Habanolide® – Patent, Twin and Environmental Data
Habanolide® – Patent, Twin and Environmental Data
A raw material that has been on the market for over three decades and has an almost identical twin at a competitor. The story of Habanolide® is an investigation into contradictions – from the patent to the competing product to the environmental data.
Contents
- The Patent Behind Habanolide
- The House's Second Generation
- The Twin at the Competition
- What the Environmental Authorities Actually Measured
- Where Habanolide Actually Appears
- Frequently Asked Questions
1. The Patent Behind Habanolide
On 27 October 1989, Firmenich filed an application in Switzerland for the use of unsaturated macrocyclic lactones as perfuming ingredients. This became European patent EP 0 424 787 B1 (inventors: Peter Fankhauser and Piero Fantini, granted 1996). Claim 1 protects a mixture containing at least 60% pentadecenolides whose double bond in position 11 or 12 has E configuration – among them trans-pentadec-12-en-15-olide, chemically (12E)-oxacyclohexadec-12-en-2-one: Habanolide. The name is slightly misleading: "pentadecenolide" counts the 15 carbon atoms; with the oxygen, the ring has 16 members. The patent expired in 2010.
This also puts the timeline in order: development in the late 1980s, patent application in 1989, registration of the Habanolide® trademark on March 5, 1992 (no. 584055). The date "1969" cited by a single trade database does not fit.
2. The House's Second Generation
dsm-firmenich calls itself the "House of Musk" – pointing to the 1939 Nobel Prize in Chemistry, awarded to Leopold Ružička for elucidating the structure of large ring molecules such as muscone and civetone. This earlier generation of macrocyclic musk notes was found in nature and isolated in the 1920s/30s: Exaltolide® (from angelica root oil), muscone (from the musk deer's gland), civetone (from the civet cat's secretion).
Habanolide belongs to a second, younger group: synthetic molecules developed specifically in Firmenich's research laboratories from the late 1980s onward – alongside Exaltenone® and Muscenone® Delta. The structural difference from the first generation is concrete: Exaltolide is a saturated 16-membered lactone, while Habanolide carries a double bond in the same ring. The deliberately introduced double bond is no coincidence: for macrocyclic musk compounds it generally holds that unsaturated variants are more odor-intensive than their saturated precursors.
3. The Twin at the Competition
Anyone reading through raw-material databases on macrocyclic musk notes will eventually run into a confusing observation: Symrise's Globalide® (CAS 34902-57-3) appears in some sources practically as a synonym for Habanolide. That is a simplification, but not pure invention.
The independent safety assessment by the Research Institute for Fragrance Materials (RIFM) – published in Food and Chemical Toxicology, Volume 164, 2022, under the title "Oxacyclohexadecen-2-one, CAS Registry Number 34902-57-3" – explicitly lists CAS 111879-80-2 (Habanolide) as an isomer of CAS 34902-57-3 (Globalide), with the reasoning: "Included because the materials are isomers." Both share the same molecular formula C15H26O2 and the same 16-membered ring system, but differ in the position and geometry of the double bond. Interestingly, Symrise's own product information for Globalide lists both CAS numbers simultaneously (34902-57-3 and 111879-80-2) and describes the material as an "isomer mixture" – whereas the manufacturer's data for Habanolide name only CAS 111879-80-2, i.e. the specific (12E)-isomer.
The takeaway relevant to end customers: Habanolide and Globalide are two independently registered, competing trade names for structurally and olfactorily very closely related materials – not a relabeling of an identical raw material, but not fundamentally different fragrance ingredients either.
4. What the Environmental Authorities Actually Measured
Manufacturer data for Habanolide circulate some strongly diverging physico-chemical values. The most informative independent source is an Australian regulatory report: the Full Public Report SN/10 from the National Industrial Chemicals Notification and Assessment Scheme (today AICIS), published August 22, 2002, based on a series of GLP studies from Safepharm Laboratories, Toxicol Laboratories, and Kurume Research Laboratories.
Two discrepancies stand out in particular. First, the partition coefficient log P: the manufacturer states 5.45, while Safepharm Laboratories' independent HPLC measurement instead arrived at ">6.2" – the measurement reached the method's upper calibration limit (the reference standard DDT at log Kow ≈ 6.2), so the true value could well be even higher. Second, vapor pressure: 0.00003 Pa according to the manufacturer versus 0.16 Pa according to Safepharm Laboratories at 25 °C – a factor of roughly 5000. An explanation going beyond a mere methodological imprecision could not be conclusively found in this research; most likely is a unit or transcription discrepancy on one side or the other.
The ecotoxicological measurements from the same report are more unambiguous: acute toxicity for rainbow trout LC50 = 2.4 mg/L (96h), for Daphnia magna LC50 = 0.88 mg/L (48h), algal growth inhibition EbC50 = 2.4 mg/L (72h) – values that lead to the strict GHS classification "Aquatic Acute 1" (H400/H410). At the same time, with 92% degradation in 28 days (OECD 301C) and 99% inherent biodegradability (OECD 302A), Habanolide shows surprisingly good biodegradability for such a lipophilic molecule. The authority itself concludes that, despite the theoretical bioaccumulation potential (calculated log BCF ≈ 4.6, no direct measurement), no environmental risk is expected under the reported pattern of use.
5. Where Habanolide Actually Appears
Official ingredient lists featuring Habanolide, published by the manufacturer or in a patent, could not be found in this research – fragrance formulas are almost always trade secrets. What can be clearly documented, on the other hand: according to a manufacturer press release, Habanolide pairs especially well with the renewable musk molecules Helvetolide® and Romandolide® – a combination recommendation that can be directly followed in our own range.
Frequently Asked Questions
Is Habanolide the same as Symrise's Globalide?
Not identical, but closely related: both are macrocyclic lactones with the molecular formula C15H26O2, officially listed as isomers by the independent safety assessment body RIFM. Habanolide (CAS 111879-80-2) is the specific (12E)-isomer, Globalide (CAS 34902-57-3) a more broadly defined, historically older isomer mixture.
Is there a patent on Habanolide?
Yes. EP 0 424 787 (Firmenich, priority 1989) protects the use of trans-pentadec-11/12-en-15-olides as perfuming ingredients – Habanolide is among them. The patent expired in 2010.
When was Habanolide discovered?
An exact year of discovery has not been published. The patent was filed in 1989 and the trademark registered in 1992 – so development dates to the late 1980s.
Why is Habanolide classified as environmentally hazardous even though it is biodegradable?
The GHS classification H400/H410 is based on acute toxicity to aquatic organisms (e.g. Daphnia magna LC50 0.88 mg/L), not on biodegradability. Both properties – high acute aquatic toxicity and good biodegradability (92% in 28 days) – are not chemically mutually exclusive, and according to the independent regulatory assessment (AICIS), both apply.