Ambergris substitutes - clarification of terms.

I've written already about natural ambergris (also called Ambra) and mentioned there that most perfumery uses synthetic substitutes.

Here I'm setting out some of those substitutes (mainly synthetic, but including some naturals) and trying to sort out some of the confusion resulting from the fact that there are so many different products with very similar names.


The ambreine produced from labdanum, also sometimes confusingly called Cistus oil, is a steam distilled product from Cistus ladaniferus.  I have been told by a leading producer of both labdanum absolute and cistus essential oil that the difference between the two products is as follows: Cistus oils are produced by steam distillation of the entire top-growth (twigs, leaves, stems and flowers) of the Cistus ladaniferus plant - a cistus absolute is sometimes also produced from the top-growth.  Labdanum products, by contrast,  are produced from a gum-resin found on the roots of the plant, which are first washed and then mechanically agitated to separate the gum from the rest of the roots, an essential oil, absolute and resinoid of labdanum are all produced from this gum-resin.

Ambrarome (from Synarome) and Ambrain (from IFF) are similarly extracted by proprietary processes from the labdanum resin (referred to as gum-labdanum sometimes though I think incorrectly - see details in this post for definitions). These are highly animalic in smell and designed as plant-based alternatives to the traditional animal components of perfumery.

Ambrox is a term usually used to mean Ambrox DL or one of it's synonyms: quite different from the labdanum based materials because it's a brand name for a single synthetic molecule (though a mixture of isomers) which replicates one of the components of natural ambergris.  The term ambrox is sometimes used to mean any of a range of similar products, in particular Ambroxan / Ambrofix / Orcanox that are brand names for chiral isomers [specifically (-)-Ambroxide], which though similar, are not quite the same. In my work I mainly use Ambrofix, which is made by Givaudan from a natural starting material, though I do use some of the others too.

Just to confuse matters further there is also Ambrein which is the waxy substance that is the majority component of natural ambergris, the breakdown products of which give the precious scented molecules of ambroxide and others that have been replicated by the various brand-named products above.  When pure, ambrein is odourless.  Bo Jensen provides a good description of what's going on (scroll down to the text just below the whale pictures).  I also use several of the other substitutes mentioned by Bo Jensen in his article for particular purposes.

Further confusion often arises between Ambergris (Ambra) products and Amber - a term that in perfumery is sometimes used to refer to a product made from the fossil amber by destructive distillation of the waste and low-grade amber left over form the jewellery trade.  This is described by Arctander as having a "smoky, tarlike, resinous" odour "with a distinct resemblance to the smell of tanned leather".  He mentions that there is also a rectified version of this oil, which has been steam distilled as well, but he says that this is "very little used in perfumery".

More often however amber refers to a blend of ingredients intended to give an warm scent reminiscent of both ambergris and the appearance of fossil amber (which in its raw state has virtually no odour).  Such blends normally include labdanum, vanilla, benzoin and other ingredients; are are often used as fixatives.  Some of the products named in the first paragraph fall into this category, but many perfumery houses and others will have their own blend.

Musk

Musk is one of the most common elements in perfumes - some form of musk is included in virtually every fragrance on the market, but which form varies a great deal as there are a great many options.

At one time, musk came almost exclusively from various species of Musk Deer but this has almost entirely disappeared from use for ethical and cost reasons.

Moschus moschiferus - one of the species that were the original source of musk

Most fragrances now use some form of synthetic musk, but there are a few natural sources still sometimes used.  In particular ambrette seed oil (containing the chemical widely used in synthetic form as ambrettolide) and angelica root oil (now known to contain the chemical exaltolide, though this was not recognised until long after exaltolide had been made synthetically).

Some synthetic musks are crystalline solids and as a result are often sold either pre-diluted or ‘mobilised’ in something to make them liquid and easier to handle.

There are a huge number of musks on the market, these are some of those I use particularly like or find useful:


Ambrettolide this synthetic is the same as the musk in Ambrette Seeds - a very good quality diffusive musk, slightly fruity, very smooth and exalting.
Applelide an IFF product, this is relatively short-lived for a musk but has a strong, velvety top-note that give a great deal of richness and has a fruity aspect of apples as well.
Cashmeran also from IFF is interesting - liquid and easy to handle - has a spicy quality. When used successfully it is very warming and velvety.  Not everyone considers this molecule as a musk at all.
Celestolide crystals that are slow to dissolve in ethanol. Adds more brightness than the others, very good diffusion.
Civettone isn't widely used alone or available in small amounts. It is the musk component of natural civet paste and the synthesised version is used as part of civet recreations, arguably the most powerful fixative in perfumery. 
Ethylene brassylate (also called Musk T), widely available, liquid at room temp and cheap, good fixative properties and easy to use macrocyclic musk.
Exaltolide solid at room temp but melts easily, very widely available and used macrocyclic musk with a fairly strong, sweet-musk aroma. Not everyone can smell exaltolide but it's one of the finest musks you can use.
Exaltone is the key molecule in muskrat musk and although it can now be synthesised even the synthetic version is very expensive.  It is however incredibly persistent and, arguably, one of the best fixatives known to perfumery.  More animal smelling than most synthetic musk.
Galaxolide a polycyclic musk, very widely available and used, especially in functional products. Often sold as 50% in DEP or IPM as it’s so thick a liquid as to be virtually solid otherwise. A polycyclic musk which is not biodegradable and very persistent in the environment and people.
Habanolide a macrocyclic musk from Firmenich with a strong odour and slightly waxy and metallic freshness. 
Helvetolide another Firmenich product, this is unusual in having a strong top-note as well as the more usual persistence of musks.  It also has a fruity aspect  of pears.
Muscenone is one of the components of natural deer musk, very good fixative and diffusive qualities and has a stronger musky smell than the better-known muscone:
Muscone this is the main musk that is in musk deer pods but synthesised. Lovely fine musk that has the edge over the others for its erogenic quality l-Muscone is a more expensive and even finer quality - just the L isomer.  Both forms have a nice powdery quality.
Romandolide not so widely available, similar in scent to Galaxolide but alicyclic (or linear) and biodegradable: very useful and I'm in the process of phasing out galaxolide to be replaced by romandolide in all my retail range.
Tonalid polycyclic, crystalline solid again but a bit easier to dissolve than some. Often disparagingly referred to as ‘laundry musk’ it’s nevertheless a good fixative and very widely used.  Cheap enough for functional products and gives a very clean effect.
Velvione another macrocyclic, very fine musk of great diffusion, rather like ambrettolide but less fruity and even softer. A great exalting agent, it has little scent of it's own but has a big effect in a blend and gives a distinct powdery effect.


There are plenty of others. I nearly always use musks in combination rather than using just one in a composition. In particular you can get good effects by using very tiny amounts of ambrettolide or velvione alongside one of the cheaper musks. Both work well with Exaltolide and Romandolide.

Another option is Auratouch from Givaudan - a blend of several of their musk products which I believe also includes a captive.

Synthetic musks have also been the cause of some controversy and a number of them were found to be unstable, carcinogenic or environmentally damaging.

Musk Ambrette is prohibited by IFRA and Musk Ketone is banned in some countries even though it isn't restricted by IFRA.  Musk Xylene is banned throughout the EU and prohibited by IFRA.

Muscone, a macrocyclic musk

If you want to understand the different categories of musk (based on their chemical structure) and something of the history of their production the Wikipedia article on Synthetic Musks makes excellent reading.

Ambergris

Ambergris as a perfume ingredient has a lasting fascination and is widely misunderstood - here I’ve described some of it’s story.


I don’t generally use real animal ingredients in my work - I use synthetic substitutes - however some ingredients have a special magic regardless of whether they can be used, or afforded.

A piece of top-quality ambergris
note the broken surface shows the pale grey interior 

One of the ingredients to attain legendary status is ambergris – not least because it was in use in perfumery for centuries before its origin was known – and it is a strange story. 

Ambergris, for those who don’t already know, is a product of the sperm whale. This naturally leads many people to assume that is was one of the products of the 19th century whaling industry and all the cruelty associated with that, but that would be misleading.

The process isn’t well understood, but we do know that ambergris is produced in the intestine of the whale, probably as a protective mechanism against the cuttlebones that are an inevitable consequence of its main diet, which is cuttlefish. At any rate the whale periodically ejects this stuff out in to the ocean, where its oily nature means that it floats.  There is debate about which end of the animal it comes out . . . I’m afraid the best evidence is it’s usually excreted, which might just put you off using it, even if you could afford it.  It is thought that only about 1% of sperm whales produce ambergris, so you can see why it is rare.

At this stage it isn’t much use to perfumers though – only after it has been floating about on the surface of the ocean and dried out on a beach somewhere for some considerable time does it metamorphose into the substance that, even now, commands enormous prices – it is normally collected from beaches where it washes up only after years of the action of salt, sun and sea have done their work. The hard grey-ish greasy lumps (the name comes from amber and gris: grey amber) still don’t always smell very nice prior to dilution, but then nor do quite a few other perfume ingredients, especially the animal ones.

Now that you know this story you can see that it would be quite pointless to kill sperm whales and attempt to collect the stuff from their remains – quite apart from the international whaling ban – the stuff would be nearly worthless even if you lucked out and killed the 1 in a 100 that had some inside it in the first place.

I therefore see no moral problem at all with using it – I do have an economic one sadly but also a consistency problem: each piece smells different so it’s very hard to achieve a consistent effect using natural ambergris.  Luckily there are some excellent synthetic substitutes, which work well, particularly if used in combination.

Among the synthetic alternatives is ambrofix / ambroxan / ambrox super - chemically identical with the key ingredient in natural ambergris - and that is something I use regularly.

For those with a particular desire for the ‘real thing’ I’m happy to use real natural ambergris in my bespoke work and I can make a special edition of any of my regular fragrances using it.  I get my ambergris from specialist beach collectors, mainly in New Zealand, Scotland and Ireland and make it into a tincture in ethanol myself.

The process of making the tincture is straightforward: it is made by grinding down the ambergris,  carefully weighing the material and mixing with sufficient alcohol to make the desired strength of tincture (1-3% is the usual level).  Then with the aid of an automatic stirrer or shaker it needs agitating constantly for some months so at roughly 20-25 degrees centigrade. I then mature mine at about 28-30 degrees for 6 months or more with daily agitation by hand. The longer you keep it the better it will become: patience is vital with ambergris.

A small amount of ambergris in the latter stages of tincturing

Here you can see a tincture in progress, before use it will be filtered to remove all the sediment and a clear, yellowy liquid will result.  It has a surprisingly mild odour that nevertheless has a remarkable effect on the other ingredients of the fragrance.