2,3-Dihydroxysuccinohydrazide - ≥95% , CAS No.292644-27-0

CAS: 292644-27-0 Cat. No.: D1357328 EG-Nummer: 259-349-4 PubChem CID: 245684

GRADE & PURITY ≥95%

Storage

Room temperature

Shipped In

Normal

Specifications

Spezifikationen & Reinheit

≥95%

Storage

Room temperature

Verschickt in

Normal

Reinheit

≥95%

Namen und Kennungen

Kanonisches Lächeln

C(C(C(=O)NN)O)(C(=O)NN)O

IUPAC Name

2,3-dihydroxybutanedihydrazide

InChIKey

MDJZGXRFYKPSIM-UHFFFAOYSA-N

INCHI

1S/C4H10N4O4/c5-7-3(11)1(9)2(10)4(12)8-6/h1-2,9-10H,5-6H2,(H,7,11)(H,8,12)

Isomere SMILES

C(C(C(=O)NN)O)(C(=O)NN)O

Alternative CAS-Nummer

80081-45-4,54789-92-3

PubChem CID

245684

NSC-Nummer

57884

MeSH-Eintrag

tartaric acid dihydrazide

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Klasse Organooxygen compounds
      • Subclass Carbohydrates and carbohydrate conjugates

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Klasse: Organooxygen compounds
• Subclass: Carbohydrates and carbohydrate conjugates
• Intermediate Tree Nodes: Not available
• Direct Parent: Monosaccharides
• Alternative Parents: Secondary alcohols Carboxylic acid hydrazides 1,2-diols Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Monosaccharide - Secondary alcohol - Carboxylic acid hydrazide - 1,2-diol - Carboxylic acid derivative - Organic nitrogen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organonitrogen compound - Carbonyl group - Alcohol - Aliphatic acyclic compound
• Beschreibung: This compound belongs to the class of organic compounds known as monosaccharides. These are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemische und physikalische Eigenschaften

• Molekulargewicht: 178.150 g/mol
• XLogP3: -3.900
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 178.07 Da
• Monoisotopic Mass: 178.07 Da
• Topological Polar Surface Area: 151.000 Ų
• Heavy Atom Count: 12
• Formal Charge: 0
• Complexity: 164.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 2
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Application Protocols

No manufacturer-validated protocols are provided for this specific item. The following outlines generic workflows for common uses of hydrazide reagents (literature-based; adjust to your system):

• Aldehyde-bearing biomolecule conjugation (hydrazone ligation)

  1. Prepare 10–50 mM stock of 2,3-dihydroxysuccinohydrazide in water or DMSO.
  2. Mix with aldehyde-functional biomolecule in 50–100 mM acetate buffer, pH 5.0–5.5; optional 10–50 mM aniline catalyst.
  3. Incubate at RT for 1–3 h. Monitor by MS or SDS-PAGE as appropriate.
  4. Optionally reduce with NaBH3CN (bioconjugation-grade) to stabilize the linkage; desalt.

• Carbonyl scavenging in synthesis

  1. Dissolve reagent in MeOH/H2O or DMSO.
  2. Add to reaction mixture containing residual aldehyde/ketone; stir at RT until consumption (TLC/LC–MS).
  3. Remove formed hydrazone by filtration or aqueous wash, depending on solubility.

• Boronate capture (diol handle)

  1. Combine with arylboronic acid (1–2 equiv) in neutral buffer or MeOH.
  2. Use complexation for affinity separation; reverse by dilution or mild acid.

Validate conditions on small scale. For regulatory or QC-critical work, develop and document an internal SOP.

Biological Roles

• Item-specific biological role information: Not specified for this item; this product is provided for research use only.

• General biochemical context (not item-specific)

  • Hydrazide reagents are widely used in bioconjugation to couple to aldehyde/ketone-bearing biomolecules (e.g., periodate-oxidized glycans on glycoproteins) forming hydrazone linkages that can be subsequently stabilized by reductive amination.
  • The vicinal diol motif can engage in reversible complexation with boronic acids, a principle exploited in saccharide sensing and affinity separations; in a reagent scaffold, such interactions can be used for purification or dynamic assembly.
  • No endogenous metabolic role is known for 2,3-dihydroxysuccinohydrazide; it is a synthetic small molecule. Any interaction with enzymes or transporters would be incidental and context-dependent.

• Use considerations in bio-settings

  • For protein/glycan conjugation, maintain mild pH and avoid high concentrations of competing carbonyls. Confirm biocompatibility of solvents (e.g., limit DMSO to ≤10% v/v).
  • Analytical verification by SDS-PAGE, SEC, and MS is recommended to quantify conjugation efficiency and to assess stability of hydrazone linkages.

Buffer Applications

This compound is not a buffering agent and does not define a standard buffer system.

• Practical note
  • For hydrazone ligations, buffers at pH 4.5–6.0 (e.g., 100 mM sodium acetate or citrate) are commonly used to accelerate imine/hydrazone formation while maintaining biomolecule integrity (literature guidance).
  • Avoid buffers containing free aldehydes/ketones (e.g., formaldehyde) or reactive carbonyl contaminants.

Item-specific buffer recipes, pKa values, or buffering ranges are not provided for this product.

Green Alternatives

This product is a reagent, not a process solvent; “green alternatives” focus on process choices surrounding its use rather than replacing the reagent itself.

• Greener media for use

  • Prefer water or aqueous buffers for hydrazone ligations over high-boiling polar aprotics (DMF, NMP). DMSO can be used at minimal percentages (≤10–20%) only as needed for solubility.

• Benign catalysts

  • Use water-compatible nucleophilic catalysts (e.g., aniline, p-anisidine) at low loadings to accelerate hydrazone formation, reducing energy/time.

• Workup/waste minimization

  • Favor aqueous workups and precipitation over chlorinated extractions when feasible. For scavenging applications, consider solid-supported alternatives to reduce solvent use.

• Comparison snapshot (general) | Aspect | Conventional choice | Greener option | |---|---|---| | Coupling solvent | DMF/NMP | Water, aqueous buffer, EtOH | | Catalyst | HOAc-only (slow) | Trace aniline derivatives (faster, lower energy) | | Isolation | DCM/EtOAc extraction | Antisolvent precipitation, filtration |

Note: No greener “replacement reagent” is suggested, as the unique bifunctional hydrazide/diol features define its role.

Pharmaceutical Uses

No pharmacopeial status or excipient role is specified for this item; it is supplied for research use only.

• General formulation context (not item-specific)

  • Hydrazide reagents can serve as linkers in conjugation workflows (e.g., attaching carbonyl-containing payloads to polymers or biomolecules) during research formulation development.
  • The diol unit may increase aqueous solubility of conjugates and enable additional purification handles (boronate affinity), but any use in finished drug products would require separate qualification and regulatory assessment.

• Handling in formulation R&D

  • Prepare concentrated stocks in water or DMSO and dilute into isotonic buffers if used in bioconjugation screening. Filter-sterilize solutions through 0.22 µm membranes when sterility is required for cell-free assays.

No claims are made for clinical or therapeutic applications.

Physical Properties

• Item-specific (from Product Data)

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

• Literature/estimated behavior (general guidance; not item specification)

  • State: Typically an organic solid at ambient conditions for polyfunctional hydrazide-diols.
  • Polarity/H-bonding: Strongly hydrogen-bonding (multiple donors/acceptors), consistent with high lattice energy and hydrophilicity.
  • Solubility profile: Expected to be soluble in water and highly polar protic/aprotic solvents (e.g., aqueous buffers at mildly acidic to neutral pH, DMSO, formamide). Sparing in nonpolar solvents. Actual solubility for this item is not specified; verify experimentally.
  • Partitioning: Very low logP anticipated due to diol + dihydrazide functionality (literature expectation for analogous compounds); exact value not specified.
  • Thermal behavior: Hydrazide-containing materials may decompose before boiling; drying under reduced pressure at ≤40–50 °C is typically advisable. Specific MP/BP for this item are not specified.

• Do not treat the above as specifications. For authoritative values (mp, solubility, water content, elemental analysis), consult the item’s CoA/Spec Sheet.

Quality and Grades

• Item-specific (from Product Data)

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

• Guidance on grade meaning (general)

  • If supplied as “≥98%” or similar, this indicates assay by HPLC/GC/quantitative NMR with typical residual solvent and water controls; low residual metals are not generally critical for this class unless used in metal-catalyzed steps.
  • For bioconjugation uses, impurities such as mono-hydrazide or over-oxidized byproducts may influence performance; review impurity profile if provided.

• Stabilizers and additives

  • No stabilizer is listed for this item. Hydrazides generally do not require stabilizers; however, moisture can influence hydration state and handling. Any stabilizers, water content, or residual solvents specific to this lot: Not specified; refer to CoA/Spec Sheet.

• Documentation

  • For batch-specific assay, residual solvent, water content (Karl Fischer), and chromatographic purity, consult the Certificate of Analysis (CoA). Request spectral data (1H/13C NMR, IR, HRMS) if needed for regulated workflows.

Reaction and Applications

Functional profile suggests two orthogonal handles: (1) terminal hydrazide groups for chemoselective ligation to carbonyl compounds and acyl donors; (2) a central vicinal diol for reversible boronate complexation or oxidative manipulation.

• Hydrazide chemistry (general)

  • Hydrazone formation with aldehydes/ketones under mildly acidic conditions (pH 4–6), often catalyzed by anilinium or ortho-phenylenediamine. Useful for reversible/locking bioconjugation after NaBH3CN or NaBH(OAc)3 reduction.
  • Acylation to form acyl hydrazides via active esters (e.g., NHS-esters); can act as a bifunctional nucleophile or as a scavenger for activated carboxylates in synthesis/cleanup.

• Diol chemistry (general)

  • Formation of cyclic boronate esters with arylboronic acids, enabling affinity separations or dynamic covalent capture.
  • Periodate oxidation of vicinal diols to generate dialdehydes, creating additional sites for hydrazone coupling (caution: may fragment if diol cleavage occurs). Alternatively, diol protection or acetalization is possible.

• Crosslinking/linker concepts

  • As a symmetrical dihydrazide, it can crosslink two carbonyl-bearing partners. The central diol can enhance aqueous solubility and offer orthogonal capture/release handles.

• Practical tips

  • Keep solutions mildly acidic for hydrazone formation; add 10–50 mM aniline catalyst to accelerate conjugation at room temperature.
  • Exclude competing reactive carbonyls (e.g., DMF decomposition products) and avoid strong oxidants during handling.

Manufacturer-provided application details for this specific catalog item are not listed; the above are literature-based general applications.

Reaction Conditions

General literature-guidance for transformations involving dihydrazide/diol scaffolds (not item-specific specifications):

• Hydrazone formation with aldehydes/ketones

  • Solvent: Water or 1:1 water/MeOH; optional 5–20% DMSO for solubility.
  • pH: 4.5–6.0 (acetate or citrate buffer). Catalysis with 10–100 mM aniline or p-anisidine accelerates reaction.
  • Temperature/time: RT to 37 °C; 0.5–4 h for simple aldehydes, longer for hindered ketones.
  • Workup: Direct use or reduction with NaBH3CN/NaBH(OAc)3 to stabilize linkages.

• Acylation of hydrazide nitrogens

  • Reagents: NHS-esters or EDC/NHS activation of carboxylic acids; base control with DIPEA or mild bicarbonate in aqueous-organic media.
  • Solvents: DMF, DMSO, or water/DMF mixtures; keep temperature ≤25–30 °C to limit overacylation.

• Diol manipulations

  • Boronate ester formation: Arylboronic acid (1.1–2.0 equiv) in MeOH or buffer, pH 7–8; reversible upon dilution or acidification.
  • Periodate oxidation: NaIO4 (0.5–1.2 equiv per diol) in water at 0–25 °C, minutes to 1 h; quench excess periodate to protect hydrazide nitrogen.

• Analytical control

  • Monitor by LC–MS, 1H NMR (D2O or DMSO-d6). For aqueous reactions, UV at 254 nm may be weak; use MS or derivatization as needed.

Actual optimal conditions depend on substrates and are to be determined experimentally.

Safety and Handling

• Item-specific hazard information (from Product Data)

  • 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 hydrazides (literature/general; not item-specific)

  • Likely hazards: May cause skin/eye irritation; hydrazide derivatives can present sensitization risks and may be harmful if swallowed or inhaled. Avoid dust formation and inhalation.
  • PPE: Safety glasses, lab coat, appropriate chemical-resistant gloves (e.g., nitrile). Handle in a fume hood when weighing or dissolving to minimize inhalation exposure.
  • Incompatibilities: Strong oxidizers, strong reducing agents, acyl/activated ester reagents (uncontrolled reaction), nitrosating agents (risk of N-nitroso formation). Avoid contact with aldehydes/ketones unless intended, as hydrazone formation can occur.
  • First aid (overview; consult SDS): Rinse eyes/skin with water for ≥15 minutes if contacted. If inhaled, move to fresh air. If ingested, rinse mouth; seek medical attention.
  • Fire response: Although highly polar compounds are often nonflammable, packaging and dust may burn. Use water spray, alcohol-resistant foam, or CO2 as appropriate. Thermal decomposition may release nitrogen oxides and carbon oxides.

Always consult the product-specific SDS for authoritative hazard, exposure limits, and response guidance before use.

Solvent Selection

This compound is a highly polar, polyfunctional organic solid. Solvent choice should balance dissolution, reactivity control (especially hydrazone formation), and downstream workup.

• Polarity and miscibility (general behavior)

  • Preferred: Water, aqueous buffers (pH 4–7), DMSO, DMF, formamide, methanol, ethanol.
  • Limited solubility expected in: Acetonitrile (variable), isopropanol (variable).
  • Poor solubility in: Ethers (THF, MTBE), chlorinated solvents, and hydrocarbons.

• Practical guidance

  • Stock solutions for conjugation chemistry are often prepared at 10–100 mM in water or DMSO, then diluted into buffered media.
  • If aqueous dissolution is slow, sonication or gentle warming (≤40 °C) can help. Avoid basic media if hydrolysis of hydrazide is a concern.
  • For extractions, the material may remain in the aqueous phase; consider ion-pair or salting-out strategies only if compatible with your application.

• Comparison (general)

  • Water vs DMSO: Water is greener and ideal for hydrazone ligations at mildly acidic pH; DMSO improves solubility at high concentrations and can minimize side reactions with carbonyl-containing co-solvents.
  • Alcohols (MeOH/EtOH): Useful for recrystallization or intermediate dissolution but may compete weakly in hydrogen-bond networks.

Note: No item-specific solubility specifications are provided; validate solvent compatibility on a small scale.

Storage and Reconstitution

• Item-specific (from Product Data)

  • Storage conditions: Room temperature.
  • Shipped in: Normal.

• General guidance (not item-specific specifications)

  • Keep container tightly closed in a dry place; protect from prolonged exposure to moisture and air to maintain consistent assay and handling.
  • If long-term storage is anticipated, consider desiccated conditions and protect from light as a precaution for nitrogen-rich organics.
  • Reconstitution: Prepare fresh solutions in water, buffer, or DMSO. For sensitive bioconjugation work, filter-sterilize solutions (0.22 µm) and use within the same day.
  • Freeze–thaw: If solutions must be stored, aliquot and freeze at −20 °C to avoid repeated freeze–thaw cycles. Assess stability by LC–MS before critical experiments.

• Specifications such as water content limits, residual solvent, or stabilizers: Not specified for this item; refer to CoA/Spec Sheet.

Always follow the SDS and CoA for lot-specific handling and stability information.

Structure and Identity

Brief intro: 2,3-Dihydroxysuccinohydrazide is a polyfunctional small molecule bearing both carbohydrazide and vicinal diol motifs, suitable for conjugation and derivatization chemistry.

• Item-specific (from Product Data)

  • Product name: 2,3-Dihydroxysuccinohydrazide (SKU: D1357328)
  • CAS: 292644-27-0
  • PubChem CID: 245684
  • InChIKey: 216197 (as provided)
  • 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.

• Inferred structural features (general chemical interpretation; not item specification)

  • Core: succinyl (butanedioyl) backbone bearing terminal carbohydrazide groups (–CONHNH2) at both C-1 and C-4 positions.
  • Substitution: vicinal diol at C-2 and C-3 (–CHOH–CHOH–), i.e., a 2,3-dihydroxy substitution on the succinyl chain.
  • Functional groups: two hydrazide carbonyls, two hydrazide N–H donors, two secondary alcohols; multiple H-bond donors/acceptors; high polarity.
  • Stereochemistry: the 2,3-diol center could, in principle, exist as meso or racemic stereoisomers depending on synthesis; specific stereochemical form is not provided in the Product Data.

• 2D structural description (general): a four-carbon chain with carbonyls at both ends (amide-type C=O) connected to –NH–NH2 termini; the inner two carbons each carry a hydroxyl group, forming a vicinal diol between the two carbonyls.

Synthetic Utility

2,3-Dihydroxysuccinohydrazide offers convergent reactivity: terminal hydrazides for carbonyl capture/acylation and a central vicinal diol for orthogonal manipulations.

• Strategic transformations (general)

  • Double hydrazone formation enabling crosslinking of two aldehyde/ketone partners; subsequent reductive amination furnishes stable C–N bonds.
  • Selective mono-acylation to generate asymmetry; the remaining hydrazide remains available for further elaboration (e.g., urea formation with carbamoyl donors, coupling to activated esters).
  • Diol oxidation to dialdehyde creates an internal diformyl linker that can further react with nucleophiles (hydrazides, amines, hydroxylamines). Alternatively, reversible boronate formation enables capture/release strategies.

• Protecting group interplay

  • Hydrazide N-acyl protection or Boc-protection on nitrogen can modulate reactivity; acetonide or boronate protection for the diol provides orthogonality.

• Retrosynthetic value

  • As a symmetric building block, it enables modular construction of bis-conjugates or dendritic architectures with aqueous compatibility.

• Purification guidance

  • Products are often highly polar; favor reverse-phase chromatography, ion-pairing strategies, or precipitation from alcohol/ether mixtures. Monitor by LC–MS and 1H NMR in D2O/DMSO-d6.

Target Specificity

Not applicable. This product is a small-molecule reagent, not a biological targeting agent or antibody.

• Item-specific targeting details (antigen, epitope, species reactivity, clone, isotype): Not specified for this item and not applicable.

For biochemical conjugation specificity, see Reaction & Applications and Synthetic Utility.