2-(2-Hydroxy-4-methyl-3-cyclohexenyl)propionic acid gamma-lactone (CAS 57743-63-2) — Woody Middle to base Note Fragrance Ingredient
2-(2-Hydroxy-4-methyl-3-cyclohexenyl)propionic acid gamma-lactone
CAS 57743-63-2
What Is 2-(2-Hydroxy-4-methyl-3-cyclohexenyl)propionic acid gamma-lactone?
This synthetic lactone is a specialized fragrance ingredient primarily used by professional perfumers. It’s not commonly encountered in consumer products but may appear in niche fragrances. The compound contributes unique woody-amber nuances to sophisticated scent compositions.
Safety Profile
USE WITH AWARENESSWhat Does 2-(2-Hydroxy-4-methyl-3-cyclohexenyl)propionic acid gamma-lactone Smell Like?
This lactone delivers a complex woody-ambergris character with subtle marine undertones. Initially presenting a crisp, slightly camphoraceous top note, it evolves into a warm, musky heart reminiscent of sun-bleached driftwood. The dry-down reveals a sophisticated ambery base with faintly sweet, almost coconut-like nuances that linger close to the skin.
2D Molecular Structure
SMILES: CC1C2CCC(C)=CC2OC1=O
Chemistry, Properties & Perfumer Guide
The Chemistry
This gamma-lactone belongs to the class of cyclic esters derived from hydroxy acids. Its structure features a cyclohexenyl ring substituted with methyl and hydroxy groups, contributing to its woody-ambergris odor profile. The compound is synthesized through intramolecular esterification of the corresponding hydroxy acid under acidic conditions. The stereochemistry of the molecule significantly impacts its olfactory properties.
Physical & Chemical Properties
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 0.5-2% | Up to 5% | Used as woody-amber modifier |
| Functional Fragrance | 0.1-0.5% | Up to 1% | For sophisticated woody notes |
Classic Accords
Tip: Use sparingly in amber bases to add naturalistic woody nuances.
Alternatives & Comparisons
Macrocyclic lactone with similar musky-woody character but stronger diffusion.
Provides woody-violet nuances with better stability in alkaline formulations.
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
No IFRA restrictions currently apply to this material.
RIFM Assessment
Limited safety assessment data available through RIFM.
Sustainability
As a synthetic material, this lactone avoids natural resource depletion concerns. Modern synthesis routes aim for atom economy and reduced solvent use. The compound’s persistence in the environment has not been thoroughly studied.
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Physicochemical Properties
DTXSID: DTXSID90886239
Physical Properties
| Molecular Weight | 166.22 g/mol🔬 EPA CompTox |
| Density | 1.071 g/cm^3📊 OPERA |
| Boiling Point | 262.387 °C📊 OPERA |
| Melting Point | 58.57 °C📊 OPERA |
| Flash Point | 121.849 °C📊 OPERA |
| Refractive Index | 1.485 Dimensionless📊 OPERA |
| Molar Volume | 159.499 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 1.959 Log10 unitless📊 OPERA |
| LogD (pH 5.5) | 1.959 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 1.959 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 5.73 Log10 unitless📊 OPERA |
| Water Solubility | 0.012 mol/L📊 OPERA |
| Henry's Law Constant | 0 atm-m3/mole📊 OPERA |
Transport Properties
| Vapor Pressure | 0.009 mmHg📊 OPERA |
| Viscosity | 5.257 cP📊 OPERA |
| Surface Tension | 30.474 dyn/cm📊 OPERA |
Molecular Descriptors
| Topological Polar Surface Area | 26.3 Ų💻 Computed |
| H-Bond Donors | 0 count💻 Computed |
| H-Bond Acceptors | 2 count💻 Computed |
| Rotatable Bonds | 0 count💻 Computed |
| Aromatic Rings | 0 count💻 Computed |
| Molar Refractivity | 45.698 cm^3/mol📊 OPERA |
| Polarizability | 18.116 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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