Eicosaenoic acid (cis-8) - analytical standard,≥99%

Cat. No.: E1508895

GRADE & PURITY Analytical standard, ≥99%

Storage

Room temperature

Shipped In

Normal

Specifications

Spécifications et pureté

analytical standard,≥99%

Conditions de stockage de stockage

Room temperature

Expédié en

Normal

Grade

Étalon d'analyse

Pureté

≥99%

Application Protocols

No manufacturer-tested biological assay protocols are provided for this small-molecule standard. For analytical use, consider the following literature-style workflows:

• GC-FAME preparation (overview)

  • Weigh 0.5–2.0 mg into a sealed vial. Add 1–2 mL of 1–3% H2SO4/MeOH or 1 N HCl/MeOH. Heat at 60–80 °C for 30–90 min. Cool, neutralize with NaHCO3, extract FAMEs into isooctane/hexane, dry over Na2SO4, inject 1 µL for GC-FID/MS.

• LC-MS stock solution (free acid)

  • Dissolve to 1–5 mg/mL in MeOH or IPA (optionally with 0.1% NH4OH). Dilute into 60:40 MeOH:H2O with 1–5 mM ammonium acetate for negative-ion ESI quantitation.

• Preparation of calibration curves

  • Prepare serial dilutions covering the analytical range (e.g., 0.1–100 µg/mL). Include at least one quality-control level and assess linearity (r2), precision, and recovery.

These are general guidance examples; validate and adjust to your instrumentation and regulatory context. Item-specific recommended dilutions or application conditions are not provided in the Product Data.

Biological Roles

General biology (literature): Eicosenoic acids (C20:1) are long-chain monounsaturated fatty acids found at low to moderate levels in certain plant and marine lipids. The Δ8-cis positional isomer is less common than Δ11 (gondoic acid) but shares core biochemical behavior of monoenes.

• Structural roles

  • Components of membrane phospholipids and neutral lipids; the cis double bond introduces a kink that reduces packing density, influencing membrane fluidity and phase behavior.

• Metabolic context

  • Can arise from elongation/desaturation pathways involving stearic/oleic precursors, depending on organism-specific desaturase positional selectivity.
  • Subject to β-oxidation in peroxisomes/mitochondria; activation to acyl-CoA is required for catabolism and incorporation into complex lipids.

• Enzymatic transformations

  • Substrate for acyltransferases (formation of TAGs, phospholipids) and potentially for desaturases/elongases (organism-dependent).
  • The double bond can undergo enzymatic oxidation (e.g., lipoxygenase-like processes) in certain biological contexts, though positional specificity varies.

• Analytical standards use

  • Served as reference for profiling and quantifying positional isomers of C20:1 in lipidomics by GC-FID/MS (as FAME) or LC-MS (as free acid or adducts).

Note: This product is for research use only. No medical, nutritional, or clinical claims are made or implied. For organism-specific pathways and abundance, consult primary literature on fatty acid biosynthesis and lipidomics.

Buffer Applications

This compound is a highly hydrophobic long-chain fatty acid and is not used as a buffering agent. It has negligible water solubility and does not form classical conjugate acid/base buffer systems in aqueous media.

• Practical guidance
  • For aqueous work, solubilize via organic co-solvents (e.g., ethanol, DMSO, or isopropanol) and then dilute into media with surfactants or carriers (BSA-fatty acid complexes) if biological assays require exposure.
  • If pH control is needed, use conventional buffers (phosphate, HEPES, Tris) independent of the fatty acid. The fatty acid may interact with buffer components or proteins; verify compatibility experimentally.

For buffer recipes and pH ranges, refer to dedicated buffering agents; this section is not typically applicable to eicosenoic acid standards.

Green Alternatives

While the molecule itself is a long-chain hydrocarbon acid with limited inherent “greenness,” several choices in solvent systems and derivatization can reduce environmental and safety impacts.

• Greener solvent choices (literature/general)

  • Replace chloroform/DCM with cyclopentyl methyl ether (CPME), 2-methyltetrahydrofuran (2-MeTHF), or ethyl acetate when solubility and method performance allow.
  • For GC sample prep, prefer isooctane or heptane over hexanes blends to reduce variability and potential benzene traces.

• Greener derivatization for FAME prep

  • Instead of BF3–MeOH (toxic, corrosive), use HCl–MeOH or H2SO4–MeOH at controlled temperatures; or base-catalyzed methanolysis (NaOMe) when no free fatty acids other than the analyte are present.

• Workup and waste minimization

  • Microscale derivatization (≤1 mL reaction volume) with solid-phase extraction (SPE) cleanup minimizes solvent.
  • Use reagent recovery (rotovap/solvent recycling) where purity permits.

• Comparative snapshot (literature)

  • BF3–MeOH: Fast, strong transesterification; hazardous and moisture-sensitive; waste treatment required.
  • HCl–MeOH: Effective, simpler handling; can corrode; neutralization required.
  • NaOMe/MeOH: Mild, low-toxicity; moisture sensitive; not ideal with substantial free acids/complex matrices.

Note: No stabilizers or green certifications are specified for this item. Select greener protocols compatible with your analytical method validation.

Pharmaceutical Uses

No pharmacopeial monograph or excipient specification is provided for this item. As supplied, it is an Analytical standard for research use only.

General formulation context (literature/general):

• Long-chain fatty acids and their esters can serve as excipient components in research-stage formulations, including:
  • Lipid-based delivery systems (e.g., emulsions, self-emulsifying systems), where fatty acids modulate lipophilicity and interfacial properties.
  • Pro-moiety design (ester/amide prodrugs) in preclinical chemistry, using long-chain acyl groups to alter permeability or depot behavior (exploratory R&D only).
  • Surfactant or co-surfactant roles when converted to soaps or partial glycerides.

Considerations

• Oxidative stability: Unsaturation can lead to peroxidation; antioxidants and oxygen control may be necessary during formulation studies.
• Regulatory: This product is not approved for human or veterinary use. Any pharmaceutical exploration must source GMP-grade materials and follow relevant pharmacopeial/ICH guidance.

Item-specific notes

• No claims are made for clinical, diagnostic, or excipient use. Packaging, stabilizers, and impurity limits appropriate for pharmaceutical submissions are Not specified for this item; refer to CoA/Spec Sheet if evaluating for method development aligned with pharmacopeial methods.

Physical Properties

Item-specific measured specifications are not provided in the Product Data; refer to the CoA/Spec Sheet for certified values. The following are literature/typical properties for monounsaturated C20 fatty acids (C20:1), provided to guide method development.

• State/appearance (literature): Waxy solid to viscous oil near ambient temperature; cis isomers often show lower melting points than saturated analogs due to chain kinking.
• Melting point (literature, C20:1 range): typically in the 10–30 °C range depending on double-bond position and purity; positional isomerism can shift mp by several degrees.
• Boiling point (literature): Decomposes before atmospheric bp; high bp expected (>300 °C). Vacuum distillation is sometimes used for purification.
• Density (literature): Approximately 0.88–0.92 g/mL at 20–25 °C for long-chain monoenes.
• Solubility (literature): Practically insoluble in water; soluble in nonpolar and moderately polar organic solvents (hexane, heptane, toluene, dichloromethane, chloroform). Limited solubility in alcohols; solubility improves with slight base (e.g., forming carboxylate in MeOH/EtOH with a trace of NH4OH).
• pKa (literature, carboxylic acid): ~4.8–5.0 in water (apparent pKa varies with micellization and medium).
• logP (literature): High hydrophobicity expected (logP > 7 for C20:1 free acid).
• Refractive index (literature, liquid monoene esters/acids): ~1.45–1.47 (temperature-dependent).

Practical notes

• For quantitative GC, convert to methyl ester (FAME) to obtain sharper peaks and reproducible retention indices.
• Solid–liquid transitions near room temperature can influence weighing accuracy; equilibrate to a consistent temperature and use pre-warmed syringes for viscous samples.

Quality and Grades

• Item-specific grade

  • Grade/Purity: Analytical standard (as provided). This designation indicates the material is intended for use as a calibration/quantitation reference in analytical methods (e.g., GC-FID/MS, LC-MS) and is manufactured/handled to minimize contaminants that could interfere with trace analysis.

• What “Analytical standard” implies (general)

  • Identity is established by appropriate spectroscopic/chromatographic methods (e.g., GC-MS, NMR, HPLC/GC purity assessment), with documentation in a Certificate of Analysis (CoA) including purity and (often) mass balance.
  • Impurities such as isomeric fatty acids, residual solvents, oxidation products (peroxides, aldehydes), and moisture are controlled to analytical-grade expectations. Exact limits: Not specified for this item; refer to CoA/Spec Sheet.
  • Packaged to reduce contamination and oxidation, often under inert gas and in amber vials for light protection (packaging specifics: Not specified for this item; refer to CoA/Spec Sheet).

• Suitability

  • Calibration of fatty acid profiles as free acids or after derivatization to methyl esters (FAMEs).
  • Spike-and-recovery, system-suitability, and retention-index locking in GC.
  • Method development for resolving positional isomers of eicosenoic acids.

• Practical guidance

  • Upon opening, record lot number and prepare aliquots to avoid repeated freeze–thaw or prolonged headspace exposure.
  • Verify any stabilizers or additives in the CoA; none are specified for this item.

Reaction and Applications

This product is supplied as an Analytical standard; its primary use is in quantitative and qualitative analysis of fatty acids. It is also a versatile long-chain carboxylic acid for synthesis.

• Analytical applications (general/literature)

  • GC profiling: Convert to methyl ester (FAME) using acidic methanol (e.g., HCl/MeOH or BF3/MeOH) for high-efficiency GC separation and retention index assignment of C20:1 isomers.
  • LC-MS workflows: Direct analysis of the free acid in negative-ion ESI; or analyze as ammonium/adducted species in APCI. Use isotope-dilution where appropriate.
  • System suitability: Establish resolution of positional isomers (Δ8 vs Δ11) on polar GC columns (e.g., cyanopropyl stationary phases) or silver-ion HPLC.

• Synthetic transformations (literature)

  • Esterification: Fischer esterification to alkyl esters; Steglich (DCC/DMAP) esterification for sensitive alcohols.
  • Amidation: Carbodiimide/HOBt or EDCI coupling to give long-chain amides and surfactant precursors.
  • Acyl chloride formation: SOCl2 or oxalyl chloride to access downstream acylation chemistry.
  • Double-bond chemistry: Selective hydrogenation to arachidic acid (C20:0); epoxidation (e.g., m-CPBA) to epoxy fatty acids; ozonolysis to yield two fragments with defined chain lengths.

• Practical tips

  • Prevent oxidation/polymerization of the double bond: use inhibitors only if compatible with analysis (none are specified for this item) and minimize air/light.
  • For trace-level analytics, employ silanized glassware, use fresh solvents, and verify blank backgrounds.

Item-specific manufacturer applications were not provided; the above expands typical uses of a Δ8-cis eicosenoic acid standard in research settings.

Reaction Conditions

The following are literature/general conditions commonly applied to long-chain monounsaturated fatty acids; optimize for your substrate and scale.

• Esterification (Fischer)

  • Reagents: Alcohol (MeOH, EtOH), catalytic H2SO4 or HCl.
  • Conditions: Reflux 1–6 h; remove water by Dean–Stark if using higher alcohols in toluene.
  • Notes: For GC analysis, methyl esterification (FAME) is standard. Neutralize and extract into isooctane/hexane.

• Steglich esterification

  • Reagents: DCC (or DIC), catalytic DMAP, dry DCM (or THF) at 0–25 °C, 2–16 h.
  • Notes: Filter dicyclohexylurea; wash to remove DMAP. Useful for sensitive alcohols.

• Amide coupling

  • Reagents: EDCI/HOBt (or HATU), amine, base (DIPEA), DCM/DMF, 0–25 °C, 2–12 h.
  • Notes: Minimize overacylation by slow addition; monitor by TLC/LC-MS.

• Acyl chloride formation

  • Reagents: SOCl2 (or oxalyl chloride) with catalytic DMF, 0–25 °C, 1–3 h.
  • Notes: Strictly anhydrous; quench cautiously. Follow with acylation of nucleophiles.

• Hydrogenation (C=C to C20:0)

  • Catalyst: Pd/C (5–10%), H2 (1–3 atm), EtOH/EtOAc/hexane, 20–40 °C, 1–6 h.
  • Notes: Avoid over-reduction of any additional functionalities; filter catalyst thoroughly.

• Epoxidation (Prilezhaev)

  • Reagent: m-CPBA (1.1–1.3 equiv), DCM, 0–25 °C, 1–4 h.
  • Notes: Buffer with NaHCO3 to limit acid-mediated side reactions; purify swiftly to avoid epoxide opening.

• Ozonolysis

  • Reagents: O3 in O2, −78 to −20 °C, then reductive workup (Me2S, PPh3) or oxidative (H2O2).
  • Notes: Provides chain-cleaved fragments; handle peroxides with caution.

Yields and times are typical literature ranges; always confirm on small scale and consult primary references for your exact transformation.

Safety and Handling

Hazard classification was not provided for this item; consult the SDS for authoritative information. The guidance below reflects general handling of long-chain monounsaturated fatty acids in a laboratory setting.

• GHS/SDS

  • Signal word, hazard statements, pictograms: Not specified for this item; refer to SDS.
  • Many fatty acids are not acutely hazardous but can cause skin/eye irritation; verify for this specific isomer and grade.

• Handling

  • Avoid contact with skin and eyes; wear appropriate PPE: lab coat, safety glasses or goggles, and nitrile gloves.
  • Use in a well-ventilated area; aerosol generation should be avoided.
  • Prevent prolonged exposure to air, heat, and light to minimize autoxidation (rancidification) of the cis double bond.

• Incompatibilities

  • Strong oxidizers (risk of exothermic reactions or accelerated peroxidation).
  • Strong bases/alkalies convert the acid to soaps; handle accordingly.
  • Acylation reagents (SOCl2, oxalyl chloride) react vigorously; add cautiously with cooling and inert atmosphere if used in synthesis.

• First aid (general)

  • Skin: Wash with soap and water. Remove contaminated clothing.
  • Eyes: Rinse cautiously with water for several minutes. Remove contact lenses if present and easy to do. Seek medical attention if irritation persists.
  • Ingestion: Rinse mouth. Do not induce vomiting. Seek medical advice.
  • Inhalation of aerosols/mists: Move to fresh air and monitor.

• Storage

  • Product Data indicates room-temperature storage and normal shipment. For long-term analytical integrity, store tightly closed, dry, and protected from light; optional inert gas blanket can further limit oxidation. Always defer to label/SDS instructions.

Solvent Selection

Eicosaenoic acid (cis-8) is highly hydrophobic and only sparingly soluble in water. Solvent choice depends on the application (analysis versus synthesis) and whether the free acid or a salt/derivative is used.

• Polarity and miscibility (literature/general)

  • Polarity class: Nonpolar to weakly polar solute; favors nonpolar organic solvents.
  • Good solvents: Hexane, heptane, isooctane, toluene, chloroform, dichloromethane. Moderate in ethyl acetate. Limited in methanol/ethanol unless assisted by base.
  • Poor solvents: Water and aqueous buffers (unless converted to micelles/salts or formulated with surfactants).

• Analytical dissolution

  • GC-FID/MS: Prepare solutions in hexane or isooctane; for FAME analysis, derivatize first then dissolve the FAME in the same diluents.
  • LC-MS (ESI/APCI): Use MeOH, ACN, or IPA with 0.1–1 mM ammonium acetate or ammonium formate; addition of a trace base (e.g., NH4OH) can improve ionization of the free acid.

• Synthetic handling

  • For esterification/amidation, use anhydrous toluene, DCM, or THF; ensure water-free conditions for coupling chemistry.

• Small comparison (literature)

  • Hexane vs isooctane: Isooctane is less volatile and often preferred for autosampler stability.
  • Chloroform vs DCM: Chloroform offers higher solubility for very hydrophobic analytes but is less preferred for green chemistry; DCM is more volatile and easier to remove.

Note: No item-specific solubility or UV-cutoff specifications are provided; consult CoA/Spec Sheet for any certified solvent recommendations.

Storage and Reconstitution

• Storage (item-specific)

  • Storage Conditions: Room temperature (as provided in Product Data).
  • Shipped In: Normal (ambient) conditions.
  • Keep container tightly closed in a dry place. Protect from excessive heat and light to limit oxidation of the cis double bond.

• Long-term integrity (general best practice)

  • Although room-temperature storage is acceptable per label, for extended storage consider cool, dark conditions with minimal headspace or an inert gas overlay (nitrogen/argon) to suppress autoxidation. Avoid repeated warm–cool cycles that can promote condensation and degradation.

• Reconstitution and stock solutions (general)

  • Dissolve the free acid in a suitable organic solvent: hexane, isooctane, toluene, chloroform, DCM, or MeOH/IPA (optionally with a trace of base for improved solubility).
  • Typical analytical stocks: 1–10 mg/mL, prepared in amber vials. Filter through PTFE syringe filters if particulate is present.
  • For aqueous or biological media, pre-dissolve in a miscible solvent (e.g., ethanol, DMSO) and, if required, complex with fatty-acid–free BSA or use surfactants to prevent precipitation.

• Stability

  • Avoid prolonged exposure to air and light. Prepare aliquots to limit repeated opening. No item-specific stabilizers or shelf-life are provided; refer to CoA/Spec Sheet and SDS for definitive guidance.

• Research Use Note: For research use only.

Structure and Identity

Eicosaenoic acid (cis-8) is a monounsaturated C20 fatty acid featuring one cis (Z) double bond located at the Δ8 position (counted from the carboxyl carbon). The backbone is a linear aliphatic chain terminating in a carboxylic acid.

• Item-specific identifiers (SKU E1508895):

  • CAS: Not specified for this item; refer to CoA/Spec Sheet.
  • CID: Not specified for this item; refer to CoA/Spec Sheet.
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/structural description (general):

  • Common class: Long-chain monounsaturated fatty acid (C20:1, Δ8-cis).
  • Functional groups: One terminal carboxylic acid (–CO2H); one internal cis C=C.
  • Stereochemistry: The single double bond is cis (Z), imparting a single kink to the hydrocarbon chain.
  • Chain topology (2D verbal depiction): HOOC–(CH2)6–CH=CH–(CH2)10–CH3 when the double bond is at Δ8 (illustrative spacing; exact atom-by-atom connectivity follows Δ8 assignment from the carboxyl end).

• Molecular formula (literature, for C20:1 fatty acid): C20H38O2.

• Molecular weight (literature): ~310.52 g/mol.

Notes

• The above molecular formula and mass are typical literature values for a C20 monounsaturated fatty acid; confirm exact identifiers and structure in the item’s CoA/Spec Sheet for regulatory or analytical documentation.
• Isomerism: Several positional isomers of eicosenoic acid exist (e.g., Δ5, Δ7, Δ11); this product specifies the Δ8-cis isomer.

Synthetic Utility

As a long-chain monounsaturated carboxylic acid, eicosaenoic acid (cis-8) is a useful, functionally rich intermediate for organic synthesis and materials research.

• Functional group handles

  • Carboxylic acid: Readily transformed into esters, amides, anhydrides, and acid chlorides. Enables coupling to alcohols (Steglich), amines (EDCI/HATU), and surfaces (via carbodiimide chemistry).
  • Internal cis-alkene: Amenable to selective hydrogenation (to C20:0), epoxidation (Prilezhaev), dihydroxylation (Upjohn), hydroboration–oxidation (anti-Markovnikov alcohol formation after cleavage/derivatization), and oxidative cleavage (ozonolysis/periodate workups) to produce defined fragment acids/aldehydes.

• Materials and surfactant chemistry

  • Long hydrophobe tail imparts amphiphilicity upon conversion to salts, esters, or quaternary ammonium derivatives; useful for model membranes, self-assembled monolayers, or rheology modifiers.

• Retrosynthetic value

  • Serves as a benchmark substrate for studying regiocontrol and stereoretention in transformations of cis monoenes (e.g., syn vs anti additions), and for validating selective functionalizations at remote positions.

• Isomer-specific studies

  • The Δ8 position provides a distinct chromatographic signature compared to Δ11 or Δ13 isomers; useful for developing resolution strategies (silver-ion chromatography, tailored GC phases) and mechanistic probes on isomerization under acid/metal catalysis.

Note: For reactions sensitive to oxidation, work under inert atmosphere and include radical inhibitors only if compatible with your objectives and analytical requirements.

Target Specificity

Not applicable. This product is a small-molecule fatty acid standard, not a biological macromolecule or antibody. No target, epitope, clone, or species reactivity information is relevant. Item-specific target data are not provided.

Foire aux questions

What is the purity of this product?

This product is supplied at ≥99% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

What does analytical standard mean?

analytical standard is a defined analytical purity tier suitable for quantitative analytical methods. It specifies a minimum assay percentage, controlled limits on common impurities (water, heavy metals, residue on ignition), and lot-to-lot consistency. analytical standard is one of several purity tiers — choose based on the sensitivity and regulatory requirements of your method.

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 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.