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99% Purity cis-Isolimonenol CAS 22972-51-6

99% Purity cis-Isolimonenol CAS 22972-51-6

cis-Isolimonenol CAS 22972-51-6 is a monocyclic monoterpenoid alcohol belonging to the carveol family. It features a cyclohexene ring with a hydroxyl group at position 2, a methyl group at position 1, and an isopropenyl group at position 4. The specified stereochemistry (1S,4R) indicates the absolute configuration of the two chiral centers, making it the (+)-cis isomer of carveol. The "cis" designation refers to the relative orientation of the hydroxyl and isopropenyl groups being on the same side of the cyclohexene ring plane. The molecule contains a conjugated system between the cyclohexene double bond and the hydroxyl group, influencing its chemical reactivity.

 

 

  • Nombre :

    cis-Isolimonenol
  • N.º CAS :

    22972-51-6
  • MF :

    C₁₀H₁₆O
  • MW :

    152.23
  • Pureza :

    99%
  • Apariencia :

    Colorless to pale yellow viscous liquid
  • Condición de almacenamiento :

    Should be stored away from oxidizers and handled with proper ventilation.

Chemical Properties​

IUPAC Name:​​ (1S,4R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-2-enol

Common Name:​​ cis-Isolimonenol

​CAS Registry Number:​​ 22972-51-6

​Molecular Formula:​​ C₁₀H₁₆O

​Molecular Weight:​​ 152.23 g/mol

​Physical State:​​ Colorless to pale yellow viscous liquid

​Boiling Point:​​ 216.8C at 760 mmHg

​Flash Point:​​ 87 °C

​Density:​​ 0.9398g/cm3

​Solubility:​​

Soluble in ethanol, diethyl ether, chloroform, and most organic solvents

Slightly soluble in water (~0.5 g/L at 20°C)

Miscible with fixed oils

​Stability:​​ Sensitive to air and light; may oxidize to carvone on prolonged exposure to air

 

Biological Activities​

1. Antimicrobial Properties:​​

Exhibits moderate antibacterial activity against Gram-positive bacteria (Staphylococcus aureus, Bacillus subtilis) with MIC values ranging from 125-500 μg/mL

Shows antifungal activity against Candida species and dermatophytes

Mechanism involves disruption of microbial cell membranes

​2. Antioxidant Activity:​​

Demonstrates moderate free radical scavenging ability in DPPH and ABTS assays (IC₅₀ ~150-200 μM)

Protects against lipid peroxidation in biological membranes

​3. Anti-inflammatory Effects:​​

Inhibits COX-2 expression and prostaglandin E2 production in vitro

Modulates NF-κB signaling pathway at concentrations of 50-100 μM

​4. Odorant Properties:​​

Strong herbaceous, green, caraway-like odor with minty undertones

Odor threshold: approximately 5 ppb in water

Acts as an insect semiochemical in certain plant species

​5. Enzymatic Interactions:​​

Substrate for alcohol dehydrogenases (converts to carvone)

Inhibits certain cytochrome P450 enzymes at high concentrations

 

Biosynthesis​

Natural Occurrence:​​ Found in essential oils of caraway (Carum carvi), dill (Anethum graveolens), spearmint (Mentha spicata), and various citrus species.

​Biosynthetic Pathway:​​

​1.Precursor Formation:​​ Synthesis begins with geranyl diphosphate (GPP) derived from the methylerythritol phosphate (MEP) pathway in plastids.

2.​Cyclization:​​ GPP undergoes enzymatic cyclization by limonene synthase to form (4S)-limonene.

​3.Hydroxylation:​​ Position-specific hydroxylation at C6 of limonene by cytochrome P450 enzymes (CYP71D subfamily) yields trans-carveol.

​4.Isomerization:​​ Enzymatic isomerization results in the cis-carveol isomers, with the specific (1S,4R) configuration determined by stereospecific isomerases.

5.​Regulation:​​ Biosynthesis is influenced by plant developmental stage, environmental factors, and herbivory, often increasing in response to mechanical damage.

​Alternative Route:​​ Can also be produced via microbial biotransformation of limonene using specific bacterial strains (Rhodococcus, Pseudomonas species).

 

Applications​

  • #
    Flavor and Fragrance Industry
    Used as a flavoring agent in food products (maximum use level 5-20 ppm)
    Incorporated in perfumes for green, herbaceous notes (typically 0.5-2% in final composition)
    Component of artificial spearmint and caraway flavors
     
  • #
    Pharmaceutical Research
    Intermediate in synthesis of terpenoid-based drugs
    Investigated as a chiral building block for asymmetric synthesis
    Used in studies of olfactory reception and signal transduction
     
  • #
    Agrochemical Applications
    Component of insect repellent formulations
    Used in attractant traps for pest monitoring
    Investigated as a natural preservative for stored crops
     
  • #
    Chemical Synthesis
    Valuable chiral pool reagent for stereoselective synthesis
    Starting material for preparation of carvone derivatives
    Used in studies of oxidation-reduction reactions of allylic alcohols
     
  • #
    Analytical Standards
    Certified reference material for GC-MS analysis of essential oils
    Chiral standard for enantiomeric purity determination

 

FAQs​

Q1: What is the relationship between this compound and limonene?​​

A: This carveol isomer is a direct hydroxylation product of limonene. The enzyme limonene-6-hydroxylase catalyzes the conversion of (4S)-limonene to trans-carveol, which can then isomerize to various cis-carveol isomers including the (1S,4R) configuration.

​Q2: How does the stereochemistry affect its properties?​​

A: The (1S,4R) configuration significantly influences:

Odor profile and threshold (each stereoisomer has distinct olfactory characteristics)

Biological activity (enantioselective interactions with enzymes and receptors)

Chemical reactivity in stereoselective transformations

Physical properties like optical rotation and crystallization behavior

​Q3: Is this compound safe for use in consumer products?​​

A: When used within established limits:

Generally Recognized as Safe (GRAS) for food use (FEMA No. 4222)

IFRA-approved for use in fragrances with recommended maximum dermal exposure limits

May cause sensitization in susceptible individuals at high concentrations

Should be stored away from oxidizers and handled with proper ventilation

​Q4: How is it typically isolated and purified?​​

A: Common methods include:

Fractional distillation of essential oils under reduced pressure

Preparative gas chromatography for high-purity samples

Chiral chromatography for enantiomeric separation

Crystallization of derivatives (e.g., urethanes) followed by regeneration

​Q5: What are the main stability concerns?​​

A: Primary degradation pathways:

Air oxidation to carvone (accelerated by light and heat)

Acid-catalyzed dehydration to p-cymene derivatives

Polymerization upon prolonged storage

Recommended storage: under inert atmosphere (N₂/Ar), at 2-8°C, in amber glass containers.

​Q6: Where can this specific stereoisomer be sourced?​​

A: Available from:

Specialty chemical suppliers (Sigma-Aldrich, TCI, Alfa Aesar)

Natural product extract suppliers

Custom synthesis laboratories

Purity typically ranges from 95% to >99% enantiomeric excess, with prices varying from $50-500 per gram depending on purity and quantity.

​Q7: What analytical methods are used for quality control?​​

A: Standard methods include:

Chiral GC or HPLC for enantiomeric purity determination

¹H NMR for structural confirmation and isomer ratio

Specific rotation measurement for optical purity

GC-MS for identification and impurity profiling

 

 

 

 

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