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(5S)-5-Methyl-3-(3-oxooctyl)-2(5H)-furanone
1. Basic Information
Full Name: 2(5H)-Furanone, 5-methyl-3-(3-oxooctyl)-, (5S)-
Alias: (S)-5-Methyl-3-(3-oxooctyl)furan-2(5H)-one
CAS No.: 168418-92-6
Molecular Formula: C??H??O?
Molecular Weight: 224.30
Category: Chiral furanone flavor intermediate, natural aroma reference standard, organic synthetic chiral building block, quorum sensing research reagent
2. Physical and Chemical Properties
Physical Properties
- Appearance: Pale yellow transparent oily liquid
- Odor: Rich roasted, nutty, caramel and savory meat-like aroma
- Solubility: Miscible with ethanol, propylene glycol, acetone, toluene, vegetable oils; slightly soluble in cold water
- Predicted Boiling Point: 332.8 ± 42.0 °C (760 mmHg)
- Predicted Density (20 °C): 1.035 ± 0.05 g/cm3
- Refractive Index nD20: 1.468–1.474
- Flash Point: 144.3 °C
- Hygroscopy: Non-hygroscopic
- Aqueous property: Neutral unsaturated lactone; stable in neutral cold water under ambient temperature
Chemical Properties
- Molecular structure: Chiral 5-membered unsaturated γ-lactone skeleton with S-chiral center at C5 methyl position; 3-position linked with long aliphatic ketone side chain, containing conjugated C=C lactone and aliphatic ketone carbonyl dual carbonyl structures
- Lactone reactivity: Unsaturated furanone ring undergoes Michael addition, reduction, and cyclization reactions; lactone ring can be hydrolyzed under acid/alkali heating to open-chain carboxylic acid
- Chiral characteristic: Single S optical isomer, used for chiral resolution and stereospecific flavor synthesis; racemic mixture has different olfactory intensity
- Photostability: Light-sensitive; long-term UV exposure causes partial oxidation and darkening
- Thermal stability: Stable below 130 °C; prolonged high-temperature heating accelerates side-chain ketone oxidation and lactone ring decomposition
- Compatibility: Compatible with most flavor solvents, edible oils and cosmetic substrates; incompatible with strong oxidants and concentrated alkaline solutions under heating
3. Main Application Fields
1. High-Impact Food Flavor Raw Material (Core Application)
Key chiral furanone flavor compound for roasted nut, caramel, coffee, meat, bread and savory seasoning essences; low odor threshold for enhancing long-lasting baked aroma
2. Natural Flavor GC/HPLC Reference Standard
Chiral reference substance for qualitative and quantitative analysis of furanone volatile flavor substances in food thermal processing systems
3. Organic Chiral Synthetic Intermediate
Stereopure lactone building block for synthesizing chiral pharmaceutical molecules and bioactive natural product analogues
4. Microbial Quorum Sensing Research Reagent
Model furanone compound for studying bacterial signal molecule inhibition and anti-biofilm laboratory research
4. Quality Specification Table
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