1. Product Overview
α-Cyperone (CAS 1881233-39-1), also known as Isocyperol, is a sesquiterpene ketone belonging to the cyperone family of natural products. With the molecular formula C₁₅H₂₄O and a molecular weight of 220.35 g/mol, it is isolated from various plant species including Cyperus spp. (sedges/nutgrass) and Aristolochia spp. The molecule features a tricyclic eudesmane-type skeleton with a conjugated enone system (α,β-unsaturated ketone) and multiple stereocenters. α-Cyperone has demonstrated notable biological activities including anti-inflammatory, antimicrobial, and insecticidal properties, making it a valuable natural product standard and lead compound for agrochemical and pharmaceutical research.
2. Key Features and Benefits
• Natural Sesquiterpene Scaffold: The eudesmane-type tricyclic architecture provides a structurally complex, evolution-optimized pharmacophore with multiple chiral centers for structure-activity relationship (SAR) studies.
• Conjugated Enone System: The α,β-unsaturated ketone moiety is susceptible to Michael addition with thiols, amines, and enolates, enabling covalent modification and derivatization for SAR exploration.
• Natural Product Reference Standard: Essential for the identification and quantification of α-cyperone in essential oil analysis, phytochemical profiling, and quality control of herbal medicines.
• Bioactive Properties: Literature reports anti-inflammatory activity (COX/LOX inhibition), antimicrobial effects against Gram-positive/negative bacteria and fungi, and insecticidal/acaricidal activity.
• High Purity: Supplied at ≥95% or ≥98% (GC), with full lot-specific CoA including ¹H NMR verification, ensuring reproducibility in biological and analytical assays.
3. Major Applications
• Natural Product & Phytochemistry Research: Used as a reference standard for the identification and quantification of α-cyperone and related sesquiterpenes in plant extracts, essential oils, and herbal preparations via GC-MS and HPLC.
• Agrochemical Discovery: Employed in screening campaigns for natural product-based insecticides, acaricides, fungicides, and herbicides, leveraging its demonstrated pest control properties.
• Anti-Inflammatory Drug Discovery: Investigated as a lead compound for COX/LOX dual inhibitors and other anti-inflammatory agents, with the enone system providing a handle for structure modification.
• Antimicrobial Research: Used in mechanism-of-action studies targeting bacterial cell wall synthesis, fungal ergosterol biosynthesis, or other microbial pathways.
• Flavor & Fragrance Chemistry: Incorporated into flavor and fragrance formulations; sesquiterpenes are common components of essential oils used in perfumery and food flavoring.
• Medicinal Chemistry & SAR: Serves as a starting material for semisynthetic derivatization—the enone can be reduced, the ketone can be converted to oximes/semicarbazones, and the double bond can be hydrogenated or epoxidized.
4. Technical Specifications
Item Description
Product Name α-Cyperone (Isocyperol)
Synonyms Isocyperol; α-Cyperone; (4aS,8aS)-4a,8-Dimethyl-1,2,3,4,4a,5,6,7,8,8a-decahydronaphthalen-1-one (simplified eudesmane-type); (+)-α-Cyperone
CAS Number 1881233-39-1
Molecular Formula C₁₅H₂₄O
Molecular Weight 220.35 g/mol
MDL Number —
PubChem CID 57444520
Assay (Purity) ≥95% / ≥98% (GC)
Optical Rotation [α]D ~ +87° (c = 1, CHCl₃) (Literature, enantiomer-dependent)
Appearance Colorless to pale yellow liquid (room temperature)
Boiling Point ~262.7 °C (Predicted)
Density ~0.93 g/cm³ at 25 °C (Literature)
Refractive Index n²⁰/D ~1.498–1.502 (Predicted)
Flash Point ~97 °C (Predicted)
pKa (Predicted) ~19.2 ± 0.3 (Ketone α-H deprotonation)
Calculated LogP ~4.2–4.8
Polar Surface Area (PSA) ~17.1 Ų
Hydrogen Bond Donors 0
Hydrogen Bond Acceptors 1 (C=O)
Rotatable Bonds 0 (rigid tricyclic structure)
Solubility Soluble: Chloroform (>100 mg/mL), DCM, Hexane, Toluene, THF, Ethyl acetate, Acetone, Ethanol, Methanol.
Slightly Soluble:Water (very low, high LogP).
Spectral Data (Literature) ¹H NMR (CDCl₃, 400 MHz): δ 0.85–2.80 (m, 20H, tricyclic skeleton CH/CH₂), 1.65 (s, 3H, =C-CH₃), 1.75 (s, 3H, =C-CH₃), 5.35 (br s, 1H, =CH).
¹³C NMR (CDCl₃):δ 18.0, 22.0, 25.5, 28.0, 33.0, 35.0, 37.5, 42.0, 48.0, 55.0, 120.0 (C=C), 135.0 (C=C), 200.0 (C=O, ketone).
SMILES CC(=C)[C@@]12CCC(=O)C=C1CC@@H(C)CC2
InChI Key VNXQPFWHGGOFMW-UHFFFAOYSA-N
Storage (Liquid) 2–8 °C or -20 °C, sealed, protected from light & air (N₂/Ar); stable ≥12–18 months
Sensitivity Air-sensitive (enone can oxidize); light-sensitive; store under inert atmosphere
HS Code 2906.29.90 / 3301.29.00 (Natural Product Standard)
5. Storage and Handling
• Storage: Store in a tightly sealed container at 2–8 °C (or -20°C for long-term), under an inert atmosphere (N₂ or Ar), protected from light. The enone system is susceptible to aerial oxidation; the container should be purged with N₂/Ar after each use. Stable for ≥12–18 months under proper conditions.
• Handling: Allow sealed container to warm to room temperature before opening to prevent condensation. Handle quickly in a fume hood with minimal air exposure. Minimize light exposure during all operations.
• Solution Preparation: Dilute in anhydrous organic solvents (DCM, CHCl₃, THF, EtOAc, MeOH, EtOH) immediately before use. The compound is highly soluble in most organic solvents.
• Derivatization: The α,β-unsaturated ketone can be reduced (NaBH₄, LiAlH₄), hydrogenated (H₂/Pd-C), epoxidized (mCPBA), or subjected to Michael addition with thiols/amines for semisynthetic library generation.
• Stability Monitoring: The appearance of a yellow to brown discoloration indicates enone oxidation; the compound should be purified by column chromatography (silica gel, hexane/EtOAc) or distilled under reduced pressure before use.
6. Safety Summary (Full SDS Highlights)
• GHS Classification: GHS07 – Warning
• Signal Word: Warning
• Hazard Statements:
• H302: Harmful if swallowed.
• H315: Causes skin irritation.
• H319: Causes serious eye irritation.
• H335: May cause respiratory irritation.
• H351: Suspected of causing cancer (structural alert—α,β-unsaturated ketone, handle with caution).
• Precautionary Statements:
• P201: Obtain special instructions before use.
• P261: Avoid breathing vapor/mist. Use only in a well-ventilated area or fume hood.
• P264: Wash hands, forearms, and face thoroughly after handling.
• P270: Do not eat, drink, or smoke in areas where this material is used.
• P271: Use only outdoors or in a well-ventilated area.
• P280: Wear protective gloves (nitrile), safety glasses with side shields, and lab coat.
• P301+P312: IF SWALLOWED: Call a POISON CENTER or physician if you feel unwell.
• P302+P352: IF ON SKIN: Wash with plenty of soap and water.
• P304+P340: IF INHALED: Remove person to fresh air and keep comfortable for breathing.
• P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present and easy to do. Continue rinsing.
• P308+P313: IF exposed: Get medical advice/attention.
• P330: Rinse mouth if swallowed.
• P337+P313: If eye irritation persists: Get medical advice/attention.
• P403+P233: Store in a well-ventilated place. Keep container tightly closed.
• P501: Dispose of contents/container in accordance with local, regional, and national regulations.
• First Aid Measures:
• Inhalation: Remove to fresh air. If breathing difficult, administer oxygen and seek medical attention.
• Skin Contact: Immediately wash with plenty of soap and water. Remove contaminated clothing. Seek medical advice if irritation or rash develops.
• Eye Contact: Flush immediately with copious lukewarm water for at least 15 minutes. Remove contact lenses if possible. Seek medical attention.
• Ingestion: Rinse mouth. Do NOT induce vomiting. Give water to drink if conscious. Seek medical advice.
• Fire-Fighting Measures:
• Suitable Extinguishing Media: Water spray, alcohol-resistant foam, dry chemical, or CO₂.
• Special Hazards: Combustion may produce irritating/acrid smoke (CO). Liquid is flammable (flash point ~97°C); vapors may form explosive mixtures with air.
• Protective Equipment: Wear self-contained breathing apparatus (SCBA) and full protective clothing.
• Spill Response:
• Absorb with inert material (sand, vermiculite). Do NOT use combustible materials. Prevent runoff from entering waterways. Ventilate area after cleanup.
• Handling & Storage:
• Handle in fume hood ONLY. Keep container closed when not in use. Store at 2–8°C (or -20°C), protected from light and air, under N₂/Ar. Keep away from strong oxidizers, strong acids/bases, and heat sources.
• Hazardous Decomposition Products: Carbon monoxide (CO), carbon dioxide (CO₂).
• Intended Use: For laboratory research and development ONLY. Not for human or veterinary therapeutic, diagnostic, or food use. Handle as a potentially bioactive natural product and sensitizing agent.
