Ebanol™ – Long-Lasting Sandalwood Molecule
Ebanol™ by Givaudan – The Complete Reference
Ebanol™ is one of the longest-lasting materials in perfumery – and one of the longest-proven. In use for almost four decades, it has established itself as a standard tool for authentic sandalwood. This reference goes beyond the product page: chemistry in detail, the complete sustainability and toxicology profile, as well as the origin story.
Contents
- What is Ebanol™?
- Performance overview
- Why you need it
- The isomer question – a look at the stereochemistry
- Origin – from campholenic aldehyde to the sandalwood standard
- Sustainability and ecotoxicity profile
- Toxicological profile in detail
- Stability by pH value – the complete table
- Quick reference: chemistry and safety
- Further questions
1. What is Ebanol™?
Ebanol™ (CAS 67801-20-1, EC no. 267-140-4, FEMA 4775) is a synthetic sandalwood molecule by Givaudan from the class of trisubstituted cyclopentenols. Officially it is assigned to the "woody" fragrance family, with the scent notes "woody, sandalwood, musky, powerful." With an odor threshold of only 0.2088 ng/l and a so-called odor value of over 2×10⁵ – the ratio between vapor pressure and odor threshold, which describes the olfactory impact of a material – it is among the most potent sandalwood materials of all. For comparison: an odor value of this magnitude means that even tiny air concentrations of the substance are clearly perceptible to the human nose, long before other, less diffusive materials would even be registered.
1a. Performance overview
| Criterion | Value |
|---|---|
| Usage range | 0.5–5% |
| Longevity on the blotter | 3 weeks |
| Burning effectiveness | ★★★★★ |
| Substantivity, wet | ★★★★★ |
| Substantivity, dry | ★★★★★ |
| Bloom in soap bases | ★★★★★ |
2. Why you need it
The full rationale – exceptional longevity, stability in difficult application bases, dual function as sandalwood core and modifier – you will find on the product page. Here, in addition, one aspect that has no place there: the combination of high substantivity and excellent pH stability makes Ebanol™ one of the few sandalwood materials equally suited to fine fragrance and to functional applications (detergents and cleaners, soaps, candles), without having to resort to different materials for different application fields.
3. The isomer question – a look at the stereochemistry
The official name "3-methyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol (& isomers)" reveals that Ebanol™ is not a single compound. The molecule has several stereogenic centers – positions in the molecular skeleton where different spatial arrangements of the atoms are possible without the molecular formula changing. The result is diastereomers: molecules with identical constitution but different three-dimensional structure.
Givaudan's current Certificate of Analysis reports a sum of three chromatographically distinguishable isomers (≥ 90%, method ISO 7609 polar), with a peak distribution of around 51.5%, 2.6% and 40.0%. In the scientific literature on aroma chemistry, the underlying synthesis is described as a mixture of predominantly four diastereomeric alcohols. This discrepancy is typical for complex technical aroma materials: depending on the chromatographic method and resolution, structurally very similar isomers can overlap or appear as a single common peak, even if more isomers are theoretically present.
For practice this means: the complex, multi-layered sandalwood impression of Ebanol™ arises not from a single, exactly defined molecular structure, but from the interplay of several structurally related compounds – much as natural sandalwood oil itself is a complex mixture of various santalols and minor components.
4. Origin – from campholenic aldehyde to the sandalwood standard
Ebanol™ is part of a development line of synthetic sandalwood materials that has its origin in campholenic aldehyde chemistry. In 1977, the Indian government imposed an export ban on oil from Santalum album, the classic Mysore sandalwood tree – a regulatory measure to protect the stands in Karnataka and other Indian states. This event was a major impetus for the intensive research into synthetic sandalwood aroma materials that the fragrance industry drove forward in the late 1970s and early 1980s.
In this environment, Givaudan's own Sandalore® (1976) first emerged, followed by Ebanol™: the Givaudan chemists Daniel Helmlinger and Mario Pesaro filed European patent EP 116 277 on 13 January 1983, describing a three-step synthesis route – starting from the aldol condensation of α-campholenic aldehyde with 2-butanone, followed by base-catalyzed isomerization and selective reduction to the final isomer mixture. Industrial market entry followed in 1986.
Ebanol™ thus joins a family of campholenic-aldehyde-based sandalwood materials that have shaped perfumery since the 1980s and remain among the central building blocks of contemporary woody accords today. Almost forty years after its market launch, Ebanol™ is still one of the most frequently used sandalwood materials in professional perfumery.
5. Sustainability and ecotoxicity profile
Givaudan evaluates its materials according to its own eight-part sustainability grid. For Ebanol™ the following picture results:
| Criterion | Rating |
|---|---|
| Renewable carbon content | > 50% |
| Biodegradability | Readily biodegradable |
| Ecotoxicity | Toxic (classified under GHS environmental hazard categories) |
| Waste generation in manufacturing | Does not meet expectations |
| Chemistry used | Not on the list of undesirable processes |
| Solvents used | Standard solvents |
| Process complexity | Complex (4 or more chemical steps) |
| Olfactory impact | Significant impact (high odor value) |
Remarkable is the contrast between the classification as "toxic" for aquatic organisms and the simultaneous ready biodegradability: while the material does burden aquatic organisms, it breaks down again comparatively quickly and does not accumulate permanently in the environment.
The underlying test data in detail:
| Test | Result | Method |
|---|---|---|
| Toxicity to fish (fathead minnow) | LC50: 2.3 mg/l (96 h) | OECD 203, GLP |
| Toxicity to water fleas | EC50: 1.9 mg/l (48 h) | OECD 202 |
| Toxicity to green algae | EC50: 24.0–26.0 mg/l; NOEC: 3.1 mg/l | OECD 201 |
| Biodegradability | 66% degradation in 28 days | OECD 301F, GLP |
| Mobility in soil | log Koc: 3.2 (moderately to slightly mobile) | – |
Under the German Major Accidents Ordinance, Ebanol™ is additionally classified in the category "environmental hazards E2," with quantity thresholds of 200 t (lower) and 500 t (upper threshold) – relevant for operations working with very large quantities, not for ordinary laboratory use.
6. Toxicological profile in detail
Beyond the basic data on the product page, the following study results are available:
- Genotoxicity: negative in four independent test systems – Ames test on two bacterial strains (Salmonella typhimurium and Escherichia coli), chromosome aberration test on human lymphocytes, and an in-vitro genetic test on mammalian cells
- Repeated dose (28 days, oral, rat): NOAEL 1,000 mg/kg (OECD 407) – the highest dose at which no harmful effects were yet observable
- Repeated dose (15 days): NOAEL also 1,000 mg/kg (OECD 421)
- Phototoxicity: tested negative on the guinea pig
- Reproductive toxicity: not classified on the basis of the available data
Overall, this yields a material with an unremarkable toxicological profile in intended use – the only regulatorily relevant classification concerns, as described on the product page, the aquatic environment.
7. Stability by pH value – the complete table
Givaudan tests the odor stability of Ebanol™ in nine typical application bases. The complete results:
| pH | Application base | Odor stability |
|---|---|---|
| 2 | Acidic cleaner | ★★★ (medium) |
| 3 | Fabric softener | ★★★★★ (good) |
| 3.5 | Antiperspirant | ★★★ (medium) |
| 6 | Shampoo | ★★★★★ (good) |
| 9 | All-purpose cleaner | ★★★★★ (good) |
| 9 | Liquid detergent | ★★★★★ (good) |
| 10 | Soap | ★★★★★ (good) |
| 10.5 | Washing powder | ★★★ (medium) |
| 11 | Liquid bleach | ★ (poor) |
Notable compared with many other aroma molecules: Ebanol™ shows medium to very good stability in eight of nine tested bases. Even in strongly alkaline environments such as washing powder, a medium effect is retained – only in liquid bleach (pH 11) does the rating drop clearly, which is typical for most aroma materials of this class.
8. Quick reference: chemistry and safety
You will find the complete physico-chemical data as well as the basic safety information on the product page. In summary: CAS 67801-20-1, C₁₄H₂₄O, 208.30 g/mol, Givaudan code 4697403 – classified as hazardous to water (H411), but toxicologically unremarkable and readily biodegradable.
Further questions about Ebanol™
What does the high "odor value" mean in practice?
The odor value describes the ratio between vapor pressure and odor threshold – put simply, how strongly a material goes "into the air" relative to how little of it the nose needs to perceive it at all. For Ebanol™ this value is over 2×10⁵, which makes it one of the most diffusive sandalwood materials.
Why do the isomer counts differ between the Certificate of Analysis and the technical literature?
The Certificate of Analysis tests a specific batch with a particular chromatographic method (ISO 7609 polar) and records three separate peaks. The technical literature describes the synthesis chemistry in general and assumes four diastereomeric alcohols. Both statements do not necessarily contradict each other – structurally very similar isomers can coincide under certain chromatographic conditions.
Is Ebanol™ suitable for high-pH applications?
Mostly yes. In eight of nine tested application bases it shows medium to very good stability. Only in strongly alkaline systems such as liquid bleach (pH 11) does the effect decrease clearly.
Does Ebanol™ accumulate in the environment?
No. Despite the classification as toxic to aquatic organisms, the material is readily biodegradable (66% degradation in 28 days) and does not accumulate permanently according to the PBT criteria (persistent, bioaccumulative, toxic).