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
Not available
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.
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Application Protocols
Item-specific, tested application details are not provided for this product.
General usage examples (literature; adapt to your system)
GC calibration standard for FAEEs: Prepare 0.5–2.0 mg/mL solutions in hexane or isooctane. Inject 0.5–1.0 µL using a high-temperature program ending at 300–320 °C; use FID for quantitation.
Lipase-catalyzed transesterification: Combine ethyl tridecanoate (1.0 equiv) and alternate alcohol (2–5 equiv) with immobilized CALB (10 wt%) in heptane. Agitate at 40 °C for 6–12 h, remove enzyme by filtration, and analyze conversion by GC.
Base-catalyzed methanolysis (model): Dissolve ester in MeOH (5–10 mL per mmol). Add 0.5–2 mol% NaOMe, stir at 25–50 °C, monitor by GC. Quench with saturated NH4Cl and extract with hexane.
Note
The above are general literature-style procedures intended for experienced chemists. Optimize conditions, scales, and safety controls to your laboratory’s requirements.
Biological Roles
General biochemistry context (literature; not an intended use claim)
Ethyl tridecanoate belongs to fatty acid ethyl esters (FAEEs), which can form enzymatically or non-enzymatically from fatty acids and ethanol. In biology, FAEEs can act as nonpolar storage/transport forms of fatty acyl chains and partition strongly into lipid membranes and neutral lipid droplets.
Metabolic relevance: FAEEs are substrates for esterases and lipases, yielding the corresponding fatty acid (tridecanoic acid) and ethanol upon hydrolysis. Chain length influences enzyme affinity and membrane partition coefficients.
Analytical biomarkers: Members of the FAEE family are monitored in biological matrices to study ethanol-related metabolism and lipid processing; chain length distributions inform on source lipids and enzymatic selectivity (literature context). Ethyl tridecanoate can serve as a reference compound in such studies.
Physicochemical behavior: Highly hydrophobic; exhibits strong sorption to hydrophobic phases and proteins with lipid-binding domains. Low aqueous solubility necessitates carrier solvents or emulsifiers for in vitro studies.
Note
This product is for research use only and is not intended for diagnostic or clinical applications.
Buffer Applications
Not typically applicable.
Ethyl tridecanoate is a hydrophobic, non-ionic ester with negligible water solubility and does not serve as a pH buffer component. For aqueous work, dissolve in a compatible organic cosolvent or formulate as emulsions with surfactants if required.
See Solvent Selection and Application Protocols for handling in nonaqueous or biphasic systems.
Green Alternatives
Context
Ethyl tridecanoate is typically used as a substrate/standard rather than a process solvent. Green considerations focus on sourcing and synthesis rather than replacement as a solvent.
Greener sourcing and synthesis (literature/general)
Bio-based feedstocks: Tridecanoic chains can originate from renewable lipids (plant or algal oils, tailored fermentation). Ethanol of biogenic origin supports a renewable FAEE.
Enzymatic routes: Lipase-catalyzed esterification of tridecanoic acid (or transesterification of triglycerides) with ethanol at moderate temperatures (30–60 °C) minimizes waste and avoids corrosive mineral acids.
Solvent minimization: Conducting reactions neat or in green solvents (2-MeTHF, CPME, or ethyl acetate) can reduce environmental footprint relative to chlorinated media.
Comparison highlights (general)
Mineral-acid esterification (H2SO4 in toluene) vs. lipase-catalyzed solvent-free esterification
Energy/temperature: High vs. low–moderate
Byproducts: Acidic aqueous waste vs. minimal
Catalyst recovery: Difficult vs. possible (immobilized enzymes)
Trade-offs
Enzymatic processes may require longer reaction times or higher catalyst loadings and are sensitive to water activity; however, they often deliver higher selectivity and easier workup with improved EHS profiles.
Pharmaceutical Uses
General formulation context (literature; no therapeutic claims)
Long-chain fatty acid esters can function as nonaqueous vehicles, emollients, and permeation modifiers in topical and transdermal formulations. Their high boiling points and hydrophobicity reduce volatility and enhance film formation.
Excipient considerations: Purity, peroxide value (typically relevant for unsaturated esters), residual solvents, and acid value are critical quality attributes. For saturated esters like ethyl tridecanoate, oxidative stability is comparatively good.
Regulatory status: Specific pharmacopeial monographs for ethyl tridecanoate are not commonly listed; this item’s pharmacopeial status is not specified. Verify acceptability with relevant compendia if excipient use is contemplated.
Item-specific
Pharmacopeia/grade status: Not specified for this item; refer to CoA/Spec Sheet.
This product is sold for research use only and not for use in humans or clinical applications.
Physical Properties
Item-specific specs
Not specified for this item; refer to CoA/Spec Sheet.
Literature/general reference values for long-chain ethyl esters of comparable chain length (for planning only; verify experimentally)
Physical state/appearance: Typically a colorless to pale yellow, oily liquid at ambient temperature (literature, long-chain FAEEs).
Boiling point: Commonly very high for C15 FAEEs; approximate range on the order of 300 °C at 1 atm (literature, long-chain saturated ethyl esters). Reduced pressures are recommended for distillation.
Melting point: Often below or near 0 °C for unsymmetrical long-chain esters; specific value for ethyl tridecanoate is not widely reported (literature trend).
Density (20–25 °C): Typically around 0.86–0.88 g/mL for C14–C16 ethyl esters (literature range).
Refractive index (nD20): Often ~1.438–1.445 for comparable FAEEs (literature range).
Vapor pressure: Very low at room temperature (literature trend for C15 esters).
Solubility: Practically insoluble in water; miscible with nonpolar and moderately polar organic solvents (hexanes, toluene, chloroform, DCM, EtOAc, ether, alcohols) (literature).
LogP: Expected high hydrophobicity (logP > 6; literature trend for C15 esters).
Notes
The above values are typical literature trends for similar fatty acid ethyl esters and are provided for context only. For exact specifications of this catalog item, consult the product CoA or specification sheet.
Quality and Grades
Item-specific quality
Grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on grades for this compound class (general)
Neat reagent-grade fatty acid ethyl esters are typically assessed by GC/FID or GC–MS for purity, with limits on free acid content (acid value), water (Karl Fischer), and residual solvents. For chromatographic applications, low-UV-absorbing impurities are preferred.
For quantitative work (e.g., lipidomics/internal standards), purity >98% and tightly controlled isomer/chain-length distribution are often desired. Verify absence of shorter/longer chain esters and positional isomers by GC.
Stabilizers: Long-chain saturated ethyl esters do not generally require added stabilizers; they are comparatively resistant to autoxidation versus unsaturated analogs. Nevertheless, storage under inert gas can further preserve quality.
What to check on receipt
Review CoA for: assay/purity, identity confirmation (GC/MS), acid value, water content, and residual solvent profile. If using for quantitative analysis, establish your own retention time and response factor under your GC method.
Reaction and Applications
Applications (general chemistry/literature)
Model substrate for ester hydrolysis and transesterification studies, including base- or acid-catalyzed alcoholysis and interesterification. Useful for assessing selectivity and kinetics in the fatty acid ethyl ester (FAEE) series.
Enzymatic catalysis: Widely employed with lipases (e.g., Candida antarctica lipase B) to study regioselectivity, chain-length preferences, and kinetic resolutions in nonaqueous media. Suitable for solvent-free or biphasic systems.
Analytical/lipidomics: Serves as a chain-length reference or internal standard in GC analysis of FAEEs and related lipid matrices, due to its high boiling point and clean GC behavior.
Synthetic intermediate: Hydrolysis yields tridecanoic acid; reduction affords 1-tridecanol. Transesterification enables access to alternative alkyl tridecanoates.
Practical tips
Avoid protic strong acids at high temperatures if preserving the ester; strong acids catalyze transesterification and cleavage.
For GC analysis, confirm column temperature stability (final oven temp ≥ 280–320 °C) and use split/splitless strategies appropriate for high-boiling esters.
In lipase-catalyzed reactions, maintain low water activity (molecular sieves or dry solvents) to steer equilibria toward ester synthesis; temperature 30–60 °C often balances activity and stability (literature practice).
For base-catalyzed transesterification (model biodiesel conditions), alkoxides (e.g., NaOMe) in corresponding alcohol can be used under mild heating; monitor by GC or 1H NMR (disappearance of ethoxy quartet, emergence of new alkoxy signals).
Reaction Conditions
General literature guidance (verify and optimize for your system)
Basic hydrolysis (saponification): KOH or NaOH (1–2 equiv) in MeOH/H2O or EtOH/H2O, reflux 1–4 h. Workup by acidification to obtain tridecanoic acid. Monitor by TLC or GC.
Acidic hydrolysis: Aqueous HCl or H2SO4 (1–3 M), reflux hours; slower than base hydrolysis for long-chain esters; biphasic setups benefit from cosolvents or surfactants.
Transesterification (base-catalyzed): Sodium methoxide (0.5–2 mol%) in dry MeOH at 25–60 °C; remove ethanol by azeotropic means or apply excess alcohol to drive equilibrium. Typical reactions complete within 0.5–3 h.
Transesterification (acid-catalyzed): p-TsOH (1–5 mol%) or H2SO4 (0.5–2 wt%) in alcohol solvent at 50–80 °C; water removal (Dean–Stark if using toluene) enhances conversion.
Enzymatic interesterification: Immobilized CALB (5–15 wt% vs. substrates) in heptane, isooctane, or solvent-free; 30–60 °C; equilibrium within 4–24 h depending on water activity and substrate ratios.
Reduction to alcohol: LiAlH4 (1.5–2.5 equiv) in dry ether or THF, 0 °C to reflux; quench carefully. DIBAL-H (1.0–1.2 equiv) at −78 to −40 °C can furnish the aldehyde (tridecanal) with careful control.
Analytical monitoring
GC/FID or GC–MS with high-temperature columns; 1H NMR diagnostic signals: ethoxy CH3 triplet (~1.25 ppm), CH2 quartet (~4.10 ppm), methylene envelope (1.2–1.4 ppm), α-CH2 to carbonyl (~2.3 ppm).
Safety and Handling
Item-specific hazard/GHS (from Product Data)
GHS classification: Not specified for this item; refer to SDS.
Signal word / H-statements / pictograms: Not specified for this item; refer to SDS.
General safety information for long-chain fatty acid ethyl esters (literature/typical)
Expected hazards: Generally low acute toxicity; may cause mild skin/eye irritation. Treat as combustible liquid (high flash point) and avoid inhalation of mists.
PPE: Laboratory coat, safety goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Use in a well-ventilated area or fume hood when heating or generating aerosols.
Incompatibilities: Strong oxidizing agents; strong bases or acids under heating may induce hydrolysis or transesterification. Avoid prolonged contact with reactive metals in strongly basic media.
Handling tips: Minimize skin contact due to defatting. When distilling, use reduced pressure to limit thermal decomposition. Prevent spills—material can create slip hazards.
First aid overview: Skin—wash with soap and water. Eyes—rinse cautiously with water for several minutes, remove contacts if present and easy. Inhalation—move to fresh air. Ingestion—rinse mouth; seek medical advice.
Authoritative source
Always consult the product-specific Safety Data Sheet (SDS) for definitive hazard, exposure limits, and first-aid instructions.
Solvent Selection
Applicability
Ethyl tridecanoate is primarily a hydrophobic substrate/standard rather than a routine laboratory solvent. For dissolution and handling, select appropriate carrier solvents.
Polarity and miscibility (literature/general)
Polarity class: Nonpolar to weakly polar (only one ester group amid a C15 skeleton).
Miscibility: Miscible with hydrocarbons (hexane, heptane, toluene), halogenated solvents (CH2Cl2, CHCl3), ethers (THF, diethyl ether), esters (EtOAc), and alcohols (EtOH, iPrOH). Practically insoluble in water.
Dielectric behavior: Low dielectric constant typical of long-chain esters; expect poor support for ionic chemistry unless cosolvents are used.
Practical guidance
For analytical dilutions (GC): Use nonpolar solvents (iso-octane, hexane) to mimic volatility and prevent transesterification.
For reaction media: If used as substrate in lipase-catalyzed transformations, nonpolar solvents (heptane, isooctane) or solvent-free systems are common.
Viscosity/handling: At room temperature it is an oily liquid; gentle warming (30–40 °C) can improve pipetting and mixing.
Comparison note
Compared to shorter ethyl esters (e.g., ethyl acetate), ethyl tridecanoate is far less volatile and more hydrophobic, making it suitable as a high-boiling diluent or as a model substrate in nonaqueous enzymatic catalysis, but unsuitable as a general-purpose solvent.
Storage and Reconstitution
Item-specific (from Product Data)
Storage conditions: Room temperature.
Shipped in: Normal.
General handling recommendations (literature/good practice)
Keep container tightly closed in a dry, well-ventilated place. Minimize exposure to moisture and strong light/heat. Although saturated FAEEs are relatively oxidation-resistant, storing under inert gas (nitrogen/argon) helps maintain long-term quality.
If viscosity hinders dispensing at room temperature, gently warm to 30–40 °C and mix before use.
Reconstitution: Not applicable; product is supplied neat. For analytical or reaction use, prepare solutions in compatible organic solvents (e.g., hexane, heptane, toluene, EtOAc) immediately prior to use.
Freeze–thaw: Not typically required. If stored cool, material may thicken; warm and homogenize before sampling to ensure representativity.
Shelf-life
Not specified for this item; refer to CoA/Spec Sheet. Periodic verification by GC (purity, absence of hydrolysis) is recommended for long-term storage.
Structure and Identity
Item-specific (from Product Data)
SKU: E156257
Product name: Ethyl Tridecanoate
CAS: 28267-29-0
PubChem CID: 119908
InChIKey (as provided): 298985
Storage: Room temperature
Shipping: Normal
Research use: For research use only
Literature/Computed identifiers and description (general reference; not item-specific specs)
Common description: Ethyl ester of tridecanoic acid (C13 saturated fatty acid)
Functional groups: One carboxylic ester (alkyl ethyl ester), long linear saturated alkyl chain (C13) on the acyl side, ethyl group on the alkoxy side.
2D description: A straight C13 alkyl chain terminates at a carbonyl carbon (C=O) connected to an ethoxy fragment –O–CH2–CH3; no rings, no heteroatoms beyond the ester oxygens; no stereocenters.
Class: Long-chain fatty acid ethyl ester (FAEE), hydrophobic, non-polar apart from the ester moiety.
Synthetic Utility
Functional-group leverage (general)
Ester functionality enables classic interconversions: hydrolysis to tridecanoic acid (acidic or basic), reduction to 1-tridecanol (e.g., LiAlH4, DIBAL-H to the aldehyde at low temperature), and transesterification to alternate alkyl esters (acid/base or enzymatic catalysis).
As a hydrophobic protecting/transport form of the C13 acyl unit, ethyl tridecanoate serves as a convenient, distillable intermediate for downstream derivatization to amides (via acid after saponification), anhydrides, or acid chlorides.
Applications and strategy
Lipase-mediated synthesis: Use ethyl tridecanoate as either donor or acceptor in interesterifications to probe enzyme chain-length selectivity and to assemble designer esters.
Materials and surfactants: The C13 backbone provides a balance between fluidity and hydrophobicity; derivatives (alcohols, acids, quats after further steps) can feed into surfactant or lubricant synthesis.
Analytical chemistry: As a retention-time and response-factor calibrant in GC/FID for the FAEE class.
Notes
For amide synthesis, a common route is saponification to the acid, conversion to the acyl chloride (e.g., oxalyl chloride, catalytic DMF) and coupling with amines. Alternatively, use coupling reagents (EDC/HOBt) directly from the acid obtained via hydrolysis.
Target Specificity
Not applicable.
This product is a small-molecule reagent/standard and is not an antibody, probe, or biologic. No target, epitope, clone, or species reactivity applies.
Products are supplied to verified businesses, institutions, and qualified professionals for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
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