Floating Gold

by Christopher Kemp

  In fact, Sillage de la Reine contains all natural ingredients: a spectrum of floral notes — of rose, iris, jasmine, orange blossom, and tuberose oils — tethered to the base notes provided by Tonkin musk and ambergris, in proportions that de Feydeau refuses to share.

  “I thought, ‘Well, we can play music from the eighteenth century, why not recreate the perfume from the eighteenth century?’” explains de Feydeau when I speak with her. “I had the book of perfumery of Jean-Louis Fargeon, the perfumer of Marie Antoinette, and by the other hand, I had the orders of the queen, conserved in the National Archives. I knew the tastes of the queen on matters of perfumery. There was a recipe called les mille fleurs, the thousand flowers. When you read the recipe, you have aromatic notes; you have, of course, flowery notes; and, to give this trail, to give to the perfume a trail and to give the power, you have animalic notes: the ambergris and musk.”

  Back in Grasse, another huge grey lump of ambergris has arrived from the other side of the world. After Perrin wraps it carefully in cotton, he will lovingly stow it away in his storeroom with the others. They wait in the darkness, like broken statuary. Another piece has been sold to a wealthy buyer. It is removed from storage and prepared for the final leg of its journey. It might travel to the Middle East, where it is still used as an aphrodisiac and a tonic.

  In The Iron Wall: Israel and the Arab World (2001), author Avi Shlaim recounted a moment during the strenuous September 1978 Camp David peace talks between President Carter, Egyptian President Anwar al-Sadat, and Israeli Prime Minister Menachem Begin when Sadat’s astrologer, a religious mystic called Hassan Tuhami, distributed pieces of ambergris to the Egyptian delegates, “telling them to dissolve it in their tea, for it would give them the stamina to confront the Israelis.”

  Reportedly, although several delegates followed Tuhami’s advice, “Boutros Boutros-Ghali declined the offer.”

  If not somewhere in the Middle East, Perrin’s ambergris might end up in Asia. “Sometimes Singapore,” he says, “but I don’t know the market.” Alternatively, and most often, a typical piece of ambergris will travel just a few kilometres away, destined for one of the numerous world-renowned perfumeries clustered around Grasse, on the lower slopes of the French Alps, overlooking the Mediterranean ocean.

  “It is mainly used by well-known brands like Chanel, Guerlain,” says Perrin, “but they will never buy from a finder. They will buy from a specialist.”

  For more than two hundred years, Grasse has been considered the perfume capital of the world: Galimard, established 1747; Guerlain, 1828; Molinard, 1849; Fragonard, 1926. A small city approximately 30 kilometres from the coast, with a population of around 50,000 residents, Grasse is surrounded by rose, lavender and jasmine fields. Each year in July and August, their petals are still harvested, collected like delicate fruit, and transported in sacks to nearby perfume houses like Chanel for processing. Other lesser-known companies in Grasse specialize in producing the fragrant materials for perfume manufacture. “Oh, you have Mane,” says Perrin, “you have Robertet, you have Charabot, you have many, many companies.”

  Respectively: Mane, established 1871; Robertet, 1850; Charabot, 1799.

  For most of that time, while tonnes of lavender, jasmine, and rose petals were being harvested from the surrounding fields, pieces of ambergris were arriving on the Côte d’Azur too, from across the world. There, the ambergris was made into a tincture. “It’s very complicated to actually make it into the infusion, as they call it, and then the infusion is used with the alcohol before you put the perfume essence in,” master perfumer Tony Morris told me from his home in Geneva.

  I ask Perrin if he has ever sold ambergris to established perfumeries like Chanel (est. 1909).

  “Indirectly, yes,” he says, “indirectly. These people, they have their own in-between men. It’s a bit complicated, but we have sold; in France we are selling through an agent. You know, to sell to Chanel, Guerlain, you need a special contact. So we have to sell to special perfumers who are in contact with Chanel. They will buy ten, or twenty kilos at a time, but they are very selective. They will buy top quality, and they will choose from the stock you have. So, they will buy maybe fifty kilos, plus. Regarding the prices, yes, they will buy, it depends, between ten and fourteen thousand euros a kilo. Only top quality. Top quality. They don’t buy only from myself. They buy from other companies. This is a delicate subject because you’re asking me my turnover. I can’t give you information about the price because some people, I know that you have contacted Adrienne from New Zealand, she will sell per gram, she will sell $20 per gram, but she’s a small business. One gram by one gram. We sell by the kilo.”

  It was a revelation to hear Perrin nonchalantly explain in his thick French accent how he obtains gigantic boulders of ambergris from around the world, and then sells them to some of the most established and successful perfume houses in history.

  Ambergris is valued for two unrelated properties, both of which explain its widespread use by perfumers. First, it is a powerful fixative, stabilizing fragrances so that they last much longer on the skin. Elizabeth I perfumed her gloves with ambergris not so much because she enjoyed its fragrance but because it lasted for years, surviving wash after wash. A piece of ambergris will retain its odour for three hundred years. This particular property was a source of curiosity for centuries.

  “Mr. Boyle had a Pair of Gloves in which the Smell of the Ambergrease continued for above twenty Years, and yet smelt very strong whenever he opened them,” the Dutch physician Herman Boerhaave told University of Leydig students in a 1745 lecture.

  I formed a Pastil of Musk, Ambergrease and Civet mixed in a certain Proportion, and placing it in a wooden Chest not accurately closed, it has continued there for above thirty Years, still retaining its Fragrancy in a great measure: yet it does not smell at all times equally strong; for when the Air is moist or suddenly changed, it smells more intensely, whereas at other times it is very weak. The whole Affair seems to follow from the Minuteness of the odoriferous Particles, which no One could ever discover even by the Microscope, either in the Flower itself, or flying off from it in the Air; no one could ever perceive them either by the Taste or Touch: but at the same time in these wonderful minute Particles, there is Force enough to briskly affect the Nose.

  The second, and equally important, property of ambergris is its indefinable odour, which people have always struggled to describe in a meaningful way.

  Despite failing the basic challenge of description, perfumers use a specific adjective to describe the nonspecific odour profile of ambergris: animalic — referring to the coarser and less refined notes of a fragrance that seem to lurk darkly beneath the lighter and more appealing floral tones. Since Pelletier and Caventou first isolated ambrein in 1820, chemists have deconstructed it even further, dismantling it atom by atom to find the source of its complex odour. Ironically, ambrein is odourless. But it holds within its structure all the necessary building blocks to make other aromatic compounds, each with unique and individual odour profiles.

  “The ambergris molecule,” says Dr Charles Sell, “it’s a terpenoid.”

  It is midmorning in Kent, 100 kilometres to the southeast of London, and Sell is in his office at one of the United Kingdom locations of Givaudan, one of the world’s largest fragrance and flavour manufacturers. “The terpenoid chain is cyclized at both ends,” explains Sell, the author of a book titled A Fragrant Introduction to Terpenoid Chemistry (2003). “You’ve got a decalin-type ring at one end and you’ve got a cyclohexane ring at the other end, and the chemistry that goes on breaks the chain that links the two. So, you break it down into the two smaller fragments, which are then volatile enough to reach the nose and smell. But there are lots of different molecules that are present in the brew that you get.”

  For instance, take ambrein — the odourless active compound in ambergris, isolated by Pelletier and Caventou in 1820— and trim it a little, reducing the long tricyclic chain of carbon atoms to a
lmost half its size, and the result is a different compound altogether. It is now gamma-dihydroionone, a shortened monocyclic compound. It still closely resembles one-half of ambrein. But it is no longer odourless. Instead, this abbreviated portion of ambrein smells strongly of tobacco. If a methylene group — one carbon and two hydrogen atoms — are added to ambrein, occupying the position next to the single oxygen atom that dangles at the end of the carbon chain, the result is yet another compound: 2-methylene-4-(2,2-dimethyl-6-methylenecyclohexyl) butanal.

  And this molecule — altered, but almost imperceptibly — smells like seawater. From no odour at all, to tobacco, and then to seawater: a transformation. A few subtle changes have altered the shape of the molecule completely. Its three-dimensional structure is different now. It folds over on itself in new ways. It occupies a different shape in space. When gamma-dihydroionone binds to olfactory receptors in the nose, it sets off a relay of nerve impulses in the brain, which then registers the smell of tobacco. Add a carbon and an oxygen atom to it, and it binds differently to those receptors. Suddenly, it is seawater instead. If gamma-dihydroionone now undergoes a process called cyclization, adding a second carbon ring where before there was only one, the result is another new molecule: alpha-ambrinol. Shortened and more compact than its predecessor, it has its own unique odour profile, which is described as mouldy, animal, and faecal.

  Finally, we return to the remnant of the original ambrein molecule, the portion that was trimmed away and gave rise to the gamma-dihydroionone molecule, and the succession of other degradation products that came after it. The addition of a third carbon ring to this shortened chain, a pentagonal ring to join the two hexagonal rings already present, produces a tricyclic compound called 3a,6,6,9a-tetramethyldo-decahydronaphtho[2,1-b]furan, or more simply, naphthofuran. And this molecule, which looks in so many ways like the ones that preceded it, smells like ambergris.

  Naphthofuran — also known as ambergris oxide. This nondescript molecule is the final outcome of a decade or more spent at sea. As ambergris slowly transforms from a viscous and unpleasant-smelling waste product to a pungent and resinous light grey boulder, ambrein has degraded to become ambergris oxide and a rich fragrant mixture of other organic molecules. This is steady entropy and inevitable breakdown: after years of oxidation by equatorial sunlight, almost completely submerged in seawater, the atoms are stripped away, added at one location, and then removed from another. Double bonds become single bonds; chains become rings, structures change, the shapes of molecules are altered, and new compounds emerge.

  “The compound that’s the most distinctive one for ambergris, and probably the one that has the most important role in it, is the naphthofuran,” says Sell.

  It’s got lots and lots of trade names. The Givaudan trade name for it is Ambrofix. The Firmenich trade name is Ambrox. Henkel calls it Ambroxan, and there are lots of other trade names, but that molecule is the one that, if you smell the individual pure molecules, this is the one that is most characteristic of ambergris and the one that’s impossible, or nearly impossible, to mimic from outside that odour area. There’s nothing else. We’ve got synthetic molecules now that mimic it, but in terms of the odour character, that’s the unique bit of ambergris. If you look at the descriptions that people give, one of the breakdown products is described as briny ozone, another one will be described as tobacco-like, but the naphthofuran, the only label we can put on it is ambergris, because there’s nothing else quite like it.

  If chemists try to build something like ambergris oxide in the laboratory, they fail on a fundamental level. Sell explained later via email:

  Another fascinating aspect of this is the stereochemistry, that is the arrangement of atoms in space. If you were to just clip the five-membered ring onto ambrinol (how often I have wished I could do things like that to molecules) the oxygen atom would be on the wrong side of the two six-membered rings. That is, in the way we normally draw the naphthofuran, the oxygen would be above the plane of the paper instead of below it. This molecule is known and is very much weaker than the natural version with the oxygen down.

  People have struggled for centuries to describe the odour of ambergris. Their failure to do so, says Sell, has a chemical explanation:

  Practically everything that you smell in nature is a complex chemical mixture. Ambergris doesn’t have any more components than jasmine oil or rose oil. They’re all in the hundreds of components. I think the reason why people will have difficulty describing the smell of ambergris is that there are no reference points for smell. For colour we have red, orange, yellow, green, blue, indigo, violet — the colours of the rainbow — and they’re all associated with specific wavelengths of light. So you’ve got a simple primary colour reference when you’re trying to describe a colour. With smells, every smell is different, and every smell — whether it’s a single molecule or a mixture of a thousand different molecules — it will create a pattern on the olfactory bulb in the brain. Smell is then recognition and interpretation of that pattern on the olfactory bulb.

  In other words, people struggle to describe the smell of ambergris because there is simply nothing else that smells quite like it. Only ambergris smells like ambergris. It is singular. To complicate things further, the ambergris smell is complemented, modulated, and adulterated by the presence of the other breakdown products: gamma-dihydroionone (tobacco), 2-methylene-4-(2,2-dimethyl-6-methylenecyclohexyl) butanal (seawater), and alpha-ambrinol (mould, animals, and faeces). But the naphthofuran is a hurdle that even the most imaginative of us cannot leap. There are no reference points. It is like a single remote point on a map with no landmarks anywhere by which to find it. Describing its odour to someone who has never smelled it is like trying to describe a rainbow to a blind person. Words are inadequate, but they are all we have.

  Chemists have gone to great lengths to try to produce something in the laboratory that smells like ambergris. Despite the constraints of stereochemistry, they have succeeded to some extent. The results — patented molecules with trade names like Ambermore, Cetalox, and Synambrane — are used by perfumers to provide the animalic tones of ambergris.

  “In my drawer here, I’ve got a couple of dozen molecules that are all in that odour area,” says Charles Sell. “There’s quite a range of different compounds. They’re mostly fairly big compounds. Obviously, to get the same odour, you have to act on the same receptors, and so the naphthofuran is largish; and in terms of fragrance molecules, it’s one of the bigger ones, so the other things that smell like it tend to be the bigger molecules and mostly are ethers or alcohols, very often cyclic ethers.”

  The process is simple enough: the vital starting material is clary sage, a common herb with long stems and flowers that grow in thick brush-like sprays. It was a technique first developed by the Swiss chemist Max Stoll. In 1953 Stoll traveled from the Firmenich headquarters, in Geneva, to Los Angeles, to accept the prestigious Fritzsche Award from the American Chemical Society. He had earned the award for replicating the structure of ambergris in the Firmenich laboratories four years earlier. The compound had since been patented and christened Ambrox. It revolutionized the perfume industry. And it is still used frequently in perfumery today.

  Stoll’s achievement was so notable that he spent the two weeks before he accepted the award crossing the United States, visiting universities and chemical research centres as he went.

  “To learn its chemical constituents,” reported the Washington Post in March 1953, “Dr. Stoll started with a block of natural ambergris. He conducted a long series of chemical processes in an attempt to duplicate its chemical parts and structures to produce man-made ambergris.”

  Months later Stoll and his coworkers had created a compound that was identical, they thought, to the chemical structure of natural ambergris. When they subjected it to a battery of tests, it passed all of them but one: the all-important smell test. “Neither he nor his associates could detect the odor of their product,” reported the Post. “It was put on a she
lf and further efforts were made to reconstitute ambergris.”

  In fact, their noses had failed them. Sitting on the shelf in the laboratory was a vial of what was later named Ambrox — pure, synthetic naphthofuran. It had evaded chemists for decades, and Stoll had succeeded. But no one had noticed. For six months, it waited on the shelf above him, as he sat at his workstation below, correcting his formulations, and checking and rechecking his impenetrable calculations.

  “One day the firm’s technical director, Dr. Roger Firmenich, came into the laboratory,” the Post article continued. “‘You’ve got it!’ he exclaimed. ‘The whole room smells amber.’ Dr. Stoll and his associates just stared. They hadn’t realized till then, he said, that their noses were ‘intoxicated’ by the odor they had been seeking.”

  In the past few decades, perfume houses have lowered and then lowered again the formulation costs for their fragrances, and they do this by using more and more synthetic compounds. Only a handful of houses remain that are willing to pay for the most difficult to obtain raw materials, like ambergris. Most other houses prefer to use synthetic ambergris compounds like Ambrox, which, as Luca Turin wrote in his comprehensive book with coauthor Tania Sanchez, Perfumes: The Guide (2008), “smell nothing like the natural material.”

  In fact, synthetic compounds only simulate ambergris, sometimes successfully and sometimes much less so. Ambermore is not ambergris; neither are Ambrox nor Synambrane. They impersonate certain olfactory and fixative aspects of ambergris. But they do not replicate it. Comparing genuine ambergris with a synthetic version of it is like comparing an original painting by Van Gogh with an inexpensive print of the same canvas.

  In a 2005 article for the New Yorker magazine, perfume critic Chandler Burr profiled a French perfumer whose nose was so sensitive that he could smell a vial of jasmine essence and identify not only the country in which the flowers were grown but whether the machines they were processed in were made of aluminium or stainless steel. The 2009 Forbes Magazine article that named Francis Kurkdjian one of the world’s top custom fragrance designers recounted his response to a client who requested a perfume that smelled of vetiver grass: did the client want the fragrance to smell of Haitian, Chinese, or Javanese vetiver?