Rose oxide, trans-(+)- , CAS No.5258-10-6

CAS: 5258-10-6 Cat. No.: R951080 Formula: C₁₀H₁₈O Peso molecolare: 154.250

Storage

Room temperature

Specifications

Condizioni di conservazione di stoccaggio

Room temperature

Nomi e identificatori

Sorrisi canonici

C[C@H]1CCO[C@@H](C1)C=C(C)C

IUPAC Name

(2S,4S)-4-methyl-2-(2-methylprop-1-enyl)oxane

InChIKey

CZCBTSFUTPZVKJ-VHSXEESVSA-N

INCHI

1S/C10H18O/c1-8(2)6-10-7-9(3)4-5-11-10/h6,9-10H,4-5,7H2,1-3H3/t9-,10+/m0/s1

Peso molecolare

154.250

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Classe Oxanes

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Classe: Oxanes
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Oxanes
• Alternative Parents: Oxacyclic compounds Dialkyl ethers Hydrocarbon derivatives
• Molecular Framework: Aliphatic heteromonocyclic compounds
• Substituents: Oxane - Oxacycle - Ether - Dialkyl ether - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Aliphatic heteromonocyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as oxanes. These are compounds containing an oxane (tetrahydropyran) ring, which is a six-member saturated aliphatic heterocycle with one oxygen atom and five carbon atoms.
• 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

Proprietà chimiche e fisiche

• Peso molecolare: 154.250 g/mol
• XLogP3: 2.900
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 154.136 Da
• Monoisotopic Mass: 154.136 Da
• Topological Polar Surface Area: 9.200 Ų
• Heavy Atom Count: 11
• Formal Charge: 0
• Complexity: 145.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 2
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Application Protocols

No standardized bioassay or immunotechnique protocols apply to this small-molecule product. For chemosensory assays (general research guidance):

• Stock preparation: Dissolve in high-purity ethanol, DMSO, or mineral oil to prepare concentrated stocks (e.g., 10–100 mM), then dilute into assay media to the desired final concentration while keeping co-solvent below assay tolerance (often ≤0.1–0.5%).
• Delivery: For olfactory receptor or behavioral assays, use headspace generation (sealed vials, SPME) or dynamic olfactometry with controlled vapor-phase concentrations.
• Analytics: Verify stimulus concentration by GC or GC–MS of headspace; employ chiral GC if stereospecific responses are studied.

These are general, literature-style suggestions only; adapt to your institutional SOPs. No item-specific tested applications are provided for this SKU.

Biological Roles

• General biochemical/organoleptic context (literature)

  • trans-(+)-Rose oxide is a potent odorant constituent associated with rose, lychee, and certain floral/fruity aromas. It acts as a ligand for olfactory receptors in humans and other species, making it valuable for chemosensory and neurobiology research (odor coding, receptor specificity, mixture interactions).

• Occurrence and biosynthesis (literature)

  • Naturally occurs in trace amounts in some essential oils. Biogenetically related to monoterpene pathways stemming from geranyl pyrophosphate through intermediate terpenoid alcohols (e.g., citronellol); intramolecular cyclization and oxidation furnish the tetrahydropyran framework.

• In vitro and in vivo research utilities (non-clinical)

  • Model compound for studying structure–odor relationships among cyclic ethers and allylic terpenoids.
  • Useful in behavioral assays (e.g., insect olfaction) and in receptor deorphanization studies, where defined stereochemistry (trans-(+)) can influence receptor activation potency.

• Physicochemical drivers of biointeraction (general)

  • Moderate hydrophobicity and an ether oxygen capable of H-bond acceptance support binding to hydrophobic olfactory receptor pockets with orientation-sensitive interactions; subtle stereochemical differences between cis/trans and (+)/(−) isomers yield distinct sensory profiles and thresholds.

Note: The above relates to research and biological understanding only. This product is for research use only and is not intended for human or animal diagnostic or therapeutic applications.

Buffer Applications

This compound is a neutral, water-insoluble monoterpenoid ether and is not used as a buffering agent. It does not contribute to acid–base capacity in aqueous systems and is not typically formulated into biological buffers. For experimental work, dissolve in a suitable organic co-solvent (e.g., ethanol, DMSO, or propylene glycol) before dilution into assay media if required, keeping final co-solvent content low to avoid confounding biological results.

Green Alternatives

Because this item is a defined substrate/reagent rather than a process solvent, greenness considerations focus on sourcing and transformation choices rather than substituting the molecule itself.

• Sourcing (general)

  • Renewable feedstocks: Rose oxide can be prepared from bio-based monoterpenes (e.g., citronellol, geraniol, or nerol) derived from essential oils (citronella, geranium). Selecting routes that use biogenic precursors reduces fossil carbon intensity.

• Process considerations (general)

  • Solvent selection: Prefer greener solvents (ethyl acetate, 2-MeTHF, CPME, MeOH/EtOH) over chlorinated solvents where compatible with selectivity.
  • Oxidants/reductants: Choose catalytic systems (e.g., O2 with TEMPO/metal catalysts, H2 for reductions) in place of stoichiometric oxidants like mCPBA when feasible.
  • Energy efficiency: Conduct reactions at ambient temperature/pressure when possible; leverage flow ozonolysis or continuous hydrogenation to improve safety and E-factor.

• Comparative snapshot (general guidance)

  • DCM vs. EtOAc for epoxidation: DCM often gives higher selectivity; EtOAc improves green score but may alter rates—pilot small-scale trials recommended.
  • TBHP/mCPBA vs. H2O2: Aqueous H2O2 is greener and generates water as byproduct; catalyst choice (e.g., tungsten, titanium-silicate) governs selectivity.
  • THF vs. 2-MeTHF: 2-MeTHF is bio-based, forms fewer peroxides, and eases separations with water; verify reactivity equivalence for your specific transformation.

• Waste minimization

  • Use high-atom-economy transformations (hydrogenation, hydroboration–oxidation with recyclable boron protocols) and design chromatography-free workups (crystallizable derivatives, distillation) when possible.

Pharmaceutical Uses

• Item-specific regulatory/grade status: Not specified for this item; refer to CoA/Spec Sheet.

• General, non-clinical formulation context (literature/industry practice)

  • Role as a fragrance/flavor excipient: Rose oxide is used in trace amounts to impart rose/lychee notes in non-therapeutic products and can be present as a fragrance component in topical or oral care matrices. Any use in regulated products requires conformity to applicable pharmacopeial/IFRA or internal specifications where relevant.
  • Analytical reference: Employed as a reference standard for method development (GC, GC–MS) to profile fragrance compositions or to validate extraction/quantitation methods in complex matrices.
  • Chiral/sensory standards: trans-(+) isomer serves as a stereochemically defined standard for sensory panels and for calibrating chiral separations (e.g., chiral GC columns).

No medical or therapeutic claims are made. Suitability for any GMP or clinical application depends on grade, impurity profile, residual solvents, and validated analytical controls documented on the specific lot CoA.

Physical Properties

• Item-specific (from Product Data)

  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • Storage conditions: Room temperature (per Product Data)

• Literature values (typical for rose oxide; provided for general guidance only, not specifications)

  • Physical state: Colorless to pale yellow liquid (literature)
  • Boiling point: ~224–226 °C at 1 atm (literature)
  • Density (20–25 °C): ~0.88–0.90 g/mL (literature)
  • Refractive index n20D: ~1.450–1.455 (literature)
  • Water solubility: Low; practically immiscible (literature). Miscible with common organics (e.g., ethanol, diethyl ether, hydrocarbons) (literature).
  • LogP (estimated for monoterpenoid ethers): moderate hydrophobicity; values commonly in the 2–3 range (literature/estimated).
  • pKa: Not applicable (neutral ether; no acidic/basic ionization in water under normal conditions).

• General interpretive notes (chemistry context)

  • The allylic C=C and cyclic ether confer a balance of lipophilicity and slight polarity; expect good solubility in nonpolar to mid-polar organics and poor aqueous solubility.
  • Refractive index and density are often used as identity/quality checks for aroma chemicals; compare measured lot values against literature ranges and the lot CoA.

Always treat literature values as non-binding approximations. For exact specifications and acceptance ranges, consult the CoA/Spec Sheet for this SKU.

Quality and Grades

• Item-specific status

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

• How to interpret grades for aroma chemicals/terpenoid ethers (general guidance)

  • “Analytical” or “ACS/AR” grades emphasize defined impurity profiles suitable for quantitative work.
  • “Fragrance” or “FG” designations often target sensory consistency (odor profile) with typical physico-chemical ranges (nD, density).
  • “Chiral/enantioenriched” materials: For trans-(+)-rose oxide, enantiomeric excess (ee) and diastereomeric ratio (dr) are key quality metrics because odor character and certain stereoselective syntheses are stereochemistry-sensitive.
  • HPLC or GC suitability: Aroma chemicals used in method development benefit from low non-volatile residue and consistent GC profile.

• Practical quality controls (what to look for on our CoA)

  • Identity: GC retention time vs. standard; MS spectral match; nD and density at 20 °C.
  • Purity: GC area % and specified limits for key related isomers (cis-rose oxide, other monoterpenes).
  • Chiral specification: optical rotation or chiral GC for enantiomeric assignment; diastereomer content (trans vs. cis).
  • Residual solvents/metals/water: Not specified for this item; refer to CoA/Spec Sheet.

• Implications of stabilizers (general)

  • If a trace antioxidant (e.g., BHT) is present, it may affect sensitive oxidation or polymerization studies; consult the CoA. Absence of stabilizer may increase susceptibility to slow oxidation/peroxide formation during storage.

Reaction and Applications

• Research use context (from Product Data)

  • For research use only.

• Synthetic and analytical applications (literature/general)

  • Sensory/chemosensory research: trans-(+)-rose oxide is a defined ligand for human and insect olfactory receptor studies, enabling receptor mapping, mixture suppression/synergy experiments, and psychophysical threshold work.
  • Stereoselective synthesis: Employed as a chiral benchmark odorant to evaluate asymmetric synthesis routes to tetrahydropyrans; the trans-(+) isomer serves as a comparator for enantio- and diastereoselectivity.
  • Functionalization of the allylic C=C
    • Epoxidation: mCPBA or peracetic acid at 0–25 °C affords epoxides; selectivity can be tuned with catalysts (Jacobsen, Shi) for asymmetric variants.
    • Hydroboration–oxidation: 9-BBN or BH3·THF, then H2O2/NaOH gives anti-Markovnikov alcohols.
    • Ozonolysis/oxidative cleavage: O3 at −78 to −20 °C followed by reductive or oxidative workup yields carbonyl fragments for structure–odor studies.
    • Hydrogenation: Pd/C or PtO2 at 1–5 bar H2 saturates the double bond with minimal ring impact.
  • Ether-centered chemistry
    • Acid-catalyzed rearrangements or ring-opening under strong protic/Lewis acids (BF3·Et2O) furnish linear alcohols or reconfigured ethers (use caution to preserve stereochemistry).
    • Metal-catalyzed allylic substitutions on derivatives (e.g., allylic carbonates formed from the isopropenyl group) enable C–C or C–X bond formation.

• Practical tips

  • Preserve stereochemical integrity by avoiding strong acids/heat; the trans relationship can scramble under harsh conditions.
  • Monitor by GC/MS and chiral GC when stereochemical outcome matters; aroma-active thresholds make organoleptic checks qualitative but not quantitative.

Reaction Conditions

The following are general literature-level conditions for common transformations of rose oxide and related allylic tetrahydropyrans. They are guidance only and not specifications for this item.

• Epoxidation of the terminal alkene

  • Typical: mCPBA (1.1–1.5 equiv), CH2Cl2, 0 °C → rt, 1–4 h. Work up with aqueous Na2S2O3/NaHCO3. Often gives high conversion with manageable diastereoselectivity.
  • Greener variant: In situ peracetic acid from H2O2/Ac2O or catalyst-driven H2O2 epoxidation (e.g., TS-1 in MeCN) at 0–25 °C.

• Hydroboration–oxidation

  • BH3·THF or 9-BBN (1.1–1.3 equiv), THF, 0 °C → rt, 1–3 h; then H2O2/NaOH (aq), 0–25 °C to afford primary alcohols. Typical isolated yields: good to excellent (literature).

• Hydrogenation

  • Pd/C (5–10 wt%), EtOAc or EtOH, 1–5 bar H2, rt–40 °C, 1–8 h; selectively reduces C=C while preserving the ether ring.

• Ozonolysis

  • O3 in O2 at −78 to −20 °C in MeOH/DCM, then reductive workup (Me2S, Zn/AcOH) to aldehydes/ketones; oxidative workup (H2O2) to acids. Exercise standard ozone safety.

• Acid-mediated rearrangement/ring opening

  • BF3·Et2O or strong mineral acids at 0–25 °C can induce rearrangements; closely control temperature/time to limit overreaction and stereochemical erosion.

• Analytical monitoring

  • GC/GC–MS is preferred due to volatility. For stereochemical studies, use chiral GC columns; confirm functionalization by 1H/13C NMR and, for epoxides/diols, 2D NMR.

Always conduct small-scale pilots to tune selectivity and confirm stability of the trans-(+) configuration under your exact conditions.

Safety and Handling

• Item-specific hazard data (from Product Data)

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

• General safety profile for monoterpenoid cyclic ethers (literature/analog-based guidance; defer to SDS)

  • Expected hazards: May cause skin/eye irritation and respiratory irritation; combustible liquid. Some fragrance ethers present aquatic toxicity—avoid release to the environment.
  • Peroxide formation: Ethers can form peroxides upon prolonged air/light exposure. Although saturated cyclic ethers are less prone than acyclic ethers, the presence of allylic functionality suggests oxidative sensitivity. Periodically assess aged material if critical (iodide-starch test or peroxides test strips), and minimize headspace/air exposure.

• Handling and PPE

  • Use in a fume hood with good ventilation. Wear safety glasses, lab coat, and appropriate chemically resistant gloves (e.g., nitrile). Avoid inhalation of vapors and contact with skin/eyes.
  • Keep away from heat/sparks/open flames. Use proper grounding/bonding during transfer of bulk liquid to limit static ignition risk.

• Incompatibilities and storage notes

  • Avoid strong oxidizers, strong acids, and radical initiators. Store in tightly closed amber glass at room temperature as provided (per Product Data), ideally under inert headspace for long-term stability.

• First aid (overview; consult SDS)

  • Skin/eyes: Rinse with water for several minutes; remove contaminated clothing. Seek medical attention if irritation persists.
  • Inhalation: Move to fresh air; monitor for respiratory irritation. Seek medical advice if symptoms occur.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.

Always consult the SDS for authoritative hazard, response, and disposal guidance.

Solvent Selection

This product is a substrate/reagent (a monoterpenoid ether), not primarily a solvent. Nevertheless, its solvency behavior affects experimental planning.

• Polarity and miscibility (literature/general)

  • Polarity class: Low to mid-polar, aprotic (cyclic ether). Hydrogen bond acceptor; non-donor.
  • Miscibility: Practically immiscible with water; miscible with common organic solvents (alcohols, ethers, esters, hydrocarbons, chlorinated solvents).
  • Dielectric behavior: Lower than THF; similar to other terpene-like ethers—sufficient for many neutral/organometallic transformations when used as substrate in an external solvent.

• Recommended solvent choices for working with rose oxide (general)

  • Nonpolar media (hexanes, heptane, toluene) for chromatographic handling and hydrogenations.
  • Mid-polar media (DCM, EtOAc, MeCN) for electrophilic additions and oxidations.
  • Alcoholic media (EtOH, i-PrOH) for certain catalytic oxidations or biotransformations.

• When to choose alternatives

  • If peroxide risk is a concern in ether-rich environments, prefer ethyl acetate or toluene as reaction solvents, using rose oxide only as a substrate.
  • For stereo- or chemo-selective oxidations of the allylic double bond, polar chlorinated solvents (e.g., DCM) or MeCN often improve selectivity versus hydrocarbon solvents.

• Practical notes

  • Monitor solubility across temperature; rose oxide typically dissolves readily at ambient temperature in organic solvents used for standard transformations.
  • Remove traces of acid from silica during purification if acid-sensitive (brief base-washed silica or add 0.1% Et3N) to minimize acetal/ether cleavage.

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 for rose oxide (literature/practice)

  • Container: Store in tightly closed amber glass to limit light exposure. Minimize headspace; consider inert gas blanket for long-term storage to slow oxidation.
  • Stability: Cyclic ethers are generally stable, but gradual oxidative changes can occur, especially at the allylic double bond. Periodic GC check is advisable for long-held stocks.

• Reconstitution/working solution guidance

  • This product is typically supplied neat (liquid). If a working solution is needed, dissolve in a suitable solvent (e.g., ethanol, isopropanol, DMSO, hexane, or ethyl acetate) to prepare a concentrated stock. Record solvent, concentration, and preparation date on the label.
  • Avoid aqueous storage due to low solubility and potential for emulsions; instead, prepare fresh dilutions into assay media just before use.
  • For small-aliquot handling, pre-aliquot under inert atmosphere to reduce repeated headspace oxygen exposure. Avoid repeated freeze–thaw of solutions; store solutions at 2–8 °C if compatible with solvent and experiment timeline.

Always consult the product CoA/SDS for definitive storage, stability, and compatibility information for this specific lot.

Structure and Identity

Intro: trans-(+)-Rose oxide is a chiral monoterpenoid cyclic ether best known as a high-impact rose-like odorant and a useful tetrahydropyran building block.

• Item-specific (from Product Data)

  • Product name: Rose oxide, trans-(+)-
  • CAS: 5258-10-6
  • CID (PubChem): 1712086
  • InChIKey: 57373 (as provided; consult CoA/SDS for full InChIKey string)
  • 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.

• Literature/computed identity (general reference for this substance class)

  • Common name: Rose oxide (one of four stereoisomers; this item is trans-(+)-)
  • Core scaffold: 2,6-disubstituted tetrahydropyran bearing an isopropenyl side chain and a methyl substituent; one endocyclic ether oxygen.
  • Stereochemistry: Two stereocenters in the tetrahydropyran ring define cis/trans diastereomers; “trans-(+)” denotes a specific absolute configuration and optical rotation sign.

• Structural description in words (general)

  • Six-membered, saturated oxygen heterocycle (tetrahydropyran) with a trans relationship between the ring methyl and the allylic side chain. The side chain contains a terminal C=C (isopropenyl), enabling electrophilic additions and oxidations, while the ether oxygen imparts moderate polarity and H-bond basicity.

Note: Where exact identifiers for this catalog lot are not listed above, consult the Certificate of Analysis (CoA) for authoritative item-specific identity details.

Synthetic Utility

• Functional groups and reactivity (general)

  • Allylic terminal alkene (isopropenyl): amenable to electrophilic additions, oxidations (epoxidation, dihydroxylation), hydrofunctionalizations (hydroboration–oxidation), and metal-catalyzed transformations (hydroformylation, cross-metathesis).
  • Cyclic ether (tetrahydropyran): Lewis/basic site for coordination; can undergo acid-catalyzed ring opening or rearrangement under forcing conditions. Useful as a masked diol motif in derivatization sequences.

• Named/representative transformations

  • Epoxidation (mCPBA, peracids; Sharpless/Katsuki variants for allylic systems) followed by regioselective ring-opening provides diols or amino alcohols.
  • Hydroboration–oxidation (BH3·THF/9-BBN → H2O2/NaOH) furnishes primary alcohols from the terminal double bond.
  • Dihydroxylation (OsO4/NMO or KMnO4) gives vicinal diols for SAR studies.
  • Cross-metathesis (Grubbs/Hoveyda–Grubbs) with electron-rich olefins to diversify the side chain while retaining the tetrahydropyran core.
  • Hydrogenation (Pd/C, PtO2) to saturate the C=C, isolating the fully saturated tetrahydropyran analogs for comparative odor/surface activity studies.

• Retrosynthetic perspective

  • Rose oxide serves as both a target and a chiral probe. Its two stereocenters in the tetrahydropyran ring make it a convenient benchmark for evaluating chiral pool, organocatalytic, or metal-catalyzed enantioselective cyclizations to 2,6-disubstituted THPs.

• Practical notes

  • Maintain mild, neutral to slightly basic conditions to protect the ether ring and stereochemistry. If purification on silica is required, neutralize acidity (0.1% Et3N) or use neutral alumina to reduce isomerization.

Target Specificity

Not applicable. This product is a small-molecule monoterpenoid ether, not an antibody, enzyme, or targeted biological. No antigen/epitope, clone, isotype, or species reactivity applies.