p-Menthan-4-ol - ≥95% , CAS No.470-65-5

CAS: 470-65-5 Cat. No.: P1026744 Formula: C₁₀H₂₀O Peso molecolare: 156.260 Numero EC: 961-579-1

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Specifiche e purezza

≥95%

Condizioni di conservazione di stoccaggio

Room temperature

Purezza

≥95%

Nomi e identificatori

Sorrisi canonici

CC1CCC(CC1)(C(C)C)O

IUPAC Name

4-methyl-1-propan-2-ylcyclohexan-1-ol

InChIKey

LWKGCZOYSGKTLB-UHFFFAOYSA-N

INCHI

1S/C10H20O/c1-8(2)10(11)6-4-9(3)5-7-10/h8-9,11H,4-7H2,1-3H3

Peso molecolare

156.260

Taxonomic Classification

Taxonomy Tree

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

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Classe: Prenol lipids
• Subclass: Monoterpenoids
• Intermediate Tree Nodes: Not available
• Direct Parent: Menthane monoterpenoids
• Alternative Parents: Monocyclic monoterpenoids Cyclohexanols Tertiary alcohols Cyclic alcohols and derivatives Hydrocarbon derivatives
• Molecular Framework: Aliphatic homomonocyclic compounds
• Substituents: P-menthane monoterpenoid - Monocyclic monoterpenoid - Cyclohexanol - Tertiary alcohol - Cyclic alcohol - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Alcohol - Aliphatic homomonocyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.
• 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: 156.260 g/mol
• XLogP3: 2.800
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 156.151 Da
• Monoisotopic Mass: 156.151 Da
• Topological Polar Surface Area: 20.200 Ų
• Heavy Atom Count: 11
• Formal Charge: 0
• Complexity: 121.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• 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 vendor-validated application protocols are provided for this item in the Product Data. For general laboratory use:

• Dissolution: Prepare stock solutions in ethanol, isopropanol, or DMSO as appropriate for your assay or reaction, then dilute into working media.
• Analytical QC: Verify identity/purity by GC–MS or 1H/13C NMR; for chiral material, consider chiral GC/HPLC.
• Derivatization (analytical): Silylate or acylate prior to GC to improve peak shape and quantitation.

For bioassays or materials testing, adapt standard operating procedures to the properties of hydrophobic, moderately volatile monoterpenoid alcohols. Always validate conditions on small scale first.

Biological Roles

This product is supplied strictly for research use. No medical or clinical claims are made.

General background (literature):

• Monoterpenoid alcohols (p-menthane family) are common plant secondary metabolites derived from the mevalonate or MEP/DOXP pathways, typically formed via geranyl pyrophosphate cyclization followed by hydrogenation/isomerization.
• They often participate in ecological signaling (plant–insect interactions, defense volatilomes) and contribute to aroma profiles.
• Physicochemical properties (hydrophobicity, moderate volatility) influence their partitioning into membranes and cuticular waxes; however, specific transporters/enzymes for this exact 4-ol isomer are not established here.

Caveat:

• Specific biosynthetic enzymes, receptor interactions, or metabolic fate for p-Menthan-4-ol (CAS 470-65-5) are not provided in the Product Data; consult primary literature if your study requires pathway-level annotations.

Buffer Applications

Not typically applicable. p-Menthan-4-ol is a hydrophobic organic small molecule, not used as a buffering agent. For experimental work involving this compound in aqueous systems, consider:

• Use of cosolvents (ethanol, DMSO) at low percentages to aid dissolution, then dilute into buffered media compatible with your bioassay.
• Verify that the chosen buffer (e.g., phosphate, HEPES) does not react with your derivatization reagents if performing chemical transformations in mixed aqueous–organic conditions.

Green Alternatives

When using p-Menthan-4-ol as a substrate, the principal green considerations are solvent and reagent choices rather than the reagent itself.

• Greener solvent choices (general):

  • Replace chlorinated solvents (DCM) with ethyl acetate, 2-MeTHF, or cyclopentyl methyl ether (CPME) where reaction scope allows.
  • For extractions, prefer EtOAc or MTBE over diethyl ether to reduce peroxide risk and improve safety.

• Oxidation/esterification alternatives:

  • Oxidations: TEMPO/bleach (aqueous NaOCl) or O2/NOx catalytic systems can be greener than chromium(VI) reagents, assuming substrate compatibility.
  • Esterifications: Use catalytic organobases (DMAP) with benign dehydrating conditions or acid catalysis in green solvents instead of SOCl2/oxalyl chloride routes.

• Energy efficiency:

  • Many derivatizations proceed at ambient temperature; avoid unnecessary reflux. Use microwave or flow with heat integration where kinetic control is needed.

Comparison (general, literature):

• Traditional vs greener approach:
  • Solvent: DCM/toluene vs 2-MeTHF/EtOAc — reduced toxicity and better renewability with bio-based ethers/esters.
  • Oxidant: PCC vs TEMPO/bleach — eliminates Cr(VI) waste.
  • Workup: Brine-heavy washes vs minimal-aqueous or solvent-switch crystallization — less wastewater.

Always validate yield/selectivity trade-offs when adopting greener conditions for terpene alcohol chemistry.

Pharmaceutical Uses

No therapeutic or clinical claims are made. Item is for research use only.

Formulation and processing context (general literature):

• Monoterpenoid alcohols can serve as excipient components in topical prototype formulations (as fragrance, penetration-modulating co-solvents) or as test actives in nonclinical studies. Any such use must be supported by appropriate specifications, impurity control, and regulatory status.
• Pharmacopeial status, residual solvent limits, and compositional standards are not provided for this item; refer to CoA/Spec Sheet if excipient-like evaluation is intended.

Caution:

• Purity, stereochemistry, and residuals can affect odor profile and volatility—critical for sensory and stability testing in preformulation. Always qualify material against your internal specifications.

Physical Properties

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Purity/Grade: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
• Boiling point, melting point, density, refractive index: Not specified for this item; refer to CoA/Spec Sheet.
• Solubility (general guidance):
  • p-Menthane alcohols are typically poorly soluble in water and freely miscible with many organic solvents (ethanol, ethers, hydrocarbons) (literature, general terpenoid alcohol behavior).
• Volatility/odor: Monoterpenoid alcohols are usually moderately volatile and characteristically odorous (literature, general).
• Partitioning: Hydrophobic character is expected (positive logP typical of C10 aliphatic alcohols) (literature, general).

Notes:

• Where precise numerical specifications are required for method development (e.g., GC method temps, density-correction, UV cutoff), consult the item-specific CoA/Spec Sheet. Do not substitute literature values for specifications.

Quality and Grades

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

• Guidance on grades (general):

  • Analytical/Reagent grade: Typically suited for quantitative work; impurity profiles and water content controlled. Choose this where precise analytical or kinetic studies are sensitive to trace contaminants.
  • GC/HPLC grade: Low background and controlled UV absorbance (for HPLC) to minimize baseline noise; useful if using the compound as a reference, internal standard matrix, or in trace analyses.
  • Industrial/technical grade: May contain higher levels of isomeric and oxidation byproducts; appropriate for noncritical process development or screening.

• Stabilizers/inhibitors: Not specified for this item; refer to CoA/Spec Sheet. Many terpenoid alcohols do not require inhibitors but can slowly oxidize; headspace oxygen and light exposure should be minimized for long-term quality.

• Batch-specific documentation:

  • Certificate of Analysis will list assay method, stereochemical composition (if controlled), residual solvents, and key limits. Request the CoA aligned to your lot before qualifying for regulated workflows.

Reaction and Applications

As a saturated monoterpenoid alcohol, p-Menthan-4-ol is a versatile handle in terpene synthesis and derivatization (general literature guidance):

• Functional group interconversions:

  • Esterification/acylation: Formation of benzoates, acetates, or carbonates under standard acid chloride/anhydride or Steglich conditions.
  • Etherification: Williamson or Mitsunobu-type conversions (account for steric hindrance in tertiary/secondary positions).
  • Oxidation: Dess–Martin, TEMPO/bleach, or PCC to the corresponding ketone/aldehyde where permissible by substitution (note: tertiary alcohols resist oxidation to carbonyls).
  • Dehydration: Acid-catalyzed elimination to isomeric alkenes (terpene olefins), often regioselective under POCl3/pyridine or sulfuric acid conditions.

• Stereochemical considerations:

  • If the alcohol-bearing carbon is stereogenic, many transformations proceed with inversion (e.g., Mitsunobu) or racemization under strongly acidic conditions; protect stereochemistry using mild conditions.

• Applications in materials/fragrance chemistry (non-clinical):

  • Precursor to esters/ethers used in flavor/fragrance R&D and performance materials where hydrophobicity and volatility are tuned via derivatization.

• Analytical uses:

  • Derivatization to silyl ethers (TMS, TBDMS) can improve GC performance and reduce tailing for quantitative analysis.

Note: The specific isomer and substitution (secondary vs tertiary 4-ol) govern which transformations are viable. Verify structure/isomerization state for your lot via CoA or NMR before planning steps.

Reaction Conditions

General, literature-derived guidance for transformations of aliphatic monoterpenoid alcohols (adjust to your isomer/lot as confirmed by CoA/NMR):

• Esterification:

  • Reagents: Ac2O/DMAP (rt to 50 °C), AcCl/pyridine (0 °C to rt), DCC/DMAP in DCM or EtOAc (rt).
  • Typical times: 1–6 h; monitor by TLC/GC. Workup: aqueous bicarbonate then brine.

• Etherification/activation:

  • Mitsunobu (DEAD/DIAD, PPh3) in THF or toluene (0 °C to rt) for inversion where secondary; avoid if tertiary.
  • Tosylation/mesylation in DCM or pyridine (0–25 °C) followed by substitution with soft nucleophiles.

• Dehydration to alkenes:

  • POCl3/pyridine (0–25 °C) or acid-catalyzed (H2SO4, 60–100 °C, solvent toluene/xylene) with attention to regio-/stereoisomers. Trap alkenes in situ if desired (e.g., hydroboration immediately following).

• Oxidation (if secondary):

  • TEMPO/bleach (pH 8–9, 0–10 °C) or Dess–Martin in DCM (0–25 °C). Tertiary alcohols are not oxidized to carbonyls under these conditions.

• Analytical notes:

  • GC: silylation (BSTFA) or acylation helps reduce tailing. Use nonpolar columns (e.g., 5% phenyl) and temperature ramps starting around 60–80 °C depending on volatility.

These conditions are representative literature practices, not item-specific specifications. Optimize for your substrate’s stereochemistry and scale.

Safety and Handling

• GHS information (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 and pictograms: Not specified for this item; refer to SDS.

• General safety considerations for monoterpenoid alcohols (literature/generic):

  • Can cause skin and eye irritation; vapors may cause respiratory irritation. Avoid inhalation of vapors and prolonged skin contact.
  • Combustible/flammable organic liquid or low-melting solid; keep away from ignition sources, heat, and oxidizers.

• Recommended PPE and handling:

  • Wear lab coat, safety glasses or chemical splash goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Use in a fume hood to control vapors/odors.
  • Avoid static discharge; use grounding/bonding when transferring flammable liquids.

• Incompatibilities (general):

  • Strong oxidizing agents; strong acids may promote dehydration/isomerization.

• First aid (overview; defer to SDS for details):

  • Skin/eye contact: Rinse with water for several minutes; remove contaminated clothing. Seek medical attention if irritation persists.
  • Inhalation: Move to fresh air; monitor for respiratory discomfort.
  • Ingestion: Rinse mouth; do not induce vomiting unless directed by medical personnel.

Always consult the Aladdin SDS for authoritative hazard classifications and response measures for this specific item (CAS 470-65-5).

Solvent Selection

p-Menthan-4-ol is a hydrophobic aliphatic alcohol with low expected water solubility and broad solubility in common organic media (literature, general for monoterpenoid alcohols).

• Polarity and miscibility (general):

  • Miscible: Alcohols (ethanol, isopropanol), ethers (THF, MTBE), esters (EtOAc), and many hydrocarbons (toluene, heptane).
  • Limited/low: Water.

• Typical use scenarios:

  • As a substrate or intermediate in terpene chemistry, fragrance chemistry, or as a chiral pool-related scaffold (depending on stereochemistry).
  • As a hydrophobic cosolute/standard in GC or olfactory panels (method development requires known purity and possible derivatization to increase volatility/reproducibility).

• Choosing solvents vs alternatives:

  • For extractions: Use moderately polar organics (EtOAc, MTBE) to balance partitioning and ease of removal.
  • For reactions: Alcohol-protecting or substitution chemistry often benefits from aprotic solvents (DCM, toluene) or alcohol-compatible media (pyridine, MeCN) depending on transformation.
  • For crystallization (if solid): Mixed nonpolar/polar systems (hexanes/EtOAc) can help tune solubility; confirm physical state on CoA.

• Practical notes:

  • Dry solvents if moisture-sensitive transformations are planned (e.g., esterifications with acid chlorides). Remove peroxides from ethers used as solvents where applicable.

Storage and Reconstitution

• Storage conditions (from Product Data): Room temperature.

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

• Appearance/physical state: Not specified for this item; refer to CoA/Spec Sheet.

• General storage guidance (literature/generic for monoterpenoid alcohols):

  • Keep container tightly closed in a cool, well-ventilated place away from direct light and sources of ignition.
  • Minimize headspace oxygen to limit slow oxidative changes; consider nitrogen blanket for long-term storage.
  • Use amber glass where odor/oxidation sensitivity is a concern. Avoid reactive metal caps/liners.

• Reconstitution/preparation:

  • If solid at room temperature, warm gently (e.g., 30–40 °C water bath) to liquefy before aliquoting. If liquid, mix thoroughly before use to ensure homogeneity.
  • Prepare stock solutions in compatible organic solvents (e.g., ethanol, isopropanol, EtOAc, DMSO) as needed. Filter (0.2 µm PTFE) if particulate is observed.

• Stability notes:

  • No item-specific stability data are provided; check CoA/Spec Sheet for retest dates. For prolonged storage, aliquot to minimize repeated headspace exposure and freeze–thaw-like temperature cycling.

Structure and Identity

Brief overview: p-Menthan-4-ol is a saturated monoterpenoid alcohol belonging to the p-menthane family (C10 terpenoids). It features a cyclohexane ring bearing isopropyl and methyl substituents plus one hydroxyl group at the 4-position (p-menthane numbering).

• Item-specific identifiers from Product Data:

  • CAS: 470-65-5
  • SKU: P1026744
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet. (The value "210936" provided is not a standard InChIKey format.)
  • 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.

• Structural features (general chemistry description):

  • Core skeleton: p-menthane (a substituted cyclohexane) with one tertiary/secondary alcohol center at C-4 (depending on the specific isomer assignment in the p-menthane nomenclature system).
  • Functional groups: one aliphatic alcohol (–OH); multiple saturated C–C bonds; branched isopropyl and methyl substituents.
  • Stereochemistry: p-menthane derivatives commonly possess multiple stereocenters on the ring; p-Menthan-4-ol can exist as stereoisomers (not specified for this catalog entry).

• 2D description in words: a chair cyclohexane ring carrying an isopropyl group (–CH(CH3)2), a methyl group (–CH3), and a single hydroxyl substituent at the 4-position on the ring. The arrangement of substituents around the chair may differ among stereoisomers.

Synthetic Utility

Key reactivity stems from the aliphatic alcohol on a sterically congested p-menthane ring (general literature):

• Protection strategies:

  • Convert to silyl ethers (TBDMS, TBS), benzyl ethers, or carbonates to mask reactivity during further manipulations on the terpene skeleton.

• Activation for substitution:

  • Transform to sulfonates (tosylate/mesylate) enabling SN1/SN2′-type substitutions depending on substrate structure; tertiary centers favor carbocation pathways (rearrangement risks), whereas secondary centers allow Mitsunobu-mediated inversion.

• Redox and skeletal editing:

  • Dehydration to alkenes followed by hydrofunctionalization (hydroboration–oxidation, epoxidation, or halogenation) provides access to diverse p-menthane derivatives.
  • If secondary, selective oxidations to ketones open Baeyer–Villiger or reductive amination routes; tertiary alcohols resist oxidation and are better used via elimination.

• Chiral pool opportunities:

  • Where a defined stereochemistry is available, the alcohol-bearing center can impart asymmetry to downstream products or be leveraged as a chiral auxiliary handle after derivatization.

• Analytical derivatization:

  • Silylation or acylation improves GC detectability and peak shape; benzoates often serve as robust, characterizable derivatives for QC.

Target Specificity

Not applicable. This product is a small-molecule monoterpenoid alcohol and is not an antibody, enzyme prep, or affinity reagent. No antigen/epitope or biological target specificity is provided in the Product Data.