Neohesperidin dihydrochalcone (CAS 20702-77-6) — Sweet Base Note Fragrance Ingredient
Neohesperidin dihydrochalcone
CAS 20702-77-6
What Is Neohesperidin dihydrochalcone?
Neohesperidin dihydrochalcone is a synthetic sweetener and flavor modifier derived from citrus fruits. You’ll find it in sugar-free candies, chewing gums, and some perfumes where a sweet, long-lasting note is desired. This ingredient matters because it provides an intensely sweet, honey-like character without adding calories, making it valuable for both food and fragrance applications where sugar would be impractical.
Safety Profile
GENERALLY SAFEWhat Does Neohesperidin dihydrochalcone Smell Like?
Neohesperidin dihydrochalcone delivers an intense, lingering sweetness reminiscent of honey soaked in orange blossom water, with nuances of dried figs and candied citrus peel. Unlike sugar, it has a slight woody-herbal undertone that prevents cloying sweetness. In perfumery, it acts as a powerful fixative for sweet accords, amplifying vanilla and fruity notes while adding a polished, almost glossy sweetness that persists through the dry-down.
2D Molecular Structure
SMILES: COC1=C(O)C=C(CCC(=O)C2=C(O)C=C(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](O)[C@H]3O)C=C2O)C=C1
Chemistry, Properties & Perfumer Guide
The Chemistry
This semi-synthetic compound belongs to the dihydrochalcone class, produced by hydrogenation of neohesperidin (a flavonoid glycoside from bitter oranges). The process creates a stable, water-soluble molecule with exceptional sweetness potency (1500-1800 times sweeter than sucrose). Though chiral centers exist in its structure, the commercial material is typically used as a racemate. Its sweetness comes from specific interactions with TAS1R2/TAS1R3 taste receptors.
Physical & Chemical Properties
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 0.1-0.5% | Up to 1% | Sweetness booster |
| Functional Fragrance | 0.05-0.2% | Up to 0.5% | Masking agent |
| Candles | 0.3-1% | Up to 2% | Sweet dry-down |
Classic Accords
Tip: Use sparingly – 0.1% can dramatically sweeten an entire formula.
Alternatives & Comparisons
When a softer, more diffuse sweetness is needed without the intense persistence of neohesperidin DC.
For applications requiring water solubility and sugar-like taste profile without fragrance interference.
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
No IFRA restrictions. Classified as a flavor rather than fragrance material.
RIFM Assessment
Not evaluated by RIFM as it’s primarily a flavor ingredient.
Sustainability
While derived from citrus byproducts, industrial synthesis requires significant energy input. Some manufacturers use enzymatic methods to improve sustainability. Biodegradation studies show moderate environmental persistence.
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Layer 3 · Practical
- FEMA GRAS: 3811
- Molecular Weight: 612.60 g/mol
- LogP (XLogP): -0.30
Ingredient Data Sheet
CAS 20702-77-6Physical Properties
| Molecular Weight | 612.6 g/mol🔬 PubChem |
| LogP (Octanol-Water) | -0.3🔬 PubChem |
| Boiling Point | 372 °C🔬 EPA CompTox |
| Vapor Pressure | 0 mmHg @ 25°C📊 OPERA |
| Flash Point | 302.6 °C🔬 EPA CompTox |
| log Kp (skin permeability) | -6.65💻 Calculated |
| SMILES | CC1C(C(C(C(O1)OC2C(C(C(OC2OC3=CC(=C(C(=C3)O)C(=O)CCC4=CC(=C(C=C4)OC)O)O)CO)O)O)O)O)O🔬 PubChem |
Volatility & Performance
| Fragrance Note | Base💻 Calculated |
Odor & Flavor
| Functional Groups | ketonealcoholphenoletheraromatic💻 RDKit |
| Neohesperidin dihydrochalcone is used as a flavor enhancer.📖 Fenaroli | |
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: DTXSID3025706
Physical Properties
| Molecular Weight | 612.581 g/mol🔬 EPA CompTox |
| Density | 1.382 g/cm^3🔬 EPA CTX |
| Boiling Point | 687.787 °C📊 OPERA |
| Melting Point | 155.778 °C🔬 EPA CTX |
| Flash Point | 352.705 °C📊 OPERA |
| Refractive Index | 1.684 Dimensionless📊 OPERA |
| Molar Volume | 378.782 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 0.67 Log10 unitless🔬 EPA CTX |
| LogD (pH 5.5) | -0.104 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 0.073 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 9.59 Log10 unitless📊 OPERA |
| Water Solubility | 0.001 mol/L🔬 EPA CTX |
| Henry's Law Constant | 0 atm-m3/mole📊 OPERA |
Transport Properties
| Vapor Pressure | 0 mmHg🔬 EPA CTX |
| Surface Tension | 97.502 dyn/cm📊 OPERA |
Molecular Descriptors
| Topological Polar Surface Area | 245.29 Ų💻 Computed |
| H-Bond Donors | 9 count💻 Computed |
| H-Bond Acceptors | 15 count💻 Computed |
| Rotatable Bonds | 10 count💻 Computed |
| Aromatic Rings | 2 count💻 Computed |
| Molar Refractivity | 143.854 cm^3/mol📊 OPERA |
| Polarizability | 57.028 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.
