3,4-Dihydroxymandelic acid - Moligand™, 10 mM in DMSO , CAS No.775-01-9

CAS: 775-01-9 Cat. No.: D1494787 Fórmula: C₈H₈O₅ Peso molecular: 184.15 Beilstein Registry Number: 10493 PubChem CID: 85782

GRADE & PURITY Moligand™, 10 mM in DMSO

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Visão geral

3,4-Dihydroxymandelic acid is a metabolite of norepinephrine.

Specifications

Especificações e pureza

Moligand™, 10 mM in DMSO

Condições de armazenamento de armazenamento

Store at -80°C

Enviado em

Dry ice packs + Cold packs

Este produto requer transporte de cadeia fria. Serviços terrestres e outros serviços econômicos não estão disponíveis.

Grau

Moligand™

Nomes e identificadores

• SMILES isoméricas: C1=CC(=C(C=C1C(C(=O)O)O)O)O
• PubChem CID: 85782
• Peso molecular: 184.15
• Beilstein: 10493
• Reaxy-Rn: 2104039

Propriedades químicas e físicas

• Ponto de fusão (°C): 131 °C

Referências

1. Xin Huang, Rui Wang, Yikai Wang, Changbao Chen, Shuying Liu.  (2022)  Investigation on property differences of ginseng and American ginseng by spatial metabolomics of neurochemicals with desorption electrospray ionization mass spectrometry imaging.  JOURNAL OF ETHNOPHARMACOLOGY,      [PMID:36516905] [10.1016/j.jep.2022.116006]

Application Protocols

No assay protocols are specified for this item. As a small molecule/standard, it is not validated for immunoassays like WB/IHC/IF/FC. General research-use handling suggestions:

• LC–MS reference standard (literature practice): Prepare 1–10 mM stocks in degassed DMSO; dilute into mobile phase or aqueous buffer just before injection. Use amber vials; keep samples on ice and minimize autosampler residence time to limit oxidation.
• Enzymology/biochemical assays: Prepare fresh working solutions at the required concentration in buffer pH 3.5–6 or in aqueous ethanol. Degas buffers and include metal chelators if compatible.

Item-specific, tested applications and recommended dilutions are Not specified for this item; refer to CoA/Spec Sheet.

Biological Roles

Literature context only (no clinical claims):

• Endogenous metabolite: 3,4-Dihydroxymandelic acid (DHMA) is a known oxidative metabolite in catecholamine biochemistry. It can arise from norepinephrine/epinephrine metabolism via monoamine oxidase (MAO) and catechol‑O‑methyltransferase (COMT) pathways, interconverting with related acids such as 3,4‑dihydroxyphenylglycolic acid and vanillylmandelic acid in multi‑step sequences.

• Chemical biology features:

  • Catechol moiety enables strong, reversible binding to metal centers and metal oxides, relevant for studying metal-mediated redox chemistry and surface interactions.
  • The α‑hydroxycarboxylate motif allows participation in hydrogen-bond networks and can influence protein–ligand recognition in enzyme assays designed to probe catechol/phenol binding pockets.

• Redox behavior: Catechols are readily oxidized to o‑quinones, which can engage in Michael-type additions with nucleophiles (thiols, amines). Researchers exploit this to study oxidative stress chemistry and covalent modification of nucleophiles in vitro (controlled model systems).

• Analytical relevance: DHMA is used as a calibration/derivatization analyte in chromatographic and electrochemical detection methods for catechols and related biogenic pathways.

Note: All uses are for laboratory research only. Biological occurrence, pathways, and transformations cited above are general literature information and not specifications of this item.

Buffer Applications

This compound is not a standard laboratory buffering agent. While it contains an acidic carboxyl group (literature pKa ~3.0–3.5) and phenolic groups (pKa ~9–10), it is not commonly employed to formulate defined pH buffers.

• Practical guidance (if considered for specialized systems):

  • Any buffering capacity would be narrow around its pKa values and complicated by catechol oxidation, especially above neutral pH.
  • For robust, well-characterized buffering, prefer established systems (e.g., citrate pH 3–6, phosphate pH 6–8, Tris pH 7–9).

• Compatibility: If DHMA must be present in a buffered assay, select buffers that minimize oxidation (citrate/acetate at mildly acidic pH) and avoid transition-metal contamination. Deaeration and light protection are recommended.

Summary: Not typically applicable as a buffer. See Solvent Selection and Storage & Reconstitution for more relevant handling guidance.

Green Alternatives

This product is a solid building block/standard rather than a process solvent. Greener practice thus focuses on solvent/media choices and protection of the catechol without resorting to hazardous reagents.

• Prefer greener solvents when feasible (literature-based guidance):

  • Water (pH 3.5–6) or aqueous ethanol for handling and crystallizations, balancing solubility and stability.
  • Ethanol over methanol where possible (reduced toxicity) for esterifications or stock solutions compatible with biology.
  • Ethyl acetate or 2‑MeTHF for extractions/processing instead of chlorinated solvents, provided solubility permits.

• Oxidation‑sensitive handling without heavy metals:

  • Limit transition-metal exposure (Cu/Fe catalyze catechol oxidation). Use plastic spatulas or passivated tools.
  • Employ oxygen exclusion (N2/Ar) and amber glassware rather than adding excess chemical antioxidants.

• Example comparison (general):

  Solvent | Greenness notes | Use with DHMA (literature)

  • DMSO | Polar aprotic; low volatility; acceptable but challenging to remove | Excellent stock solvent; stable when protected from light/air
  • Ethanol | Renewable routes; lower toxicity than MeOH | Good co-solvent; suitable for prep and some assays
  • Water | Benign; no VOCs | Good at pH ~3.5–6; watch oxidation at basic pH
  • Dichloromethane | Problematic (halogenated, volatile) | Generally avoid; limited solubility anyway

Adopt minimal solvent volumes, recycle where practical, and favor catalytic over stoichiometric reagents in derivatizations.

Pharmaceutical Uses

No excipient or pharmacopeial role is specified for this item; refer to CoA/Spec Sheet for any regulatory status. The following reflects general research/manufacturing context without therapeutic claims:

• Analytical standard: Used in research and development as a reference/impurity standard for chromatographic and mass-spectrometric methods targeting catechol- and mandelate-related species.

• Process/quality support (research stage):

  • Method development: Evaluating extraction, derivatization (e.g., dansylation, silylation), and detection conditions for catechol-containing analytes.
  • System suitability: Stress-testing oxidation controls and metal-scavenging conditions in stability-indicating methods.

• Formulation R&D considerations: Due to its catechol, DHMA is oxidation-prone and not commonly considered as an excipient. Any formulation work remains at the exploratory research stage, typically employing antioxidants, low oxygen headspace, and amber packaging for stability studies.

Item-specific pharmacopeial listings, residual solvent limits, and impurity profiles are Not specified for this item; refer to CoA/Spec Sheet. All uses are strictly for research laboratory applications.

Physical Properties

Item-specific specifications are not provided in the Product Data. The following are literature/general values and guidance; do not treat as item specifications.

• Physical state/appearance: Not specified for this item; refer to CoA/Spec Sheet. (Literature: typically an off-white to tan solid due to catechol oxidation sensitivity.)
• Melting point: Decomposes on heating; discrete MP values vary by source and hydration/form (literature; values reported roughly in the 140–180 °C range depending on form). Treat with caution due to oxidation and decarboxylation tendencies.
• Boiling point: Not applicable (decomposes before boiling at atmospheric pressure) (literature).
• Density: Not specified for this item; refer to CoA/Spec Sheet.
• pKa (aqueous, 25 °C, literature ranges):
  • Carboxylic acid pKa ~3.0–3.5.
  • Phenolic OH pKa values typically in the ~9–10 range for catechols (second phenolic deprotonation much higher, >12).
• LogP/logD: Expected low logP and pH-dependent logD due to acid and phenols (literature qualitative assessment).
• Solubility (qualitative, literature):
  • Water: moderate; increases strongly above pH ~4 as the carboxylate forms; high at basic pH. Susceptible to air oxidation in alkaline solution.
  • Polar organics: soluble in methanol, ethanol; highly soluble in DMSO/DMF.
• UV–Vis: Catechol chromophore absorbs in near‑UV; oxidation causes visible darkening (literature trend). Exact cutoffs/ε: Not specified for this item; refer to CoA/Spec Sheet.
• Refractive index: Not applicable (solid) / Not specified for this item; refer to CoA/Spec Sheet.

Quality and Grades

• Grade: Moligand™ (as provided). While no formal industry definition exists for this proprietary designation, Moligand™ in our catalog denotes small-molecule library members suitable for screening and discovery workflows (e.g., biochemical/biophysical assays, fragment or ligand discovery), provided strictly for research use.

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

• Stabilizers/inhibitors: Not specified for this item; refer to CoA/Spec Sheet. Note that catechol-containing compounds are sometimes supplied with antioxidant stabilizers or packaged under inert atmosphere to limit oxidation; check the CoA for details specific to your lot.

What the grade implies for practice (general guidance):

• Identity is controlled to support library/assay reproducibility; consult the CoA for analytical data (e.g., NMR, LC–MS, HPLC purity trace) associated with your lot.
• For HTS/biochemical screening, low nonvolatile residue and compatibility with DMSO stock solutions are typical expectations; however, exact solution quality metrics (peroxide content, metal content, water content) are Not specified for this item; refer to CoA/Spec Sheet.

Packaging/format (general for library items):

• Often supplied in small vials or plates suitable for DMSO reconstitution. If plate/vial format matters, confirm with Customer Service/CoA.

Traceability:

• SKU D1494787; retain lot numbers and CoA for data integrity and audit trails.

Reaction and Applications

3,4-Dihydroxymandelic acid combines a catechol with an α‑hydroxycarboxylic acid, enabling diverse chemistry and utility.

• Analytical/standards (literature use): Reference/derivatization standard in studies of catecholamine metabolism and catechol-containing systems; often handled as DMSO concentrates for LC–MS workflows.

• Coordination/chelation: The ortho‑dihydroxy motif and neighboring α‑hydroxycarboxylate furnish bidentate/tridentate binding to many transition metals. Useful in preparing model complexes, surface anchors, and metal–organic assemblies.

• Protection/derivatization strategies:

  • Catechol protection: O‑methylation (MeI/Me2SO4), O‑benzylation (BnBr, K2CO3, acetone/DMF), or O‑acylation (Ac2O, pyridine) to stabilize against oxidation during multistep synthesis.
  • Carboxyl protection: Esterification (MeOH–HCl, Fischer) or DCC/DMAP‑mediated formation of alkyl/aryl esters. α‑Hydroxy can be silylated or acylated selectively under control.

• Transformations (literature/general):

  • Oxidation of the benzylic secondary alcohol to the corresponding α‑keto acid (e.g., TEMPO/bleach, Dess–Martin, or Swern), enabling further decarboxylation or coupling.
  • Amide formation via activation of the carboxylate (EDC/HOBt, HATU) for conjugates and probes.
  • Decarboxylation under radical/thermal conditions to give catecholic benzylic alcohols/derivatives.

• Practical tips:

  • Maintain inert atmosphere and light protection for catechol intermediates; use acid-washed glassware to reduce trace metals.
  • For selective O‑functionalization, preform metal catecholates (e.g., Na/K salt) to direct reactivity; quench carefully to avoid oxidation.

All applications are for research use only.

Reaction Conditions

General, literature-based guidance for typical transformations of 3,4-dihydroxymandelic acid. These are not item specifications; optimize for your system.

• Stock solution preparation (analytical use): 10–50 mM in anhydrous, degassed DMSO; vortex, brief sonication if needed. Store aliquots at −20 to −80 °C in amber vials. Dilute into aqueous buffers immediately before use.

• Catechol protection (O‑benzylation):

  • Reagents: BnBr (1.5–2.5 equiv), K2CO3 (3–4 equiv), dry acetone or DMF, 0.05–0.1 equiv TBAB optional.
  • Conditions: 0–25 °C, 2–16 h under N2. Work up with aqueous NH4Cl; purify by column chromatography. Alternative: BnCl/NaH in THF at 0 °C to rt (handle NaH precautions).

• Esterification (carboxyl protection):

  • Fischer: ROH (excess), catalytic H2SO4 or HCl(g), 0–25 °C to reflux; remove water (Dean–Stark for higher alcohols).
  • Steglich: ROH (1.2–2.0 equiv), DCC (1.2–1.5 equiv), DMAP (0.1 equiv), CH2Cl2 or EtOAc, 0 °C to rt.

• Oxidation to α‑keto acid:

  • Dess–Martin periodinane (1.3 equiv), CH2Cl2, 0 °C to rt, 1–3 h.
  • TEMPO/NaOCl (pH 8.5–9, biphasic), 0–5 °C, then rt; buffer carefully to limit catechol oxidation.

• Amide coupling:

  • HATU or EDC·HCl (1.1–1.5 equiv), HOAt/HOBt additive, DIPEA (2–3 equiv), DMF or NMP, 0 °C to rt, 1–16 h.

• Stability controls:

  • Exclude oxygen/light; add trace antioxidant (e.g., 0.1% ascorbate) if compatible. Minimize base strength and residence time in basic media.

Reported yields vary widely depending on protection strategy and substrate; monitor closely by LC–MS/HPLC.

Safety and Handling

Hazard classification for this specific item is not provided in the Product Data. Always consult the SDS for authoritative guidance.

• GHS/SDS: Not specified for this item; refer to SDS.
• Primary hazards (general, literature-based):
  • Irritation to eyes/skin/respiratory tract typical of organic acids and phenolics.
  • Catechols can auto‑oxidize to quinones, potentially generating reactive oxygen species; avoid strong bases, air, and light during handling to limit oxidation byproducts.
• PPE: Safety glasses, lab coat, and appropriate chemical-resistant gloves (e.g., nitrile). Handle powders in a fume hood to minimize dust inhalation.
• Storage incompatibilities: Avoid strong oxidizers, strong bases (which accelerate autoxidation), and transition-metal contaminants (copper/iron catalyze catechol oxidation). Keep away from light and air when possible.
• First‑aid overview (general):
  • Inhalation: Move to fresh air; seek medical attention if symptoms persist.
  • Skin/eyes: Rinse with water for at least 15 minutes; remove contaminated clothing; seek medical advice.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
• Handling tips specific to catechols (practical):
  • Work quickly with minimal air exposure; use amber glassware.
  • Prepare solutions freshly; purge with inert gas for sensitive work.
  • Maintain mildly acidic to neutral pH during solution prep to reduce oxidation.
• Waste: Collect phenolic/organic acid waste according to institutional and local regulations; segregate from oxidizers.

Solvent Selection

3,4-Dihydroxymandelic acid is a highly polar, hydrogen‑bonding solid with acid and phenolic functions. Solvent choice should balance solubility, stability (resistance to catechol oxidation), and downstream compatibility.

• Miscibility/solubility profile (literature trends):

  • Water: Good solubility above pH ~4 (carboxylate formation); limited in deionized water at low pH. Oxidation accelerates at basic pH; minimize air/light and consider degassing and metal chelators (e.g., EDTA) if alkaline solutions are required.
  • Alcohols: Methanol/ethanol generally dissolve well; isopropanol shows moderate solubility.
  • Dipolar aprotics: DMSO and DMF provide high solubility; DMSO is preferred for library stocks.
  • Nonpolar solvents (EtOAc, MTBE, hexanes): Poor solubility unless converted to neutral derivatives (esters/ethers) or paired with ion-pairing agents.

• Practical scenarios:

  • Screening stocks: 10–50 mM in dry, degassed DMSO; aliquot and store at −20 to −80 °C. Dilute into assay buffer immediately before use.
  • Preparative workup: Dissolve in minimal MeOH/H2O mixtures or adjust pH slightly basic to extract into aqueous; acidify to precipitate the free acid when needed.

• Stability considerations by solvent:

  • Aqueous basic media: fastest oxidation/darkening; use inert atmosphere and antioxidants if unavoidable.
  • Alcohols/DMSO: improved stability; still protect from light and air.

• When to choose alternatives:

  • For biophysical assays sensitive to DMSO, consider aqueous buffers at pH 3.5–6 or aqueous ethanol; confirm analyte stability empirically.

Storage and Reconstitution

• Storage conditions (as provided): Store at −80 °C.
• Shipping: Shipped on dry ice packs + cold packs.
• Research use note: For research use only.

Best practices (general, for catechol-containing solids):

• Keep container tightly closed under dry, inert atmosphere. Use amber vials to limit photodegradation/oxidation.
• After first opening, minimize headspace oxygen: backfill with nitrogen/argon; re‑cap promptly. Consider desiccant in secondary containment.

Reconstitution guidance (general):

• DMSO stocks: Dissolve to 10–50 mM in anhydrous, degassed DMSO. Vortex and briefly sonicate if needed. Filter (0.2 µm PTFE) if particulate persists.
• Aqueous solutions: For immediate use, dissolve in water or buffer adjusted to pH ~3.5–6 to balance solubility and stability. Avoid prolonged exposure above neutral pH. Degas solutions and protect from light.
• Aliquoting: Dispense single‑use aliquots to avoid repeated freeze–thaw. Label with concentration, solvent, and date.

Stability notes:

• Catechols are prone to air oxidation, especially in basic/oxygenated media; solutions may darken. Prepare fresh before critical experiments.
• Do not store solutions at room temperature. For short‑term (hours–days), keep at 2–8 °C protected from light; for longer term, freeze at −20 to −80 °C.

Any item-specific stabilizers, water content, or impurity limits are Not specified for this item; refer to CoA/Spec Sheet.

Structure and Identity

3,4-Dihydroxymandelic acid (often abbreviated DHMA) is a catechol-bearing α‑hydroxycarboxylic acid structurally related to mandelic acid.

• SKU: D1494787
• CAS: 775-01-9 (literature)
• PubChem CID: 85782 (literature)
• Molecular formula: C8H8O5 (literature)
• Molecular weight: ~184.15 g/mol (literature)
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.

Structural features (descriptive, literature-based):

• Aromatic ring bearing a 3,4‑dihydroxy (catechol) substitution pattern.
• Benzylic stereogenic center at the mandelic (α‑hydroxy) carbon: –CH(OH)–CO2H. Commercial material is typically racemic unless otherwise stated (no stereochemical specification provided for this item).
• Functional groups: phenolic diol (two Ar–OH), secondary alcohol (benzylic), and carboxylic acid.

2D structure in words:

• A substituted benzene ring with hydroxyls at the 3- and 4‑positions; at the 1‑position is a –CH(OH)–CO2H side chain. The proximity of the catechol and α‑hydroxycarboxylate enables strong intra/intermolecular hydrogen bonding and metal chelation (literature).

Synthetic Utility

Functional groups and reactivity (literature-based):

• Catechol (3,4‑diol): strong H‑bond donor/acceptor; oxidizable to o‑quinone; readily O‑alkylated/acylated/benzylated; forms stable catecholate salts and metal complexes.
• α‑Hydroxycarboxylic acid: enables esterification, amidation (after activation), lactonization with neighboring groups, and selective oxidation to α‑keto acids.

Strategic applications:

• Bifunctional chelating building block for anchoring to inorganic surfaces (e.g., metal oxides) while projecting a carboxylate/derivative for further coupling (linker chemistry, materials interfaces).
• Precursor to catechol‑containing monomers and crosslinkers; after suitable protection, can be incorporated into polymers or adhesives mimicking mussel-inspired adhesion.
• Scaffold for probe synthesis: derivatize the carboxyl (amide coupling via EDC/HOBt or HATU) while protecting the catechol (e.g., O‑benzyl). Subsequent global deprotection yields the active catechol motif.

Named/typical reactions (general):

• Fischer esterification (ROH/H+), Steglich esterification (DCC/DMAP), and carbodiimide couplings for amide/ester formation.
• TEMPO/Dess–Martin/Swern oxidation of the benzylic secondary alcohol to α‑keto acids, enabling further decarboxylation or aldol-type chemistry.
• Electrophilic O‑alkylation with alkyl halides or sulfate esters; catalytic hydrogenolysis for O‑benzyl deprotection (Pd/C, H2).

Practical notes:

• Conduct O‑functionalizations under inert atmosphere; monitor by LC–MS due to possible oxidation byproducts.
• Use mildly acidic workups and metal scavengers to maintain catechol integrity.

Target Specificity

Not applicable to this product type. 3,4-Dihydroxymandelic acid is a small molecule, not an antibody, protein, or nucleic-acid reagent. No antigen/epitope specificity, clone, isotype, or species reactivity applies.