Butyl sorbate , CAS No.7367-78-4

CAS: 7367-78-4 Cat. No.: B1061822 Formula: C₁₀H₁₆O₂ Peso molecolare: 168.23 Numero EC: 230-911-0 PubChem CID: 5369076

Storage

Room temperature

Specifications

Condizioni di conservazione di stoccaggio

Room temperature

Nomi e identificatori

• Sorrisi canonici: CCCCOC(=O)C=CC=CC
• IUPAC Name: butyl (2E,4E)-hexa-2,4-dienoate
• InChIKey: SCVZKPKDMFXESQ-VSAQMIDASA-N
• INCHI: 1S/C10H16O2/c1-3-5-7-8-10(11)12-9-6-4-2/h3,5,7-8H,4,6,9H2,1-2H3/b5-3+,8-7+
• Isomeri SMILES: CCCCOC(=O)/C=C/C=C/C
• PubChem CID: 5369076
• Peso molecolare: 168.23

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Classe Fatty Acyls
      • Subclass Fatty acid esters

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Classe: Fatty Acyls
• Subclass: Fatty acid esters
• Intermediate Tree Nodes: Not available
• Direct Parent: Fatty acid esters
• Alternative Parents: Enoate esters Monocarboxylic acids and derivatives Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Fatty acid ester - Alpha,beta-unsaturated carboxylic ester - Enoate ester - Carboxylic acid ester - Monocarboxylic acid or derivatives - 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 fatty acid esters. These are carboxylic ester derivatives of a fatty acid.
• External Descriptors: Wax monoesters

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: 168.230 g/mol
• XLogP3: 2.800
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 168.115 Da
• Monoisotopic Mass: 168.115 Da
• Topological Polar Surface Area: 26.300 Ų
• Heavy Atom Count: 12
• Formal Charge: 0
• Complexity: 169.000
• 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

Not applicable. This listing is not an antibody/assay kit and has no WB/IHC/IF/FC protocols or dilution guidance.

General handling suggestions (for small-molecule reagents)

• For solution preparation, weigh accurately and dissolve in a suitable organic solvent (e.g., ethanol, DMSO, EtOAc) to make concentrated stocks; filter through 0.22 µm PTFE if particulate control is required.
• For microbiology or biochemical assays (if pursued in research settings), control final co-solvent content (often ≤1–2% v/v) and include vehicle controls. Item-specific assay conditions are not provided.

Biological Roles

General literature context (not product claims)

• Sorbate family: Sorbic acid and its alkyl esters have been extensively studied for their inhibitory effects on yeasts, molds, and some bacteria in acidic environments. Mechanistic studies suggest interference with membrane-associated processes and intracellular pH homeostasis, modulated by pH and lipophilicity.
• Lipophilicity tuning: Increasing alkyl chain length (e.g., butyl vs. methyl) typically increases membrane partitioning, which can influence observed antimicrobial potency in microbiological assays; quantitative effects depend on organism and conditions.
• Metabolic/biodegradation: Esterases can hydrolyze alkyl sorbates to sorbic acid and the corresponding alcohol in biological systems; rates depend on enzyme source and medium.
• Photobiology/oxidation: Conjugated dienes can undergo photo-oxidation (e.g., singlet-oxygen addition) generating peroxides/epoxides that are of interest in oxidative stress models.

Important notes

• This product is designated For research use only. No food, cosmetic, diagnostic, or therapeutic uses are implied.
• Item-specific bioactivity data, MIC values, and regulatory statuses are Not specified for this item; consult primary literature if such data are required for experimental design.

Buffer Applications

Not typically applicable. Butyl sorbate is a neutral, hydrophobic ester with low water solubility and does not serve as a conventional buffering agent.

Practical note

• If experiments require aqueous environments (e.g., microbiology assays), it is commonly introduced via a co-solvent (ethanol, DMSO) or emulsified formulations. Optimize solvent content to avoid confounding biological effects. No item-specific aqueous solubility data are provided; refer to CoA/Spec Sheet or determine empirically.

Green Alternatives

Context

• Butyl sorbate is a hydrophobic conjugated ester. Green chemistry considerations relate primarily to solvent choice, synthesis, and handling rather than to the substrate per se.

Greener options/approaches (general guidance)

• Solvent selection: Prefer bio-based or low-toxicity solvents (e.g., 2-MeTHF, Cyrene, ethyl acetate, dimethyl carbonate) over chlorinated or petroleum aromatics when compatible with reactivity and analytics.
• Synthesis: Enzymatic esterification (lipase-catalyzed) of sorbic acid with n-butanol in solvent-free or green solvent systems can reduce energy input and waste relative to mineral acid catalysis (literature).
• Stabilization and storage: Use minimal antioxidants and light-protective packaging to prolong shelf life, reducing waste from degradation.

Comparison snapshot (general, literature)

• Toluene vs. 2-MeTHF: 2-MeTHF is renewable, often offers similar solubility for conjugated esters, and facilitates phase separation; however, it can contain residual water and form peroxides—monitor accordingly.
• DCM vs. EtOAc: Ethyl acetate is biodegradable and less problematic from a regulatory standpoint; it often dissolves sorbate esters sufficiently for reactions and workups.
• Hexanes vs. Heptane/iPP (isoparaffins): Heptane or isoparaffinic solvents may reduce VOC classification impacts and offer improved safety profiles.

Trade-offs

• Some green solvents have higher boiling points, complicating removal. Peroxide formation is still a concern for ethers; institute peroxide testing where applicable.

Pharmaceutical Uses

Scope and limitations

• This product is supplied For research use only. No pharmacopeial compliance or suitability for pharmaceutical manufacturing is implied by this listing.

General literature context (non-item-specific)

• Alkyl sorbates have been investigated as preservative agents in topical and oral formulations due to their lipophilicity and volatility profiles compared with sorbic acid or potassium sorbate. Selection is driven by solvent system, pH, and compatibility with excipients.
• Butyl sorbate specifically is less commonly referenced in major pharmacopeias compared with sorbic acid/potassium sorbate. Its utility, where explored, relates to nonaqueous or oily vehicles where an ester form is preferable.

Formulation considerations (general)

• Hydrolysis risk: Avoid strong acid/base environments and prolonged aqueous exposure; monitor for sorbic acid and n-butanol formation.
• Partitioning: Expect strong partition into lipid/oil phases; adjust emulsifier systems accordingly if used in emulsions.

Item-specific regulatory/compendial status, impurity limits, and residual solvent profiles are Not specified for this item; refer to CoA/Spec Sheet and applicable regulations if evaluating for regulated uses.

Physical Properties

Item-specific specifications

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

General/literature reference values for butyl sorbate (for context only)

• Physical state: typically a colorless to pale liquid ester (literature)
• Polarity/functional class: moderately polar, aprotic, hydrophobic ester with a conjugated diene (general)
• Water solubility: low; expected to be sparingly soluble in water and miscible with many organic solvents such as hexanes, toluene, diethyl ether, and alcohols (general/literature trends for long-chain sorbate esters)
• Volatility: lower volatility than methyl/ethyl sorbate analogs due to the butyl chain (general)
• UV absorbance: conjugated diene/enoate typically shows strong π–π* absorption in the 220–260 nm region with extended tailing; exact maxima and cutoff depend on solvent and isomer ratio (literature, not item-specific)

Important cautions on interpretation

• Do not use the above as product specifications. Actual MP/BP, density, refractive index, UV cutoff, water/peroxide/metal content, and other QC metrics are Not specified for this item; refer to CoA/Spec Sheet.

Quality and Grades

Item-specific grade/purity information

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

How to interpret common grades for an ester like butyl sorbate (general guidance)

• Analytical/Reagent grade: Typically assures low levels of common inorganic/organic impurities; suitable for most syntheses and analytical sample preparation.
• HPLC/UV grade: Tight control of UV-absorbing impurities and baseline drift; desirable if the compound is to be used as an internal standard or chromatographic reference in UV-detected systems. Note: conjugated dienes inherently absorb in UV; “UV grade” relates to impurity profile, not eliminating intrinsic absorbance.
• Food/pharma grades: Governed by separate compendial monographs (if available). For research-only materials like this item, no food/pharmacopeial suitability is implied.

What to check on the CoA/Spec Sheet (practical tips)

• Identity: NMR, GC/LC purity, IR (C=O and C=C bands), and isomer ratio (E,E content) if reported.
• Purity: GC/LC area %, limits for residual solvents, water (Karl Fischer), and acid/alcohol residues.
• Stabilization/packaging: Presence of antioxidants, headspace nitrogen, amber glass—if used—to minimize oxidation/isomerization.

Note: This product is for research use only (per Product Data).

Reaction and Applications

Typical research uses (general literature on sorbate esters)

• Model conjugated diene–enoate: Useful in studying conjugation effects, E/Z isomerization, and excited-state photochemistry. The diene conjugated with an ester carbonyl provides characteristic UV/vis signatures and reactivity.
• Radical and electrophilic additions: The conjugated chain can undergo radical additions (e.g., thiol–ene type across one double bond) and halofunctionalization under controlled conditions.
• Diels–Alder chemistry (as diene): Under appropriate conditions, sorbate esters can participate as electron-rich dienes with suitable dienophiles; the ester modulates diene reactivity and regioselectivity.
• Hydrogenation: Stepwise or full hydrogenation affords partially or fully saturated butyl esters (e.g., toward butyl hex- or hexanoate) enabling studies on selective reduction of conjugated systems (Pd/C, PtO2, Ni; H2).
• Oxidation/autoxidation: Conjugated dienes are substrates for singlet-oxygen or radical autoxidation, enabling mechanistic lipid-peroxidation analog studies.

Practical considerations

• Isomer control: Light and acids/bases can induce E/Z isomerization; protect from light, and control pH/base strength to retain E,E configuration when needed.
• Competing pathways: Under basic/nucleophilic conditions, conjugate (1,4-/1,6-) additions may compete with simple substitution; monitor by GC/LC–MS.
• Hydrolysis/transesterification: Avoid prolonged exposure to strong acids/bases or alcoholates to prevent ester cleavage or scrambling; rigorously dry solvents for kinetic studies.

Notes

• The Manufacturer Applications field is not provided for this item; applications above are based on general literature precedent for sorbate esters and are not item-specific specifications.

Reaction Conditions

General literature guidance (not item-specific specifications)

• Hydrogenation: Pd/C (5–10 wt% on carbon), H2 1–5 bar, 20–50 °C, solvent such as EtOAc, EtOH, or hexanes; monitor by GC to stop at monoene stage or proceed to full saturation. Typical times: 0.5–6 h depending on catalyst loading.
• Diels–Alder (as diene): Combine with electron-poor dienophiles (e.g., maleic anhydride derivatives) in toluene or chlorobenzene, 60–120 °C; Lewis acids (AlCl3, TiCl4) may accelerate but can promote side reactions—screen milder catalysts first. Times: hours to overnight.
• Conjugate additions: Base catalysts (DBU, tertiary amines) or soft nucleophiles (thiols) in polar aprotic solvents (THF, MeCN, DMF), 0–25 °C, 1–24 h. Control stoichiometry and temperature to manage 1,4 vs. 1,6 selectivity.
• Epoxidation: mCPBA or peracetic acid in DCM/CH2Cl2 at 0–25 °C; buffer the medium to limit epoxide opening; sequential epoxidations possible across both C=C bonds. Typical times: 0.5–4 h.
• Photochemistry: UV-A/B irradiation (e.g., 300–365 nm) in degassed solvent with or without sensitizer; maintain inert atmosphere (N2/Ar) to control photo-oxidation; monitor E/Z ratios by NMR/GC.

Practical controls

• Dry, oxygen-free conditions reduce autoxidation and side reactions during base-catalyzed or photochemical experiments.
• Use amber glassware or wrap vessels in foil for light-sensitive studies.

Yields

• Strongly condition-dependent; consult primary literature for the specific transformation. No item-specific yields are provided.

Safety and Handling

Authoritative source: Always consult the product SDS for definitive hazard classifications, PPE, and emergency measures.

GHS classification (item-specific)

• Signal word: Not specified for this item; refer to SDS.
• H-statements: Not specified for this item; refer to SDS.
• Pictograms: Not specified for this item; refer to SDS.

General safety guidance for conjugated ester liquids (non-item-specific)

• Likely hazards: Organic liquids may cause skin/eye irritation and may be harmful if swallowed or inhaled. Conjugated dienoates can be sensitive to light/air, undergoing slow oxidative changes.
• PPE: Use lab coat, safety glasses or splash goggles, and appropriate chemically resistant gloves (e.g., nitrile). Work in a fume hood to avoid inhalation of vapors/aerosols.
• Handling: Avoid breathing vapors/mist; avoid contact with skin and eyes. Keep away from strong oxidizers. Prevent prolonged exposure to light and elevated temperatures to minimize peroxidation/isomerization.
• Incompatibilities: Strong acids/bases (risk of hydrolysis/transesterification), strong oxidizing agents (risk of exothermic reaction/oxidation), strong nucleophiles under basic conditions (Michael additions possible on activated double bond).
• First aid (general):
  • Inhalation: Move to fresh air; seek medical advice if symptoms persist.
  • Skin/eye contact: Rinse with water for several minutes; remove contaminated clothing; obtain medical attention if irritation continues.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
• Fire safety: Treat as a combustible organic liquid. Use CO2, dry chemical, or foam. Cool containers with water spray from a safe distance.

Waste disposal

• Collect organic residues as halogen-free organic waste unless local regulations dictate otherwise. Follow institutional and regulatory requirements.

Solvent Selection

Chemical class and polarity

• Butyl sorbate is a hydrophobic, moderately polar aprotic ester with a conjugated diene. It partitions strongly into nonpolar and moderately polar organic phases.

Miscibility and preferred media (general/literature)

• Expected to be miscible or highly soluble in: hexanes/heptane, cyclohexane, toluene, chlorinated solvents (e.g., DCM), ethers (Et2O, MTBE, THF), and alcohols (MeOH to BuOH). Sparingly soluble in water.

When to choose this substrate vs alternatives

• For reactivity studies of conjugated dienoates where the butyl group modulates lipophilicity and volatility compared to methyl/ethyl sorbate.
• As a model substrate in photochemistry, autoxidation, or radical addition studies where an n-butyl ester offers different steric/electronic context than shorter-chain esters.

Small comparison (general)

• Methyl/Ethyl sorbate: higher volatility, lower hydrophobicity; convenient for GC handling, faster evaporation.
• Butyl sorbate: lower volatility; improved handling when slower evaporation is desired; greater solubility in very nonpolar media.
• Sorbic acid: acidic, water/MeOH compatibility differs; less suitable where neutral ester functionality is required.

Practical tips

• For kinetic or photochemical work, use spectroscopic-grade solvents to minimize background absorbance in the 220–300 nm region.
• If performing base-catalyzed reactions (e.g., Michael-type additions), dry polar aprotic solvents (THF, MeCN, DMF) often improve reproducibility; exclude moisture to limit hydrolysis.

Storage and Reconstitution

Storage (item-specific)

• Storage conditions: Room temperature (per Product Data).
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.

Best practices (general for conjugated esters)

• Protect from light (store in amber glass) and air where possible; consider nitrogen headspace to minimize oxidative changes and E/Z isomerization.
• Keep container tightly closed. Avoid prolonged exposure to elevated temperatures.
• Segregate from strong oxidizers, acids, and bases.

Reconstitution and stock solutions

• Solubility: Readily soluble in common organic solvents; select solvent compatible with the intended application. Aqueous solubility is low—use co-solvents/emulsifiers if needed.
• Preparing stocks: Make concentrated solutions (e.g., 100–1000 mg/mL) in ethanol, DMSO, EtOAc, or hexanes as appropriate. Filter if necessary using PTFE membranes. Record solvent, concentration, and date.
• Stability of solutions: Monitor for changes (color, UV profile, GC purity). Store light-protected at room temperature or refrigerated depending on solvent volatility and laboratory policy.

Expiration/retention

• No item-specific shelf-life is provided. For critical applications, periodically re-verify identity/purity (e.g., GC/LC, 1H NMR).

Research use note

• For research use only (per Product Data).

Structure and Identity

Overview: Butyl sorbate is the butyl ester of sorbic acid, i.e., butyl (E,E)-2,4-hexadienoate. It features a conjugated 1,3-diene chain terminated by a carboxylate ester, giving a delocalized π-system that influences its reactivity and spectroscopic properties.

• Item-specific identifiers (from Product Data)

  • SKU: B1061822
  • Product name: Butyl sorbate
  • CAS: 7367-78-4
  • CID: 5369076
  • InChIKey: 332621 (as provided)
  • Storage conditions: Room temperature

• Literature identity details (for reference; not specifications for this item)

  • Preferred name: Butyl (E,E)-2,4-hexadienoate (butyl sorbate)
  • Structural features: conjugated 1,3-diene (C2–C3 and C4–C5), terminal methyl at C6, ester carbonyl at C1 linked to an n-butyl –O–(CH2)3CH3 chain; typically E,E geometry around both double bonds for the sorbate scaffold.
  • Approximate 2D description: n-butyl–O–C(=O)–CH=CH–CH=CH–CH3 in a roughly extended, planar diene segment conjugated with the carbonyl (an α,β,γ,δ-unsaturated ester).
  • Molecular formula (literature): C10H16O2
  • Molecular weight (literature): ~168.23 g/mol
  • Example SMILES (literature): CCCCOC(=O)/C=C/C=C/C

Notes

• Values in “literature” are general reference data; consult the item’s CoA/Spec Sheet for definitive identification parameters for this specific lot.

Synthetic Utility

Functional group analysis

• Conjugated 1,3-diene adjacent to an ester carbonyl (α,β,γ,δ-unsaturated ester) provides a versatile platform for pericyclic, radical, and polar transformations.

Representative transformations (literature)

• Diene chemistry: Acts as a diene in Diels–Alder reactions with strong dienophiles; regio-/stereochemical outcomes can be tuned by Lewis acids and solvent.
• Selective hydrogenation: Stepwise reduction of one or both double bonds (e.g., Pd/C, Pt, Ni catalysts) allows access to monoenes and the saturated butyl hexanoate. Reaction control via pressure, temperature, and catalyst choice.
• Michael-type additions: Nucleophiles (e.g., thiols, malonates) can add conjugatively under base catalysis; 1,4- vs 1,6-selectivity may depend on conditions and substitution.
• Halofunctionalization/epoxidation: Electrophilic halogenation or peracid epoxidation across the diene affords functionalized esters; sequence control is key to avoid overreaction.
• Photochemical E/Z isomerization: UV irradiation induces isomerization; photosensitizers enable controlled studies of conjugated system dynamics.

Strategic roles

• Lipophilicity handle: The n-butyl ester improves solubility in nonpolar media versus methyl/ethyl esters, aiding extractions and phase separations.
• Protecting/transport form: Esterification of sorbic acid masks acidity, enabling neutral conditions in multistep sequences; later hydrolysis/regioselective transformations can unmask the acid.

Target Specificity

Not applicable. This product is a small-molecule reagent and does not have antigen/epitope targets, clone information, isotypes, or species reactivity.

Item-specific note

• No Target Specificity data are provided for this item.