Succinyl phosphonate - ≥98% , CAS No.26647-82-5

CAS: 26647-82-5 Cat. No.: S768914 Formula: C₄H₇O₆P Molecular Weight: 182.07

GRADE & PURITY ≥98%

Storage

Store at 2-8°C

Shipped In

Wet ice

Overview

Succinyl phosphonate is an inhibitor of alpha-ketoglutarate dehydrogenase.

Specifications

Specifications & Purity

≥98%

Storage

Store at 2-8°C

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥98%

Names and Identifiers

Canonical Smiles

C(CC(=O)P(=O)(O)O)C(=O)O

InChIKey

XUHDEWZJMFKPOD-UHFFFAOYSA-N

INCHI

1S/C4H7O6P/c5-3(6)1-2-4(7)11(8,9)10/h1-2H2,(H,5,6)(H2,8,9,10)

Isomeric SMILES

C(CC(=O)P(=O)(O)O)C(=O)O

Molecular Weight

182.07

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Fatty Acyls
      • Subclass Fatty acids and conjugates

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Fatty Acyls
• Subclass: Fatty acids and conjugates
• Intermediate Tree Nodes: Not available
• Direct Parent: Fatty acids and conjugates
• Alternative Parents: Organic phosphonic acids Monocarboxylic acids and derivatives Carboxylic acids Organophosphorus compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Fatty acid - Organophosphonic acid derivative - Organophosphonic acid - Monocarboxylic acid or derivatives - Carboxylic acid - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organophosphorus compound - Organooxygen compound - Carbonyl group - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as fatty acids and conjugates. These are aliphatic monocarboxylic acids with a saturated or unsaturated aliphatic tail (with at least 4 Carbon atoms).
• 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

Chemical and Physical Properties

• Molecular Weight: 182.070 g/mol
• XLogP3: -2.400
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 181.998 Da
• Monoisotopic Mass: 181.998 Da
• Topological Polar Surface Area: 112.000 Ų
• Heavy Atom Count: 11
• Formal Charge: 0
• Complexity: 215.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• 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

Not applicable—no tested bioassay protocols or analytical methods are specified for this item.

General suggestions (literature/general; not item-specific)

• Stock solutions: Prepare 10–100 mM in water or DMSO depending on solubility; filter through 0.22 μm for biochemical assays.
• Enzyme assays: Titrate across pH to account for multiple ionizations; include metal chelation controls if the target is metallo-dependent.
• Analytics: Use 31P NMR for identity and purity; HPLC with ELSD or UV at 210 nm; LC/MS in negative mode for confirmation.

For validated, application-specific protocols, consult primary literature once the exact structure and ionization state are confirmed from the CoA/Spec Sheet.

Biological Roles

Item-specific facts (from Product Data)

• None provided beyond research-use-only notice.

Literature/general discussion (not item-specific)

• Phosphonates are carbon–phosphorus analogs of phosphates and can act as stable mimics of tetrahedral phosphate intermediates in enzyme-catalyzed reactions. Because the C–P bond is not enzymatically hydrolyzed by most phosphatases, phosphonates often serve as competitive inhibitors or transition-state analogs in biochemical studies.
• A “succinyl” motif echoes metabolites in central carbon metabolism (e.g., succinate/succinyl derivatives). Researchers sometimes explore succinyl-phosphonate scaffolds to probe enzymes that bind succinyl-containing substrates. Actual binding or inhibition depends sensitively on the precise structure, ionization state, and stereoelectronics.
• The multiple acidic groups confer high charge density at physiological pH, which generally limits passive membrane permeability and favors extracellular or enzyme-active-site studies in vitro rather than cellular uptake without a carrier or prodrug strategy.

Caveats

• No biological target, potency, or mechanism is specified for this catalog item. Any biological role should be established empirically for the batch in hand using appropriate controls, and all use is for research only.

Buffer Applications

Relevance

• As a small-molecule acid/phosphonate, this compound is not a standard buffering agent like phosphate, HEPES, or acetate.

General guidance (literature/general)

• While not typically used to maintain pH, phosphonate-containing acids can contribute to buffering capacity within a narrow pH window around their pKa values. However, their primary use is as analytes, inhibitors, or ligands rather than as buffers.
• If preparing aqueous solutions for assays, select an appropriate external buffer system (e.g., phosphate, HEPES, MOPS, or Tris) at a concentration that does not interfere with the biochemical target. Consider possible metal chelation by phosphonates, which can affect buffer components that contain metal cofactors.

Practical notes

• Adjust solution pH after dissolving the compound, as ionization can shift final pH.
• Filter-sterilize solutions for biological assays to avoid heat exposure that may cause decomposition.

Item-specific buffer information

• Not specified for this item; refer to CoA/Spec Sheet for any recommendations regarding compatible buffers or pH ranges.

Green Alternatives

Context

• Item-specific green metrics are not provided. The guidance below addresses general greener handling and substitution strategies for phosphonate chemistry.

Strategies (literature/general)

• Prefer water as solvent when compatible with your transformation or assay; many phosphonates are highly water-soluble in salt form.
• Use DMSO in small percentages as a cosolvent rather than neat where possible; DMSO has favorable safety and environmental profiles compared with many dipolar aprotics.
• Avoid chlorinated solvents for routine handling; if organic extraction is needed, consider alcohols or esters where feasible.
• Minimize derivatization steps (e.g., transient esterification) unless strictly required; each protection/deprotection cycle adds waste.

Compact comparison (general)

• Water: nonflammable, benign, excellent for ionic compounds; may require pH adjustment.
• DMSO: high solvating power, low volatility; can transport solutes through skin—use PPE.
• DMF/NMP: effective but carry greater regulatory and reproductive-toxicity concerns; relegate to cases where alternatives fail.

Operational green tips

• Use aqueous workups without halogenated solvents when possible.
• Recover and reuse aqueous buffer streams for early screening rounds if cross-contamination risk is managed.
• Right-size batches to reduce surplus solution disposal.

Note

• For process development, conduct solvent selection via solvent guides (e.g., CHEM21/ACS GCI) and verify that chosen media maintain compound stability and assay integrity.

Pharmaceutical Uses

Scope

• No pharmacopeial status, excipient role, or formulation guidance is specified for this item. This product is supplied strictly for research use only.

Literature/general context (not item-specific)

• Phosphonates have been explored as research tools in medicinal chemistry due to their metabolic stability and ability to mimic phosphate esters. However, their high polarity often necessitates salt forms or prodrug strategies (e.g., phosphonate esters) for permeability in formulation research.
• In preclinical research settings, such molecules can serve as reference standards, enzyme probes, or mechanistic controls in ADME assays. Any use in drug product manufacturing would require comprehensive quality, impurity, and regulatory dossiers not provided here.

Formulation considerations (general)

• Aqueous salt solutions are typical for in vitro assays. For in vivo research (outside the scope of this catalog’s intended use), specialized enabling strategies are often required; no such guidance is provided for this product.

Statement

• No therapeutic or clinical claims are made or implied. For any application beyond bench research, consult regulatory guidance and develop a full CMC package.

Physical Properties

Item-specific facts (from Product Data)

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Density: Not specified for this item; refer to CoA/Spec Sheet.
• Melting point: Not specified for this item; refer to CoA/Spec Sheet.
• Boiling point: Not specified for this item; refer to CoA/Spec Sheet.
• Solubility: Not specified for this item; refer to CoA/Spec Sheet.
• LogP, pKa, refractive index: Not specified for this item; refer to CoA/Spec Sheet.

Literature/general physical behavior for phosphonates (not item-specific)

• Ionization: Phosphonic acids are typically diprotic with two acidic protons on phosphorus; additional carboxyl groups (if present) add further acidity. Reported pKa values for simple phosphonic acids are often around pKa1 ~1–2 and pKa2 ~6–8 (literature, compound-dependent). Carboxylates typically show pKa ~2–5 (literature, structure-dependent).
• Phase and form: Many low-molecular-weight phosphonates are crystalline solids or amorphous powders, often hygroscopic due to multiple acidic/ionic sites.
• Solubility profile: High aqueous solubility is common for phosphonic acids and their sodium/potassium salts; solubility in nonpolar organic solvents is generally poor. Polar aprotic solvents (DMSO, DMF) can dissolve many phosphonates (literature).
• Thermal behavior: Rather than exhibiting a sharp boiling point, multifunctional acids often decompose or char at elevated temperatures; drying/lyophilization is commonly used to prepare solid material.

Practical notes

• Prepare stock solutions in deionized water or aqueous buffer when feasible. For nonaqueous applications, DMSO stock solutions are commonly used in screening libraries. Verify concentration by weight and pH/neutralization state as appropriate.

Quality & Grades

Item-specific facts (from Product Data)

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

Guidance on grades and implications (general; not item-specific)

• Research grade: Suitable for discovery biology, enzymology, and synthetic method development. If HPLC or screening assays are sensitive to impurities, request or review the CoA for assay purity, residual solvents, inorganic content, and water content.
• Chromatography/UV considerations: Phosphonates typically have minimal UV chromophores; purity confirmation is often by HPLC with low-wavelength detection (e.g., 210 nm), ELSD, or ion chromatography. For NMR, 31P and 1H/13C provide orthogonal identity/purity confirmation.
• Counterions and form: Many phosphonates are offered as free acids or sodium/potassium salts. The exact form strongly affects molecular weight, solution pH, and solubility. Verify the counterion and hydration state on the CoA/Spec Sheet before preparing solutions.
• Stabilizers: Generally not required for inorganic-acid-like organophosphorus acids; however, moisture content can drift. If water content is controlled (e.g., Karl Fischer), this will appear on the CoA.

Recommendations

• Before critical assays, confirm: identity (NMR, HRMS), purity (HPLC/IC), inorganic content/anion balance, and pH of prepared solutions. Document batch-specific details from the CoA to ensure reproducibility across campaigns.

Reaction & Applications

Item-specific facts (from Product Data)

• Manufacturer application notes: Not specified for this item.

General applications for succinyl-phosphonate-type compounds (literature/general)

• Enzyme chemistry tools: Phosphonate motifs serve as stable, tetrahedral mimics of phosphate transition states. Succinyl-like backbones are used as probe scaffolds for enzymes that recognize succinate/succinyl fragments in metabolism (e.g., dehydrogenase or ligase families). These uses are research-only and require structure confirmation for target fit.
• Coordination and materials: Multidentate acid groups (phosphonic + carboxylic) can chelate metal ions, enabling studies in scale inhibition, surface modification, and metal–organic assemblies.
• Analogue synthesis: Carboxyl functions (if present) can be temporarily protected and later coupled to amines (amide formation) to access conjugates, probes, or immobilized ligands. Phosphonic acid can be esterified to tune lipophilicity or as protecting groups.

Practical execution

• Solution preparation: Use aqueous buffers or DMSO for stock solutions; filter-sterilize if biological assays are planned.
• Metal sensitivity: Phosphonates bind metal ions; use metal-free plastics or acid-washed glassware for precise biochemical measurements.
• pH control: Activity in enzyme assays is often pH-dependent due to ionization; prepare buffers across relevant pH windows to map SAR.

Note

• Specific reactivity or inhibitory profiles for this exact catalog item are not provided; consult primary literature and confirm identity and form via CoA before designing experiments.

Reaction Conditions

Item-specific reaction conditions are not provided. The following are general, literature-based guidelines for handling phosphonate/carboxylate chemistry; adjust to the confirmed structure and scale.

Esterification of phosphonic acids (general)

• Typical solvents: Toluene, benzene, or chlorobenzene with reflux in excess alcohol; or use POCl3/SOCl2 to form phosphonochloridate intermediates in DCM/THF at 0–25 °C then couple with alcohols/amines.
• Bases/catalysts: Pyridine, triethylamine, or DMAP when forming esters/anhydrides.

Amide coupling (for carboxyl group, if present)

• Solvents: DMF, DMSO, NMP, or aqueous-organic mixtures.
• Agents: EDC·HCl with NHS or HOBt; DIC/HOAt; PyBOP for challenging couplings.
• Temperatures: 0–25 °C, typically 1–16 h; monitor by LC/MS or HPLC.

Salt formation and neutralization

• Dissolve in water; titrate with NaOH/KOH to desired pH (e.g., pH 7–8 for neutral salts). Lyophilize to isolate salts.

Analytical monitoring

• 31P NMR (δP sensitive to protonation state), 1H/13C NMR for backbone, and LC/MS with negative ESI.

Workup tips

• Avoid silica gel for strongly acidic species; use ion-exchange chromatography or reverse-phase HPLC. If silica is used, pre-neutralize with triethylamine or use buffered eluents.

Note

• Verify compatibility with the specific item’s form (acid vs salt, hydration state) from the CoA before selecting reagents and conditions.

Safety & Handling

Item-specific facts (from Product Data)

• GHS classification, pictograms, H-statements, signal word: Not specified for this item; refer to SDS.
• Storage: Store at 2–8 °C. Shipped on wet ice.

General safety guidance for phosphonic/carboxylic acids (literature/general; not item-specific)

• Hazards: Polyacidic compounds can be irritating to skin, eyes, and mucous membranes. Dusts or aerosols may cause respiratory tract irritation. Salt forms can still be irritating.
• PPE: Use lab coat, safety glasses or goggles, and appropriate chemically resistant gloves (e.g., nitrile). Handle powders/solids in a fume hood to minimize inhalation of dust.
• Incompatibilities: Avoid strong bases (exothermic neutralization), strong oxidizers, and reactive acid chlorinating agents (e.g., thionyl chloride) unless under controlled synthetic conditions with appropriate engineering controls.
• First aid overview: In case of skin/eye contact, rinse with water for at least 15 minutes; remove contaminated clothing. If inhaled, move to fresh air. If ingested, rinse mouth; do not induce vomiting; seek medical attention. Always follow institutional SOPs.
• Fire safety: Many phosphonate salts are nonflammable; however, organic components may burn. Use water spray, CO2, dry chemical, or foam as appropriate for the surrounding fire. Combustion may release phosphorus oxides.

Authoritative source

• Consult the product-specific Safety Data Sheet (SDS) for definitive hazard classification, exposure limits, and spill/cleanup procedures.

Solvent Selection

Item-specific facts (from Product Data)

• Not specified for this item; refer to CoA/Spec Sheet for any solubility annotations.

General solvent guidance for phosphonate-containing acids/salts (literature/general)

• Primary solvents: Water and aqueous buffers are generally preferred due to high polarity and ionizable groups. Adjust pH to improve dissolution if supplied as free acid.
• Secondary solvents: DMSO and DMF dissolve many highly polar organics; DMSO stocks (10–100 mM) are common for screening. Methanol and ethanol may be partially effective; acetone, ethyl acetate, and hydrocarbons are typically poor.
• Dielectric considerations: High-dielectric media (water ε ~80; DMSO ε ~47) favor dissolution of ionic species. Low-dielectric solvents generally do not.

When to choose vs alternatives

• Choose aqueous systems when the experimental context allows ionic media (biochemical assays, ion-exchange, crystallization screens).
• Choose DMSO for compatibility with HTS plate formats and when aqueous solubility is insufficient at the desired concentration.
• If organometallic or water-intolerant steps are required, derivatization (e.g., transient esterification of the phosphonate or carboxyl) may be needed to enable solubility in aprotic solvents.

Practical tips

• Pre-wet with a small volume of water or DMSO before dilution into buffer. For free acids, titrate with NaOH or appropriate base to target pH for maximum solubility.

Storage & Reconstitution

Item-specific facts (from Product Data)

• Storage conditions: Store at 2–8 °C.
• Shipping: Shipped on wet ice.
• Appearance, solvent of reconstitution, concentration limits: Not specified for this item; refer to CoA/Spec Sheet.

General guidance (literature/general)

• Protection from moisture: Many phosphonates are hygroscopic. Keep container tightly closed. If the material is supplied as a hydrate or in solution, retain the original packaging to preserve concentration.
• Long-term storage: For solids, desiccation under inert gas is prudent. For aqueous solutions, refrigeration (2–8 °C) is typical; for extended storage, aliquot and freeze (−20 °C) if the compound is stable to freezing—verify on a small sample first.
• Reconstitution: Prefer deionized water or buffer at target pH. If solubility is limited, dissolve first in a minimal volume of DMSO, then dilute with water/buffer while mixing. Record the final pH.
• Freeze–thaw: Minimize cycles by aliquoting. Inspect for precipitation upon thawing; gently warm and mix to redissolve if appropriate.

Documentation

• Always record lot number, preparation date, solvent, pH, and concentration for traceability. Confirm identity/purity after extended storage by NMR or HPLC as needed.

Structure & Identity

Item-specific facts (from Product Data)

• Product name: Succinyl phosphonate (SKU: S768914)
• CAS: 26647-82-5
• PubChem CID: 46209593
• InChIKey: 427471 (as provided; note this is not a standard-format InChIKey string)
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.

Literature/general identity notes (not item-specific)

• “Succinyl phosphonate” commonly refers to a phosphonate analog of a succinyl fragment; structures reported in literature typically contain a phosphonic acid (–PO3H2) motif appended to a succinyl-like C4 backbone bearing carboxyl functionality. Such entities are highly polar, often isolated as acids or salts.
• Functional groups expected in representative succinyl phosphonate species: phosphonic acid (tetrahedral phosphorus, P(V)), carboxylic acid(s), and an aliphatic chain. These groups confer multiple ionizable sites and strong hydrogen-bonding capacity.

2D structural description (literature/general)

• The 2D sketch generally comprises a four‑carbon chain reminiscent of succinate, with one terminus bearing a carboxyl group and another position bearing a phosphonate group (P(=O)(OH)2). The phosphorus is tetrahedral with a P=O bond and two P–OH bonds; the carbon chain is saturated and may present an additional carboxylate depending on exact substitution pattern.

Important note

• Exact constitutional details (isomer/salt form, counterions, stereochemistry if any) for this catalog item are not specified above and should be confirmed from the CoA/Spec Sheet or SDS before use.

Synthetic Utility

General reactivity features (literature/general; not item-specific)

• Phosphonic acid functionality: Amenable to esterification (e.g., via alcohols under acidic conditions or using chlorinating agents to form phosphonochloridates), enabling protection or modulation of lipophilicity. The resulting dialkyl phosphonates are commonplace synthetic handles.
• Carboxyl functionality (if present in the succinyl portion): Can be activated with carbodiimides (EDC/HOBt, DIC/DMAP) or converted to mixed anhydrides for amide coupling to amines or immobilization on amine-functionalized resins.
• Metal binding: The juxtaposition of phosphonate and carboxylate groups creates chelating ligation sites useful for assembling metal–organic frameworks or surface grafting onto metal oxides (TiO2, ZrO2, Al2O3).

Representative transformations

• Protection strategy: Convert phosphonic acid to its diester to permit operations in nonaqueous media; deprotect under TMSBr or bromotrimethylsilane/methanol sequences to regenerate the acid.
• Conjugation: EDC/NHS activation of a carboxyl group to couple with amines, generating amide-linked conjugates containing a persistent phosphonate moiety.
• Salt selection: Prepare sodium/potassium salts to enhance aqueous solubility for subsequent reactions or assays.

Practical tips

• Ensure rigorous drying when performing esterifications; water severely suppresses yields.
• Track phosphorus by 31P NMR to monitor conversion and purity across steps.

Note

• Exact functional group count and positions for this catalog item are not specified; adapt conditions to the confirmed structure from the CoA.

Target Specificity

Not applicable to this product category.

• This item is a small molecule, not an antibody or biological affinity reagent. No antigen, epitope, species reactivity, clone, or isotype information applies.
• If used as an enzyme probe or ligand in research, any target preference must be established empirically for the specific structure and lot; no item-specific target data are provided.

Frequently Asked Questions

What is the purity of this product?

This product is supplied at ≥98% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at 2–8 °C. Refrigerated storage is required to maintain the specified shelf life.

How is this product shipped?

This product ships chilled on wet ice. Unpack on arrival and transfer it to the storage condition stated above.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 26647-82-5, the molecular formula is C4H7O6P, and the molecular weight is 182.07 g/mol. InChIKey XUHDEWZJMFKPOD-UHFFFAOYSA-N.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.