Sitolactone (δ-Lactone): Chemical Properties, Applications, and Industrial Relevance
Introduction
Sitolactone, also known as delta-Lactone or δ-Lactone, is a member of the lactone family—a class of cyclic esters valued for their pleasant aroma, reactivity, and utility in synthesis. Sitolactone occurs naturally in certain plant oils and can be produced synthetically through intramolecular esterification of hydroxy acids.
Because of its unique ring structure and stability, Sitolactone is widely applied in flavor and fragrance research, polymer chemistry, and biochemical studies. It is regarded as a non-hazardous industrial compound when handled under standard laboratory protocols, making it fully compliant for regulated trade and research use.
Informational: Chemical Identity and Core Properties
| Property | Specification |
|---|---|
| Chemical Name | Sitolactone (delta-Lactone) |
| IUPAC Name | 5-Hydroxyhexanoic acid lactone (generic example for δ-lactones) |
| Chemical Formula | C₆H₁₀O₂ (varies slightly by chain length) |
| Molecular Weight | ~114.14 g/mol |
| CAS Number | 695-06-7 (representative δ-lactone) |
| Chemical Family | Cyclic ester (lactone) |
| Appearance | Colorless to pale yellow liquid |
| Odor | Creamy, coconut-like; characteristic sweet aroma |
| Boiling Point | 225 – 230 °C |
| Melting Point | ~-3 °C |
| Solubility | Slightly soluble in water; miscible with ethanol, ether, and oils |
| Flash Point | 100 – 110 °C (closed cup) |
| Stability | Stable under ambient conditions; hydrolyzes in strong acids or bases |
Chemical Overview
Delta-lactones are five-membered cyclic esters containing a carbonyl and an ether oxygen in the ring. Sitolactone’s structure makes it a moderately polar, thermally stable molecule, ideal for reactions requiring controlled ester functionality. It is frequently used as a reference standard in analytical chemistry and as a building block in organic synthesis.
Navigational: Industrial and Research Applications
1. Flavor and Fragrance Research
Sitolactone and related δ-lactones contribute to the creamy, coconut, and fruity notes in food flavoring and perfumery. In analytical contexts, they serve as flavor profile markers in dairy, chocolate, and tropical fruit studies.
2. Organic Synthesis
Because lactones can undergo ring-opening polymerization, Sitolactone is used in the development of biodegradable polyesters and functional monomers. Its reactivity also makes it useful in forming hydroxyacid derivatives for pharmaceutical intermediates.
3. Biochemical and Agricultural Research
Researchers employ Sitolactone in studying enzyme-catalyzed ester hydrolysis, biosynthetic lactonization, and plant volatile emissions. It also appears in experimental work on pheromone analogs and signal compounds.
4. Material Science
Delta-lactones are precursors in designing bioplastics and eco-friendly coatings, offering a balance between flexibility and biodegradability.
Commercial: Grades, Packaging, and Supply
Sitolactone is commercially produced under strict quality control for analytical, research, and industrial applications.
| Grade | Purity Range | Common Use |
|---|---|---|
| Analytical (≥ 99%) | 99 – 99.5 % | Calibration standards, GC-MS reference compounds |
| Research (≥ 95%) | 95 – 98 % | Organic synthesis, lactone polymerization studies |
| Industrial (≥ 90%) | 90 – 95 % | Fragrance and flavor formulation, resin development |
Packaging & Storage
- Standard packaging: 25 mL glass vials (lab scale), 1 L amber bottles, or 25 kg drums for bulk use.
- Storage conditions: Keep tightly sealed, away from heat and strong oxidizing agents.
- Shelf life: 24 months under recommended conditions.
All suppliers should comply with ISO 9001, REACH, and GHS labeling requirements.
Safety, Handling, and Environmental Profile
Although Sitolactone is considered low-toxicity, general chemical hygiene practices apply.
| Hazard Symbol | Classification | Precaution |
|---|---|---|
| ⚠️ | Irritant (mild) | Avoid eye and prolonged skin contact |
| ♻️ | Readily biodegradable | Dispose of according to local waste regulations |
| 🔥 | Combustible liquid | Keep away from ignition sources |
Handling Tips
- Use nitrile gloves and protective eyewear.
- Work under ventilated conditions to avoid vapor accumulation.
- Clean spills using absorbent materials; rinse surfaces with ethanol and water.
Environmental Considerations
Delta-lactones are biodegradable and exhibit low bioaccumulation potential, making them suitable for sustainable chemical formulations.
Transactional: Regulatory Compliance and Market Access
| Region | Regulatory Status | Governing Body |
|---|---|---|
| United States | Listed as non-hazardous under TSCA | EPA / OSHA |
| European Union | Registered under REACH | ECHA |
| United Kingdom | Covered by UK-REACH | HSE |
| Canada | DSL-listed substance | Environment Canada |
| Asia-Pacific | Allowed for industrial R&D | K-REACH / NICNAS / CSCL |
Supply Chain and Trade Notes
Sitolactone is available through authorized chemical distributors, laboratory reagent suppliers, and flavor chemistry companies. Procurement should always ensure:
- Valid Safety Data Sheet (SDS) and Certificate of Analysis (COA)
- Verified origin and purity documentation
- Compliance with customs and labeling regulations
Comparative Table: Sitolactone vs Other Lactones
| Lactone Type | Ring Size | Common Name | Primary Aroma / Application |
|---|---|---|---|
| Gamma-Lactone (γ-Lactone) | 5-membered | γ-Decalactone | Peach, apricot aroma; used in food flavoring |
| Delta-Lactone (δ-Lactone) | 6-membered | Sitolactone | Creamy, coconut aroma; fragrance, polymer chemistry |
| Epsilon-Lactone (ε-Lactone) | 7-membered | ε-Caprolactone | Monomer for biodegradable polyesters |
| Macro-Lactone | ≥ 12-membered | Muscone | Musk notes; perfumery and bio-signal research |
Research & Market Outlook
Interest in biodegradable lactones has surged as industries pursue sustainable, plant-based chemicals. Sitolactone’s compatibility with renewable feedstocks and its mild aromatic profile position it as an attractive ingredient in:
- Green polymer synthesis (bio-plastics, eco-adhesives)
- Natural fragrance compounds
- Flavor chemistry innovation
- Catalytic reaction studies for ester formation and hydrolysis
The global demand for δ-lactones is projected to grow as cosmetic, food, and environmental industries transition toward non-petroleum-based organic intermediates.
Conclusion
Sitolactone (delta-Lactone) represents a cornerstone in the chemistry of cyclic esters—combining chemical versatility, pleasant sensory attributes, and low environmental impact. Its widespread use in flavor, fragrance, and materials science underscores its dual role as both a functional reagent and a sustainable chemical model.
When sourced from certified chemical suppliers and handled under standard laboratory protocols, Sitolactone remains a safe, valuable, and compliant material for modern research and industrial development.
Keywords
Sitolactone • delta-Lactone • cyclic ester • lactone synthesis • fragrance intermediate • biodegradable lactone • flavor chemistry compound • organic synthesis reagent • REACH-compliant chemical • sustainable chemical raw material
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Packaging and Storage
- Packaging: Available in 200kg drums, aluminum foil bags, or cartons
- Storage Conditions: Cool and dry storage environment
- Shelf Life: 2 years
Supply and Lead Time
- MOQ: 1 kg
- Monthly Supply Capacity: Up to 5000 kg
- Lead Time:
- 1-25 kg: 3 days
- 26-100 kg: 7 days
- 101-1000 kg: 15 days
- Orders exceeding 1000 kg: Negotiable
Applications
- Delta-lactone is widely utilized as an intermediate in the synthesis of various high-end steroid drugs and derivatives, such as mifepristone, estradiol, 19-normethylene 4-androstenedione, and other pharmaceutical compounds.
Sample Availability: Yes, available upon request.
