This compound belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms.
External Descriptors
Fatty alcohols
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.
Certificats (CoA, COO, BSE/TSE et tableau d'analyse)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Propriétés chimiques et physiques
Poids moléculaire
184.320 g/mol
XLogP3
4.200
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
1
Rotatable Bond Count
9
Exact Mass
184.183 Da
Monoisotopic Mass
184.183 Da
Topological Polar Surface Area
20.200 Ų
Heavy Atom Count
13
Formal Charge
0
Complexity
108.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
1
Undefined Bond Stereocenter Count
0
The total count of all stereochemical bonds
1
Covalently-Bonded Unit Count
1
Calculateurs de solution
Molarity Calculator
Determine the necessary mass, volume, or concentration for preparing a solution.
Dilution Calculator
Determine the dilution needed to prepare a stock solution.
Reconstitution Calculator
Avis
Avis des clients
Application Protocols
Not applicable as a validated biological assay reagent. No WB/IHC/IF/FC or similar application protocols are provided for this small-molecule substrate. For synthetic and materials applications, refer to the “Reaction Conditions” and “Synthetic Utility” sections for general procedural guidance and adapt to your specific transformation.
Biological Roles
This catalog item is for research use only. No clinical or therapeutic claims are made.
Literature/General context for alkenyl fatty alcohols:
Fatty alcohols (C12–C18) occur in biological systems as minor constituents of wax esters and as intermediates in lipid metabolism via fatty acyl-CoA reductases. Unsaturation (one C=C) can influence membrane packing and melting behavior of derived lipids.
Alkenyl alcohols can be enzymatically converted to corresponding esters (waxes), ethers, or oxidized to aldehydes/acids; these transformations affect surfactant behavior, micellization, and interfacial properties relevant to biophysical studies.
In model membranes, incorporation of unsaturated long-chain amphiphiles modulates fluidity and phase separation; double-bond position and geometry change transition temperatures and domain morphology.
As hydrophobic modifiers, C12 alkenyl alcohols can be used to tailor hydrophobic interactions in protein–lipid or polymer–lipid assemblies in vitro.
Notes: Specific biochemical pathways, potencies, or cellular activities for SKU D1039013 are not specified and should not be inferred. If biological assays are planned, confirm isomeric purity (double-bond position/E–Z) as it can affect biophysical outcomes.
Buffer Applications
Not typically applicable. 8-Dodecenol is a hydrophobic, non-ionic long-chain alcohol and is not used as a buffering agent. For experimental systems requiring aqueous handling, consider:
Using co-solvents (e.g., ≤2–5% DMSO, ethanol, or 2-propanol) or surfactants (Tween, Triton) to disperse the compound.
Preparing emulsions or liposome-like dispersions if interfacial studies are intended.
Buffer formulation details (pKa, buffering ranges) are not relevant to this substrate.
Green Alternatives
Considerations (general): long-chain alkenyl alcohols like 8-dodecenol are often derived from petrochemical or bio-based oleochemical routes. Greener choices focus on sourcing, solvent selection, and reagent economy rather than replacing the substrate itself.
Greener processing choices (literature/general):
Bio-based sourcing: select materials produced from natural fatty alcohol cuts (oleochemical) when available; lower carbon footprint compared with petrochemical synthesis.
Solvent selection: prefer 2-MeTHF, cyclopentyl methyl ether (CPME), ethyl acetate, or propylene carbonate in place of chlorinated solvents when reaction compatibility permits.
Catalysis: use catalytic esterifications (solid acids, enzymes such as CAL-B) under solvent-minimized or solvent-free conditions.
Oxidations: replace chromium(VI) reagents with TEMPO/NaOCl, Oxone, or electrochemical methods; employ aqueous biphasic systems to reduce VOCs.
Example comparison (general; not item-specific):
| Aspect | Conventional choice | Greener alternative | Trade-offs |
|---|---|---|---|
| Solvent for esterification | CH2Cl2 | EtOAc or 2-MeTHF | Slightly different rates/selectivity; easier solvent recovery |
| Epoxidation | mCPBA in CH2Cl2 | H2O2 with tungstate or Mn catalysts in MeOH/H2O | Requires optimization; safer oxidant |
| Oxidation to aldehyde | Swern (DMSO/oxalyl chloride) | DMP or TEMPO/NaOCl | Cost vs. halide waste vs. aqueous handling |
Waste minimization: employ continuous extraction or reactive distillation for water removal in Fischer esterifications; recycle nonpolar solvents via fractional distillation.
Pharmaceutical Uses
Item-specific (Product Data): Grade/purity and pharmacopeial status are not specified for this item; refer to CoA/Spec Sheet. For research use only.
Literature/General formulation context:
Long-chain fatty alcohols are sometimes employed as excipient components in topical and transdermal formulations (e.g., emollients, co-emulsifiers, consistency agents) or as hydrophobes in controlled-release matrices. Unsaturation can soften texture and lower melting points relative to saturated analogs.
8-Dodecenol derivatives (esters, ethers, acrylates) may serve as functional monomers or additives in medical-device coatings or adhesive systems; such uses require dedicated quality and biocompatibility assessments not implied here.
For pre-formulation screening, characterize: peroxide value, acid value, residual solvents, and isomeric composition, as these can impact stability and odor.
No pharmacopeial monograph or excipient grade is claimed for SKU D1039013 based on the provided data.
Physical Properties
Item-specific (Product Data):
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
Literature/General values for C12 mono-unsaturated fatty alcohols (for context; not item specifications):
Approx. molecular formula: C12H24O; formula mass ~184.32 g/mol (literature, typical for dodecen-1-ol isomers).
Physical state: typically a colorless to pale liquid or low-melting wax; viscosity increases on cooling.
Boiling point: often reported in the 250–280 °C range at 1 atm for C12 alkenyl alcohols; substantially lower under reduced pressure (literature). Exact value depends on isomer and purity.
Melting point: may be near or below room temperature; unsaturation depresses melting relative to saturated dodecanol (literature).
Density (20–25 °C): commonly ~0.82–0.84 g/mL for long-chain alkenyl alcohols (literature).
Solubility: insoluble in water; miscible with nonpolar and moderately polar organic solvents (hexanes, toluene, Et2O, THF, CH2Cl2); limited solubility in acetonitrile; immiscible with highly polar protic solvents like water (literature trends).
LogP: expected >4 due to long hydrocarbon chain (literature estimate).
Refractive index: typically around nD 1.44–1.46 (literature, chain-length and unsaturation dependent).
Notes: All numerical values above are general literature expectations for C12 alkenyl alcohols and are not specifications for SKU D1039013.
Quality and Grades
Item-specific (Product Data):
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/Inhibitors: Not specified for this item; refer to CoA/Spec Sheet.
Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on interpreting grades (general):
Research grade fatty alcohols are typically suitable for synthesis, formulation screening, and materials studies. Specifications may include GC purity, residual solvents, water content, and isomeric composition (position of C=C, E/Z ratio, and terminal vs internal alcohol).
For reaction-critical applications (e.g., polymerization, surface chemistry), request the CoA for: GC area % purity, hydroxyl value/acid value, peroxide value, isomer distribution, and metal traces if catalytic processes are planned.
Low-UV or HPLC-grade designations (if applicable) indicate minimized UV-active impurities for analytical compatibility. Inhibitors are uncommon for fatty alcohols, but some lots may include antioxidants; verify before use in radical chemistry.
Practical tips:
If stereochemistry or double-bond position is important, confirm by 1H/13C NMR and GC–MS. Residual saturation/di-unsaturation levels can impact physical properties and reactivity.
For moisture-sensitive derivatizations (e.g., acid chloride esterifications), consider drying the alcohol by azeotropy or molecular sieves even though long-chain alcohols are weakly hygroscopic.
Alkene functionalization: epoxidation (mCPBA, peracids), dihydroxylation (OsO4/NMO; Upjohn), hydroboration–oxidation (BH3·THF then H2O2/NaOH) to give regioselective diols or isomeric alcohols, ozonolysis to fragment the chain.
Alcohol derivatization: esterification (Fischer, Steglich, acid chloride), carbonate/urethane formation, tosylation/mesylation to enable substitution, etherification (Williamson) to produce surfactant-like ethers.
Oxidation/reduction: Swern/DMP/TPAP to aldehydes; Jones/Pinnick to acids; catalytic hydrogenation to saturated dodecanol or to saturate the C=C selectively.
Radical and thiol–ene additions across the double bond for constructing functionalized surfactants and macromonomers.
Application spaces:
Intermediates for surfactants, lubricants, dispersants, plasticizers, and specialty esters (e.g., acrylates, methacrylates) for coatings and UV-curable materials.
Model compound for studying micellization/monolayer formation and hydrophobic interactions in soft-matter systems; precursor for phase-change materials via ester networks.
Practical tips (general):
Dry the substrate before moisture-sensitive couplings (azeotrope or molecular sieves). Although long-chain alcohols are weakly hygroscopic, trace water can suppress carbodiimide esterifications.
Double-bond position and E/Z geometry can affect reaction regio-/stereochemistry and melting points; verify by NMR before selective oxidations or polymerizations.
For heterogeneous systems (e.g., TEMPO/NaOCl oxidations), use phase-transfer catalysts or emulsifiers to enhance mass transfer.
Reaction Conditions
General literature guidance for transforming alkenyl fatty alcohols like 8-dodecenol (not specifications):
Epoxidation of the C=C:
Reagents: mCPBA (1.1–1.5 equiv) in CH2Cl2, 0–25 °C, 1–6 h; buffer with NaHCO3 to suppress epoxide opening. Typical isolated yields: 70–90% for clean substrates.
Greener variant: H2O2 (30%) with tungstate or Ti-silicate catalysts in MeOH or MeOH/H2O at 0–25 °C; monitor to avoid over-oxidation.
Hydroboration–oxidation:
BH3·THF or 9-BBN (1.1–1.5 equiv), 0–25 °C; then H2O2/NaOH. Anti-Markovnikov alcohols form; reaction in THF, 0–4 h. Yields commonly 70–95%.
Esterification (Steglich):
Carboxylic acid (1.1 equiv), DCC or EDCI, catalytic DMAP in CH2Cl2 or THF, 0–25 °C, 2–16 h. Work up by urea filtration; 75–95% typical.
Oxidation to aldehyde (DMP):
DMP (1.3 equiv) in CH2Cl2, 0–25 °C, 0.5–2 h; quench with NaHCO3/Na2S2O3. Typical yields 75–90%.
Hydrogenation:
Pd/C (5–10 wt%), H2 (1–3 atm), EtOH or EtOAc, 20–40 °C, 2–8 h to saturate C=C; minimal over-reduction at the alcohol. Yields ~90%.
Notes:
Long-chain substrates may exhibit slow mixing; ensure efficient stirring or use small amounts of co-solvent/surfactant.
Confirm double-bond position/E–Z prior to regioselective steps. Monitor by GC or 1H NMR (allylic/olefinic resonances). All conditions above are general literature ranges and require optimization for your specific isomer and scale.
Safety and Handling
Item-specific (Product Data):
GHS classification, signal word, pictograms, and H-statements: Not specified for this item; refer to the SDS.
Storage conditions: Room temperature.
General safety considerations for long-chain alkenyl alcohols (literature/typical):
Hazards: combustible liquid; may cause skin and eye irritation; ingestion and inhalation of mists may be harmful. Low volatility reduces acute inhalation risk but does not eliminate it.
Peroxide formation: not typically prone like ethers; however, unsaturated substrates can auto-oxidize over prolonged air exposure. Keep containers tightly closed and minimize headspace oxygen for long-term storage.
Incompatibilities: strong oxidizers (risk of exothermic reaction/oxidation to aldehydes/acids), strong acids (possible dehydration), and strong bases (may promote isomerization/condensation under heating).
Recommended PPE: safety glasses or face shield, lab coat, and chemical-resistant gloves (e.g., nitrile). Use in a fume hood when heating, distilling, or aerosolizing.
First aid (summary; defer to SDS):
Skin/eye contact: rinse with water for ≥15 minutes; remove contaminated clothing; seek medical attention for persistent irritation.
Inhalation: move to fresh air; provide oxygen if needed; seek medical attention if symptoms persist.
Ingestion: rinse mouth; do not induce vomiting; seek medical advice.
Firefighting: use CO2, dry chemical, or foam; water spray to cool containers. Combustion may produce CO, CO2, and irritating fumes.
Solvent Selection
This product is a hydrophobic, long-chain alkenyl alcohol and is generally used as a substrate or building block rather than as a reaction solvent.
Polarity and miscibility (literature/general):
Polarity class: low-polarity protic organic compound with strong hydrophobic character.
Water miscibility: effectively insoluble in water.
Organic solubility: good in nonpolar/aprotic media (hexanes, heptane, toluene), ethers (THF, MTBE), chlorinated solvents (CH2Cl2, CHCl3); moderate in alcohols like ethanol at room temperature; limited in acetonitrile and acetone due to hydrophobic chain.
Choosing media for transformations of 8-dodecenol (general guidance):
Esterifications/Carbonate formation: toluene, CH2Cl2, or neat conditions with Dean–Stark (for acid-catalyzed routes). For DMAP/EDC routes, use CH2Cl2 or THF.
Oxidations to aldehydes/acids: CH2Cl2, EtOAc, or MeCN depending on reagent system (e.g., Dess–Martin in CH2Cl2; TEMPO/bleach in biphasic toluene/aqueous NaOCl with phase-transfer catalyst).
Hydroboration–oxidation or epoxidation at the alkene: THF (hydroboration), CH2Cl2 (mCPBA epoxidation) are typical.
Comparison snapshot (general):
Hexanes: maximizes solubility and phase separation; poor for polar reagents.
Toluene: good substrate solubility; tolerates higher temps; compatible with acid catalysis.
CH2Cl2: balances solubility and reactivity for many derivatizations; easy workup; environmental considerations apply.
Storage and Reconstitution
Item-specific (Product Data):
Storage conditions: Room temperature.
Other storage details (container type, stabilizers, shelf life): Not specified for this item; refer to CoA/Spec Sheet.
General handling guidance for long-chain alkenyl alcohols:
Store tightly closed in an amber glass bottle to limit light exposure and oxidative degradation of the C=C. Minimize headspace air for long-term storage; consider inert gas blanket for sensitive applications.
Avoid prolonged exposure to strong light, heat, or oxidants. If low-temperature solidification occurs, gently warm (e.g., 30–40 °C water bath) to fully liquefy before dispensing; mix thoroughly to ensure homogeneity.
If exceptionally low peroxide values are critical (e.g., in radical polymerizations), test periodically and, if needed, pass through a short plug of basic alumina just prior to use.
Reconstitution/Preparation for use:
Typically used neat or dissolved in a compatible organic solvent (e.g., hexanes, toluene, CH2Cl2, THF). For aqueous dispersions, employ co-solvents or surfactants and high-shear mixing or sonication.
Research use only notice: As provided in Product Data, this material is designated for research use only.
Structure and Identity
Item-specific (Product Data):
SKU: D1039013
Product name: 8-Dodecenol
CAS: 42513-42-8
InChIKey: Not specified for this item; refer to CoA/Spec Sheet. (the provided token “435343” is not a valid InChIKey)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
8-Dodecenol generally refers to a C12 alkenyl alcohol (a “fatty alcohol”) bearing one carbon–carbon double bond and one hydroxyl group. Specific constitutional isomers include terminal (–CH2OH) or internal alcohols and E/Z alkene geometry; exact structure should be confirmed from the CoA.
Typical molecular formula for mono-unsaturated C12 alcohols: C12H24O (literature). Exact empirical details for this catalog item are not specified; verify on the CoA.
Structural features: long, flexible aliphatic chain; one isolated C=C (alkenyl) functionality; one alcohol (–OH) capable of hydrogen bonding and derivatization (esters/ethers/carbonates). No rings; no heteroatoms other than oxygen; expected to be a non-volatile, hydrophobic liquid/low-melting solid depending on isomer and purity.
2D description: a 12‑carbon zig–zag chain containing one C=C unit and one hydroxymethyl or secondary alcohol terminus depending on isomer assignment; the double bond may be E or Z. Confirm stereochemical configuration on the supplied specification sheet.
Synthetic Utility
Functional handles:
Alcohol (–OH): enables formation of esters (acylation), carbonates/urethanes, sulfonates (tosylate/mesylate) for SN2 substitutions, and ether formation (Williamson). Oxidation to aldehyde/acid provides access to semiochemicals and surfactant acids.
Alkene (C=C): supports epoxidation, hydroboration–oxidation to shift the hydroxyl position, halogenation, ozonolysis for chain scission, and thiol–ene conjugations. Hydrogenation affords saturated dodecanol.
Retrosynthetic value:
Serves as a bifunctional amphiphile for constructing telechelics and macromonomers; can be converted to acrylates/methacrylates or to glycidyl ethers for polymer chemistry.
Ozonolysis or Lemieux–Johnson cleavage maps the double-bond position and provides access to shorter-chain aldehydes/acids.
Selectivity considerations (general):
Protecting groups: silyl ethers (TBS/TIPS) stabilize the alcohol during oxidative alkene transformations; alternatively, perform chemoselective epoxidation that tolerates free –OH (with appropriate media).
Regio-/stereocontrol: hydroboration typically delivers anti-Markovnikov addition; E/Z configuration affects diastereoselectivity in epoxidations and dihydroxylations.
Practical notes:
For nucleophilic substitutions on derived sulfonates, heat in polar aprotic solvents (DMF/DMSO) can be required; long chains may phase-separate—use co-solvents or surfactants as needed.
Purification often relies on Kugelrohr or short-path distillation under high vacuum due to high boiling points and low polarity.
Target Specificity
Not applicable. This product is a small-molecule alkenyl alcohol, not a biological targeting reagent (e.g., antibody, ligand with defined receptor selectivity). No target, epitope, clone, isotype, or species reactivity is associated with SKU D1039013.
Nous utilisons des cookies pour garantir le bon fonctionnement du site et, lorsque cela est autorisé, pour améliorer votre expérience. Vous pouvez gérer vos préférences à tout moment dans les Paramètres. Pour en savoir plus, consultez notre Politique relative aux cookies.
Souhaitez-vous que nous vous envoyions un message lorsque des réductions seront disponibles?
Me rappeler plus tard
Merci ! Veuillez vérifier votre boîte de réception e-mail pour confirmer.
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.
