(S)-(+)-1,2-Propanediol - Moligand™, 10 mM in DMSO , CAS No.4254-15-3

CAS: 4254-15-3 Cat. No.: S1499247 Formula: C₃H₈O₂ Peso molecolare: 76.09 Beilstein Registry Number: 1718871 Numero EC: 610-039-0

GRADE & PURITY Moligand™, 10 mM in DMSO

Storage

Desiccated,Store at -80°C

Shipped In

Dry ice packs + Cold packs

Panoramica

(S)-(+)-1,2-Propanediol is an endogenous metabolite .

Specifications

Specifiche e purezza

Moligand™, 10 mM in DMSO

Condizioni di conservazione di stoccaggio

Desiccated,Store at -80°C

Spedito in

Dry ice packs + Cold packs

Questo prodotto richiede spedizione a catena fredda. I servizi di terra e altri servizi economici non sono disponibili.

Grado

Moligand™

Nomi e identificatori

• Isomeri SMILES: C[C@@H](CO)O
• WGK Germania: 1
• Peso molecolare: 76.09
• Beilstein: 1718871
• Reaxy-Rn: 1340498
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1340498&ln=

Proprietà chimiche e fisiche

• Indice di rifrazione: 1.432
• Rotazione specifica [α]: 16.5 ° (neat)
• Punto di infiammabilità (°F): 103 °C
• Punto di infiammabilità (°C): 103°C
• Punto di ebollizione (°C): 186-188°C

Riferimenti

1. Chen-Yan Zheng, Hai-Long Qian, Cheng Yang, Xu-Qin Ran, Xiu-Ping Yan.  (2023)  Pure Covalent-Organic Framework Membrane as a Label-Free Biomimetic Nanochannel for Sensitive and Selective Sensing of Chiral Flavor Substances.  ACS Sensors,      [PMID:38054443] [10.1021/acssensors.3c01849]

Application Protocols

No antibody- or assay-validated application protocols are provided for this small-molecule reagent.

• Tested applications (WB, IHC, IF, FC): Not applicable
• Recommended dilutions: Not applicable
• Positive controls: Not applicable

General usage suggestions (literature/practice):

• As a co-solvent, prepare stock solutions by mixing with water, alcohols, or DMSO; filter if required for analytical work.
• For chiral building-block use, document stereochemical integrity (e.g., optical rotation, chiral HPLC) upon receipt and after extended storage.

For any specific application in your workflow, develop and qualify an internal SOP. Refer to the product’s CoA and SDS for item-specific handling details.

Biological Roles

The discussion below concerns general biochemistry of 1,2-propanediol and is not specific to any clinical or diagnostic application.

• Occurrence and metabolism (literature/general)

  • In microbes, 1,2-propanediol can arise from degradation of rhamnose and fucose, entering 1,2-propanediol utilization (pdu) pathways that convert it to propionaldehyde and propionate/1-propanol, often within bacterial microcompartments.
  • In mammals, propylene glycol can be metabolized by alcohol and aldehyde dehydrogenases to lactaldehyde and lactate/pyruvate; it can enter gluconeogenic pathways. Metabolism is capacity-limited and differs from ethylene glycol (which forms oxalate).

• Physicochemical roles in biology (literature)

  • Acts as a cryo/lyoprotectant co-solvent, stabilizing proteins and membranes by modulating water activity and hydrogen-bond networks.
  • Serves as a compatible solute/co-solvent in enzymatic reactions, sometimes enhancing substrate solubility; at higher levels it may inhibit or denature enzymes.

• Toxicology context (literature/general)

  • Generally low acute toxicity; high doses can cause osmotic and CNS effects. Not a known bioaccumulative substance due to high water solubility and rapid metabolism.

Note: The above summarizes general biochemical behavior. This catalog item is for research use only and not for use in humans or animals. No medical or clinical claims are made.

Buffer Applications

(S)-1,2-Propanediol is not a buffering agent and does not establish a defined pH range like classical buffers (e.g., phosphate, Tris, HEPES). Accordingly, it is not typically used to prepare buffer systems.

• Practical laboratory use (literature/general)

  • As a co-solvent or cryoprotectant added to aqueous buffers to enhance solubility of hydrophobic analytes or to depress freezing point for cold storage and low-temperature assays.
  • Typical working concentrations vary widely (1–40% v/v) depending on protein/assay tolerance and solubility needs; optimization is empirical.

• Compatibility notes

  • High concentrations can alter enzyme kinetics, protein stability, and spectroscopic baselines due to refractive index and viscosity changes; run solvent controls.
  • Strongly affects freezing behavior; confirm storage temperatures and glass transition for freeze–thaw protocols.

For true buffering capacity, select appropriate buffer systems (phosphate, acetate, Good’s buffers) and consider adding (S)-1,2-propanediol only as a co-solvent modifier if needed.

Green Alternatives

From a green chemistry standpoint, (S)-1,2-propanediol is comparatively benign among organic solvents/reagents: low volatility, good biodegradability, and relatively favorable toxicological profile (literature). Consider the following when selecting it or alternatives.

• Advantages (literature/general)

  • Low VOC emissions due to high boiling point and low vapor pressure.
  • Miscibility with water enables aqueous or high-water-content media, reducing need for hazardous solvents.
  • Derived industrially from both petrochemical and bio-based routes (e.g., glycerol hydrogenolysis), supporting renewable sourcing.

• Potential drawbacks

  • High viscosity hampers mass transfer in some systems.
  • Strong hydrogen-bonding can complicate product isolation and drying.

• Alternatives and trade-offs (literature)

  • Glycerol: Greener and more renewable; higher viscosity and melting point, potentially limiting.
  • Ethanol/water: Very green, low toxicity and easy removal; lower solvating power for highly polar solutes vs diols.
  • 2-Methyltetrahydrofuran (2-MeTHF): Bio-derived ether with good processability; forms peroxides over time and is flammable; less polar than diols.
  • Propylene carbonate: Polar aprotic, high boiling point, often biodegradable; different reactivity profile (cyclic carbonate), not protic.

Small comparison (literature/general)

• (S)-1,2-propanediol vs glycerol: Lower viscosity/easier handling; slightly less hydrophilic.
• (S)-1,2-propanediol vs ethylene glycol: Similar solvent power; propanediol favored for reduced health hazards.

Selection guidance: For polar, protic, low-volatility media or for chiral diol building-block chemistry, (S)-1,2-propanediol is a reasonable “greener” choice; for rapid workup and easy removal, ethanol/water may be preferable.

Pharmaceutical Uses

No therapeutic claims are made. The following reflects general formulation practice from literature and pharmacopeial compendia for propylene glycol-type materials; applicability to this specific chiral grade should be evaluated case-by-case.

• Typical roles in formulation (literature/general)

  • Solvent/co-solvent for poorly water-soluble actives in research formulations, pre-formulation studies, and ex vivo work.
  • Humectant and plasticizer in semi-solid and liquid dosage form development (e.g., gels, creams) in laboratory research.
  • Penetration enhancer in topical research formulations; effects are formulation- and active-dependent.

• Compendial notes

  • Propylene glycol appears in multiple pharmacopeias as an excipient; however, enantiomer-specific listings for (S)-isomer are uncommon. Verify regulatory status and impurity limits for any regulated use.

• Compatibility and constraints

  • Miscible with water, ethanol, PEGs, glycerol; may extract plasticizers from some polymers—use compatible container materials (e.g., glass, select HDPE).
  • High levels can impact osmolarity and may cause irritation; conduct appropriate risk assessments in any nonclinical handling contexts.

This Aladdin product is designated For research use only and is not intended for human or animal administration.

Physical Properties

The following are typical physicochemical properties of (S)-1,2-propanediol; values are representative of the enantiopure compound and essentially match racemic propylene glycol. They are provided for reference and are not item-specific specifications.

• State/appearance: Colorless, viscous liquid; hygroscopic (literature)
• Boiling point: ~188–189 °C at 1 atm (literature)
• Melting point: ~−59 °C (literature)
• Density: ~1.035–1.040 g/mL at 20 °C (literature)
• Refractive index: nD20 ~1.431 (literature)
• Vapor pressure: Very low at ambient temperature (literature)
• Solubility profile (qualitative, literature)
  • Water: Miscible in all proportions
  • Alcohols (MeOH, EtOH, i-PrOH): Miscible
  • Polar aprotics (DMSO, DMF, NMP): Miscible
  • Ethers (THF, 2-MeTHF): Miscible/soluble
  • Hydrocarbons (hexanes, heptane): Low solubility
• Partitioning: LogP (octanol/water) ≈ −0.9 (literature)
• Acidity/basicity: Neutral diol; alcohol pKa ≳ 15 (water, literature); conjugate-acid pKa ≈ −2 to −3 (literature)
• Viscosity: High relative to monohydric alcohols; markedly temperature-dependent (literature)
• Hygroscopicity: Absorbs atmospheric moisture; water content increases on exposure to air (literature)

Item-specific specifications (for QC release) such as water content, metals, UV cutoff, residual solvents, and exact refractive index are Not specified for this item; refer to CoA/Spec Sheet.

Quality and Grades

• Catalog grade: Moligand™ (as provided in Product Data)

  • Context: Moligand™ indicates suitability for use in molecular screening libraries, ligand discovery, and structure–activity relationship (SAR) exploration. Such materials are typically selected for high purity, structural fidelity (including enantiopurity where applicable), and stable handling characteristics in high-throughput settings.
  • Implications for (S)-(+)-1,2-propanediol:
    • Enantiomerically defined S-configuration is expected for chiral applications (verify enantiomeric excess on CoA if critical).
    • Clean spectral identity supports use as a chiral building block or auxiliary in asymmetric synthesis campaigns.

• What this grade does not state:

  • Water content, metals profile, residual solvents, UV cutoff, and exact purity percentage: Not specified for this item; refer to CoA/Spec Sheet.
  • Stabilizers: None indicated in Product Data; if present, they will be declared on the CoA.

• Fit-for-purpose guidance (general):

  • Medicinal chemistry/HTE: Moligand™ materials are appropriate for plate-based dispensing, aliquoting, and storage protocols commonly used in screening. Confirm solubility in intended matrices (e.g., DMSO, aqueous co-solvent systems).
  • Chiral synthesis: If optical rotation or ee is critical, request CoA chiroptical data or chromatographic verification (e.g., chiral GC/HPLC).

• Documentation: Batch-specific CoA/Spec Sheet provides authoritative release criteria; request prior to regulated or data-critical work.

Reaction and Applications

As an enantiomerically defined vicinal diol, (S)-(+)-1,2-propanediol serves multiple roles in synthesis and method development.

• Roles in synthesis (literature/general)

  • Chiral building block: The S-stereocenter can be transferred or elaborated via selective functionalization (e.g., oxidation to hydroxyketones/α-hydroxyacids, substitution at C1 after activation).
  • Protecting group chemistry: Formation of 5-membered cyclic acetals/ketals with carbonyl compounds; (S)-diol-derived acetals can impart chirality into auxiliaries.
  • Auxiliary/ligand precursor: Precursor to chiral acetals/orthoesters and to diol-derived ligands for asymmetric catalysis (e.g., salen-type or phosphinite frameworks via further functionalization; literature).
  • Carbonate chemistry: Conversion to cyclic carbonates (e.g., via CO2 activation with dehydrating agents or phosgene-equivalents) for green solvent or monomer research.
  • Esterification/transesterification: Readily forms mono- and diesters under acid or enzyme catalysis; kinetic resolution opportunities exist with enantioselective acylation.

• Practical notes

  • Water sensitivity: Hygroscopic; dry before use for moisture-sensitive transformations (molecular sieves, azeotropic removal with toluene/Dean–Stark after prior derivatization as acetal/ketal, or vacuum drying).
  • Selectivity: Secondary vs primary OH can be differentiated using sterically demanding acylating agents or selective oxidants (e.g., TEMPO for primary oxidation, Dess–Martin for secondary; literature).
  • Activation: Convert OH groups to mesylates/tosylates for nucleophilic substitution or cyclization sequences.

• Examples (literature)

  • Preparation of chiral cyclic sulfates from diols for stereospecific substitution (cyclic sulfate methodology).
  • Preparation of chiral epoxides from vicinal diols via selective sulfonation followed by base-induced cyclization.

Reaction Conditions

Representative conditions for common transformations of 1,2-propanediol are summarized for literature guidance; optimize for your substrate and scale.

• Selective oxidations (literature)

  • Primary OH → aldehyde: TEMPO (1–5 mol%), NaOCl (1.5–2.0 eq), pH ~9, 0–5 °C to rt, 0.5–3 h; extractive workup. Typical yields 70–90% on small scale.
  • Secondary OH → ketone: Dess–Martin periodinane (1.3 eq) in CH2Cl2, 0 °C to rt, 1–2 h; or Swern (oxalyl chloride/DMSO, −78 °C → 0 °C). Yields 70–95%.

• Esterifications/transesterifications (literature)

  • Acid-catalyzed: p-TsOH (1–5 mol%) in toluene or toluene/heptane with Dean–Stark for water removal; reflux, 2–12 h → mono/diesters (control via stoichiometry).
  • Enzymatic (kinetic resolution): Vinyl acetate or isopropenyl acetate, lipase (CAL-B), 25–50 °C in MTBE, TBME, or solvent-free; monitor ee and conversion.

• Acetonide (isopropylidene) protection (literature)

  • Acetone, catalytic p-TsOH or CSA, 0 °C to rt, 1–6 h; remove acid, neutralize, and concentrate. Alternatively, 2,2-dimethoxypropane with catalytic acid for water-free conditions.

• Sulfonate formation and displacement (literature)

  • MsCl or TsCl (1.1–1.5 eq) with Et3N or pyridine, 0 °C to rt in CH2Cl2 or DMF, 1–3 h; subsequent SN2 displacement with nucleophiles (e.g., halides, azide) at 0–80 °C depending on solvent/nucleophile.

• Cyclic carbonate formation (literature)

  • CO2 (1–10 bar), organic base (DBU/TBD) and dehydrating co-reagent (e.g., CDI) or halide catalyst; 25–80 °C, several hours to overnight.

Notes: Reaction media often benefit from drying (molecular sieves). Given the substrate’s protic nature, strongly basic reagents may induce elimination or rearrangement only at elevated temperatures; monitor carefully.

Safety and Handling

Safety information below is general to 1,2-propanediol and provided for laboratory risk assessment. Item-specific GHS/SDS data were not provided.

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

General laboratory guidance (literature/practice):

• Hazards: (S)-1,2-propanediol is generally considered to have low acute toxicity and low volatility; may cause mild eye/skin irritation. Prolonged or repeated exposure to large quantities can cause CNS effects if ingested (literature).
• PPE: Wear safety glasses, lab coat, and appropriate chemical-resistant gloves (e.g., nitrile). Use in well-ventilated area.
• Handling: Hygroscopic; minimize air exposure to limit water uptake. For moisture-sensitive applications, handle under inert atmosphere and use anhydrous techniques.
• Storage incompatibilities: Strong oxidizers; acid chlorides/anhydrides; isocyanates; strong dehydrating agents. Glycols can react with oxidants to form aldehydes/ketones/acids.
• First aid (overview; defer to SDS):
  • Inhalation: Move to fresh air; seek medical attention if symptoms persist.
  • Skin: Wash with soap and water; remove contaminated clothing.
  • Eyes: Rinse cautiously with water for several minutes; seek medical advice if irritation continues.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
• Spill/cleanup: Contain with inert absorbent; collect for disposal. Slippery when spilled.
• Fire response: Not easily ignited; use water spray, alcohol-resistant foam, dry chemical, or CO2. Thermal decomposition may produce irritant vapors.

Always consult the product-specific SDS for authoritative hazard, exposure limits, and emergency measures.

Solvent Selection

This product is itself a polar protic organic liquid used primarily as a reagent, co-solvent, and medium modifier rather than a general-purpose chromatographic solvent.

• Polarity and miscibility (literature/general):

  • Class: Polar protic diol; strong hydrogen-bond donor and acceptor.
  • Miscibility: Fully miscible with water, alcohols, and many polar aprotic solvents (DMSO, DMF, NMP); limited solubility in aliphatic hydrocarbons.
  • Volatility: Low; high boiling point reduces evaporative loss and VOC burden.

• When to choose (S)-1,2-propanediol as a solvent/co-solvent

  • To increase the polarity and hydrogen-bonding capacity of a medium (e.g., boosting solubility of polyols, carbohydrates, polar APIs/intermediates in research contexts).
  • For low-temperature baths where freezing depression is needed (mixtures with water/alcohols), while avoiding flammability of more volatile alcohols.
  • As a benign co-solvent in catalytic hydrogenation or biocatalytic media (literature), mindful of enzyme compatibility.

• Alternatives and comparisons (literature)

  • Glycerol: Higher polarity/viscosity; better for extreme hydrophilicity but harder to handle/transfer.
  • Ethylene glycol: Similar polarity; lower viscosity than glycerol but greater toxicological concerns.
  • Polyethylene glycol (PEG-200/400): Excellent solvating power; substantially higher viscosity and different volatility.

Note: For chromatographic applications (HPLC/GC), (S)-1,2-propanediol is not a routine mobile phase component; prefer MeOH, ACN, IPA, or water-based systems unless method development specifically calls for glycol modifiers.

Storage and Reconstitution

• Storage conditions (from Product Data)

  • Desiccated, Store at −80 °C.
  • Shipped on dry ice packs + cold packs.

• Packaging/handling recommendations (practice)

  • Upon receipt, keep frozen until first use. Allow container to equilibrate to room temperature in a desiccator before opening to prevent moisture condensation—compound is hygroscopic.
  • After first opening, aliquot into dry, airtight vials (e.g., borosilicate glass) under inert gas if feasible to minimize water uptake; clearly label aliquots.
  • For frequent access, consider maintaining a working aliquot at −20 °C (if permissible for your application) and reserve primary stock at −80 °C to limit freeze–thaw cycles.

• Stability notes (literature/general)

  • 1,2-Propanediol is chemically stable under neutral, anhydrous conditions; avoid strong oxidizers and prolonged exposure to elevated temperatures.
  • Freeze–thaw: No crystallization expected at typical freezer temperatures due to low melting point; viscosity increases markedly at subzero temperatures.

• Reconstitution/dispensing

  • Neat liquid; no reconstitution required. If preparing solutions, use dry, oxygen-free solvents where moisture/oxygen-sensitive transformations are planned.
  • For analytical work, consider 0.2 μm filtration of prepared solutions to remove particulates.

• Item-specific shelf life, assay, water content limits: Not specified for this item; refer to CoA/Spec Sheet.

Always follow institutional chemical hygiene practices and consult the SDS for detailed guidance.

Structure and Identity

Brief description: (S)-(+)-1,2-Propanediol is the single-enantiomer form of propylene glycol bearing two vicinal alcohols and one stereogenic center at C2.

• Item identifiers (from Product Data)

  • SKU: S1499247
  • Product Name: (S)-(+)-1,2-Propanediol
  • CAS: 4254-15-3
  • Grade: Moligand™
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Identity and composition (literature/general)

  • Common names: (S)-propylene glycol; (S)-1,2-propylene glycol; (S)-1,2-propanediol
  • Molecular formula: C3H8O2 (literature)
  • Molecular weight: 76.09 g/mol (literature)
  • Stereochemistry: Single chiral center at C2 with S-configuration; optical rotation is positive for the S-enantiomer (literature)

• Structural features (descriptive)

  • Functional groups: Two primary/secondary alcohols in a vicinal 1,2-diol motif (–CH(OH)–CH2OH)
  • Backbone: Three-carbon propane chain substituted by a methyl at C2 and hydroxyls at C1 and C2
  • Hydrogen-bonding: Strong H-bond donor/acceptor due to two hydroxyls; forms extensive intermolecular H-bond networks
  • 2D structure in words: A central chiral carbon bearing a methyl group, a hydroxyl group, and a methylene bearing a terminal hydroxyl; the remaining substituent is hydrogen. No rings or additional heteroatoms.

• Registry cross-references (general)

  • PubChem CID: 439846 (literature)

Note: Structural identifiers (SMILES/InChI/InChIKey) specific to this exact catalog item may be provided on the CoA; consult the CoA/Spec Sheet for authoritative identity data.

Synthetic Utility

(S)-(+)-1,2-Propanediol is a versatile chiral synthon whose vicinal diol and stereogenic center enable diverse transformations (literature/general):

• Functional group interconversions

  • Selective oxidation: Primary alcohol → aldehyde/acid (e.g., TEMPO/bleach, Swern); secondary alcohol → ketone (Dess–Martin, PCC). Control chemoselectivity via reagent choice and protecting groups.
  • Protection strategies: Convert to acetonide (isopropylidene) or benzylidene acetals to lock conformation and differentiate OH groups.
  • Leaving group installation: Mesylate/tosylate formation at primary or secondary OH for SN2/SN1 substitutions and intramolecular cyclizations.
  • Carbonate/oxalate formation: Route to cyclic carbonates or mixed carbonates for further diversification.

• Stereochemical relay and chiral pool use

  • Use the existing S-configuration to set new stereocenters via substrate-controlled reactions (e.g., Evans–Tishchenko-type reductions on derived hydroxyaldehydes, or Sharpless asymmetric-like relay using chiral auxiliaries derived from the diol).
  • Kinetic resolution: Enzymatic acylation (lipases) can differentiate the two OH groups, delivering enantioenriched monoesters with predictable selectivity.

• Linker/ligand precursor

  • Diol serves as a scaffold for bidentate ligands upon phosphorylation, boronation (boronate esters), or acetalization with chiral aldehydes.

• Practical considerations

  • Drying: Remove adventitious water prior to moisture-sensitive steps (sieves, co-evaporation with toluene under vacuum).
  • Workup: Strong hydrogen-bonding can retain products; consider salting-out, phase-splitting with brine/MTBE, or derivatization to more hydrophobic intermediates for extraction.

These utilities make (S)-1,2-propanediol a valuable chiral pool starting material for small-molecule synthesis.

Target Specificity

This product is a small-molecule reagent and does not target biological antigens or epitopes.

• Target/epitope: Not applicable
• Species reactivity/clone/isotype: Not applicable
• Item-specific target data: Not specified for this item; refer to CoA/Spec Sheet.

For biochemical specificity in catalysis or binding studies, see the Synthetic Utility and Reaction & Applications sections for relevant chemical selectivity rather than biological target specificity.