Olfactory Chemistry: Hedione- My Fair Jasmine

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When you look back at perfumery there are some specific moments where the use of a new aroma chemical sparks a flurry of creativity. In 1966 perfumer Edmond Roudnitska introduced the world to Hedione in the classic men’s perfume Christian Dior Eau Sauvage.

Hedione was a synthetic jasmine discovered by chemist Edouard Demole. Dr. Demole was part of the team at Firmenich who discovered that the component in natural jasmine essential oil was a molecule called Methyl Jasmonate. From a synthetic perspective the double bond was problematic as far as synthesizing and making large quantities of this molecule. Dr. Demole discovered if he removed the double bond he formed a transparent version of jasmine chemically called Methyl Dihydrojasmonate and trademarked as Hedione.

hedione1

For many jasmine essential oil was a very difficult ingredient to use in moderation. Not only for the strong floral character but also for the presence of strong-smelling indoles in high percentage it made jasmine something which was strong. Maybe too strong. Hedione was a version of jasmine in which Dr. Demole played Henry Higgins and cleaned up jasmine removing the filthy skanky indoles. He also made it much less overwhelming. Hedione provides a unique middle ground between volatile top note and heavier base note. It is probably overstating things a bit to call Hedione the missing link for many perfumers looking for a diffusive floral transparency but it has been a part of thousands of perfumes over the last fifty years.

You will notice that unlike the drawing of Methyl Jasmonate which has the dashed and solid wedges to designate a specific geometry I didn’t draw Hedione that way because it is a mixture of all four possible variations. The chemists at Firmenich would go on to continue to synthesize ever more specific structures of that mixture. It would take thirty-seven years, in 1993, when it was discovered if you had a mixture of the two compounds shown below you got an enriched effect by having the two compounds where the side chains were on the same side of the molecule. This is called cis- in chemistry speak. In the structure of Methyl Jasmonate above that would be called trans- when the side chains are on different sides.

hedionehcparadisone

The mixture would be called Hedione HC which stood for “High Cis” meaning a high percentage of the cis-isomers. It would take three more years to develop a synthesis of the single isomer responsible for most of the effect in Hedione, and Hedione HC. That is the structure on the right and it is called Paradisone.  Paradisone is Hedione on steroids as now there is nothing to attenuate the power. The shy Eliza Doolittle of Hedione has become a stunning version which turns heads.

Perfumer Alberto Morillas has been one of the more contemporary perfumers who uses these molecules in interesting ways. One of the more recent uses of both Hedione and Paradisone was in 2013’s Penhaligon’s Iris Prima. Together they make the jasmine and iris heart feel like it has no horizon, almost infinitely expansive.

It may have taken forty years for the chemists at Firmenich to finally arrive at Paradisone but it all started with a simple reduction of a double bond on the natural molecule.

Mark Behnke

Book Review: Fragrant- The Secret Life of Scent by Mandy Aftel- Essential Oil Reading

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When I reviewed Mandy Aftel’s recent release Palimpsest she mentioned it was inspired by the research she did for her new book, “Fragrant- The Secret Life of Scent”. I received my review copy a little over a week ago and spent this past weekend completely enthralled by Ms. Aftel’s new book. This is Ms. Aftel’s fourth book on scent and it is by far her most accessible.

Ms. Aftel starts off with an introduction on how she fell in love with making natural perfume after a number of previous careers. She realized that scent was important to her and that she wanted to learn how to create perfume. She immersed herself in the history of perfumery and after her years as a perfumer she has come up with a simple truism, “Scent is a portal to these basic human appetites- for the far-off, the familiar, the transcendent, the strange, and the beautiful-that have motivated us since the origins of our species.” That sentence encapsulates what great perfume does for me and what it aspires to.

MandyAuthorPhoto

Mandy Aftel (Photo: Foster Curry)

For this book Ms. Aftel decided to focus on five raw ingredients: cinnamon, mint, frankincense, ambergris, and jasmine. Each ingredient gets its own chapter. It starts with a history of the ingredient but there are delightful tangents as well. One of my favorites comes from the Cinnamon chapter where she found a set of five rules for perfumers in ancient Constantinople. It directs where the perfumers can ply their trade so the pleasant smells will drift up into the Royal Palace nearby. They are also directed that, “They are not to stock poor quality goods in their shops: a sweet smell and a bad smell do not go together.” I think there are some modern perfumeries which could be reminded of these old rules.

The last section of each chapter is dedicated to experiencing the ingredient as a raw material and it includes recipes for different fragrances and ways to use it in cooking. For an even richer experience for these last sections; on the Aftelier website there is a Companion Kit which has all five of the ingredients to allow you to actually play along as you read. I received one of the Companion Kits and it greatly enhanced my experience. Plus there is enough to allow the reader to choose to use some in whatever way seems apt.

Ms. Aftel’s previous career as a writer along with her experience as a natural perfumer allows for a perfect synergy as the author is also the expert. It is an important distinction when it comes to describing a sensory experience in words. I believe it is Ms. Aftel’s intimate relationship with these materials which allow for her to communicate about them so effectively and beautifully.

There are very few books which can reach outside the small circle of those of us who are obsessed with perfume. I believe Fragrant is going to be a book which does have a much wider reach because it is as easy to read as a true-life adventure. For those of us who love perfume and the raw ingredients within them Fragrant is going to give you new perspective on these ingredients. I learned so much I didn’t know about ingredients I thought I knew a lot about.

The section of my bookshelf which houses the books on scent and perfume that I think are essential is pretty small. With the publication of Fragrant it just got one volume bigger.

Disclosure: This review was based on a copy of Fragrant provided by Riverhead Books.

Mark Behnke

The Gold Standard: Jasmine- Serge Lutens Sarrasins

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This is going to be a version of The Gold Standard where some are going to disagree vehemently. The reason for that is there really are two versions of jasmine in perfumery. Which one you like best is all about your tolerance for the more vivid notes of unadulterated jasmine. Jasmine when it is extracted also carries a significant amount of a chemical class called indoles. Indoles are a very pungent chemical and some people, like me, love them; others run away. This is why you see jasmine in both forms in perfumes. There is the straight indolic jasmine and there are the cleaned-up greatly reduced in indoles jasmine. One is a child of the night and the other is a freshly scrubbed ingénue. My choice for The Gold Standard in jasmine is a perfume which not only proudly displays the indoles at the core of jasmine but doubles down with even more skank in the base. That perfume is Serge Lutens Sarrasins.

Christopher-Sheldrake

Christopher Sheldrake

Sarrasins came out at the very end of 2007 and perfumer Christopher Sheldrake turns in one of his most simple compositions, ever, for Serge Lutens. There are five listed notes but each of them when used in their most natural form provide nuance to burn. It is instructional that if your raw materials are suitably complex you don’t need to gild the lily, or the jasmine, in this case.

Bergamot is listed as a note and it is sort of like a matador note as it is the only representative of the light in the entire development. As soon as you notice it is gone under one of the most indolic jasmines I’ve encountered in a perfume. It was exactly what I wanted as the sweet floral character is countered with a raw dirty accord. This jasmine has dirty smudges on her cheeks and her debutante days are well behind her and she is all the more interesting for it. Most perfumers would just let the indoles naturally carry the day but M. Sheldrake decides to add a slug of castoreum. It almost feels like the jasmine is growing fur as if it is a carnivorous flower in a Hogwarts greenhouse. A wonderfully redolent patchouli swaggers in and labdanum applies the last bit of intensity.

Sarrasins has 12-14 hour longevity and average sillage.

serge sarrasins

It is almost ridiculous to say they don’t make them like they used to when I am referring to perfume made seven years ago. Sarrasins feels like a perfume which is out of step with current aesthetics and would’ve been at home on a counter containing the original Patou Joy and Chanel No. 5. For all of that it feels like a perfume unstuck from time, it also feels timeless in its uncompromising adherence to the style of Serge Lutens circa 2007. There is no other fragrance which exemplifies indolic jasmine better than Sarrasins.

Disclosure: This review is based on a bottle I purchased.

Mark Behnke