cis,trans-Muconic acid - ≥97% , CAS No.1119-73-9

CAS: 1119-73-9 Cat. No.: C1027231 Formula: C₆H₆O₄ Peso molecolare: 142.110

GRADE & PURITY ≥97%

Storage

Room temperature

Specifications

Specifiche e purezza

≥97%

Condizioni di conservazione di stoccaggio

Room temperature

Purezza

≥97%

Nomi e identificatori

Sorrisi canonici

C(=C/C(=O)O)\C=C/C(=O)O

IUPAC Name

(2Z,4E)-hexa-2,4-dienedioic acid

InChIKey

TXXHDPDFNKHHGW-HSFFGMMNSA-N

INCHI

1S/C6H6O4/c7-5(8)3-1-2-4-6(9)10/h1-4H,(H,7,8)(H,9,10)/b3-1-,4-2+

Peso molecolare

142.110

Taxonomic Classification

Taxonomy Tree

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

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Classe: Fatty Acyls
• Subclass: Fatty acids and conjugates
• Intermediate Tree Nodes: Not available
• Direct Parent: Medium-chain fatty acids
• Alternative Parents: Unsaturated fatty acids Dicarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Medium-chain fatty acid - Unsaturated fatty acid - Dicarboxylic acid or derivatives - Carboxylic acid - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aliphatic acyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
• External Descriptors: muconic acid

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

Proprietà chimiche e fisiche

• Peso molecolare: 142.110 g/mol
• XLogP3: 0.200
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 142.027 Da
• Monoisotopic Mass: 142.027 Da
• Topological Polar Surface Area: 74.600 Ų
• Heavy Atom Count: 10
• Formal Charge: 0
• Complexity: 168.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 2
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 2
• Covalently-Bonded Unit Count: 1

Application Protocols

No tested biological assay protocols (e.g., WB, IHC, IF, FC) are provided for this item in the Product Data. Typical laboratory uses are synthetic and materials oriented (e.g., esterification to muconates, hydrogenation studies, enzymology of aromatic catabolism intermediates).

General preparation examples (literature-based, for reference):

• Stock solutions for analytical use: dissolve at 100–500 mM in DMSO or water with slight basification (e.g., 1–5 mM NaOH) to aid solubility; filter through 0.22 μm for clarity.
• Enzymology assays: prepare sodium muconate by neutralizing with equimolar NaOH; adjust ionic strength with KCl; confirm isomer state by UV/NMR if stereospecific enzymes are studied.

For application-specific, validated protocols, consult primary literature or develop method parameters empirically.

Biological Roles

General biochemistry context (literature; no medical claims):

• Aromatic catabolism intermediate: Muconic acid is a central metabolite in the β-ketoadipate pathway, arising from catechol or protocatechuate ring-cleavage via intradiol dioxygenases. The cis,trans isomer can appear upon isomerization of cis,cis-muconate by muconate cycloisomerase enzymes en route to muconolactone and ultimately β-ketoadipate.
• Enzymatic handling: isomerization and cycloisomerization steps are stereospecific; the E/Z configuration affects enzyme compatibility and flux through the pathway. Salts of muconate are commonly used in enzymology studies probing dioxygenase/cycloisomerase mechanisms.
• Microbial production: engineered microbes can overproduce muconic acid from glucose via the shikimate/catechol route, making it a target molecule in industrial biotechnology as a precursor to adipic acid and specialty polymers.
• Physicochemical influence: as a dicarboxylate at physiological pH, muconate engages in metal chelation and can influence transport across membranes via dicarboxylate transporters in microbes.

Note: Biological roles above describe general metabolism and research relevance; this product is for research use only.

Buffer Applications

Not a standard laboratory buffer component. As a dicarboxylic acid, cis,trans-muconic acid could, in principle, act as a weak buffering agent near its pKa values (literature generally places the two pKa values in the ~3–5 range), but it is not commonly used for buffering.

If used experimentally (general guidance):

• Prepare a sodium muconate buffer by titrating the acid with NaOH to the desired pH; buffering capacity will be modest and limited to acidic pH.
• Consider ionic strength and potential metal chelation effects in enzyme assays.
• For routine buffering between pH 3–6, conventional systems (citrate, acetate, MES) are preferred due to well-characterized properties and availability.

Item-specific buffer specifications: Not specified for this item; refer to CoA/Spec Sheet.

Green Alternatives

Context: This product is not a solvent; “green alternatives” considerations focus on process choices when using cis,trans-muconic acid as a bio-based platform chemical.

Greener process choices (literature/guidance):

• Bio-based sourcing: muconic acid can be produced via microbial pathways from renewable sugars or from lignin-derived aromatics, offering a lower carbon footprint compared with petro-derived adipic acid precursors.
• Solvent selection: prefer water or bio-based alcohols (EtOH) where possible. Employ biphasic water/green solvent systems for esterifications and hydrogenations to reduce reliance on chlorinated solvents.
• Catalysis: use heterogeneous catalysts (Pd/C, Raney Ni) in aqueous ethanol for hydrogenation to adipic acid, enabling catalyst recovery and lower E-factors.
• Energy: run esterifications under microwave or reactive distillation with azeotrope management to reduce time/energy.

Small comparison (general):

• Traditional approach: chlorinated solvents (CH2Cl2), oxalyl chloride, stoichiometric reagents.
• Greener variant: dimethyl carbonate or green acylation reagents; enzymatic esterification in solvent-free or ionic-liquid media; water/EtOH as reaction media when feasible.

Trade-offs:

• Aqueous systems may require salt management and corrosion-resistant equipment.
• Bio-based routes may introduce isomer/impurity profiles requiring additional purification; plan analytics accordingly.

Pharmaceutical Uses

This product is offered for research use only. No pharmacopeial grade or excipient status is specified for this item.

General formulation context (literature/inference without clinical claims):

• Functional group utility: as a dicarboxylic acid, muconic acid can form salts, esters, and amides; such derivatives may be explored as intermediates in medicinal chemistry or as components in polymeric excipients.
• Material science: dialkyl muconates are investigated for UV-absorbing coatings and specialty polymers that could, in principle, find roles in packaging or device materials; these are outside drug product excipient norms.

Item-specific statements:

• Grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
• Regulatory listing: No Ph. Eur./USP monograph references are provided for this listing.

For any work that touches regulated contexts, ensure suitability by consulting the lot-specific CoA and relevant pharmacopeial/ICH guidance.

Physical Properties

Item-specific specifications: Not specified for this item; refer to CoA/Spec Sheet.

Literature/general values (for cis,trans-muconic acid; values vary with isomeric purity):

• Appearance: white to off-white crystalline solid (literature)
• Molecular formula: C6H6O4; FW ~142.11 g/mol (literature)
• Melting point: typically reported around 200–210 °C (may soften/dec.) (literature)
• Boiling point: not practical; decomposes before boiling under ambient pressure (literature)
• Density: ~1.6–1.7 g/cm³ (solid, estimated from related diacids; consult primary data) (literature)
• pKa values: two acidic protons; reports generally place pKa1 and pKa2 in the ~3–5 range depending on medium and isomer (literature)
• Solubility: sparingly soluble in cold water; increased solubility in hot water and in aqueous base (to give muconate salts). Soluble in polar protic solvents (MeOH, EtOH) and DMSO; low solubility in nonpolar solvents (literature)
• LogP (neutral form): expected negative to slightly positive due to two CO2H groups; increases upon esterification (literature)
• UV/Vis: conjugated diene shows π→π* absorption in the near-UV (ca. 220–270 nm) with solvent/isomer dependence (literature)

Notes:

• Exact numeric specifications for this catalog item are not provided; verify property values relevant to your protocol using the CoA/SDS and primary literature.

Quality and Grades

Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.

Guidance for interpreting grades (general information for planning):

• Research grade vs. analytical grade: analytical/reagent grades typically include tighter controls on assay purity (e.g., >98–99%), inorganic residues, and moisture; research grade prioritizes suitability for general lab use.
• Isomeric purity: for geometric isomers such as cis,trans-muconic acid, specifications may include isomer ratio or maximum content of cis,cis and trans,trans isomers. If your application is isomer-sensitive (e.g., polymerization kinetics, spectroscopic reference standards), verify by NMR/HPLC.
• Residual solvents/metals: not specified for this item; consult CoA if your catalytic or polymer applications are metal-sensitive.
• Stabilizers: none are typical for this material; it is generally supplied neat. If stabilizers or anti-caking agents are present, they will appear on the CoA.

Recommendations:

• For polymer or medicinal chemistry workflows demanding low UV background or known water content, request current CoA/SDS for assay, moisture (Karl Fischer), and any chromatography traces.
• If lot-to-lot stereochemical consistency is critical, confirm with vendor-supplied chromatographic/NMR data.

Reaction and Applications

Applications (general, literature-based):

• Platform chemical: cis,trans-muconic acid is a bio-based C6 unsaturated diacid used as a precursor to adipic acid via catalytic hydrogenation (Pd, Ni, or Ru systems). It serves as an intermediate toward nylons and polyurethanes.
• Polyester/diester monomer: conversion to dialkyl muconates (e.g., dimethyl diester) gives monomers for free-radical or step-growth polymerization to yield specialty polymers and resins with tunable glass-transition temperatures and UV-absorbing properties.
• Functional-group interconversions:
  • Diacyl chloride formation (SOCl2 or oxalyl chloride) enabling amide/anhydride synthesis.
  • Esterification/transesterification to tailor solubility and reactivity.
  • Salt formation (Na, K, ammonium muconates) for aqueous catalysis or materials applications.
• Diene chemistry: the conjugated diene can participate in Diels–Alder cycloadditions with activated dienophiles (e.g., maleimides, acrylates) or undergo selective hydrogenation/epoxidation/ozonolysis to diversify scaffolds.
• Polymer crosslinking/UV-curable systems: muconate esters act as multifunctional crosslinkers; the conjugation imparts UV absorbance useful in coatings and lithography.

Practical notes:

• Drying: if moisture control is critical (e.g., for acyl chloride formation), dry the solid under vacuum at ambient to 40 °C; avoid overheating to prevent isomerization or dehydration side reactions.
• Isomer considerations: reactivity and polymerization behavior can vary with E/Z content. Verify isomer ratio by 1H NMR (vinyl coupling constants) prior to stereosensitive transformations.
• Degassing: for radical polymerizations of muconate esters, degas monomer solutions and employ oxygen scavengers to minimize inhibition.

Reaction Conditions

General literature guidance (illustrative; optimize per your system):

• Esterification (Fischer):
  • Conditions: ROH (MeOH/EtOH), catalytic H2SO4 or p-TsOH, reflux 2–12 h; remove water (Dean–Stark for higher alcohols) to drive to completion.
  • Workup: neutralize, extract; typical isolated yields for diesters 70–95% depending on alcohol and isomer purity.
• Acyl chloride formation:
  • Reagents: SOCl2 (2–5 equiv) or oxalyl chloride (1.5–3 equiv) with DMF catalyst, CH2Cl2 or toluene, 0–25 °C then to reflux if needed, 1–4 h.
  • Notes: ensure dry conditions; monitor by IR (loss of C=O(OH) stretch, appearance of acyl chloride band).
• Hydrogenation to adipic acid:
  • Catalyst/media: Pd/C or Raney Ni; solvent water/EtOH or acetic acid; H2 5–50 bar; 25–100 °C; 2–16 h.
  • Remarks: start from muconate salts for better solubility; over-hydrogenation of impurities can occur—use carbonyl analysis to confirm.
• Diels–Alder cycloadditions:
  • Partners: maleimides, acrylates, or electron-poor alkenes; solvent DMF, toluene, or ionic liquids; 80–140 °C (thermal) or Lewis-acid-catalyzed at lower T.
  • Stereochemistry: E/Z geometry and substitution pattern control endo/exo ratios and regiochemistry.
• Oxidations:
  • Epoxidation: mCPBA (1.1–2.2 equiv), CH2Cl2, 0–25 °C; subsequent ring opening diversifies products.
  • Ozonolysis: O3 at −78 to 0 °C in MeOH or CH2Cl2; reductive workup (Me2S) affords fragment diacids/dicarbonyls.

These conditions are representative literature ranges; consult primary sources and scale-appropriate safety reviews before execution.

Safety and Handling

Item-specific hazard data from Product Data:

• GHS classification, pictograms, signal word, and H-statements: Not specified for this item; refer to SDS.

General safety considerations for dicarboxylic acids and this structure (literature/best practice; not a substitute for SDS):

• Expected hazards: may cause skin/eye irritation; dust may irritate respiratory tract. Not known as highly acute-toxic, but handle as a laboratory chemical.
• PPE: lab coat, safety glasses or goggles, suitable gloves (e.g., nitrile). Use dust control (weighing in fume hood) to avoid inhalation.
• Storage: per Product Data, store at room temperature in a tightly closed container. Protect from moisture to prevent caking; avoid strong bases/acids if not intended, strong oxidizers, and reactive dehydrating agents.
• Incompatibilities: strong oxidizing agents (risk of exotherm), strong bases/acids (neutralization/esterification), acid chlorinating agents (SOCl2, oxalyl chloride) unless for intended synthesis.
• First aid (overview):
  • 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; remove contact lenses if present and easy; seek medical advice if irritation persists.
  • Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
• Fire: organic solid; use water spray, CO2, foam, or dry chemical. Combustion may produce CO, CO2.
• Spill response: avoid dust formation; collect mechanically; wash area with water while preventing entry into drains as appropriate.

Always consult the product’s SDS for authoritative, up-to-date hazard and handling information.

Solvent Selection

Applicability: cis,trans-Muconic acid is a polar, bifunctional solid; solvent choice primarily addresses dissolution for reactions (esterification, acylation, hydrogenation) or analytical preparation.

General solvent behavior (literature):

• Polarity class: polar protic/aqueous media are most effective when partially or fully deprotonated (muconate salts). Polar aprotic solvents can solvate the neutral diacid.
• Miscibility/solubility trends: sparingly soluble in cold water; better in hot water and in basic aqueous media. Good solubility in DMSO and DMF; moderate in methanol/ethanol (warming aids dissolution); poor in nonpolar hydrocarbons and chlorinated solvents.
• Dielectric constants (literature, solvent examples): water ~80, DMSO ~47, DMF ~38, MeOH ~33, EtOH ~25 — use higher-permittivity media to assist dissolution/ionization.

When to choose what:

• Synthesis of esters: MeOH/EtOH with acid catalysis (H2SO4, TsOH); remove water via Dean–Stark (for higher alcohols) or use molecular sieves.
• Formation of acyl chlorides/anhydrides: employ inert aprotic media (CH2Cl2, toluene) with chlorinating/dehydrating agents; begin by forming a suspension if solubility is limited.
• Hydrogenation to adipic acid derivatives: aqueous or alcoholic media; muconate salts in water/EtOH improve catalyst contact.
• Analytical prep: dissolve in DMSO to prepare concentrated stocks; then dilute with water/buffer/MeOH as needed.

Practical tips:

• Mild basification (e.g., NaHCO3, Na2CO3) to pH 7–8 markedly increases aqueous solubility by forming sodium muconate.
• Warm solutions (40–60 °C) to accelerate dissolution; avoid prolonged heating under strongly acidic/basic conditions unless intended to react.

Storage and Reconstitution

Item-specific storage from Product Data:

• Storage conditions: Room temperature.
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
• Appearance: Not specified for this item; refer to CoA/Spec Sheet.

General guidance (literature/practice):

• Container: store in airtight, moisture-protected containers to prevent caking and facilitate accurate weighing.
• Light: the conjugated diene can slowly isomerize; store away from strong light/UV. Amber bottles are recommended for long-term storage.
• Stability: stable as a solid under ambient conditions; avoid prolonged exposure to strong acids/bases unless intended.

Reconstitution/preparation of solutions:

• Aqueous: dissolve in water; adjust pH toward neutrality with NaOH/KOH to form soluble muconate salts. Gentle warming (30–50 °C) aids dissolution.
• Organic: use DMSO or lower alcohols (MeOH/EtOH) for concentrated stocks; sonication can help.
• Sterile filtration: pass through 0.22 μm membranes if solutions are intended for biological assays.
• Freeze–thaw: for aqueous solutions, aliquot and store refrigerated or frozen to minimize microbial growth; avoid repeated freeze–thaw cycles that can alter concentration due to precipitation.

Always refer to the lot-specific CoA/SDS for definitive handling and stability details.

Structure and Identity

Item-specific (from Product Data):

• SKU: C1027231
• Product name: cis,trans-Muconic acid
• CAS: 1119-73-9
• PubChem CID: 5280614
• InChIKey: 352818 (as provided)
• Storage: Room temperature

Literature/typical identifiers and structural description (general, for reference):

• Common name: cis,trans-Muconic acid; (E,Z)-hexa-2,4-dienedioic acid
• Molecular formula: C6H6O4 (literature)
• Molecular weight: ~142.11 g/mol (literature)
• SMILES (representative, stereochemistry shown for one E and one Z double bond): O=C(O)/C=C/C=C\C(=O)O (literature)
• InChIKey (for muconic acid isomers are distinct; consult primary database for the exact (E,Z) key) (literature)

Structural features (general):

• Linear C6 backbone bearing a conjugated 1,3-diene (–CH=CH–CH=CH–) flanked by two terminal carboxylic acids.
• Geometric isomerism: one C=C bond is E (trans) and the other is Z (cis). No stereogenic centers.
• Functional groups: two carboxylic acids (dicarboxylic acid), conjugated diene; highly polar termini with a hydrophobic, unsaturated core.
• 2D description: HOOC–CH=CH–CH=CH–COOH with alternating single/double bonds; planarity favored in the diene segment due to conjugation.

Synthetic Utility

Functional handles and transformations (literature):

• Carboxyl groups:
  • Esterification (Fischer, Steglich) to dialkyl muconates; esters enable radical polymerization and alter solubility/reactivity.
  • Activation to acid chlorides (SOCl2, (COCl)2) or mixed anhydrides for amide/anhydride coupling.
  • Salt formation (Na/K/NH4) to increase aqueous handling and enable phase-transfer catalysis.
• Conjugated diene:
  • Hydrogenation to adipic acid (full saturation) or partial hydrogenation to monoenes.
  • Diels–Alder cycloadditions with activated dienophiles to build cyclohexene scaffolds; carboxylates direct regioselectivity.
  • Electrophilic addition/oxidation: epoxidation (peracids), dihydroxylation (OsO4/NMO), ozonolysis to shorter diacids/oxoacids.
  • Metal-catalyzed difunctionalizations (e.g., hydroboration–oxidation after esterification to improve compatibility).

Retrosynthetic value:

• A convergent C6 synthon with two terminal acids and internal unsaturation; enables late-stage diversification via orthogonal functional group chemistry (end-group derivatization independent from diene manipulation).

Practical notes:

• Isomer control: E/Z geometry can influence cycloaddition rates and polymerization behavior; verify and, if needed, isomerize under controlled conditions.
• Protecting-group strategy: convert acids to esters for compatibility with many diene transformations and to improve solubility in organic media.

Target Specificity

Not applicable. This product is a small-molecule dicarboxylic acid, not a biological targeting reagent (e.g., antibody, probe). No target/epitope specificity data are provided in the Product Data.