Category Archives: aroma chemistry

Chemistry Flash – Ambroxan

As week by week the day is getting shorter and it becomes dark outside much earlier I think most of us spend more time at home these days. It also gets colder, the first snow of this winter might fall any moment and Christmas is right behind the corner I though this may be a good opportunity for a chemistry lesson about one of these “warming” ingredients that we “love” in our winter perfumes.

The full name of this compound is (3aR,5aS,9aS,9bR)-3a,6,6,9a-tetramethyl-2,4,5,5a,7,8,9,9b-octahydro-1H-benzo[e][1]benzofuran but to average perfume user it is known as ambroxan. It’s an aromachemical of molecular weight of 236,39 grams, formulae C16H28O. It belongs to the class of tetranorlabdane oxide and is valued in perfumery.

Ambergris or a grey amber is one of the most expensive raw materials that can be used by perfumers. It is extremely rare as it is obtained from cachalot (sperm whales.) cachalot are currently on the IUNC Red List of Endangered Species and they’re classified as “vulnerable” which means that their species might soon be endangered if their survival and reproduction are threatened. It’s their digestive system (which can be as long as 300 meters) where ambergris is produced. There were times when poachers killed sperm whales and were selling the grey amber.

The boulder of ambergris forms in a cachalot stomach as a result of irritating the delicate intestinal lining of sperm whales. It mostly happens because of squid beaks, this species loves eating squids. The mass is growing bigger, moves farther the digestive system, finally it becomes the indigestible solid that blocks the rectum. As a response the organism increases water absorption in the intestines, eventually the mass of squid beaks turns into a rock.

As the Cachalot continues its life, the rock grows bigger and bigger. Sometimes a whale is able to expel ambergris from its body but sometimes it becomes impossible, the boulder completely blocks the excretory system. It has fatal results, a whale dies. Its monstrous body will become food for sharks and other organisms. At some point the stone of grey amber will be released into the sea. Because its density is smaller than of water, it floats on the waves, and this can happen for decades. At first it’s a solid, viscous matter of grey to black color that has a marine and fecal odor. During its journey before landing on some beach it ages and gains earthy and sweet aroma.

Ambroxan doesn’t occur in natural ambergris. The main ingredient of this material – ambrein can be separated from the grey amber stones by heating them with alcohol and then allowing the solution to cool down. White crystals of ambrein crystallize. The interesting thing is that ambrein is almost odorless. However by a process of oxidation it can break in two, forming molecules of ambrox and ambrinol. These two possess intensive aroma and are main odour component of ambre gris.

Due to sperm whales being a vulnerable species and due to the cost of obtaining this rare perfume material, modern perfumery found a way how to introduce a smell of ambergris into perfume without affecting cachalot population. The chemical equivalent, ambroxan was developed. It’s structure is identical with ambrox derived from ambrein. Nowadays there are many methods to synthesise ambroxan, they’re described in chemical publications.

To mention just a few there are ways starting with compounds such as (-)-drimenol, labdanolic acid, (-)-sclareol. Synthetic ambroxan is used in perfumes to add them a fragrance of musk and it also plays a role of a fixative (it makes a fragrance last longer.) Ambroxan was first obtained via a synthesis pathway in 1950. Ambroxan is a trade name for Henkel, Quest uses it as Amberlyn and Firmenich as Ambrox. Nowadays it’s hard to find a perfume without the addition of this synthetic aroma molecule. There are even a couple of brand which somehow started specializing in using in their perfume creations.

Here’s a list of couple of perfumes containing ambroxan:

  • Juliette Has a Gun: Oil Fiction, Anyway, Not a Perfume*
  • Escentric Molecules: Escentric 02, Molecule 02*
  • Le Labo: Baie Rose 26, Another 13
  • Frederic Malle: French Lover, Geranium pour Monsieur
  • D&G: Light Blue

For more fascinating information about ambergris read this article.

* – means that a perfume is pure ambroxan in alcohol. Is it still perfume?

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June perfume workshop report, part 1 of 2

Last Friday I took a lovely weekend trip to Warsaw. Another perfume workshop organized by Quality Missala perfumeries took its place in the capital city. Warsaw is not as close to me as Wrocław but since all my exams are finished I decided to go on a weekend voyage there. My decision was also influenced by the fact that the theme of June workshop was really right up my alley as it was about citrus & exotic fruit. As you know citrus is one of my favourite groups so I just had to be there.

I arrived in Warsaw on Friday afternoon and the workshop was starting at 11 a.m on Saturday. After I checked in at the hotel I was staying I took a stroll around Warsaw city centre. The next day, after a small breakfast, I took a tram to Bemowo, one of the districts of Warsaw, where Quality Missala perfumery house is located. There, at the conference hall above the actual perfumery the workshop was held. The day was hot, luckily we had some mild air conditioning and cold drinks there.

Everyone was treated with a fruit punch made of juicy citrus and pieces of strawberries were floating in it too, cold mint water with lemon and a strawberry cheesecake. We were ready to start sniffing.

The scheme of this workshop was done in a similar manner like the previous meetings. First Ania gave us some chemical, technological and botanical background, she told us about different processes of obtaining essential oils from different citrus, exotic fruits and that they can be obtained from different parts of the fruit. This time I took some notes to make this report easier to write. In this part I will share my thoughts on all the essences tested. In part 2 I will feature all the perfumes tried.

First was bergamot essence. It was really acidic, with a sweet and sour feeling. Very juicy and mouth-watering. It had a very happy smell, it would perfectly fit to some sweet, creamy desserts. Essence we tried was made from Italian bergamot.

Grapefruit was up next. It had a juicy, tart smell, uplifting and invigorating. I really liked this essence of American grapefruit. It didn’t smell like an actual fruit but like a glass of juice.

Lemon from California had a very happy smell and it was literally bursting with joy. The intensity of the smell was quite in your face but I enjoyed it. This essence was obtained by the cold pressing of the citrus which means the that the oil came from squeezing and pressing the whole fruit in cold or room temperature. Then it was filtered to separate any particles of the pulp from the oil and juice.

For an interesting comparison we got another lemon essential oil to smell. It was lemon from Calabria. It was sweeter on my skin and reminded me of Nimm2 lemon candies. I love their taste and smell. After a few hours both lemons lost their citrus edge and they smelled really green, of leaves and twigs. Interesting.

Another aroma we tried was one of Mexican lime. It was delicious and it smelled almost like Mojito drink but without mint and alcohol. It had a relaxing scent to me.

Next was neroli which I think was my favourite essence of that day. Neroli is an essential oil obtained from bitter orange flowers in a process of water distillation. It had a floral, clean and soapy smell which was couple of times intensive that the simplest neroli fragrances available. Simply gorgeous. Neroli’s relative – petit grain, the essence of bitter orange flowers, leaves and twigs was next in the lime to smell. Oh my God, it was awful. It was sweaty, almost beefy in style. Very bad thing to wear alone! Essence tried was of petit grain from Paraguay.

Then we tried the perfume oil made from the orange pulp. What a happy and vigorous scent that was. Like a freshly squeezed juice and the smell was actually pretty close to Atelier Cologne Orange Sanguine. Simple and charming smell, pretty edible. Tangerine had a very subtle, slightly sweet vibe but on the whole it was really hard to smell anything from the strip. Sicilian tangerine had a little bit more intensive aroma but still it was very light.

Essence of yuzu was just ok, I didn’t fell for it but it didn’t repel me either. Then we samples the smell of melon. It was a synthetic combination of different aroma chemicals to recreate the real melon aroma. It is impossible to obtain the natural lemon extract. It possessed kind of sweet, honeyed, watery aroma. Mango we tried was also artificial. It’s possible to obtain natural essence of it but it’s totally against the economy, it’s so expensive. I could barely smell it, only some subtle, fruity-oily nuances. We also has a synthetic peach, aldehyde C-14 that smelled creamy and lactonic. It had that mild fruity vibe combined with the smell of fuzzy peel.

Last two perfume oils we tried were banana and coco. They shared some similarities. Both were milky and tender, but coco had an additional fluffiness and a lot of creamy, desserty vibe I liked.

After a finished workshop we talked a lot, spend some more time downstairs in a perfumery, we tried what we wanted without sticking to the citrus-exotic theme. We just had a lot of fun. Then a few newly met friends I knew earlier online and I went to have a dinner together. We exchanged our experiences, sniffed some samples as everyone had something to show to the others. I didn’t even notice when the time passed and from 10 in the morning in was 7 in the evening. I had a great time!

Stay tuned, in a few days I will post part 2 to tell you about perfumes for each of these fruits.

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