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
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
No application assay protocols (e.g., WB, IHC, IF, FC) are applicable to this small-molecule building block. For practical laboratory use, refer to the Reaction Conditions, Solvent Selection, and Synthetic Utility sections for step-by-step synthetic guidance.
Research Use Note: For research use only (as provided in product data).
Biological Roles
This substance is a synthetic, bifunctional analogue of long-chain fatty acid derivatives and is not known as a natural metabolite.
Endogenous occurrence: No established role; the ethyl ester substituent is non-natural in typical lipid metabolism.
Biophysical behavior (general): The C12 hydrocarbon segment imparts strong hydrophobicity; the terminal acid (and, after hydrolysis, a second acid) increases amphiphilicity and potential for self-assembly in micellar or thin-film contexts.
Biochemical handling: Carboxylic acids may form salts with amines or metal cations; esters can be susceptible to nonspecific esterases in biological matrices, but such considerations are outside the scope of research-use chemicals unless specifically studied.
Use in model systems: Long-chain bifunctional acids can serve as surrogates for constructing lipid-mimetic materials, membrane anchors, or to study hydrophobic spacer effects in conjugates under in vitro conditions.
Note: No medical, diagnostic, or therapeutic use is intended or implied. Any biological testing must be designed and interpreted under appropriate institutional approvals. For research use only (as stated in product data).
Buffer Applications
Not typically applicable. 11-Ethoxycarbonyldodecanoic acid is a hydrophobic organic building block rather than a buffering reagent. It lacks a pH range suitable for maintaining buffer capacity in aqueous systems. For aqueous work, it may form soluble salts in basic media, but this is not a standard buffering application.
Recommendation: Refer instead to the Solvent Selection, Reaction & Applications, and Synthetic Utility sections for practical usage guidance.
Green Alternatives
Greener practices for working with long-chain carboxylic acid/ester building blocks focus on solvent selection, coupling reagents, and minimizing halogenated waste. The compound itself is a saturated hydrocarbon derivative; the main leverage points are process choices.
Greener solvent substitutions (general guidance):
Replace DCM/CHCl3 with 2-MeTHF, CPME, or EtOAc for many coupling and workup steps.
Prefer EtOAc/Heptane biphasic systems over DCM/Hexanes for extractions and chromatography.
Use MeCN or 2-MeTHF instead of THF where peroxide risk or energy intensity is a concern.
Comparison (literature-based, qualitative):
DCM vs EtOAc: EtOAc has lower toxicity and is biodegradable; solubility for long-chain substrates is generally good; slightly higher polarity can aid coupling.
THF vs 2-MeTHF: 2-MeTHF is bio-based, forms fewer peroxides, and allows water-tolerant couplings; similar dissolving power for fatty derivatives.
DMF vs Cyrene/NBP: in some amide couplings, Cyrene (dihydrolevoglucosenone) or N‑butylpyrrolidone can replace DMF; verify reactivity and workup feasibility at scale.
Reagent choices:
Coupling: consider DMTMM or CDI as alternatives to carbodiimides to reduce urea waste; enzymatic esterification (lipases) can enable solvent-lean processes at mild temperatures.
Bases: aqueous carbonate/bicarbonate for selective saponification instead of strong hydroxide when feasible to reduce corrosive hazards.
Process intensification:
Employ mechanochemistry (ball milling) for some couplings to reduce solvent use.
Use microwave or flow to shorten reaction times and energy consumption, validating selectivity (particularly for ester integrity).
Pharmaceutical Uses
No pharmacopeial or excipient status is provided for this item.
Regulatory status: Not specified for this item; refer to CoA/Spec Sheet.
Typical role (general, research context): hydrophobic spacer or intermediate for generating dicarboxylic acids, amides, and ester derivatives used in materials, pro-moiety studies, or lipid-mimetic constructs. Not for human or veterinary use.
Formulation notes: In preclinical formulation chemistry, long-chain acids/esters may be dissolved in biocompatible solvents (e.g., ethanol, PEGs) or formulated as salts; however, such practices require case-by-case toxicological evaluation and are outside the intended use for this catalog item.
Important: This product is supplied strictly for research use only (as stated in product data). No therapeutic, diagnostic, or clinical claims are made or should be inferred.
Physical Properties
Item-specific specifications are not provided in the current product record. The following notes reflect general/literature expectations for saturated, long-chain bifunctional fatty-acid derivatives and should be used as guidance only.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Melting point: Not specified for this item; refer to CoA/Spec Sheet. (Long-chain, saturated acids/esters often are waxy solids or low-melting solids; actual MP depends on exact structure and purity.)
Boiling point/thermal behavior: Not specified for this item; refer to CoA/Spec Sheet. (Such compounds typically decompose before boiling at ambient pressure.)
Density: Not specified for this item; refer to CoA/Spec Sheet.
Refractive index: Not specified for this item; refer to CoA/Spec Sheet.
LogP/partitioning (literature expectation): Highly hydrophobic due to a C12 chain; overall amphiphilic character from the acid group but poor water solubility in neutral form.
pKa (literature expectation): Carboxylic acid pKa typically ~4–5 in water for saturated aliphatic acids; the internal ethyl ester is neutral and non-ionizable under physiological pH.
Solubility (literature expectation):
Water: very low at neutral pH; solubility increases in basic aqueous media via carboxylate formation.
Organic solvents: soluble in common organics (e.g., dichloromethane, chloroform, THF, acetone, ethyl acetate); soluble in alcohols; good solubility in nonpolar solvents (toluene, hexanes) when warmed.
For definitive, lot-specific values (e.g., MP range, water content, residual solvents), consult the CoA/Spec Sheet.
Quality and Grades
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 (general):
Research-grade organic building blocks are typically supplied with assay purity suitable for synthetic use. When purity is stated (e.g., ≥95%, ≥98%), it typically reflects area% by GC/HPLC or NMR integration. Absent a stated value here, consult the product label/CoA for the assay method and acceptance criteria.
Residual solvents, water content (Karl Fischer), and limits on inorganic impurities/heavy metals are batch-dependent; without item-specific values, these should be taken from the CoA.
Stabilizers: None are specified for this item. If present in a particular lot (e.g., added antioxidant), it will be disclosed on the CoA/label.
What to check on receipt:
Confirm identity by 1H/13C NMR and HRMS as needed. The compound’s two carbonyl environments (acid and ester) should be clearly distinguishable in both IR (two C=O bands) and NMR (distinct methylene environments near each functionality; ethyl ester quartet/triplet when present).
Assess acid value or neutralization equivalent if relevant for stoichiometric reactions.
For any chromatography-sensitive applications (e.g., derivatization analytics), consider additional purification (short-path, recrystallization, or flash) based on CoA data.
Reaction and Applications
With both a terminal carboxylic acid and an internal ethyl ester, 11-ethoxycarbonyldodecanoic acid is a versatile bifunctional building block for constructing amphiphiles, spacers, and surface-active motifs.
Representative applications (general/literature):
Stepwise functionalization: convert the terminal acid to amides/esters (EDC/HOBt or HATU/DIPEA in DCM/DMF) while retaining the internal ethyl ester as a masked acyl equivalent. The internal ester can later be hydrolyzed to unveil a second acid for further coupling (orthogonal protection concept).
Spacer/linker design: the C12 segment serves as a hydrophobic spacer between polar headgroups; useful in preparing gemini surfactants, polymer-tethered fatty-acid motifs, and SAM precursors on hydrophobic surfaces.
Transesterification: exchange the ethyl group under acid (e.g., catalytic TsOH in ROH) or base (sodium alkoxide in ROH) to introduce tailored alcohol residues.
Selective hydrolysis: saponify the ethyl ester (aq. base in THF/MeOH) to generate a diacid, enabling subsequent diacyl chloride formation for polymer, crosslinker, or dendrimer synthesis.
Activation chemistry: formation of mixed anhydrides, acid chlorides (SOCl2, oxalyl chloride) from the terminal acid for further acylations; careful conditions minimize unintended ester cleavage.
Click-adjacent strategies: preinstall azide/alkyne handles via amide coupling at the acid, then post-functionalize the remaining ester-derived acid after hydrolysis.
Practical tips:
Maintain anhydrous conditions when preserving the internal ester; include molecular sieves when using carbodiimides.
Monitor by 1H NMR: ethyl ester quartet (–OCH2–) and triplet (–CH3) provide convenient handles to track transformations.
For sequential deprotection, use milder bases (K2CO3) and lower temperatures to favor selective ester saponification over other side reactions.
Reaction Conditions
The following conditions are general literature guidance for long-chain carboxylic acids bearing an internal ethyl ester. Optimize for your specific substrate, scale, and purity requirements.
Amide formation at terminal acid:
Reagents: EDC·HCl (1.2–1.5 eq), HOBt or Oxyma (0.1–1.0 eq), amine (1.1–1.5 eq), base (DIPEA 2–3 eq).
Solvent: DCM, DMF, or MeCN (anhydrous).
Temperature/time: 0–25 °C, 2–16 h. Typical isolated yields: 70–95% (literature, substrate-dependent).
Solvent: DCM or THF, 0–25 °C, 4–16 h. Remove DCU by filtration.
Selective saponification of internal ethyl ester (to diacid):
Reagents: K2CO3 (2–4 eq) or NaOH (1–2 eq) in MeOH/H2O or THF/H2O (3:1 to 9:1).
Temperature/time: 0–25 °C, 1–6 h; monitor by TLC/LC-MS. Quench into dilute acid, extract promptly to avoid over-hydrolysis elsewhere.
Transesterification:
Base-catalyzed: NaOMe or KOtBu (0.05–0.2 eq) in corresponding ROH, 25–60 °C, 1–6 h.
Acid-catalyzed: p-TsOH (1–5 mol%) in ROH, Dean–Stark (if applicable), 50–80 °C.
Acid chloride formation (terminal acid):
Reagents: SOCl2 (3–5 eq), catalytic DMF.
Solvent-free or in toluene/DCM; 0–70 °C, 1–3 h. Protect the internal ester by controlling time/temperature.
Workup/purification tips:
Partition between EtOAc and aqueous phases; adjust pH to move acid/ester selectively.
Use normal-phase silica; hexanes/EtOAc or toluene/EtOAc gradients accommodate hydrophobicity. Avoid prolonged exposure to basic silica to protect ester integrity.
Safety and Handling
GHS/SDS details specific to this catalog item are not provided. Handle as a typical long-chain carboxylic acid/ester derivative and defer to the SDS for authoritative guidance.
GHS classification: Not specified for this item; refer to SDS.
Signal word/H-statements/Pictograms: Not specified for this item; refer to SDS.
General laboratory precautions (good practice):
PPE: lab coat, safety glasses, and appropriate chemically resistant gloves (e.g., nitrile). Avoid skin/eye contact and inhalation of dust or aerosols.
Ventilation: handle powders/particulates in a fume hood to avoid inhalation; avoid generating dust.
Incompatibilities: strong oxidizers; strong bases/acids (will induce saponification/hydrolysis of the ester or neutralization of the acid). Moisture promotes ester hydrolysis over extended times.
Thermal stability: long-chain esters/acids typically stable at ambient conditions; avoid prolonged heating above ~120–150 °C to minimize decomposition.
Spill/cleanup: contain solids with inert absorbent, collect mechanically; wash residues with suitable solvent while observing compatibility and waste rules.
First aid (overview):
Skin: wash with soap and water; remove contaminated clothing.
Eyes: rinse cautiously with water for several minutes; remove contact lenses if present.
Inhalation: move to fresh air; seek medical attention if symptoms persist.
Ingestion: rinse mouth; do not induce vomiting; seek medical advice.
Waste: dispose according to institutional, local, and national regulations for organic chemicals/esters/acids.
Solvent Selection
This compound is a hydrophobic, long-chain carboxylic acid bearing an internal ethyl ester. Solvent choice should balance dissolving power for a C12 chain with compatibility to the desired transformation of the acid or ester functionality.
Water: poor solubility at neutral pH; forms soluble carboxylate salts in basic aqueous media.
Polar aprotic: good solubility in DCM/CHCl3, THF, DMF, DMSO, acetonitrile (often requires slight warming for the less polar options).
Polar protic: soluble in MeOH/EtOH/i-PrOH; note these can participate in ester exchange under acidic/basic conditions.
Nonpolar: soluble in toluene and alkanes; may require warming for hexanes.
Selection guidance:
For coupling at the acid (amide/ester formation): use dry DCM, DMF, or MeCN to support carbodiimide or uronium coupling systems; add base (DIPEA) as needed.
For selective hydrolysis of the ethyl ester: aqueous THF/MeOH with base (NaOH/K2CO3) or aqueous dioxane; control temperature to avoid affecting the terminal acid.
For transesterification: anhydrous alcohol solvents (MeOH, EtOH) with catalytic acid/base.
For hydrophobic assembly/surface work: toluene or heptane can promote monolayer formation or phase transfer.
Quick comparison (general):
DCM: fast dissolution, easy removal, low boiling; halogenated waste burden.
THF: good balance of polarity; peroxide formation risk—use inhibitor checks and fresh solvent.
DMF/DMSO: strong solvents for difficult dissolutions; higher boiling, challenging removal; consider for coupling chemistry.
Toluene: compatible with high-temperature reactions and hydrophobic matrices.
Keep tightly closed in a dry, inert atmosphere to minimize ester hydrolysis and acid/base-catalyzed degradation. Desiccation (P2O5 or silica gel) is recommended for long-term storage.
Protect from prolonged exposure to moisture, strong light, and heat. Store in amber glass if prolonged light exposure is expected.
If the material is a low-melting solid/waxy: gently warm (30–40 °C) to liquefy for accurate weighing/pipetting; cool before long-term storage.
Solution preparation:
Prepare stock solutions in dry organic solvents (e.g., DCM, THF, EtOAc, MeCN, or anhydrous alcohols) immediately before use.
For basic aqueous handling (e.g., saponification), prepare solutions fresh; avoid extended storage in water to prevent unintended hydrolysis.
Avoid repeated freeze–thaw cycles for solutions; aliquot as needed. For maximum stability, store solutions under inert gas at 2–8 °C and use within a few days.
Specifications not provided:
Appearance, assay, water content, and stabilizers: Not specified for this item; refer to CoA/Spec Sheet.
Always consult the product label and SDS for definitive handling and storage recommendations.
Structure and Identity
Brief description: 11-Ethoxycarbonyldodecanoic acid is a long-chain, saturated, bifunctional aliphatic compound bearing a terminal carboxylic acid and an internal ethoxycarbonyl (carbethoxy) substituent. It is useful as a hydrophobic spacer/building block in synthesis.
SKU: E136467
Product name: 11-Ethoxycarbonyldodecanoic Acid
CAS: 66003-63-2
PubChem CID: 560435 (catalog reference)
InChIKey: 380689 (as provided in product data)
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.
Structural features (general/literature description):
Functional groups: one carboxylic acid (–CO2H) and one ethyl ester substituent (–CO2Et) positioned along a saturated C12 backbone.
Saturation/stereochemistry: saturated, no rings; the substituted methylene at C-11 (by IUPAC numbering of dodecanoic acid) is sp3 and achiral unless asymmetry arises from substitution pattern.
2D structure in words: a linear dodecanoic acid chain with an ethoxycarbonyl group pendant near the terminal end of the chain (remote from the acid), providing both an acidic handle and a protected (ester) acyl equivalent.
Note: Item-specific identifiers beyond those listed above are not provided in the current product record; consult the CoA/Spec Sheet for definitive structure representation (SMILES/InChI) and elemental composition.
Synthetic Utility
Key reactivity arises from the coexistence of a terminal carboxylic acid (reactive, polar handle) and an internal ethyl ester (masked acyl function) along a hydrophobic C12 scaffold.
Orthogonal functionalization: Perform amide/ester couplings at the terminal acid under standard peptide-coupling conditions while preserving the ethyl ester. Subsequent selective saponification unveils a diacid for further elaboration, enabling sequential conjugation strategies.
Divergent routes to diacids and diesters:
Hydrolysis (base or acid) of the internal ethyl ester → diacid; convert to diacyl chloride (SOCl2 or Ghosez’s reagent) for polymerization, dendrimer branching, or crosslinker synthesis.
Esterification of the terminal acid (Fischer or Steglich) → diester; useful for hydrophobic plasticizers or monomer feeds.
Transesterification: Exchange the ethyl group with sterically/ electronically tuned alcohols to modulate downstream reactivity or solubility.
Reductive manipulations: The terminal acid can be reduced to alcohol (BH3·THF, LiAlH4) furnishing a hydroxy-terminated carbethoxy derivative; subsequent chemistry includes carbonate formation, urethanes, or further oxidation.
Click-enabling handles: Install azide/alkyne motifs via amide coupling at the acid end; after ester hydrolysis, the second acid allows a second conjugation, advantageous in bifunctional probe design.
Surface modification: The hydrophobic chain anchors to nonpolar substrates; the acid/ester termini facilitate covalent attachment of functional headgroups for SAMs or polymer brushes.
Analytical cues: IR shows two distinct C=O stretches (acid ~1700–1725 cm⁻¹ broad; ester ~1735–1750 cm⁻¹); 1H NMR displays ethyl ester quartet (~4.1–4.3 ppm) and triplet (~1.2–1.3 ppm) alongside the methylene envelope.
Target Specificity
Not applicable. This product is a small-molecule organic building block and is not an antibody, probe, or biologic with defined target binding parameters.
Antigen/epitope/clone/isotype: Not applicable.
Species reactivity: Not applicable.
Preguntas frecuentes
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 room temperature.
How is this product shipped?
This product ships under standard ambient conditions. No temperature-controlled packaging is required.
What are the CAS number, molecular formula and molecular weight?
The CAS Number is 66003-63-2, the molecular formula is C14H26O4, and the molecular weight is 258.36 g/mol. InChIKey VJOPNKODAZUCRH-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.
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