D-​Arabinose-C , CAS No.D1451659

CAS: D1451659 Cat. No.: D1451659 Summenformel: ₁₃C₅H₁₀O₅ Molekulargewicht: 155.09

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Übersicht

D- Arabinose- 13 C 5 is 13 C labeled D- Arabinose. D-Arabinose, a monosaccharide, shows strong growth inhibition against the Caenorhabditis elegans with an IC 50 of 7.5 mM.

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: 155.09

Application Protocols

No validated bioassay/immunoassay application protocols are provided for this item.

General guidance (literature/general)

• Preparation of stock solutions: dissolve in sterile water or buffer (e.g., PBS) with gentle warming if needed; filter-sterilize (0.22 µm) for cell-free biochemical assays. Verify compatibility with any biological system prior to use.
• Analytical standard use: prepare gravimetrically in water; for HPAEC-PAD, store aliquots at −20 °C; for GC analysis, derivatize to aldononitrile acetate or TMS ethers per established methods.
• Glycosylation workflows: dry thoroughly, protect diols as needed, and use anhydrous solvents under inert atmosphere; follow reaction conditions in the Reaction Conditions tab.

Item-specific recommendations (WB/IHC/IF/FC, dilutions, positive controls)

• Not applicable; no such data are specified for this item.

Biological Roles

Literature/general biology (no medical claims)

• D-Arabinose is a naturally occurring aldopentose. In many bacteria (notably mycobacteria), the D-arabinofuranose unit is a key component of arabinogalactan within the cell wall, impacting structural integrity and permeability.
• Metabolism: some microbes can utilize D-arabinose via isomerases/kinases/aldolases feeding into central carbon metabolism. Metabolic capacity is species dependent; E. coli predominantly uses L-arabinose, whereas D-arabinose catabolism occurs in select organisms.
• Biochemical behavior: as a reducing sugar, D-arabinose can form Schiff bases with amines and undergo Amadori rearrangements under appropriate conditions, relevant to glycation chemistry in vitro.
• Structural chemistry: equilibrates between furanose and pyranose anomers; the furanose is often favored in biological glycoconjugates.
• Analytical use: serves as an internal/external standard in carbohydrate quantification and as a model substrate for glycosidase/glycosyltransferase studies.

Item-specific biological role

• This product is designated for research use only. No additional item-specific biological annotations are provided.

Buffer Applications

Applicability

• D-Arabinose is not a buffering agent and does not provide meaningful buffering capacity in typical laboratory pH ranges.

Practical use in solutions (literature/general)

• Additive/stabilizer: sugars can act as osmolytes and protein stabilizers in vitro, modulating viscosity and protecting against aggregation; effectiveness is system dependent and should be empirically determined.
• Cryo/lyoprotection: carbohydrates are often included in lyophilization formulations to protect biomolecules during drying; selection and concentration optimization are required.

Guidance

• For buffered systems, pair D-arabinose with appropriate buffers (e.g., phosphate, HEPES, MOPS) targeting the experimental pH; confirm compatibility with enzymes and avoid conditions that promote sugar degradation (strong acid/base, high heat).

Item-specific note

• No buffer recipes or validated buffer applications are provided for this item.

Green Alternatives

Context

• D-Arabinose is a biobased, renewable carbohydrate typically derived from biomass; it is inherently low toxicity and water compatible. As such, it often aligns with green chemistry principles.

Greener handling considerations (literature/general)

• Solvent choice: prefer water as the reaction/processing medium where possible; avoid high-boiling polar aprotics when an aqueous or alcohol medium suffices.
• Protection minimization: adopt protecting-group-free or minimal-protection strategies to reduce steps, reagents, and waste.
• Catalysis: use organocatalysts or benign Lewis acids (e.g., boronic acids for diol complexation) in place of heavier metals when forming glycosidic bonds.

Comparison examples

• Aqueous biocatalysis vs anhydrous derivatization
  • Aqueous enzymatic transformations: high atom economy, mild conditions, easier workup.
  • Anhydrous DMSO/DMF derivatizations: broader scope but increased EHS footprint; ensure solvent recovery.

Waste and energy

• Carbohydrate processes can generate large volumes of aqueous waste; apply concentration/reuse strategies and membrane separations.
• Lower energy crystallizations from water/ethanol blends can replace high-temperature solvent operations.

Note

• If this item is isotopically labeled, enrichment processes may carry a higher environmental cost; plan experiments to maximize data per unit material and recover unused material when feasible.

Pharmaceutical Uses

Scope

• No therapeutic or clinical claims are made for this product. Research use only.

Literature/general formulation/manufacturing context

• Excipients: while D-ribose and sucrose are common, D-arabinose is less typical as a standalone excipient; however, carbohydrates in general can function as bulking agents, stabilizers, or tonicity modifiers in experimental formulations.
• Synthetic intermediate: the arabinose scaffold underlies various arabinoside structures; D-arabinofuranosyl donors are key in the preparation of arabinose-containing glycoconjugates and can serve in the synthesis of investigational compounds.
• Analytical reference: used as a reference standard in QC/analytical method development for carbohydrate profiling.

Regulatory/standards

• No pharmacopeial monograph is cited here for D-arabinose. Any use in regulated settings would require qualification to appropriate standards (identity, purity, microbial limits, endotoxin if parenteral exposure is anticipated).

Item-specific details

• Grade/purity and compliance status: Not specified for this item; refer to CoA/Spec Sheet.

Physical Properties

Item-specific specifications

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

Literature/general physical data for D-arabinose (unlabeled)

• Melting point: ~153–154 °C (literature; anhydrous crystalline D-arabinose). Hydrates/syrups may show broadened ranges.
• Solubility: highly soluble in water; sparingly to moderately soluble in lower alcohols (e.g., methanol, ethanol); essentially insoluble in nonpolar solvents (literature).
• Density: not commonly tabulated for the solid; solutions approximate densities >1.00 g/mL depending on concentration (literature).
• pKa: not applicable (neutral polyol/aldehyde). Neighboring hydroxyls can display apparent acidities in complexation, but no discrete pKa for buffering utility (literature).
• logP (octanol/water): strongly negative; highly hydrophilic carbohydrate (literature; various estimated cLogP around −3 to −4).
• Optical rotation: D-arabinose is dextrorotatory; [α] values depend on solvent, temperature, and mutarotation state (literature).
• Hygroscopicity: carbohydrates can be hygroscopic; storage under dry conditions is recommended (general guidance).

Important note

• No item-specific numerical specs (e.g., water content, metal content, UV cutoff, isotopic enrichment) are provided: 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.

Guidance on grades for D-arabinose materials (literature/general)

• Research/Biochemical grade: suitable for general biochemical assays, enzymology, and carbohydrate chemistry; typically controlled for ash, heavy metals, and microbial bioburden.
• Cell culture grade: may include sterility/microbial limits and endotoxin specifications to support in vitro use (not specified for this item).
• Isotopic grade (if “-C” indicates carbon labeling): characterized by isotopic enrichment (e.g., 13C) and isotopomer distribution. For quantitative NMR/MS work, enrichment (atom %) and labeling position are critical. Not specified for this item; refer to CoA/Spec Sheet.

What to look for on the CoA/Spec Sheet

• Identity: NMR (1H/13C), specific optical rotation, HPLC purity, and chromatographic profile of anomers.
• Purity: % area by HPLC, residual solvents, water content (Karl Fischer), ash/metals (ICP), microbial counts.
• For isotopically labeled materials: enrichment level, labeling position(s), and verification by HRMS/13C NMR.

Stabilizers/additives

• None indicated for this product. If present in similar products (e.g., anti-caking agents), they should be disclosed on the CoA. For this item: Not specified.

Reaction and Applications

Applications (literature/general)

• Carbohydrate standard: used as a calibration/response standard in sugar analysis (HPAEC-PAD, GC after derivatization, LC-MS as adducts) and in total carbohydrate assays.
• Chiral pool starting material: three stereocenters make D-arabinose a valuable precursor to enantiopure polyols, 1,2,3,4-tetrahydrofuran derivatives, and heterocycles.
• Glycosylation chemistry: conversion to D-arabinofuranosyl donors (e.g., trichloroacetimidates, thioglycosides) for assembly of arabinans, arabinogalactans, and arabinosides.
• Derivatization: acetylation (pentaacetate), benzylation, silylation, and acetonide protections enable selective transformations; oxidation to D-arabinonic acid; reduction to arabitol.
• Isotopic tracing (if carbon-labeled): 13C-labeled D-arabinose can support metabolic flux analysis in microbes that catabolize D-arabinose, or NMR probe studies of glycosylation mechanisms. For this item, isotopic details are not specified.

Practical tips

• Drying: for non-aqueous derivatizations, dry material under high vacuum over P2O5 or in a desiccator; co-evaporation with dry toluene or acetonitrile helps remove residual water.
• Anomer control: mutarotation in solution can affect NMR integrations; allow solutions to equilibrate or control temperature/solvent to favor a defined anomer.
• Protecting group strategy: choose orthogonal protections (acetonide for vic‑diols; benzyl/PMB for permanent protections) to guide regioselective glycosylations.
• Analytical: use HPAEC-PAD for direct sugar quantitation; derivatize with aldononitrile acetate or trimethylsilyl ethers for GC; use 1H/13C NMR with D2O for structure/anomer ratio.

Reaction Conditions

General conditions for common transformations of D-arabinose (literature; adjust per substrate and scale)

• Acetylation to pentaacetate: Ac2O (5–10 eq per OH) in pyridine or Ac2O/catalytic DMAP, 0 °C to rt, 2–12 h. Workup with aqueous quench; typical yields high (70–95%).
• Trichloroacetimidate donor formation: from peracetylated hemiacetal; use CCl3CN (2–3 eq), base (K2CO3/DBU), CH2Cl2 or MeCN, 0 °C to rt, 1–4 h.
• Glycosylation using trichloroacetimidate donor: acceptor ROH, catalyst TMSOTf (1–10 mol%), dry CH2Cl2 or toluene, −78 to 0 °C, 0.5–6 h; control anomeric selectivity via protecting groups and temperature.
• Acetonide protection: acetone with catalytic H2SO4 or p‑TsOH, rt to reflux; monitor to avoid dehydration; neutralize and isolate under reduced pressure.
• Benzylation: generate alkoxides (NaH, DMF) then BnBr; 0 °C to rt, 2–16 h; ensure anhydrous conditions.
• Oxidation to arabinonic acid: TEMPO (5–10 mol%), NaOCl (bleach), NaBr, pH ~10–11, 0–5 °C to rt, 1–3 h; or catalytic TEMPO with O2 and Cu catalysts in water.
• Reduction to arabitol: NaBH4 (1–2 eq) in MeOH/H2O at 0–5 °C; quench cautiously; isolate polyol.

Analytical/controls

• Monitor by TLC (anisaldehyde or orcinol stain for carbohydrates), HPLC, or 1H/13C NMR. Be mindful of mutarotation—allow solutions to equilibrate before final measurements.

Note

• Conditions are typical literature guidance; optimize for scale, protecting groups, and desired anomeric outcomes.

Safety and Handling

Hazard classification (item-specific)

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

General safety considerations for carbohydrates (literature/general)

• Expected low acute toxicity; handle as a laboratory chemical. Avoid inhalation of dusts and contact with eyes.
• Combustible dust hazard may exist for fine powders; minimize dust generation and ignition sources.
• Reducing sugars can participate in Maillard-type reactions with amines upon heating; avoid strong heating with amine-containing materials.
• Incompatibilities: strong oxidizers (may cause vigorous reactions); strong acids/bases can promote degradation (caramelization, aldol condensations) at elevated temperature.

PPE and handling

• Wear lab coat, safety glasses, and appropriate gloves (e.g., nitrile). Handle powders in a fume hood or with local exhaust if dust may form.
• Hygroscopic tendency: keep container tightly closed to avoid moisture uptake and caking.

First-aid (overview; defer to SDS)

• Inhalation: move to fresh air; seek medical advice if symptoms persist.
• Skin/eye contact: rinse with water for at least 15 minutes; remove contaminated clothing.
• Ingestion: rinse mouth; do not induce vomiting; seek medical attention if unwell.

Waste disposal

• Dispose of in accordance with institutional, local, and national regulations. Aqueous sugar solutions are typically nonhazardous but confirm via SDS and local rules.

Solvent Selection

Applicability

• D-Arabinose is a highly polar, hydrogen-bonding carbohydrate; solvent choice is driven by its strong hydrophilicity and multiple hydroxyl groups.

Preferred solvents (literature/general)

• Water: primary solvent; rapid dissolution at room temperature with stirring.
• Aqueous buffers: for biochemical assays; maintain pH stability (neutral to mildly acidic preferred to limit degradation).
• Polar protic organics: methanol, ethanol—limited to moderate solubility; often used for recrystallization or precipitation from water.
• Polar aprotic: DMSO and DMF can dissolve sugars at moderate levels; useful for derivatization chemistry; ensure biocompatibility if used in bioassays.

Avoid

• Nonpolar solvents (e.g., hexane, toluene, diethyl ether): essentially insoluble.

Selection tips

• For enzymatic/biochemical work, use water or buffered saline; adjust ionic strength and temperature to avoid mutarotation artifacts in kinetic measurements.
• For protection/derivatization, use anhydrous DMF/DMSO or acetone (for acetonide formation) with appropriate catalysts; remove residual solvent thoroughly after reaction.

Comparison (literature)

• Water vs DMSO: water maximizes biocompatibility; DMSO permits higher concentrations for derivatization and NMR but may interfere with enzymes.
• Ethanol/methanol: useful for crystallization and precipitation of arabinose derivatives; flammable and may participate in acetal exchange under acid catalysis.

Storage and Reconstitution

Storage (item-specific)

• Store at −20 °C (per Product Data). Keep tightly closed. Protect from moisture.
• Shipped in: Ice chest + ice pads (per Product Data).

General handling

• Hygroscopic solid: minimize time at ambient humidity; dispense quickly and recap. Consider storing under inert atmosphere or with desiccant.
• Aliquoting: if frequent use is anticipated, aliquot into moisture-tight containers to avoid repeated freeze–thaw and condensation on opening.

Reconstitution (literature/general)

• Solvents: water is preferred; aqueous buffers for biochemical work. For non-aqueous derivatization, use dry DMSO/DMF.
• Concentration: prepare stock solutions appropriate to application (e.g., 0.1–1.0 M for assay standards). Filter sterilize (0.22 µm) if sterility is required.
• Stability in solution: sugars can undergo slow degradation, especially at elevated temperature and extreme pH. Store aqueous stocks at 2–8 °C for short term (days) or at −20 °C for longer term (weeks to months). Avoid strong acids/bases and prolonged heating.

Specifications not provided

• Stabilizers, water content, isotopic enrichment, and exact solubility limits: Not specified for this item; refer to CoA/Spec Sheet.

Research use

• For research use only (per Product Data).

Structure and Identity

Item-specific identifiers (from Product Data)

• SKU: D1451659
• Product Name: D-Arabinose-C
• CAS: D1451659 (as provided by catalog)
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
• 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.

Notes on identity and structure (literature/general)

• D-Arabinose is a five‑carbon aldopentose (a reducing monosaccharide) typically existing in equilibrium between open‑chain aldehyde and cyclic furanose/pyranose forms in aqueous solution.
• Functional groups: one aldehyde (open chain), four secondary alcohols; in cyclic forms: multiple hemiacetal centers.
• Stereochemistry: D-series configuration; three stereogenic centers in the open-chain form. The prevalent cyclic form in many contexts is D-arabinofuranose.
• Typical literature identifiers for unlabeled D-arabinose: molecular formula C5H10O5; molecular weight ~150.13 g/mol. If this product is a carbon‑labeled variant (the “-C” suffix), the labeling position and enrichment are not specified for this item.
• 2D description (literature): an open-chain sequence HO–CH2–CH(OH)–CH(OH)–CH(OH)–CHO that cyclizes intramolecularly (C4–O attacking C1) to give a five‑membered furanose ring bearing three hydroxyl substituents and a primary hydroxymethyl group.

Synthetic Utility

Literature/general synthetic utility of D-arabinose

• Chiral pool feedstock: provides three defined stereocenters for constructing complex polyhydroxylated targets and heterocycles with predictable relative configurations.
• Protection strategies: acetonide formation across 1,2- or 2,3-diols (acetone, catalytic acid); benzyl/PMB protections via alkoxide formation (NaH/Ag2O) and alkyl halides; silyl protections (TBS/TIPS) enabling selective downstream manipulations.
• Oxidation/reduction: TEMPO/NaOCl or PDC oxidations to D-arabinonic acid or lactone; NaBH4 reduction of the aldehyde to arabitol; periodate cleavage of vic-diols to smaller fragments for structure probing.
• Glycosyl donor preparation: conversion to peracetylated arabinose pentaacetate, then to trichloroacetimidate donors (CCl3CN, base) or thioglycosides (PhSH, BF3·Et2O) for subsequent glycosylations.
• Cyclizations/annulations: intramolecular cyclizations to tetrahydrofuran/tetrahydropyran motifs; application in natural product fragment synthesis.

Isotopic applications (if carbon-labeled)

• 13C-label facilitates NMR assignment of anomeric and ring carbons in intermediates and products; supports mechanistic studies of glycosylation and rearrangements. Labeling specifics for this item are not provided.

Target Specificity

Not applicable to this product category.

• This item is a small-molecule carbohydrate, not a biologic/antibody. No antigen/epitope or species reactivity applies.
• Item-specific target data: Not specified for this item.