salts: If catalytic or enzymatic assays are sensitive to trace metals or anions, consult the CoA for elemental/ionic impurities. Do not assume specifications in the absence of documentation.

Recommendations

• For quantitative or regulatory‑sensitive work, request a current CoA/Spec Sheet defining identity tests, assay, water content, and impurity profiles for SKU D1452511.

Reaction and Applications

General research applications for D-talitol and related hexitols (literature/general)

• Carbohydrate chemistry platform: D‑Talitol serves as a stereochemically defined hexitol for constructing chiral building blocks. Selective protection (e.g., formation of 1,2‑ or 1,3‑acetonides; cyclic boronate esters) allows differentiation of vicinal diols.
• Oxidation/re-oxidation sequences: TEMPO/bleach or catalytic nitroxyl oxidations can convert terminal primary alcohols to aldehydes/acids; periodic oxidation (NaIO4) cleaves 1,2‑diols to carbonyl fragments for degradation mapping.
• Ester/ether derivatization: Formation of sulfonates (tosylates/mesylates) enables substitution or intramolecular cyclizations to cyclic ethers. Mitsunobu conditions can invert configuration at secondary alcohol positions to access other diastereomers.
• Complexation and sensing: Reversible boronic acid/diol complexation underpins affinity separations and sensor development; binding strength reflects diol geometry and can be probed with talitol isomers.
• Analytical standards: Useful as a reference material for chromatography of sugar alcohols (e.g., HPAEC‑PAD, GC after silylation) or for NMR chemical shift libraries.
• Potential isotopic applications: If isotopically labeled at C1 (to be confirmed on CoA), the compound can serve in carbon‑flux tracing or mechanistic studies. This is a general note—no isotopic enrichment is specified for this SKU.

Practical tips

• Water removal is key during acetalization; employ 3 Å molecular sieves and catalytic acid (e.g., p‑TsOH) in acetone.
• For selective oxidations, protect non-target diols to avoid over‑oxidation; monitor by TLC (borate‑impregnated plates) or LC with RI/PAD detection.
• Polyols can foam and char upon overheating; use oil baths with accurate control for any thermal steps.

Reaction Conditions

Typical literature conditions for transformations of hexitol polyols (not product‑specific)

• Acetonide protection: D‑Talitol + acetone (or 2,2‑dimethoxypropane), catalytic p‑TsOH or CSA, room temperature to reflux; drive equilibrium by water removal (molecular sieves). Reaction times: 2–24 h depending on selectivity desired.
• Benzylidene acetal formation: Benzaldehyde dimethyl acetal, catalytic acid in DMF or toluene; 0–25 °C; affords 4,6‑ or 3,4‑selective protection depending on conditions.
• Periodate cleavage: NaIO4 (1–2 eq per vic‑diol) in aqueous buffer (pH 4–6), 0–25 °C, 0.5–4 h; monitor by iodate formation or LC. Cleaves 1,2‑diols to aldehydes/ketones.
• Selective oxidation: TEMPO (1–5 mol%), NaOCl (pH 9–10, NaHCO3/Na2CO3 buffer), 0–10 °C for primary alcohols; quench with Na2S2O3. Alternatively, PDC/PCC in dichloromethane (less green), or electrochemical methods in water.
• Tosylation/mesylation: p‑TsCl (1.1–2.0 eq/OH to be activated), pyridine or Et3N, 0 °C to rt, 1–16 h; for mesylates, MsCl/Et3N, CH2Cl2, 0–5 °C.
• Mitsunobu inversion: DIAD/DEAD (1.1–1.5 eq), PPh3 (1.2–1.8 eq), carboxylic acid nucleophile, THF or toluene, 0 °C to rt; protect other OH groups to control chemoselectivity.
• Silylation/acetylation (analytical derivatization): BSTFA + 1% TMCS, 60–70 °C, 30–60 min (GC‑MS); or Ac2O/pyridine, rt to 50 °C, 1–4 h for per‑O‑acetates.

Yields and selectivity

• Highly substrate‑ and condition‑dependent; protection step yields typically 60–90% for favored diol pairs; oxidative conversions of primary OH to aldehydes often >80% under TEMPO/NaOCl.

Notes

• Rigorous drying and controlled addition are important due to extensive hydrogen bonding and water carryover.
• For stereochemical integrity, avoid conditions that promote 1,2‑shifts or pinacol rearrangements unless intended.

Safety and Handling

Item-specific hazard information (from Product Data)

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

General safety profile (literature/general for sugar alcohols; not a substitute for SDS)

• Expected hazards: Low acute toxicity profile typical of carbohydrate polyols. Dust may cause mechanical eye/respiratory irritation. Combustible dust hazard is possible if finely divided material becomes airborne in sufficient concentration.
• Incompatibilities: Strong oxidizers (can promote exothermic oxidation); strong dehydrating agents; avoid contact with reactive acid chlorides/anhydrides unless intended for derivatization. Thermal decomposition may occur if overheated.
• Peroxide formation: Not applicable (no ether functionality).

Personal protective equipment (PPE)

• Recommended: Lab coat, safety glasses or splash goggles, and appropriate gloves (e.g., nitrile). Use a dust mask/respirator if generating aerosols or fine dust.

Handling and hygiene

• Minimize dust generation; weigh in a draft-free area. For moisture-sensitive work, handle quickly and re-seal under dry conditions.
• Avoid ingestion and inhalation. Wash hands thoroughly after handling.

First aid (overview; follow SDS/site SOPs)

• Inhalation: Move to fresh air; seek medical attention if symptoms persist.
• Eye contact: Rinse cautiously with water for several minutes; remove contact lenses if present and easy to do.
• Skin contact: Wash with soap and water; remove contaminated clothing.
• Ingestion: Rinse mouth; seek advice if unwell.

Fire fighting

• Suitable media: Water spray, dry chemical, CO2, or foam. Dust control measures are important to prevent dispersion.

Solvent Selection

Fit-for-purpose guidance (general for hexitols like D-talitol)

• Polarity class: Highly polar, polyhydroxy compound capable of extensive hydrogen bonding.
• Preferred solvents: Water is the primary solvent due to very high solubility and chemical compatibility. Aqueous buffers (pH ~2–10) are generally suitable; avoid strong dehydrating acids.
• Organic cosolvents: Methanol and ethanol dissolve many hexitols effectively; solubility in isopropanol is lower but nonzero. DMSO and DMF provide excellent solubility for NMR or nonaqueous reactions. Solubility is poor in ethers, ketones with low polarity (e.g., MTBE, CPME), chlorinated solvents, and hydrocarbons.

Selection by application

• Biochemical assays: Use water or aqueous buffer; adjust ionic strength to minimize matrix effects. For highly concentrated stocks, DMSO or glycerol can be used but consider downstream compatibility.
• NMR analysis: D2O provides clean spectra for polyols; DMSO‑d6 can improve dispersion of hydroxyl resonances and suppress exchange.
• Derivatization chemistry: For acetal/ketal protection, employ acetone or 2,2‑dimethoxypropane with catalytic acid; water removal (Dean–Stark or molecular sieves) is critical.

Comparison snapshot (general)

• Water: Best solubility, green, benign.
• Methanol/ethanol: Good solubility; flammable; can participate in acetal exchange.
• DMSO/DMF: Excellent solvency; high boiling; consider workup challenges.

Note

• No item‑specific solvent restrictions are provided. Verify compatibility with your intended reaction conditions and consult the product CoA/SDS for any stabilizer or additive that might influence solvent choice.

Storage and Reconstitution

Item-specific instructions (from Product Data)

• Storage Conditions: Store at −20 °C.
• Shipped In: Ice chest + ice pads.
• Research Use Note: For research use only.

General best practices for this compound class (literature/general)

• Container: Keep tightly closed in a clean, dry container. Polyols can be hygroscopic; include a desiccant in secondary containment when stored at sub‑ambient temperatures.
• Light/moisture sensitivity: Not light‑sensitive, but prolonged exposure to ambient humidity can change mass and complicate quantitative work. Allow vials to warm to room temperature in a desiccator before opening to avoid condensation.
• Reconstitution: Dissolve in ultrapure water or aqueous buffer. For high‑concentration stocks, gentle warming (25–37 °C) and stirring may be used. Filter sterilize (0.22 µm) if required for biological assays.
• Aliquoting: If repeated access is expected, prepare single‑use aliquots and store at −20 °C to minimize freeze–thaw cycles.
• Stability: Solid polyols are generally stable for extended periods at −20 °C. Aqueous solutions are typically stable for weeks at 2–8 °C; for long‑term storage, freeze at −20 °C or below. Avoid microbial contamination; include sodium azide or sterile technique if appropriate for non‑enzymatic applications.

Documentation

• For shelf life, exact purity limits, and any stabilizers, consult the lot‑specific CoA/Spec Sheet and SDS for SKU D1452511.

Structure and Identity

Item-specific identifiers (from Product Data)

• SKU: D1452511
• Product Name: D-Talitol-1-C
• CAS: Not specified for this item; refer to CoA/Spec Sheet.
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.

General structural description (literature/general)

• Compound class: Polyhydroxy alcohol (hexitol), the fully reduced (alditol) form of the aldose sugar D-talose.
• Functional groups: Six secondary/primary alcohols (–CH2OH termini and four internal –CHOH), no carbonyls, no carboxyls, no heteroatoms beyond oxygen.
• Chirality: Four stereogenic centers along the C2–C5 backbone (specific D-talitol configuration corresponds to reduction of D-talose; all-carbon chain, no rings). Diastereomeric to sorbitol, mannitol, iditol, galactitol, etc.
• 2D description (words): A straight six‑carbon chain bearing hydroxyl groups on every carbon; primary alcohols at C1 and C6, secondary alcohols at C2–C5 with a D-talose-derived stereochemical pattern. In common depictions, the molecule is drawn in an extended zig‑zag with alternating wedge/dash OH substituents.

Molecular formula and molecular weight

• Item-specific (Product Data): Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet. Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
• Literature/general for hexitols like D-talitol: Empirical formula C6H14O6; formula weight ~182.17 g/mol (literature).

Synthetic Utility

General synthetic roles (literature/general for D-talitol and related hexitols)

• Chiral pool starting material: Provides four contiguous stereocenters to access complex motifs. Strategic protection (acetonides, benzylidene acetals) differentiates diols for stepwise functionalization.
• Leaving‑group installation: Conversion to ditosylates/mesylates enables nucleophilic substitution, cyclizations (to tetrahydrofuran/tetrahydropyran derivatives), and iterative chain editing.
• Redox manipulation: Selective oxidation of primary alcohol(s) to aldehydes/acids, followed by Wittig/olefination or amidation, expands scaffold diversity.
• Fragmentation chemistry: Periodate cleavage of 1,2‑diols provides carbonyl fragments that retain stereochemical information, aiding in degradation analyses and synthesis planning.
• Boronate chemistry: Cyclic boronate esters act as temporary protecting groups and as handles for separation or sensing; equilibria can be exploited for dynamic covalent assembly.
• Derivatization for analysis: Per‑O‑silylation (e.g., TMS derivatives) or per‑O‑acetylation renders the compound GC‑amenable and enhances MS response for quantitative methods.

Notes on selectivity and tactics

• Regioselective protection often leverages differential reactivity between primary and secondary OH groups; neighboring‑group participation and conformational bias of acetonides guide outcomes.
• Mitsunobu inversion permits access to alternative diastereomers at targeted positions; use orthogonal protection to avoid scrambling.
• If isotopic enrichment at C1 is confirmed for this SKU (not specified), it can be preserved through many protection/activation sequences with careful choice of conditions to avoid carbon‑skeletal rearrangements.

Target Specificity

Not applicable.

• This product is a small‑molecule polyol, not a biological targeting reagent (e.g., antibody, ligand with defined receptor specificity). No antigen, epitope, species reactivity, clone, or isotype information is relevant.
• Item-specific targeting data are not provided in the Product Data.