This compound belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
External Descriptors
a sesquiterpenoid
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 assay-specific application protocols are provided for this item in the Product Data.
General laboratory uses (literature/typical):
GC–MS standard preparation: prepare 0.1–1.0 mg/mL solutions in isooctane or hexane; include internal standards (e.g., n-alkanes) for retention index calibration. Store aliquots tightly sealed at 2–8 °C for short-term stability, protected from light.
NMR sample: dissolve ~5–20 mg in 0.6 mL CDCl3; acquire 1H/13C, and 2D (HSQC/HMBC) to assign olefinic and bridgehead signals. Avoid prolonged sample exposure to air/UV.
Reaction screening: run 0.05–0.2 mmol scale tests under inert gas in crimped vials to rapidly assess selectivity before scale-up.
Note: These are general, literature-style guidelines offered for research planning. For validated, SKU-specific protocols, refer to documentation accompanying your lot or contact technical support.
Biological Roles
This section provides general biochemical context for alpha-santalene as a plant terpenoid; it does not describe medical or clinical uses.
General roles (literature):
Biosynthesis: alpha-santalene is a sesquiterpene formed from farnesyl pyrophosphate (FPP) via terpene cyclase-catalyzed cyclization in sandalwood and related species.
Ecological function: volatile sesquiterpenes like alpha-santalene contribute to plant–insect and plant–microbe interactions, serving as semiochemicals, attractants, or deterrents depending on context.
Metabolic fate: in planta and during storage/exposure to air, alpha-santalene can oxidize enzymatically or non-enzymatically to santalenols and further to aldehydes/ketones (e.g., santalal derivatives), altering aroma profiles.
Physicochemical behavior: hydrophobic, membrane-partitioning compound; in biological matrices it tends to associate with lipophilic phases and bind to hydrophobic protein pockets non-specifically.
Research use implications:
Analytical standards: used as a reference in metabolomics of essential oils and in authentication of sandalwood-related natural products by GC–MS profiling.
Enzymology: substrate or product marker in studies of santalene synthases and engineered terpene biosynthesis pathways.
Note: Any biological context above is general, literature-based information intended for research planning and interpretation. This catalog item is for research use only.
Buffer Applications
alpha-Santalene is a nonpolar hydrocarbon and is not used to prepare aqueous buffer systems. It is insoluble in water and has no acid/base functionality to contribute to buffering capacity.
Practical guidance:
For experiments requiring aqueous phases, dissolve or pre-disperse alpha-santalene in a compatible organic co-solvent (e.g., ethanol, isopropanol, DMSO, or a surfactant system) before partitioning into biphasic setups.
If your work involves emulsions or microemulsions for biotransformations, select surfactants/emulsifiers and co-solvents based on enzyme/process compatibility; alpha-santalene itself does not buffer pH.
For buffer recipes and pH control, refer to established buffering agents (phosphate, Tris, HEPES, acetate, etc.).
Green Alternatives
As alpha-santalene is a substrate rather than a solvent or reagent, “greener alternatives” focus on the transformation conditions and solvents employed when working with it.
Greener considerations (literature/general):
Solvents: replace chlorinated solvents where possible. Ethyl acetate, 2-methyltetrahydrofuran (2-MeTHF), cyclopentyl methyl ether (CPME), or toluene can substitute for DCM/CHCl3 in many oxidations and epoxidations, with attention to selectivity.
Oxidants: favor O2 (with catalysts), H2O2, oxone, or TEMPO/bleach systems over chromium- or manganese-based stoichiometric oxidants for allylic oxidation and alcohol formation.
Reductions/hydrogenations: use H2 gas with heterogeneous catalysts (Pd/C, Ni) in benign solvents rather than hydride reagents where applicable.
Workup/waste: minimize peracid residues; neutralize and separate organic peroxide-containing wastes carefully; use solvent recovery where feasible.
Illustrative comparison (general; not item-specific):
DCM + mCPBA vs. EtOAc + in situ dioxirane (oxone/acetone): the latter reduces halogenated solvent use and avoids chloroacetic byproducts, though it may require optimization for selectivity.
SeO2 allylic oxidation vs. catalytic aerobic oxidation (Cu/Mn/NHC systems): catalytic aerobic methods reduce selenium waste but can be slower and may need rigorous O2 control.
Trade-offs: Greener systems may shift regio-/stereoselectivity on the polyunsaturated, sterically demanding santalene scaffold; pilot small-scale screens before scale-up.
Pharmaceutical Uses
No pharmaceutical excipient or compendial status is specified for this item.
Item-specific:
Grade/compendial compliance: Not specified for this item; refer to CoA/Spec Sheet.
General context (non-therapeutic):
Terpene hydrocarbons like alpha-santalene are primarily studied in fragrance/flavor chemistry and natural products research. In pharmaceutical R&D laboratories they may be used as analytical standards, synthetic intermediates toward more functionalized sesquiterpenoids, or as model hydrophobes in formulation studies.
If used in formulation research, alpha-santalene would typically act as a hydrophobic component within an oil phase, but it is not a standard pharmaceutical excipient and would require thorough safety/tox assessment for any non-research application.
Compliance reminder: This product is supplied for research use only. It is not intended for human or veterinary use, diagnostic procedures, foods, or cosmetics.
Physical Properties
Item-specific (from Product Data):
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Storage: Room temperature (per Product Data).
Literature/General (for reference only; not item specifications):
Physical state: typically a colorless to pale yellow, oily liquid with a characteristic woody, sandalwood-like odor (terpene typical).
Boiling point: often reported in the ~250–270 °C range at 1 atm for sesquiterpene hydrocarbons like alpha-santalene; lower apparent b.p. under reduced pressure (literature).
Density: commonly ~0.90–0.95 g/mL at 20–25 °C (literature, terpene class).
Refractive index: often around nD20 ~1.49–1.51 (literature ranges for related santalenes).
LogP: high (estimated >4), reflecting strong hydrophobicity (computed/literature for C15 hydrocarbons).
Solubility: insoluble in water; miscible with nonpolar and moderately polar organic solvents (hexanes, toluene, ether, dichloromethane, acetone) (literature).
Practical notes for use (general):
Viscosity and volatility: less volatile than monoterpenes; manageable vapor pressure but can slowly evaporate—work in closed vessels to minimize loss.
Optical rotation may be reported for stereochemically defined material in the literature; verify against CoA for this SKU.
All numeric values above are provided as literature/general context and should not be taken as specifications for this catalog item.
Quality and Grades
Item-specific quality information:
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers: Not specified for this item; refer to CoA/Spec Sheet.
Context and expectations (general):
For sesquiterpene hydrocarbons such as alpha-santalene, quality is typically assessed by GC-FID/GC–MS purity and by stereochemical integrity (ratio of alpha- vs. other santalenes, and enantiomeric purity where applicable). If chiral purity is relevant to your work, request enantiomeric excess (ee) data or chiral GC.
Common impurity profiles: other santalene isomers (beta-, epi-), oxidized congeners (santalenols, santalal) if exposed to air/light, and residual synthesis/isolates (terpene hydrocarbons) are typical.
UV profile: terpenes often have minimal UV absorbance above ~210–220 nm; if you require LC-UV compatibility, verify UV cutoff and background absorbance with the CoA.
Analytical recommendations (general best practice):
Confirm identity by GC–MS with characteristic hydrocarbon fragmentation, and by 1H/13C NMR showing olefinic protons/carbons and the bicyclic framework.
If you need trace specifications (water, peroxides, metals), these are Not specified for this item; refer to CoA/Spec Sheet.
If you require a defined grade (e.g., ≥98% GC, fragrance grade, or chiral grade), contact us with your specification; we can often provide lot-resolved CoAs or custom material.
Reaction and Applications
alpha-Santalene is a versatile sesquiterpene hydrocarbon used as a substrate, reference standard, and synthetic intermediate in terpene chemistry and fragrance-related synthesis.
Typical reaction families and uses (literature/general):
Selective oxidations: allylic oxidation (e.g., SeO2- or Cr-free catalytic variants) to access santalenols; radical autoxidation under controlled conditions can furnish peroxides/alcohols (use caution).
Epoxidation: peracid (mCPBA), in situ dioxirane (from acetone/oxone), or Jacobsen–Katsuki (if chiral induction desired) to access epoxy-santalenes for further functionalization.
Hydroboration–oxidation: anti-Markovnikov hydration of exocyclic/endocyclic alkenes to give corresponding alcohols; regioselectivity can be tuned by steric approach control and borane choice (BH3·THF vs. 9-BBN).
Hydrogenation: catalytic hydrogenation (Pd/C, PtO2, Rh/C) to saturate one or more double bonds; pressure and catalyst loading control partial vs. full saturation.
Electrophilic additions: halogenation/bromohydroxylation of alkenes; subsequent eliminations enable rearranged frameworks.
Photochemical/radical reactions: visible/UV-induced transformations at allylic positions or double bonds; consider oxygen exclusion and radical inhibitors as needed.
Practical tips:
Use inert atmosphere and light protection to minimize unintended autoxidation during prolonged reactions.
Monitor by GC–FID or GC–MS given volatility and complexity of isomer mixtures; NMR assignment benefits from 2D methods (HSQC/HMBC/NOESY) due to overlapping olefinic signals.
If stereochemistry is critical, consider chiral catalysis or kinetic resolutions to control/assess new stereocenter formation in functionalized derivatives.
Reaction Conditions
The following are literature-style, general conditions commonly applied to sesquiterpene hydrocarbons like alpha-santalene. They are guidance only and not product specifications.
Hydroboration–oxidation: 0.9–1.2 equiv 9-BBN or BH3·THF in anhydrous THF, 0–25 °C, 1–3 h; oxidative workup with H2O2/NaOH at 0–25 °C affords anti-Markovnikov alcohols. Regioselectivity depends on double-bond substitution; monitor by GC–MS/NMR.
Epoxidation: mCPBA (1.1–1.5 equiv) in DCM or toluene at 0–25 °C, 1–6 h; buffer with NaHCO3 to suppress acid-mediated rearrangements. Alternatively, in situ dioxirane (oxone/acetone, NaHCO3, 0–10 °C) provides complementary selectivity.
Allylic oxidation: SeO2 (5–20 mol%) with tert-butyl hydroperoxide in toluene, 60–90 °C, 2–16 h; or catalytic Pd/Cu with O2 (1 atm) in toluene/AcOH at 25–60 °C for greener variants. Product distribution is sensitive to temperature and oxygen.
Hydrogenation: 5–10 wt% Pd/C (1–5 mol% Pd) in EtOH, EtOAc, or hexanes under 1–5 bar H2, 25–40 °C, 1–8 h. For partial hydrogenation, use lower pressure/shorter times or less active catalysts (e.g., Lindlar, Rh/Al2O3).
Halofunctionalization: NBS (1.1 equiv) with catalytic light or radical initiator in CCl4 or greener alternatives (MeCN/toluene) at 0–25 °C for allylic bromination; quench promptly to limit overbromination.
Typical monitoring: GC–FID/GC–MS due to volatility; 1H NMR (CDCl3) for rapid assessment. Yields in the 50–85% range are common but depend strongly on selectivity and isomer purity.
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: Not specified for this item; refer to SDS.
Pictograms: Not specified for this item; refer to SDS.
General safety considerations for sesquiterpene hydrocarbons (literature/typical):
Flammability: combustible liquid; vapors may form flammable mixtures with air. Keep away from ignition sources and hot surfaces.
Irritation/sensitization: terpenes can cause skin and eye irritation in some users; avoid prolonged contact. Use appropriate PPE (lab coat, nitrile gloves, safety glasses/goggles).
Inhalation: avoid breathing vapors or aerosols; handle in a fume hood when transferring/batching.
Environmental: harmful to aquatic organisms with long-lasting effects is common for hydrophobic terpenes; prevent release to drains (check SDS for classification).
Storage and incompatibilities (general guidance):
Storage: per Product Data, room temperature. For best stability, store tightly sealed, under inert gas (N2/Ar) if possible, protected from light and air to minimize autoxidation.
Incompatibilities: strong oxidizers; radical initiators; avoid prolonged exposure to air/UV which can promote peroxidation/oxidation.
First-aid overview (general):
Skin: wash with soap and water; remove contaminated clothing.
Eyes: rinse cautiously with water for several minutes; seek medical attention if irritation persists.
Inhalation: move to fresh air; seek medical advice if symptoms occur.
Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
Always consult the product’s SDS for authoritative, SKU-specific safety information.
Solvent Selection
Applicability: alpha-Santalene is a hydrophobic substrate/standard rather than a solvent. Solvent choice pertains to its handling and reactions.
General solvent compatibility (literature):
Polarity class: nonpolar hydrocarbon.
Miscibility: insoluble in water; freely soluble in nonpolar and moderately polar organic solvents (hexanes, heptane, petroleum ether, toluene, diethyl ether, dichloromethane, chloroform). Limited solubility in alcohols; solubility improves in isopropanol vs. methanol.
Dielectric context: prefer low- to mid-dielectric solvents for stability and to minimize undesired polar reactions (e.g., avoid strong protic/oxidizing media).
Selection tips by use case:
Analytical GC: dilute in isooctane, hexane, or dichloromethane for stable injection profiles.
NMR: CDCl3 provides good solubility and well-resolved olefinic signals; C6D6 may sharpen signals and minimize exchange.
Oxidations/functionalizations: choose solvent to match reagent—e.g., DCM for peracid epoxidation; toluene for radical/photochemical steps; THF for hydroboration.
Comparison (general):
Hexanes vs. toluene: hexanes maximize volatility for easy removal; toluene provides higher boiling point for elevated-temperature reactions.
DCM vs. ethyl acetate: DCM offers greater nonpolar solubility and inertness; EtOAc is a greener alternative with adequate solubility for many terpene transformations.
Always dry solvents when reactions are moisture-sensitive (e.g., hydroboration, metal-catalyzed couplings) and consider oxygen exclusion to limit substrate autoxidation.
Storage and Reconstitution
Item-specific storage:
Storage conditions: Room temperature (per Product Data).
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
General best practices for terpenes (literature/typical):
Container: store in amber glass with PTFE-lined cap to minimize light/oxygen ingress and adsorption.
Atmosphere: if possible, blanket headspace with inert gas (N2 or Ar) to slow autoxidation.
Light/air: protect from light and minimize repeated opening; consider aliquoting into smaller vials for multi-use to reduce air exposure.
Temperature: room temperature is acceptable for short to medium term; for long-term stability, cool, dark storage (e.g., 2–8 °C) may further reduce oxidation without risking crystallization (liquid).
Reconstitution:
Not applicable—alpha-santalene is supplied as a neat organic compound. If dilution is required, prepare solutions in suitable solvents (hexanes, toluene, DCM, EtOH) immediately before use. Mix thoroughly to ensure homogeneity.
Stability notes:
Water content, peroxide content, and inhibitor/stabilizer presence are Not specified for this item; refer to CoA/Spec Sheet. If critical, assay peroxides periodically (iodometric test) and consider adding trace BHT when appropriate for research needs.
Structure and Identity
alpha-Santalene is a plant-derived sesquiterpene hydrocarbon commonly found in sandalwood oil. It is a bicyclic, highly unsaturated terpene with three isoprene units.
Item-specific (from Product Data):
CAS: 512-61-8
PubChem CID: 94164
InChIKey: 191264 (as provided)
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/General identity (for reference only; not item specifications):
Typical molecular formula (literature): C15H24 (sesquiterpene hydrocarbon)
Structural features: bicyclic carbon skeleton with multiple trisubstituted/disubstituted double bonds; no heteroatoms; hydrocarbon framework derived biosynthetically from farnesyl pyrophosphate via cyclization.
2D description: a fused/bicyclic terpene ring system bearing one exocyclic and one or more endocyclic C=C bonds; overall nonpolar, compact framework with several allylic positions.
Notes:
Stereochemistry: alpha-santalene occurs as a defined stereoisomer among the santalene family; configurations at the bridgehead/tertiary centers define the “alpha” isomer. Exact stereochemical description should be confirmed against the product’s CoA/SDS or authoritative structural databases.
Synthetic Utility
alpha-Santalene’s densely substituted, bicyclic framework with multiple alkenes makes it a valuable scaffold for generating higher-value sesquiterpenoids.
Key functional handles (literature/general):
Multiple alkenes: enable chemoselective transformations (e.g., selective epoxidation or hydroboration) to differentiate exocyclic vs. endocyclic double bonds.
Allylic C–H sites: amenable to oxidation (e.g., SeO2, Pd/Cu-catalyzed aerobic systems) to introduce alcohols/carbonyls without disrupting the carbon skeleton.
Strained bicyclic geometry: can bias reagent approach and control regio-/stereoselectivity in additions.
Typical synthetic routes:
Access to santalenols/santalols: via hydroboration–oxidation or directed epoxidation followed by ring opening to furnish tertiary/secondary alcohols with defined stereochemistry.
Carbonyl derivatives (santalal-type): achieved by allylic oxidation or alcohol oxidation under mild conditions (e.g., TEMPO/bleach, Dess–Martin for secondary alcohols derived from santalene).
Hydrogenated congeners: partial or full hydrogenation to probe structure–odor relationships or to simplify NMR assignments.
Retrosynthetic value:
The hydrocarbon core serves as a chiral pool starting point when enantioenriched alpha-santalene is used (if available), enabling downstream asymmetric derivatizations without de novo cyclization.
Analytical control:
Because mixtures of santalene isomers can co-occur, rigorous GC method development (temperature programming, nonpolar stationary phases) is recommended to track selectivity during stepwise functionalization.
Target Specificity
Not applicable. This product is a small-molecule sesquiterpene, not a biological macromolecule or antibody. No antigen/epitope, clone, isotype, or species reactivity information applies.
For molecular selectivity in chemical reactions with alpha-santalene, see the Synthetic Utility and Reaction Conditions tabs.
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