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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28 thoughts on “Chemistry Flash – Ambroxan

  1. Jordan River says:

    Excellent, now I know more than I did a few minutes ago. Have you read Floating Gold by Christopher Kemp? I see it in your link above; it is a great read on the natural ingredient. Thank you for the Chemistry Flash on the synthetic/s.

  2. jillie says:

    Oh poor whale! Thank you for explaining this so well.

  3. shellyw says:

    I really enjoyed the Floating Gold book you linked to. The eccentrics could not been written as well if it had been a novel. Thank you for the science aspect.

  4. Tora says:

    Thank you for this tutorial. I had no idea that the ambergris could have fatal effects on the whale. I thought it was a natural exudate that the whale released regularly. I look forward to reading the link you sent along with this. I have been fascinated by the scent and story of ambergris ever since I first smelled the oil a woman wore at a wedding in the 90’s. Madini perfumes used to and maybe still does make a perfume oil of ambergris. It is very earthy and smoky and strong. I am glad to have learned more about this intriguing substance. Thank you.

    • lucasai says:

      Yes, the ambergris boulder can sometimes be lethat for a whale, when it grows too big and cannot be exudated (it blocks the intestines) and whale can’t go “poo”
      I’ve never smelled pure ambergris oil but I bet it’s very strong and animalic.

  5. hajusuuri says:

    Oh the poor whale. Real ambergis sounds fascinating and disgusting at the same time. Truth be told, if I know that a perfume has the read ambergis, I probably would avoid it. Your post reminds me that aromachemicals can be your friend….of course, as long as the synthetic aspects don’t smell artificial, if you know what I mean.

    This past summer, I went to western Massachusetts for a few days. During that trip, I visited The Clark which had on display John Singer Sargant’s painting Fumée d’Ambre Gris (Smoke of Ambergris). According to the caption of that painting “The painting depicts an exotically dressed woman inhaling the smoke of ambergris — a resinous substance found in tropical seawater. Ambergris was believed to ward off evil spirits and also served as an aphrodisiac.

  6. Undina says:

    I think you did a great job explaining both natural and synthetic ingredients – detailed enough to be informative but not too long to become boring. But I’m not sure I agreewith this part: “… how to introduce a smell of ambergris into perfume without affecting cachalot population.” It’s not ambergris that endangers those whales (since grey ambergris isn’t that valuable) so its use in perfumery shouldn’t have any effect on their population, should it?

    • lucasai says:

      Thank for a compliment that I’ve found a balance between informative and not too boring. As for the part you don’t agree – maybe I misinterpreted this part of the article I based my post on? Grey amber or ambergris is expensive so it seems to me that I understood it right. But I won’t bet on it

      • Undina says:

        I might be wrong as well, so I won’t argue, but from the articles that I’ve read the “fresh” ambergris is the least desirable and whales were hunted for the other products of their bodies. Anyway, it’s good that they are protected and the only product that can be used is the one found the natural way.

  7. Elizabeth Watson says:

    What a fascinating post–thanks for this. I look forward to reading the Floating Gold excerpt during my lunch hour!

  8. me says:

    There is a reference to ambergris in Herman Melville’s novel of 19th century whaling, “Moby Dick”. In addition to being a novel about obsession, good and evil, the novel is also an exhaustive detailing of 19th Century whaling. The narrator, describes how the ship turns itself into a rendering factory after a whale is killed notes that in addition to boiling the fat into sperm oil (the main product and one which allowed ordinary people to have interior lighting at night) the whalers obtained a precious ingredient from the stomach for perfume. The narrator (Call him Ishmael) comments that fine ladies would be shocked to know their sweet perfumes come from the whales stomach. I have always wondered whether the 19th century whaling industry enabled a commercial perfume industry to develop by making this key ingredient available in commercially reliable (although expensive quantities).

    Given what we now know about whales social systems and intelligence, (not to mention sperm whale’s precarious existence), I too would not use a perfume which used actually ambergris, even it was sourced from the rare material washed ashore.

  9. Christopher Kemp says:

    I wrote the book Floating Gold, that you’ve linked to here. Thanks for the link! I’d really welcome the thoughts and comments of any readers who have come across the book.

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