Santalol - ≥70%, mixture of isomers , CAS No.11031-45-1

CAS: 11031-45-1 Cat. No.: S302191 Formula: C₁₅H₂₄O Peso molecolare: 220.35 Numero EC: 234-262-4

GRADE & PURITY ≥70%, mixture of isomers

Synonyms

(E)-2-methyl-5-(2-methyl-3-methylenebicyclo[2.2.1]heptan-2-yl)pent-2-en-1-ol | (E)-2-methyl-5-(2-methyl-3-methylidene-2-bicyclo[2.2.1]heptanyl)pent-2-en-1-ol

Storage

Protected from light,Store at -20°C

Shipped In

Ice chest + Ice pads

Panoramica

Santalol, α- and β-isomers are used as analytical standards for the quantification of the analytes in fragrances using flow-modulation comprehensive two-dimensional gas chromatography coupled to mass spectrometry (FM GCxGC/MS).

Specifications

Sinonimi

(E)-2-methyl-5-(2-methyl-3-methylenebicyclo[2.2.1]heptan-2-yl)pent-2-en-1-ol | (E)-2-methyl-5-(2-methyl-3-methylidene-2-bicyclo[2.2.1]heptanyl)pent-2-en-1-ol

Specifiche e purezza

≥70%, mixture of isomers

Condizioni di conservazione di stoccaggio

Protected from light,Store at -20°C

Spedito in

Ice chest + Ice pads

Questo prodotto richiede spedizione a catena fredda. I servizi di terra e altri servizi economici non sono disponibili.

Purezza

≥70%

Nomi e identificatori

• Pubchem Sid: 488198025
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488198025
• Sorrisi canonici: CC(=CCCC1(C2CCC(C2)C1=C)C)CO
• IUPAC Name: (E)-2-methyl-5-[(1S,2S,4R)-2-methyl-3-methylidene-2-bicyclo[2.2.1]heptanyl]pent-2-en-1-ol
• InChIKey: OJYKYCDSGQGTRJ-INLOORNJSA-N
• INCHI: 1S/C15H24O/c1-11(10-16)5-4-8-15(3)12(2)13-6-7-14(15)9-13/h5,13-14,16H,2,4,6-10H2,1,3H3/b11-5+/t13-,14+,15-/m1/s1
• Isomeri SMILES: C/C(=C\CC[C@]1([C@H]2CC[C@H](C2)C1=C)C)/CO
• CAS alternativo: 77-42-9
• Peso molecolare: 220.35

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Classe Prenol lipids
      • Subclass Sesquiterpenoids

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Classe: Prenol lipids
• Subclass: Sesquiterpenoids
• Intermediate Tree Nodes: Not available
• Direct Parent: Sesquiterpenoids
• Alternative Parents: Fatty alcohols Primary alcohols Hydrocarbon derivatives
• Molecular Framework: Aliphatic homopolycyclic compounds
• Substituents: Sesquiterpenoid - Fatty alcohol - Fatty acyl - Organic oxygen compound - Hydrocarbon derivative - Primary alcohol - Organooxygen compound - Alcohol - Aliphatic homopolycyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
• 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

• Sensibilità: light sensitive
• Indice di rifrazione: n20/D 1.507
• Punto di ebollizione (°C): 101-103 °C
• Peso molecolare: 220.350 g/mol
• XLogP3: 4.000
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 220.183 Da
• Monoisotopic Mass: 220.183 Da
• Topological Polar Surface Area: 20.200 Ų
• Heavy Atom Count: 16
• Formal Charge: 0
• Complexity: 315.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 3
• 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 item-specific tested application protocols are provided for this product. General research-use suggestions (not item-specific):

• GC–MS reference solution: prepare 1–2 mg/mL in GC-grade isooctane or hexane; store aliquots at −20 °C protected from light; equilibrate to room temperature before use.
• LC method development: dissolve at 0.1–1 mg/mL in acetonitrile or methanol; use C18 columns with water/acetonitrile + 0.1% formic acid for reverse-phase separations, or normal-phase silica with hexane/IPA for isomer resolution.
• Bioassays: prepare 100–1000× stocks in DMSO or ethanol; keep final organic cosolvent ≤0.1–1% v/v in assay medium; include solvent controls.

For validated, item-specific protocols and performance characteristics, refer to the CoA/Spec Sheet.

Biological Roles

Context (literature; not item-specific): Santalol denotes a class of sesquiterpene alcohols occurring predominantly in sandalwood (Santalum album and related species). They arise from terpene biosynthesis and can participate in ecological interactions.

• Biosynthetic origin

  • Derived from farnesyl pyrophosphate via cyclization (e.g., santalene synthases) followed by P450-mediated allylic hydroxylations to yield α-/β-santalol isomers.

• Biological function and distribution

  • Major constituents of sandalwood essential oil; composition and stereochemistry vary with species, geography, and extraction method.
  • Terpenoid alcohols like santalol may act as semiochemicals in plant–insect interactions and contribute to plant defense and pollinator attraction (general terpenoid roles, literature).

• Biotransformations

  • Subject to enzymatic oxidation (alcohol dehydrogenases) and conjugation (glucuronidation) in biological systems; readily incorporated into model membranes or lipid phases due to hydrophobicity.

• Research relevance

  • Used as reference standards in metabolomic/volatilomic profiling, authentication of botanical materials, and studies of terpene biosynthetic pathways.

No clinical or therapeutic claims are made; this product is for research use only.

Buffer Applications

Santalol is a hydrophobic neutral organic compound and is not used to prepare aqueous buffer systems. For experiments requiring santalol exposure in biological media, prepare stock solutions in DMSO or ethanol and dilute into the buffer to the required final concentration, ensuring the cosolvent remains at a level compatible with your system (commonly ≤0.1–1% v/v).

Green Alternatives

While santalol itself is a target analyte/building block rather than a process solvent, greener choices can be made around its use and derivatization.

• Solvent selection (literature guidance)

  • Prefer bio-based, greener solvents where feasible: 2-methyltetrahydrofuran (2-MeTHF), cyclopentyl methyl ether (CPME), ethyl acetate, and ethanol as alternatives to chlorinated solvents or toluene.

• Comparison snapshot (general)

  • DCM vs Ethyl acetate: EtOAc offers lower toxicity and better biodegradability; suitable for extractions and many workups involving terpenoids.
  • Toluene vs 2-MeTHF: 2-MeTHF is bio-derived and often matches solubility for terpene chemistry; facilitates phase separation with water.
  • Hexane vs Heptane/Isooctane: heptane and isooctane reduce neurotoxicity concerns associated with n-hexane.

• Process considerations

  • Employ catalytic and solvent-minimized transformations (e.g., TEMPO-catalyzed oxidations with bleach) rather than stoichiometric heavy-metal reagents.
  • Use peroxide-free ethers and limit energy input via room-temperature or flow protocols where applicable.

Note: Greener choices should be balanced with selectivity needs for allylic alcohol chemistry; validate performance before scaling.

Pharmaceutical Uses

No pharmacopeial grade or excipient designation is provided for this item.

• Item-specific status

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

• Literature context (not item-specific)

  • Santalol is studied in formulation science as a hydrophobic fragrance component or model sesquiterpene for permeation and stability studies.
  • In research on semisolid dosage forms, it may be incorporated into creams/ointments as a volatile/semi-volatile component to assess rheology and release behavior.

• Formulation considerations (general)

  • Solubilize in suitable carriers (ethanol, medium-chain triglycerides, PEGs) before incorporation into aqueous systems.
  • Monitor for oxidative degradation; antioxidants (e.g., BHT) and light protection can improve stability in prototype formulations.

This information is provided for laboratory/formulation research context only; no clinical or therapeutic uses are implied.

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.

• Literature/general properties for santalol isomers/mixtures (for context; not item-specific specifications)

  • Physical state: typically a colorless to pale yellow viscous liquid with characteristic sandalwood odor (literature).
  • Boiling point: commonly reported ~300–310 °C at 1 atm for α-/β-santalol isomers (literature).
  • Density: typically ~0.95–0.98 g/mL at 20–25 °C (literature).
  • Refractive index (n20/D): frequently reported ~1.49–1.51 (literature).
  • LogP: expected high hydrophobicity; typical cLogP ~3.5–4.5 (computed/literature for sesquiterpene alcohols).
  • Solubility: low in water; miscible with common organic solvents (ethanol, methanol, acetone, ether, dichloromethane, hydrocarbons) (literature).
  • pKa: alcohol O–H ~16–18 in water (literature, generic for secondary alcohols); considerably more acidic in DMSO (~29 for ROH scale).

• Practical implications

  • Poor aqueous solubility suggests preparing concentrated stocks in ethanol or DMSO for biological/analytical studies.
  • High boiling point and low vapor pressure reduce evaporative loss during handling but prolong removal of residual solvent.

Note: Exact numeric specifications for this catalog item are not provided above; refer to the item’s CoA/Spec Sheet for authoritative values.

Quality and Grades

• Item-specific status

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

• Context and expectations for this material type

  • For terpenoid standards and fragrance components, quality descriptors may include chemical purity (GC area %), isomer ratio (e.g., α-/β-), and residual solvent limits. High-purity material is recommended for analytical method development (GC–MS, GC–FID, HPLC) and reaction studies.
  • If the item is stabilized or contains defined isomer ratios, this will be explicitly listed on the label/CoA. No stabilizer is stated in the Product Data for this item.

• Practical guidance

  • Verify by GC–MS or GC–FID for isomer composition and potential oxidation products (e.g., santalal, santalone) before quantitative work.
  • For chiral studies, consider chiral GC to assess enantiomeric excess where relevant.
  • Low UV background is generally expected, but if using in UV-based analysis, check baseline at your detection wavelength.

Refer to the product’s CoA/Spec Sheet for definitive purity, impurities, and any stabilizers used.

Reaction and Applications

Santalol’s allylic secondary alcohol and terpene backbone make it a versatile handle for derivatization and as a reference material in natural products and fragrance chemistry.

• Representative applications (literature; not item-specific)

  • Oxidation: selective allylic alcohol oxidations (e.g., Dess–Martin, TEMPO/bleach, Swern) to corresponding aldehydes/ketones (e.g., santalal), enabling downstream condensations.
  • Esterification/Acylation: formation of benzoates/acetates (DCC/DMAP or acid chloride/Et3N) to modulate volatility and chromatographic behavior.
  • Protection: silyl ether protection (TBDMS/TBDPS) to prevent dehydration/isomerization during multistep synthesis.
  • Dehydration/Isomerization: acid-catalyzed elimination to santalene/santene-type olefins; mechanistic probes for terpene rearrangements.
  • Hydrogenation: partial or full hydrogenation of C=C bonds (Pd/C, H2) to study structure–odor relationships or generate saturated alcohols.
  • Analytical standard: GC–MS reference for sandalwood oil profiling; internal/external standardization in essential oil authentication studies.

• Practical tips

  • Minimize light/oxygen exposure to avoid autoxidation; work under inert atmosphere for sensitive transformations.
  • Use mild conditions for oxidation to preserve double-bond geometry; monitor by GC to avoid overoxidation.
  • For chiral/isomer-resolved work, employ chiral stationary phases or derivatize to Mosher esters for NMR/GC analysis.

Reaction Conditions

Typical conditions used with allylic terpene alcohols such as santalol (literature guidance; optimize per application):

• Oxidation to aldehyde/ketone

  • Dess–Martin periodinane (1.3–1.5 eq) in DCM, 0–25 °C, 1–3 h; quench with Na2S2O3/NaHCO3; often high yields with minimal alkene isomerization.
  • TEMPO/NaOCl (pH ~9, CH2Cl2/H2O biphasic, 0–5 °C), catalytic TEMPO and KBr; rapid reaction with good selectivity.

• Esterification

  • Acyl chloride (1.1 eq), Et3N (2 eq), catalytic DMAP, DCM, 0–25 °C, 1–4 h; or DCC/DMAP with carboxylic acid in DCM/DMF at rt.

• Dehydration to olefins

  • POCl3/pyridine or TsCl/pyridine at 0–25 °C; or catalytic p-TsOH in toluene with azeotropic removal of water; monitor to limit rearrangement.

• Hydrogenation

  • H2 (1–3 bar), Pd/C (5–10 wt%), EtOH or EtOAc, 25–40 °C, 1–6 h; sequential hydrogenation of double bonds possible.

• Epoxidation

  • mCPBA (1.1 eq) in DCM at 0–5 °C; work up with Na2SO3/NaHCO3 to remove acids; regioselectivity governed by alkene substitution.

Practical notes

• Exclude light/oxygen where allylic oxidation or isomerization is problematic; employ inert atmosphere.
• Track isomer ratios and E/Z geometry by GC or 1H NMR (vinylic coupling constants) to guide condition selection.

Safety and Handling

• Item-specific hazard information (from Product Data)

  • GHS Classification: Not specified for this item; refer to SDS.
  • Signal Word: Not specified for this item; refer to SDS.
  • H-Statements: Not specified for this item; refer to SDS.
  • Pictograms: Not specified for this item; refer to SDS.

• General safety considerations for sesquiterpene alcohols (literature; not item-specific)

  • May cause skin/eye irritation and, in some individuals, sensitization on repeated exposure. Avoid inhalation of vapors/aerosols and direct skin contact.
  • Typically combustible; keep away from heat/sparks/open flames. Although many santalols have relatively high flash points, treat as a combustible organic liquid.

• PPE and handling

  • Wear lab coat, safety glasses or goggles, and suitable chemically resistant gloves (e.g., nitrile). Handle in a fume hood to minimize inhalation exposure.
  • Prevent environmental release; collect waste in halogen-free organic liquid containers unless otherwise specified by your EHS program.

• Incompatibilities and stability

  • Avoid strong oxidizers (risk of exothermic reaction) and strong acids/bases that can promote dehydration/isomerization.
  • Protect from light to minimize peroxidation/allylic oxidation and isomerization; store under inert gas if long-term.

• First aid (general guidance; defer to SDS)

  • 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 attention if symptoms occur.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.

Always consult the product-specific SDS for authoritative safety and regulatory information.

Solvent Selection

Santalol is a hydrophobic sesquiterpene alcohol; solvent choice centers on dissolving power, volatility, and compatibility with downstream assays.

• General polarity/miscibility (literature)

  • Polarity: nonpolar to weakly polar solute; high affinity for nonpolar and moderately polar organic solvents.
  • Miscibility: readily soluble in ethanol, methanol, isopropanol, acetone, ethyl acetate, dichloromethane, toluene, hexanes; poorly soluble in water.

• Typical use scenarios

  • Analytical standards: dissolve in GC-grade hexane or isooctane; for LC applications, ethanol, acetonitrile, or methanol are common.
  • Bioassays: prepare concentrated stocks in DMSO or ethanol; final assay solvent content commonly kept ≤0.1–1% v/v to avoid solvent effects.
  • Synthesis: use nonprotic solvents (toluene, hexanes, DCM, THF) for protection/esterification; protic alcohol solvents for transesterification or solubilization.

• Practical comparison (literature guidance)

  • Hexane/isooctane: ideal for GC; fastest evaporation; lowest polarity.
  • Ethanol/methanol: good solubility; compatible with many biological assays; moderate evaporation rate.
  • DMSO: maximal solubilization for stock solutions; difficult to remove; use sparingly.

Note: Choose solvent based on intended application and analytical method requirements; verify solubility and stability empirically.

Storage and Reconstitution

• Item-specific storage and shipping (from Product Data)

  • Storage conditions: Protected from light, Store at −20 °C.
  • Shipped in: Ice chest + ice pads.
  • Research use note: For research use only.

• Practical guidance

  • Upon receipt: Keep container tightly closed; minimize headspace and consider storing under inert gas (N2/Ar) to limit oxidation/isomerization.
  • Aliquoting: If frequent access is expected, aliquot into amber vials to avoid repeated freeze–thaw and light exposure.
  • Reconstitution/stock solutions: For analytical or bioassay use, dissolve in ethanol, isopropanol, acetonitrile, or DMSO to prepare concentrated stocks (e.g., 10–100 mg/mL depending on application). Mix thoroughly to ensure homogeneity.
  • Stability: Terpene alcohols can slowly oxidize; incorporate light protection and limit oxygen exposure. Periodically verify integrity by GC–MS or NMR if stored long term.

Note: Where exact solubility limits, stabilizers, or shelf-life are required, consult the product’s CoA/Spec Sheet and SDS.

Structure and Identity

Brief overview: Santalol is a sesquiterpenoid alcohol best known as a principal component of sandalwood oil. Commercial "santalol" may denote a mixture of isomeric santalols (e.g., α- and β-santalol).

• Item-specific (from Product Data)

  • SKU: S302191
  • Product name: Santalol
  • CAS: 11031-45-1
  • InChIKey: 260038
  • 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 structural information (for context; not item-specific)

  • Core scaffold: sesquiterpene (C15) backbone derived from farnesyl diphosphate; contains an allylic secondary alcohol and multiple alkenes.
  • Typical formula for individual santalol isomers: C15H24O (literature).
  • Typical MW for isomeric santalols: ~220.35 g/mol (literature).
  • Isomerism: α- and β-santalol are constitutional isomers; natural samples often enriched in (Z)-configured allylic alcohols and may possess defined stereocenters depending on origin.
  • 2D description: a branched C15 hydrocarbon framework with one hydroxyl group (–OH) at an allylic, often secondary carbon; two or more C=C bonds in the carbon chain or small ring; no heteroatoms other than the single oxygen.

• Note on identity

  • Because “santalol” may refer to an isomeric mixture, definitive identifiers (exact SMILES/InChIKey, stereodescriptors) depend on the specific isomer or mixture composition. Consult the CoA for definitive identity for this item.

Synthetic Utility

Santalol’s functionality and terpene framework enable diverse transformations valuable in natural products and fragrance chemistry.

• Functional group reactivity (literature)

  • Allylic secondary alcohol: amenable to oxidation (to aldehydes/ketones), esterification, etherification, and selective dehydration.
  • Alkenes: support epoxidation (mCPBA), dihydroxylation (OsO4/NMO), hydroboration–oxidation (BH3·THF then H2O2/NaOH), and hydrogenation (Pd/C, H2).

• Protecting group strategies

  • Silyl ethers (TBDMS/TBDPS) preserve the alcohol under acidic/basic conditions during manipulations of the olefins.

• Retrosynthetic value

  • Serves as a chiral/isomer-defined starting material for accessing santalene, santalal, and structurally related sesquiterpenoids via oxidation/reduction and rearrangement sequences.

• Named/representative reactions (general)

  • Mitsunobu inversion to access the corresponding inverted-configuration derivatives (if stereogenic at C–OH).
  • Sharpless allylic oxidation conditions can probe selectivity at the allylic position.
  • Johnson–Claisen or Ireland–Claisen rearrangements on allylic derivatives to reconfigure the carbon skeleton.

• Analytical utility

  • GC–MS calibration and method validation for essential oil authentication and stability studies.

Target Specificity

Not applicable. This product is a small-molecule sesquiterpene alcohol and not a biological targeting reagent. No antigen, clone, or species reactivity information applies.