3-Phenylpropyl cinnamate (CAS 122-68-9) — Balsamic Middle to base Note Fragrance Ingredient
3-Phenylpropyl cinnamate
CAS 122-68-9
What Is 3-Phenylpropyl cinnamate?
3-Phenylpropyl cinnamate is a synthetic fragrance ingredient with a warm, balsamic scent profile. It’s often found in perfumes, candles, and body care products where a rich, honeyed sweetness is desired. This ester contributes to oriental and amber accords, adding depth and longevity. As a synthetic molecule, it provides consistent quality and avoids the variability of natural extracts. It’s particularly valued for its ability to round out floral compositions and enhance vanilla-like notes without being overly gourmand.
Safety Profile
USE WITH AWARENESSWhat Does 3-Phenylpropyl cinnamate Smell Like?
3-Phenylpropyl cinnamate unfolds like liquid amber warmed by the sun – a golden, resinous heart wrapped in honeyed sweetness. The opening carries a subtle cinnamon-like spice that quickly mellows into a plush base reminiscent of dried figs soaked in vanilla syrup. Unlike simpler cinnamates, this phenylpropyl variant has remarkable tenacity, evolving over hours from a bright top to a velvety dry-down that clings to skin like fine perfume oil. Its balsamic character bridges floral and woody accords, adding a luminous quality to oriental compositions without overwhelming delicate notes.
In Famous Fragrances
Fragrance associations may not reflect actual formulations.
Used as a sophisticated modifier for the vanilla base, adding resinous depth that prevents the sweetness from becoming cloying. Works synergistically with ethyl maltol to create the iconic ‘Guerlainade’ signature.
Provides a smooth transition between the sharp herbal top notes and dense labdanum base. Its honeyed facets amplify the amber illusion while maintaining transparency.
2D Molecular Structure
SMILES: O=C(OCCCC1=CC=CC=C1)C=CC1=CC=CC=C1
Chemistry, Properties & Perfumer Guide
The Chemistry
3-Phenylpropyl cinnamate belongs to the ester class, formed through Fischer esterification between cinnamic acid and 3-phenylpropanol. The phenylpropyl chain increases molecular weight compared to simpler cinnamates, contributing to its enhanced longevity. While not found in nature, its structural relatives occur in balsams and resins. Industrial synthesis typically employs acid-catalyzed reactions under controlled conditions to prevent transesterification. The molecule’s planar structure allows for strong π-π stacking interactions, explaining its tenacious fragrance profile and moderate volatility.
Physical & Chemical Properties
| Appearance | Colorless to pale yellow viscous liquid |
|---|---|
| Boiling Point | ~300 °C (estimated) |
| Density | ~1.05 g/cm³ (estimated) |
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 0.5-2% | Up to 5% | Amber/oriental bases |
| Home Fragrance | 1-3% | Up to 8% | Candle wax compatibility |
Classic Accords
Tip: Use with ionones to create a seamless floral-amber transition in oriental compositions.
Alternatives & Comparisons
More affordable with sharper initial impact but less dry-down complexity. Prefer when cost is a factor or for brighter compositions.
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
Not currently restricted under IFRA standards. Classified as a potential sensitizer at high concentrations (>10%).
RIFM Assessment
Under evaluation by RIFM. Preliminary data suggests safe use at current industry levels.
Sustainability
As a synthetic material, 3-phenylpropyl cinnamate avoids agricultural land use and seasonal variability. Production typically uses green chemistry principles with high atom economy. The cinnamic acid feedstock can be derived from biomass fermentation, reducing petroleum dependence. Energy-intensive distillation steps required for natural analogues are eliminated.
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Physicochemical Properties
DTXSID: DTXSID9047411
Physical Properties
| Molecular Weight | 266.34 g/mol🔬 EPA CompTox |
| Density | 1.077 g/cm^3🔬 EPA CTX |
| Boiling Point | 383.331 °C📊 OPERA |
| Melting Point | 44.198 °C📊 OPERA |
| Flash Point | 260.7 °C🔬 EPA CTX |
| Refractive Index | 1.589 Dimensionless📊 OPERA |
| Molar Volume | 244.113 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 4.076 Log10 unitless📊 OPERA |
| LogD (pH 5.5) | 4.076 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 4.076 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 8.63 Log10 unitless📊 OPERA |
| Water Solubility | 0 mol/L📊 OPERA |
| Henry's Law Constant | 0 atm-m3/mole📊 OPERA |
Transport Properties
| Vapor Pressure | 0 mmHg📊 OPERA |
| Surface Tension | 42.498 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 | 6 count💻 Computed |
| Aromatic Rings | 2 count💻 Computed |
| Molar Refractivity | 82.303 cm^3/mol📊 OPERA |
| Polarizability | 32.628 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.
