5-Hydroxy-2,4-decadienoic acid delta-lactone (CAS 27593-23-3) — Sweet Middle Note Fragrance Ingredient
5-Hydroxy-2,4-decadienoic acid delta-lactone
CAS 27593-23-3
What Is 5-Hydroxy-2,4-decadienoic acid delta-lactone?
5-Hydroxy-2,4-decadienoic acid delta-lactone is a synthetic fragrance compound primarily used in perfumery. It’s not commonly encountered in everyday products but plays a specialized role in creating certain scent profiles. This lactone contributes unique olfactory characteristics that are valued by perfumers for adding depth and complexity to fragrance compositions.
Safety Profile
GENERALLY SAFEWhat Does 5-Hydroxy-2,4-decadienoic acid delta-lactone Smell Like?
This lactone delivers a rich, fatty character with subtle fruity undertones. The scent evolves from an initial waxy, slightly animalic impression to reveal deeper buttery nuances. In dry-down, it contributes a creamy, lactonic quality reminiscent of ripe peaches or coconut flesh. The molecule’s structure gives it excellent tenacity, allowing its smooth, fatty notes to persist through the heart phase of a fragrance.
2D Molecular Structure
SMILES: CCCCCC1=CC=CC(=O)O1
Chemistry, Properties & Perfumer Guide
The Chemistry
5-Hydroxy-2,4-decadienoic acid delta-lactone belongs to the class of unsaturated lactones. While not found in nature, it’s synthesized through controlled oxidation processes of fatty acids. The molecule’s delta-lactone ring structure contributes to its stability and distinctive odor profile. Its unsaturated carbon chain allows for interesting interactions with other fragrance components.
Physical & Chemical Properties
| Molecular Type | Synthetic lactone |
|---|
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 0.5-2% | Up to 5% | Used as a modifier for fruity or creamy accords |
| Functional Fragrance | 0.1-0.5% | Up to 1% | Adds depth to household product scents |
Classic Accords
Tip: Use sparingly in fruity compositions to add naturalistic fatty undertones.
Alternatives & Comparisons
For a more pronounced peach character with similar lactonic properties.
When a longer-lasting, more coconut-like lactonic effect is desired.
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
Not currently restricted by IFRA standards.
RIFM Assessment
Limited safety assessment data available through RIFM.
Sustainability
As a synthetic material, this lactone’s environmental impact is primarily related to its manufacturing process. Being produced in controlled laboratory settings allows for precise quality control and reduced ecological footprint compared to some natural alternatives. The compound’s efficiency in formulations means it’s typically used at low concentrations.
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Ingredient Data Sheet
CAS 27593-23-3Physical Properties
| Molecular Weight | 166.22 g/mol🔬 PubChem |
| LogP (Octanol-Water) | 3🔬 PubChem |
| Boiling Point | 285 °C🔬 EPA CompTox |
| log Kp (skin permeability) | -1.584💻 Calculated |
| SMILES | CCCCCC1=CC=CC(=O)O1🔬 PubChem |
Volatility & Performance
| Fragrance Note | Base💻 Calculated |
Odor & Flavor
| Primary Descriptors | butterycoconutcreamypeach• leffingwell |
| Functional Groups | aromatic💻 RDKit |
Sensory Thresholds
| Odor Detection Threshold | 0.15 ppm📖 van Gemert |
Physical data: PubChem (NIH/NLM), U.S. EPA CompTox Dashboard, EPA OPERA models, RDKit. Odor & flavor: Arctander (Perfume & Flavor Chemicals), Fenaroli's Handbook of Flavor Ingredients, Leffingwell. Thresholds: van Gemert (Compilations of Odour Threshold Values). Regulatory: IFRA Standards 51st, FEMA GRAS. Trade names: Surburg (Common Fragrance & Flavor Materials). All data compiled and cross-referenced for perfumertools.com.
Physicochemical Properties
DTXSID: DTXSID0047589
Physical Properties
| Molecular Weight | 166.22 g/mol🔬 EPA CompTox |
| Density | 1.005 g/cm^3🔬 EPA CTX |
| Boiling Point | 285.5 °C🔬 EPA CTX |
| Melting Point | 18.861 °C📊 OPERA |
| Flash Point | 117.28 °C📊 OPERA |
| Refractive Index | 1.482 Dimensionless📊 OPERA |
| Molar Volume | 165.667 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 3.023 Log10 unitless📊 OPERA |
| LogD (pH 5.5) | 3.023 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 3.023 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 6.08 Log10 unitless📊 OPERA |
| Water Solubility | 0.018 mol/L📊 OPERA |
| Henry's Law Constant | 0 atm-m3/mole📊 OPERA |
Transport Properties
| Vapor Pressure | 0.006 mmHg📊 OPERA |
| Viscosity | 2.703 cP📊 OPERA |
| Surface Tension | 33.3 dyn/cm📊 OPERA |
Molecular Descriptors
| Topological Polar Surface Area | 30.21 Ų💻 Computed |
| H-Bond Donors | 0 count💻 Computed |
| H-Bond Acceptors | 2 count💻 Computed |
| Rotatable Bonds | 4 count💻 Computed |
| Aromatic Rings | 1 count💻 Computed |
| Molar Refractivity | 47.223 cm^3/mol📊 OPERA |
| Polarizability | 18.721 Å^3📊 OPERA |
Data Sources:
🔬 EPA Experimental data from U.S. EPA CompTox Chemicals Dashboard & CTX APIs. 📊 OPERA Predicted using EPA's OPERA QSAR models. 💻 Computed Calculated from SMILES using RDKit.
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