Dihydro Myrcenol

• 📂 CAS N° — 18479-58-8

• 🏭 Manifacturer — Symrise

• ⚖️ MW — 156,26 g/mol

• 📝 Odor Type — Fresh (listed as citrus, but its much more aromatic - lavender like to me)

• 📈 Odour Strength — weak

• 👃🏼 Odor Profile — Fresh floral smell, someway close to linalool, detergent, blue, household, lavender-like, glass cleaner.

• Arctander, 1969: It has a lime-like citrusy-floral while sweet odor of considerable tenacity.

• 👅 Flavor Profile — green aldehydic herbal terpenic soapy lime tropical

• ⚗️ Uses — It is used predominantly in soap fragrances and as a powerful supporting note in citrus and lime-type perfumes. Use to boost top notes in fougere accords. Use instead of lavender in fougeres or alongside lavender or even alone. Dihydromyrcenol has become a kind of important flavoring and fragrance ingredient. It is also widely used in daily chemical fragrance formulation. Dihydromyrcenol imparts a powerful, fresh lime-like, citrusy-floral and sweet odor with little or no terpenic undertones.

WHAT IS DIHYDROMYRCENOL?

Perfumes are often viewed as complementary, as small details in an overall greater composition of personality and character, but can often be seen as time machines; fragrances or odors that bring us back to imagine a specific time, a clear image, and an incredibly vivid scenario. Continuing the journey among the most defining synthetic molecules, the following article will talk about one such molecule; one that evokes the lucid sense of childhood and brings back to the memory of white, immaculate clean sheets hanged to dry in the warm sun. Follow us down while we immerse ourselves in the history and olfactory description of a molecule that redefined the concept of freshness: Dihydromyrcenol.

Dihydromyrcenol is a fragrance ingredient used in cosmetics, fine fragrances, shampoos, toilet soaps, and other toiletries as well as in non-cosmetic products such as household cleaners and detergents. Its worldwide use is greater than >1000 metric tons per year (IFRA, 2004). A colorless, somewhat viscous liquid that is a mixture of approximately 50% 2,6-dimethyl-7-octen-2-ol and 50% 2,6-dimethyl-7-octen-2-yl formate. It has apparently not been reported to occur in nature. [1]

Dihydromyrcenol is an organic compound from the group of the acyclic terpenoidal alcohols. It is a fragrance with a powerful, fresh, lavender like, sweet citrus and floral fragrance, which is synthetically prepared. The pure substance appears as a colorless viscous liquid, which is practically insoluble in water. 

DIHYDROMYRCENOL AND THE NEW FRESHNESS WAVE

The history surrounding the first synthesis of Dihydromyrcenol appears to be uncertain, especially if we consider the fact that not many sources have been able to concur on which year the synthetic molecule was first created. Much of the information reported seems to point to the late 60s and early 70s as the probable year of production; while, when it comes to its paternity, although it appears to be uncertain to which chemist to attribute its paternity, it is known that the molecule was developed inside the International Flavors & Fragrances (IFF) laboratories.

The necessity for a new, synthetic, and eco-sustainable molecule arose from the governmental regulation on the use of animal musks which, in turn, was generated by the new sentiment of the cruelty-free wave. Although initially the molecule was conceived as a possible way to bring a fresh, clean, and marine nuance to cleaning products and laundry, the above-mentioned events represented an essential propelling force for Dihydromyrcenol becoming, shortly thereafter, a key component to many fragrances.

Although many tend to list Azarro Pour Homme (1978) as the first fragrance to list the synthetic molecule among its constituents, deeper research might show differently. In fact, Chandler Burr in his The Perfect Scent: A Year Inside the Perfume Industry in Paris and New York (2008) highlighted that the well-renowned French perfumer Jean-Claude Ellena noticed the presence of the molecule several years prior to its first thought injection in the world of perfumery.

Burr, while interviewing the French perfumer, highlighted how much Ellena actively disliked the synthetic molecule, ascribing the birth of what Ellena addressed as a “hygienic trend” to Paco Rabanne Pour Homme (1973). According to Burr, Ellena thought that: “(…) you could pinpoint the beginning of the hygienic trend as Paco Rabanne Pour Homme(1973), which **was leading away from leather and ferns and spices and straight into the fluorescent-lit drugstore detergent aisle(…)”. Ellena’s pejorative observations were directed at the presence of around 2 to 5% Dihydromyrcenol in Rabanne’s new fragrance, which absolved the role of enhancer for the levander facets of the concoction.

As many sources tend to point out, there were many other fragrances that closely followed the beaten path created by Rabanne, namely the above-mentioned Azarro Pour Homme, a truly remarkable approach to the synthetic molecule was adopted by the perfumer Pierre Wargnye. In fact, while working on a new fragrance for Guy Laroche, Wargnye decided to exponentially heighten the percentage of Dihydromyrcenol from the conventional 2/5% to an astonishing 10%. This choice led to the commercialization of the highly praised and renowned Drakkar Noir (1982), which instantly became a fragrant, scented manifesto of the eighties and the new freshness. In his portentous labor, Wargnye decided not to merely use the Dihydromyrcenol as a head note which simply aimed to enhance the properties of the lavender spike -which he preferred to the lavender vera due to its stronger camphoric notes-, but instead used it to impart a peculiar aromatic breeziness fostered by concentrated bursts of Dihydromyrcenol.

Probably inspired by Wargnye’s innovation, in 1988 Pierre Bourdon, who at the time was working under Davidoff, created a fundamental fragrance that gave a completely fresh approach to the molecule. Bourdon, appointed by Davidoff to recreate a more affordable version of one of his part works, namely Green Irish Tweed (1985) **by Creed, decided to increment the concentration of Dihydromyrcenol to 20%. This decision resulted in what Burr doesn’t shy away from describing as “an apotheosis” for the molecule, that found one of its most important representations in Davidoff’s Cool Water (1988) a universally respected “high school kids’ cologne” remembered for its characteristic salty and ozonic notes.

However, if anyone wondered how is Dihydromyrcenol fairing in the current landscape of perfumery, the answer might be more direct than a person might think. In fact, although the molecule has found, and still finds a fairly good amount of success, its application has been relegated to a specific, albeit incredibly vast, branch of masculine fragrances such as cK One (1994) by Calvin Klein, Light Blue (2001) by Dolce & Gabbana, Eternity Aqua for Men (2010) by Calvin Klein, and many more. As noted by Burr, although many of the above-mentioned master perfumers showed interesting and innovative angles to approach the molecule, the abuse of Dihydromyrcenol in the current market projected it directly into the immobility of the status quo, transforming it into a proper cliché of perfumery.

Olfactory profile and fields of application

When discussing the applications and olfactory profile of Dihydromyrcenol, it is possible to state that the monoterpenoid possesses one of the most recognizable odors in chemistry. In fact, thanks to its fresh, detergent-like, and borderline aseptic scent, the molecule has found a wide amount of success in a vast array of hygienic products such as shampoos, toilet soaps, decorative cosmetics, toiletries, household cleaners and detergents and, last but not least, in perfumery.

Dihydromyrcenol has often been described as a viscous, coloreless liquid with high volatility which cannot be dissolved in water. Its olfactory profile is characterized by peculiarly fresh, lime-like, linen-like, and floral notes, accompanied by a few terpenic undernotes, which may be either present in low amounts or absent as a whole, and it is often associated with a pleasant lavender-like aspect.

Regarding the use of the monoterpenoid in perfumery, it is important to stress that, although possessing a very distinct odor, the molecule has found fecund territory in this aromatic field of interest. The importance of said molecule in perfumery has been highlighted by many perfumers and companies, among which is possible to list Symrise that did not refrain from defining the monoterpenoid as “(…)one of the most important fragrance ingredients”.

Symrise's statement did not merely stem from the wide market-spread demand for the molecule, or its environmentally friendly approach to perfumery and chemistry as a whole; which the molecule actively promotes by not requiring the use of natural raw material. In fact, its flexibility is one of the factors that add relevancy to an already almost essential molecule.

That said, the flexibility ascribed to Dihydromyrcenol derives from its ability to be used as either a head note, thus enhancing and boosting various floral or citrusy aspects of the fragrance, or as a more front-and-center component of the perfume. The molecule can also add a peculiar freshness that can often be perceived as aquatic in more modern iterations, or enrich other central components of the perfume taking on different facets such as salty and ozonic. For this specific reason, it is mandatory for the perfumer to have a precise idea of how to use the liquid in the fragrance, in order not to lead his or her fragrance to acquire the smell of what Ellena might describe as “(…) the fluorescent-lit drugstore detergent aisle.”

Production

There are two preparation methods. One is to chlorinate Dihydromyrcene and then be hydrolyzed in alkaline water. The other process is esterifying Dihydromyrcene by acetic acid or formic acid, and then produce Dihydromyrcenol through saponification and hydrolysis under the alkaline condition. (Germany Patent: 1668280)

NOTE

Soviet spice experts had been researched the flavor quality in mixtures of Dihydromyrcenol and Myrcenyl Acetate. Results of the study show that when the contents of Myrcenyl acetate above 10%, Dihydromyrcenol had the best flavor quality.

Sources:

• Fragrance material review on dihydromyrcenol—D. McGinty *, C.S. Letizia, A.M. Api

• National Center for Biotechnology Information (2020). PubChem Compound Summary for CID 29096, Dihydromyrcenol. Retrieved November 24, 2020 from https://pubchem.ncbi.nlm.nih.gov/compound/Dihydromyrcenol.

• The Perfect Scent: A Year Inside the Perfume Industry in Paris and New York - Chandler Burr pp. 426, 427, 428, 429

• The Chemistry of Fragrances - David Pybus and Charles Sell

• https://www.scentspiracy.com/synthetics/dihydromyrcenol

• https://www.sylvaine-delacourte.com/en/guide/the-new-freshness-facet

• https://www.symrise.com/our-stories/everything-flows/

• https://www.fragrantica.com/news/Unter-den-Linden-Linden-Blossom-in-Perfumery-17777.html

• https://ifragranceofficial.com/an-introduction-to-musks/

• https://www.fragrenza.com/blogs/notes-in-perfumery/dihydromyrcenol-in-perfumery

• https://www.carrementbelle.com/blog/en/2021/10/20/new-freshness-olfactory-facet-perfume/

• https://qualiacomputing.com/tag/state-space/

• http://www.thegoodscentscompany.com/data/rw1006052.html

• https://pubchem.ncbi.nlm.nih.gov/compound/Dihydromyrcenol

• https://oneseedperfumes.com/blogs/news/the-problem-with-synthetic-musk