Ethyl geranyl ether , CAS No.40267-72-9

CAS: 40267-72-9 Cat. No.: E1041546 EC番号: 254-867-7 PubChem CID: 5365847

Storage

Room temperature

Specifications

保管条件

Room temperature

名前と識別子

• カノニカル・スマイル: CCOCC=C(C)CCC=C(C)C
• IUPAC Name: (2E)-1-ethoxy-3,7-dimethylocta-2,6-diene
• InChIKey: LOUIMJFJROISMD-FMIVXFBMSA-N
• INCHI: 1S/C12H22O/c1-5-13-10-9-12(4)8-6-7-11(2)3/h7,9H,5-6,8,10H2,1-4H3/b12-9+
• 異性体SMILES: CCOC/C=C(\C)/CCC=C(C)C
• 代替CAS番号: 40267-72-9,22882-89-9,22882-91-3
• PubChem CID: 5365847

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • 分類 Prenol lipids
      • Subclass Monoterpenoids

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• 分類: Prenol lipids
• Subclass: Monoterpenoids
• Intermediate Tree Nodes: Not available
• Direct Parent: Acyclic monoterpenoids
• Alternative Parents: Dialkyl ethers Hydrocarbon derivatives
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Acyclic monoterpenoid - Ether - Dialkyl ether - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Aliphatic acyclic compound
• 説明: This compound belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle.
• External Descriptors: Not available

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

化学的性質と物理的性質

• 分子量: 182.300 g/mol
• XLogP3: 3.800
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 6
• Exact Mass: 182.167 Da
• Monoisotopic Mass: 182.167 Da
• Topological Polar Surface Area: 9.200 Ų
• Heavy Atom Count: 13
• Formal Charge: 0
• Complexity: 174.000
• 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

Application Protocols

No validated bioassay or immunoassay protocols are associated with this small-molecule reagent. For synthetic use, typical protocols include:

• GC–MS identity/purity check

  • Prepare ~1 mg/mL in hexane or DCM; inject 1 µL on a nonpolar column (e.g., 5% phenyl-methylpolysiloxane); monitor for expected allylic fragments. Include peroxide check if stored long-term.

• Epoxidation screening

  • Dissolve substrate (0.1–0.5 M) in dry DCM; cool to 0–5 °C; add mCPBA (1.05 equiv per alkene) portionwise; stir 1–2 h; quench with saturated NaHCO3; extract, dry, and analyze by NMR/GC.

These examples are general literature-style workflows and are not item-specific validated methods. Adjust conditions to your scale and safety protocols.

Biological Roles

Ethyl geranyl ether is a synthetic ether of a monoterpenoid (geraniol). While geraniol and related terpenes occur widely in plants and participate in flavor/aroma profiles, the ethyl ether is primarily a research chemical.

• General biochemical context (literature)

  • Terpenoid backbones (isoprenoids) are ubiquitous in biology (e.g., prenylation, carotenoids, sterols). The geranyl motif mimics early intermediates in the mevalonate/MEP pathways.
  • Etherification of the primary alcohol removes hydrogen-bonding capacity and significantly alters polarity and membrane partitioning relative to geraniol, which can influence model membrane studies or binding to hydrophobic protein pockets.

• Use in research settings

  • Probe molecule for studying allylic oxidation/selectivity and metabolic oxidation models in microsomal systems (non-clinical, in vitro), where ether stability can simplify product analysis compared to alcohol substrates.
  • Hydrophobic carrier or scent model in formulation science to evaluate volatility, release, and oxidative stability of unsaturated terpenoid ethers.

No medical or clinical roles are claimed or implied. For biological testing, ensure appropriate controls (e.g., geraniol vs ether) to separate effects of hydrogen-bonding and polarity.

Buffer Applications

Not typically applicable. Ethyl geranyl ether is a nonpolar organic substrate and does not function as a buffering agent. In aqueous systems it partitions to an organic phase or forms emulsions. For work involving this compound in biphasic or emulsion systems, focus on solvent/emulsifier selection (e.g., inclusion of surfactants or cosolvents) rather than buffer composition.

Green Alternatives

This product is a substrate/building block rather than a process solvent. Green considerations focus on solvent and reagent choices used with it.

• Greener solvent choices (literature guidance)

  • Replace chlorinated solvents (DCM) with cyclopentyl methyl ether (CPME) or 2‑MeTHF where compatible to reduce halogenated waste.
  • Use toluene or anisole instead of benzene; consider bio-based esters (EtOAc) when polarity allows.
  • For extractions, consider heptane or methylcyclohexane instead of hexane blends containing n‑hexane.

• Oxidant/electrophile choices

  • Prefer hydrogen peroxide with appropriate catalysts (e.g., phosphotungstate) over peracids for epoxidations when feasible.
  • Employ catalytic, atom-economic processes (olefin metathesis, hydroboration with catalytic HB sources) over stoichiometric halogenations.

• Comparison snapshot (general)

  • DCM vs CPME: similar solvating power for many transformations; CPME offers higher boiling point, lower toxicity, and reduced peroxide formation relative to MTBE/THF but still requires periodic testing.
  • Peracids vs H2O2 systems: H2O2 generates benign byproduct (water), but may need catalysts and offers narrower substrate scope.

Note: The compound itself is a petroleum/bio-based hydrocarbon ether; greener sourcing may include biogenic geraniol feedstocks. Always evaluate LCA and waste minimization in your specific process.

Pharmaceutical Uses

This product is offered for research use only and is not intended for human or animal use in drug, food, or cosmetic applications.

• Formulation science context (general)
  • As a hydrophobic, unsaturated ether, it can serve as a model excipient-interacting molecule in pre-formulation research (e.g., studying volatility, oxidative stability, or aroma retention in non-aqueous systems). However, it is not a compendial excipient and has no pharmacopeia monograph.
  • The ether is less polar than geraniol, which can alter solubility in lipid vehicles and polymer matrices, providing a contrast substrate in screening studies.

No therapeutic claims are made. Any use in pharmaceutical R&D should be limited to laboratory-scale experimentation with appropriate safety review.

Physical Properties

• Item-specific specifications (this catalog item)

  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
  • Density, refractive index, water content, UV cutoff, metal content: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/general properties for ethyl geranyl ether (non-spec, for reference only)

  • Physical state: typically a colorless, hydrophobic liquid with a mild terpene-like odor (literature, typical for geranyl ethers).
  • Molecular weight: ~182.30 g/mol (from C12H22O).
  • Solubility: expected to be insoluble in water; miscible with common organic solvents such as hexanes, ethers, and aromatics (literature expectation for nonpolar terpene ethers).
  • Volatility/boiling behavior: medium–high boiling for a C12 ether; significantly less volatile than short-chain dialkyl ethers (general trend; consult primary data for exact bp).
  • Partitioning: high hydrophobicity with an elevated logP is expected for a C12 alkyl/allylic ether (general trend; consult primary data for measured logP).

Note: All numerical physical constants (bp, mp, density, nD, pKa/logP) are not specified for this item; consult the product CoA or SDS for authoritative values if required for method development or safety review.

Quality and Grades

• Item-specific quality information

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

• Interpreting grades (general guidance)

  • Research/analytical grades typically specify assay purity (GC), limits on related terpenoid impurities (e.g., neryl/isogeranyl ethers), and residual solvents. For chromatographic applications, low UV-absorbing impurities are desirable.
  • If stabilized, common antioxidants for unsaturated terpenes (e.g., BHT) may be present to suppress autoxidation; this can influence downstream reactions or bioassays and should be disclosed on the CoA.
  • Odor/organoleptic notes, while common in fragrance-grade materials, are not substitutes for analytical specifications in research reagents.

• Recommended verification

  • Confirm identity/purity by GC–MS or 1H/13C NMR. Monitor for peroxide content if long-term storage is anticipated.
  • For sensitive applications (e.g., kinetic studies or polymerization), request current CoA/SDS for exact impurity and stabilizer profile.

Reaction and Applications

As an unsaturated allylic ether, ethyl geranyl ether is a versatile substrate for transformation of the isoprenoid chain while the ether oxygen protects the primary alcohol function.

• Typical reactions on the diene (literature)

  • Electrophilic additions: hydrohalogenation, halohydrin formation, and hydration across the C=C bonds under controlled conditions.
  • Oxidations: epoxidation (e.g., mCPBA), dihydroxylation (OsO4/NMO, KMnO4), allylic oxidation (SeO2) to access enones or allylic alcohols after subsequent manipulations.
  • Ozonolysis/oxidative cleavage to fragment the isoprenoid chain into carbonyl derivatives.
  • Hydroboration–oxidation to generate regioselective alcohols; the ether function stays intact under standard conditions.
  • Olefin metathesis (RCM/CM) with ruthenium carbene catalysts on suitably designed derivatives.

• Ether stability and manipulations

  • The ethyl ether is generally robust to bases and many nucleophiles; it can be cleaved under Lewis acidic conditions (e.g., BBr3/BCl3 or AlCl3 variants) to regenerate geraniol, though conditions must be tuned to avoid double-bond isomerization.
  • Under strong protic acids, allylic rearrangements and dehydration side reactions may occur; use non-nucleophilic acids if activation of the ether is required.

• Practical tips

  • Work under inert atmosphere for air-sensitive steps to limit peroxide/autoxidation of the diene.
  • For selective functionalization of one C=C bond, temperature control and choice of reagent sterics are important given the similar substitution patterns.
  • Monitor by GC–FID/GC–MS; the ether is GC-amenable and exhibits characteristic allylic fragment ions.

Reaction Conditions

General literature guidance for common transformations on allylic dienyl ethers like ethyl geranyl ether (non-binding; optimize per substrate):

• Epoxidation

  • Reagents: mCPBA (1.0–1.2 equiv per C=C) in DCM or toluene, 0–25 °C, 1–4 h; buffer with NaHCO3 to moderate acidity. Alternative: H2O2/UHP with catalytic tungstate in MeCN or alcohol solvents at 20–40 °C.

• Dihydroxylation

  • OsO4 (0.5–2 mol%) with NMO or K3[Fe(CN)6] in tBuOH/H2O or acetone/H2O at 0–25 °C; quench with bisulfite; delivers vicinal diols from each alkene.

• Allylic oxidation

  • SeO2 (0.5–1.0 equiv) with TBHP in toluene, 60–90 °C; monitor for overoxidation. Alternative: Mn-catalyzed allylic C–H oxidation with peroxides under milder conditions.

• Hydroboration–oxidation

  • 9‑BBN (1.1–2.2 equiv) or BH3·THF in THF/THF alternative (e.g., 2‑MeTHF), 0–25 °C; oxidation with H2O2/NaOH to furnish alcohols; ether remains intact.

• Olefin metathesis

  • Grubbs/Hoveyda–Grubbs catalysts (2–10 mol%) in DCM, toluene, or chlorobenzene; 25–60 °C under N2/Ar with degassed solvent.

• Deprotection (ether cleavage; use caution)

  • BBr3 or BCl3 in DCM, −78 to 0 °C, quench carefully; risk of double-bond isomerization/cationic rearrangement exists—verify by NMR/GC.

Safety note: Use inert atmosphere to limit peroxide formation/autoxidation; verify absence of peroxides before concentrating organic solutions of this ether.

Safety and Handling

• Product Data safety fields

  • Signal word: Not specified for this item; refer to SDS.
  • H-statements / GHS classification / pictograms: Not specified for this item; refer to SDS.

• General safety considerations for terpene ethers (literature/good practice)

  • Flammability: treat as a combustible organic liquid; keep away from heat, sparks, and open flame. Use explosion-proof ventilation where vapor accumulation is possible.
  • Peroxide formation: ethers can form peroxides during prolonged air/oxygen exposure, especially upon light contact. While allylic ethers are less notorious than dialkyl ethers like THF/diethyl ether, periodic testing and proper storage are prudent.
  • Reactivity: avoid strong oxidizers; double bonds are susceptible to autoxidation. Strong acids may promote cleavage/isomerization; strong bases generally tolerated by ethers but may induce isomerization at allylic positions under forcing conditions.
  • PPE: lab coat, nitrile gloves, and splash goggles as minimum. Use in a fume hood to control vapors and prevent inhalation exposure.
  • First aid (overview; defer to SDS): in case of skin contact, wash with soap and water; for eye contact, rinse cautiously with water for several minutes and seek medical attention if irritation persists; if inhaled, move to fresh air; if ingested, do not induce vomiting—seek medical advice.

Always consult the product-specific SDS for authoritative hazard classification, exposure limits, and spill/firefighting procedures.

Solvent Selection

Ethyl geranyl ether is a hydrophobic, non-protic organic compound used predominantly as a substrate/building block rather than as a bulk solvent.

• Polarity and miscibility (general)

  • Polarity: low; behaves similarly to other C10–C12 aliphatic/allylic ethers.
  • Water miscibility: effectively immiscible; forms separate phase in aqueous systems.
  • Organic miscibility: miscible with hydrocarbons (hexanes, heptane), ethers (MTBE, TBME), aromatics (toluene), chlorinated solvents (DCM) and moderately polar organics (ethyl acetate).

• When choosing solvents for this substrate

  • For synthesis on the allylic diene motif: use nonpolar to moderately polar, aprotic solvents (hexanes, toluene, EtOAc, MTBE) to preserve ether integrity and limit acid-promoted side reactions.
  • For oxidation or electrophilic additions: dry, oxygen-controlled aromatic solvents (toluene) or DCM are common to moderate reactivity and heat.
  • For metathesis on the diene: use degassed toluene, DCM, or chlorobenzene under inert atmosphere.

• Comparison (general)

  • Versus alcohol (geraniol): ether lacks H-bonding and is less polar, improving solubility in apolar media and stability toward acids/bases, but removes the handle for hydrogen bonding or derivatization at O.

Note: This product is not intended as a chromatography-grade solvent. Use a suitable eluent (e.g., hexanes/EtOAc) when handling this compound on silica.

Storage and Reconstitution

• Item-specific storage (from Product Data)

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

• General handling guidance (literature/best practice)

  • Keep container tightly closed under dry, inert atmosphere (e.g., nitrogen) to limit autoxidation and potential peroxide formation in the ether and at allylic positions.
  • Store away from light and sources of heat; consider amber glass. Avoid contact with strong oxidizers and strong acids.
  • If long-term storage is anticipated, periodic peroxide testing of opened containers is prudent for ethers. Do not distill to dryness.

• Reconstitution/Preparation

  • Liquid reagent; use as supplied. If solid impurities/crystals are observed at low temperature, warm gently to ambient and mix thoroughly before use.
  • For moisture-sensitive transformations, dry over molecular sieves (3Å/4Å) or pass through a short alumina plug; verify that adsorbents do not promote isomerization of the diene.

Research Use Only: This material is intended solely for laboratory research. Refer to the product CoA and SDS for definitive storage and handling instructions.

Structure and Identity

Ethyl geranyl ether is an acyclic terpene ether derived from geraniol, in which the hydroxyl hydrogen is replaced by an ethyl group, yielding a non-protic, hydrophobic allylic ether.

• Item identifiers (from Product Data)

  • CAS: 40267-72-9
  • CID: 5365847
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Composition (literature/computed)

  • Molecular formula: C12H22O (literature, consistent with an ethyl ether of geraniol)
  • Molecular weight: ~182.30 g/mol (calculated from C12H22O)

• Structural features (general chemistry)

  • Functional groups: one ether (R–O–R′), two isolated trisubstituted C=C double bonds (isoprenoid pattern), several allylic C–H sites.
  • Backbone: a 10‑carbon geranyl chain (3,7-dimethyl-2,6-octadienyl) linked via oxygen to an ethyl group.
  • Stereochemistry: acyclic with E/Z geometry typically depicted as E at both internal double bonds for the geranyl isomer; as an ether, no stereocenters are present.
  • 2D description: an ethoxy substituent attached to the primary carbon of a 3,7-dimethyl-2,6-octadienyl chain; two C=C bonds separated by three sp3 carbons.

Synthetic Utility

Ethyl geranyl ether is a protected geraniol equivalent that preserves the oxidation state at C1 while enabling diverse manipulations of the isoprenoid chain.

• Protective features

  • O‑Ethyl protection blocks nucleophilic/oxidative events at the primary alcohol and provides enhanced stability under basic conditions relative to the free alcohol.
  • Deprotection under Lewis acidic conditions (e.g., BBr3, BCl3) or via iodination/reductive pathways can regenerate geraniol (optimize to minimize double-bond isomerization).

• Transformations on the carbon skeleton (literature)

  • Epoxidation at C2=C3 and/or C6=C7 followed by regioselective ring opening to build 1,2- and 6,7‑diols or haloalcohols.
  • Allylic oxidation (SeO2/TBHP variants) to introduce enone or allylic alcohol motifs post-deprotection.
  • Ozonolysis to access linear C=O fragments useful for terpene fragment coupling.
  • Cross-metathesis with acrylates or styrenes to elaborate the terminal or internal olefins.

• Retrosynthetic value

  • Serves as a geranyl synthon in cascades where the alcohol would interfere (e.g., acid-catalyzed cyclizations, polymerizations, metal-catalyzed processes sensitive to protic substrates).

Target Specificity

Not applicable. This product is a small-molecule organic reagent and is not an antibody, enzyme, or biological targeting agent. No target, epitope, isotype, or species reactivity information applies.