2H-Pyran, tetrahydro-4-methyl-2-phenyl-, (2R,4R)-rel- (CAS 149713-24-6) — Woody Experimental Note Fragrance Ingredient
2H-Pyran, tetrahydro-4-methyl-2-phenyl-, (2R,4R)-rel-
CAS 149713-24-6
What Is 2H-Pyran, tetrahydro-4-methyl-2-phenyl-, (2R,4R)-rel-?
This synthetic fragrance ingredient is a specialized chemical compound primarily used by professional perfumers in niche and experimental fragrances. Consumers might encounter trace amounts in avant-garde perfumes where novel aromas are prized. Though obscure, such molecules allow perfumers to create unique scent profiles that can’t be achieved with traditional materials.
Safety Profile
PROFESSIONAL USEWhat Does 2H-Pyran, tetrahydro-4-methyl-2-phenyl-, (2R,4R)-rel- Smell Like?
The aroma profile of this synthetic pyran derivative remains largely undocumented in public literature. Based on structural analogs, it likely exhibits a complex bouquet balancing herbal, woody, and faintly floral characteristics with possible metallic undertones. The phenyl group suggests aromatic warmth while the tetrahydro-2H-pyran structure may contribute fresh, slightly green nuances. Performance would depend heavily on stereochemistry – the (2R,4R) configuration potentially offering sharper top notes than other stereoisomers.
2D Molecular Structure
SMILES: C[C@@H]1CCO[C@H](C1)C1=CC=CC=C1
Chemistry, Properties & Perfumer Guide
The Chemistry
This chiral molecule belongs to the tetrahydropyran class, featuring a phenyl substituent at the 2-position and a methyl group at the 4-position. The specified (2R,4R) relative configuration suggests stereospecific synthesis would be required for perfumery applications, likely involving asymmetric hydrogenation or chiral auxiliary methods. Such compounds are typically prepared through Prins cyclization or oxymercuration-demercuration routes starting from appropriate allylic alcohols. The electron-rich oxygen heterocycle makes it moderately polar, while the aromatic ring provides lipophilic character.
Physical & Chemical Properties
| Molecular Class | Chiral tetrahydropyran derivative |
|---|---|
| Stereochemistry | (2R,4R)-relative configuration |
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Experimental Fragrances | <1% | Trace-2% | Novelty modifier only |
| Academic Research | N/A | N/A | Structure-odor relationship studies |
Classic Accords
Tip: Conduct extensive stability testing before incorporating into prototypes.
Alternatives & Comparisons
More studied aromatic heterocycle with similar structural features and better documented olfactory properties.
Established pyran derivative offering floral-green notes with comprehensive safety data.
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
No IFRA restriction data available – assume restricted until proven otherwise.
RIFM Assessment
No RIFM assessment found for this specific stereoisomer.
Sustainability
As a synthetic specialty chemical, environmental impact depends heavily on production methods. Lack of commercial scale data makes lifecycle assessment difficult. Potential advantages over natural analogs include reduced land/water use and consistent quality, but energy-intensive synthesis may offset benefits. Proper waste solvent recovery would be essential for sustainable production.
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Physicochemical Properties
DTXSID: DTXSID10889000
Physical Properties
| Molecular Weight | 176.259 g/mol🔬 EPA CompTox |
| Density | 0.997 g/cm^3📊 OPERA |
| Boiling Point | 258.893 °C📊 OPERA |
| Melting Point | 47.181 °C📊 OPERA |
| Flash Point | 106.949 °C📊 OPERA |
| Refractive Index | 1.504 Dimensionless📊 OPERA |
| Molar Volume | 181.673 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 3.094 Log10 unitless📊 OPERA |
| LogD (pH 5.5) | 3.094 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 3.094 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 5.77 Log10 unitless📊 OPERA |
| Water Solubility | 0.001 mol/L📊 OPERA |
| Henry's Law Constant | 0 atm-m3/mole📊 OPERA |
Transport Properties
| Vapor Pressure | 0.014 mmHg📊 OPERA |
| Viscosity | 6.805 cP📊 OPERA |
| Surface Tension | 34.772 dyn/cm📊 OPERA |
| Thermal Conductivity | 126.158 mW/(m*K)📊 OPERA |
Molecular Descriptors
| Topological Polar Surface Area | 9.23 Ų💻 Computed |
| H-Bond Donors | 0 count💻 Computed |
| H-Bond Acceptors | 1 count💻 Computed |
| Rotatable Bonds | 1 count💻 Computed |
| Aromatic Rings | 1 count💻 Computed |
| Molar Refractivity | 53.816 cm^3/mol📊 OPERA |
| Polarizability | 21.334 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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