o-Methoxycinnamaldehyde (CAS 1504-74-1) — Spicy Middle Note Fragrance Ingredient
o-Methoxycinnamaldehyde
CAS 1504-74-1
What Is o-Methoxycinnamaldehyde?
o-Methoxycinnamaldehyde is a synthetic fragrance ingredient with a warm, spicy-cinnamon character. It’s found in perfumes, candles, and some flavored products. This molecule enhances oriental and gourmand fragrances with its sweet-balsamic depth. Perfumers value o-methoxycinnamaldehyde for its ability to bridge spicy top notes with woody base notes. It adds complexity to vanilla and amber accords while providing excellent longevity.
Safety Profile
USE WITH AWARENESSWhat Does o-Methoxycinnamaldehyde Smell Like?
o-Methoxycinnamaldehyde unfolds with an initial burst of cinnamon-dusted oranges that quickly settles into a rich, honeyed warmth. The methoxy group softens the harsh edges of cinnamaldehyde, creating a velvety spice reminiscent of Mexican hot chocolate. As it dries down, the molecule reveals a suede-like texture with whispers of tobacco leaf and dried figs. Unlike its parent compound, it maintains a delicate balance between sweetness and spice without becoming cloying, making it ideal for modern gourmand compositions.
In Famous Fragrances
Fragrance associations may not reflect actual formulations.
Used as a sophisticated spice enhancer, o-methoxycinnamaldehyde amplifies the fragrance’s cinnamon accord while preventing it from becoming overly food-like. It bridges the pink pepper top to the leather base.
This molecule contributes to Angel’s legendary gourmand character, adding a polished cinnamon facet that complements the patchouli-chocolate heart without overwhelming the composition.
2D Molecular Structure
SMILES: COC1=CC=CC=C1C=CC=O
Chemistry, Properties & Perfumer Guide
The Chemistry
o-Methoxycinnamaldehyde is a methoxylated derivative of cinnamaldehyde, belonging to the phenylpropanoid class. The methoxy group at the ortho position significantly alters both the odor profile and chemical reactivity compared to its parent compound. Industrially produced via Claisen-Schmidt condensation of o-methoxybenzaldehyde with acetaldehyde, this synthetic route yields high purity material. The molecule’s planar structure and conjugated π-system contribute to its stability and intense olfactory properties.
Physical & Chemical Properties
| Appearance | Pale yellow liquid |
|---|---|
| Boiling Point | 285 °C |
| Density | 1.12 g/cm³ |
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 0.5-2% | Up to 3% | Spice modifier in oriental compositions |
| Home Fragrance | 0.1-0.5% | Up to 1% | Warming agent in candle blends |
Classic Accords
Tip: Combine with ionones to create a baked goods effect without excessive sweetness.
Alternatives & Comparisons
For stronger cinnamon impact when phototoxicity isn’t a concern. More aggressive and less refined than the methoxy derivative.
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
Not currently restricted by IFRA standards.
EU Allergen Declaration
Not listed in EU allergen regulation (EC) No 1223/2009.
GHS Classification
RIFM Assessment
RIFM evaluation ongoing; preliminary data suggests moderate skin sensitization potential.
Sustainability
As a synthetic material, o-methoxycinnamaldehyde avoids agricultural land use. Production from petrochemical precursors raises carbon footprint concerns, but high odor potency minimizes required quantities. No known biotechnology production routes currently exist.
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Physicochemical Properties
DTXSID: DTXSID2025551
Physical Properties
| Molecular Weight | 162.188 g/mol🔬 EPA CompTox |
| Density | 1.053 g/cm^3📊 OPERA |
| Boiling Point | 277.308 °C📊 OPERA |
| Melting Point | 40.715 °C📊 OPERA |
| Flash Point | 134.5 °C🔬 EPA CTX |
| Refractive Index | 1.559 Dimensionless📊 OPERA |
| Molar Volume | 151.73 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 1.947 Log10 unitless📊 OPERA |
| LogD (pH 5.5) | 1.947 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 1.947 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 5.84 Log10 unitless📊 OPERA |
| Water Solubility | 0.01 mol/L📊 OPERA |
| Henry's Law Constant | 0 atm-m3/mole📊 OPERA |
Transport Properties
| Vapor Pressure | 0.01 mmHg📊 OPERA |
| Viscosity | 2.393 cP📊 OPERA |
| Surface Tension | 36.728 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 | 3 count💻 Computed |
| Aromatic Rings | 1 count💻 Computed |
| Molar Refractivity | 49.008 cm^3/mol📊 OPERA |
| Polarizability | 19.428 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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