Stars & Garters - Molecules with Silly or Unusual Names

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From Paul May's website at Bristol University
(This was featured in New Scientist magazine, Jan 17th 2000)

Believe it or not, some chemists do have a sense of humour, and this page is a testament to that. Here we'll show you some real molecules that have unusual, ridiculous or downright silly names. If you know of any other potential candidates for this page, please let me know.

Arsole
Yes, believe it or not, there is actually a molecule called Arsole... and it's a ring! It is the arsenic equivalent of pyrrole, and although it is rarely found in its pure form, it is occasionally seen as a sidegroup in the form of organic arsolyls. For more information, see the paper with probably the best title of any scientific paper I've ever come across: "Studies on the Chemistry of the Arsoles", G. Markl and H. Hauptmann, J.Organomet.Chem., 248 (1983) 269. Contrary to popular belief, however, the arsoles are not aromatic...

Adamantane
This molecule always brings a smile to the lips of undergrads when they first hear its name, especially in the UK. For those not in the know, Adam Ant was an English pop star in the early 1980's famous for silly songs and strange make-up.

Bastardane
This is actually a close relative of adamantane, and its proper name is ethano-bridged noradamantane. However because it had the unusual ethano bridge, and was therefore a variation from the standard types of structure found in the field of hydrocarbon cage rearrangements, it came to be known as bastardane - the "unwanted child".
[A. Nickon and E.F. Silversmith, 'Organic Chemistry: The Name Game', Pergamon, 1987].

Buckminster Fullerene
This is the famous soccerball-shaped molecule that won its discoverers the Nobel prize for Chemistry in 1996. It is named after the architect Buckminster Fuller who designed the geodesic dome exhibited at Expo '67 in Montreal, from which Sir Harry Kroto got the idea how 60 Carbon atoms could be arranged in a perfectly symmetrical fashion. Because the name of the molecule is a bit of a mouthful, it is often referred to just as a Bucky Ball.

Megaphone
Despite having a ridiculous name, the molecule is quite ordinary. It gets its name from being both a constituent of Aniba Megaphylla roots and a ketone.
[S.M. Kupchan et al, 'J.Org.Chem.', 43 (1987) 586].

Munchnones
No, these aren't the favourite compound of the Munchkins from The Wizard of Oz, but are in fact a type of mesoionic compound. These are ring structures in which the positive and negative charge are delocalised, and which cannot be represented satisfactorily by any one polar structure. They got their name when Huisgen called them after the city Munich (Munchen), after similar compounds were called sydnones after Sydney.
Huisgen et al. Chem. Ber. 1970, 103, 2611. Thanks to Matthew J. Dowd, Virginia Commonwealth University, Richmond, VA, for supplying this one.

Unununium
I know this is technically an element, not a molecule, but it's got such a ridiculous name I thought I'd include it. This is actually element number 111, and is so new it doesn't have a proper name yet. So until it's named after a dead chemist (or physicist) it rejoices in the IUPAC temporary systematic name of unununium. Let's just hope this element doesn't form ring or cage structures, otherwise we might end up with unununium onions...
[See Pure and Appl. Chem. 51 (1979) 381 for the naming scheme].

Cummingtonite
This mineral must have the silliest name of them all. Its official name is magnesium iron silicate hydroxide, and it has the formula (Mg,Fe)7Si18O22(OH)2. It got its name from the locality where it was first found, Cummington, Massachusetts, USA.

Putrescine and Cadaverine
Putrescine originates in putrefying and rotting flesh, and is quite literally, the smell of death. It contains two amine groups, one at either end of the molecule, and is one of the breakdown products of some of the amino-acids found in animals, including humans. Although the molecule is a poisonous solid, as flesh decays the vapour pressure of the putrescine it contains becomes sufficiently large to allow its disgusting odour to be detected. It is usuallyaccompanied by cadaverine (named after the cadavers that give rise to it), a poisonous syrupy liquid with an equally disgusting smell. Putrescine and cadaverine also contribute towards the smells of some living processes. Since they are both poisonous, the body normally excretes them in whatever way is quickest and most convenient. For example, the smell of semen and urine are 'enriched' by the presence of these molecules, as is the odour of bad breath.

Dickite
Dickite, Al2Si2O5(OH)4, is a (kaolin) clay-like mineral which exhibits mica-like layers with silicate sheets of 6-membered rings bonded to aluminium oxide/hydroxide layers. Dickite is used in ceramics, as paint filler, rubber, plastics and glossy paper. It got its name from the geologist that discovered it around the 1890s, Dr. W. Thomas Dick, of Lanarkshire, Scotland.

Moronic Acid
This is a triterpenoid organic acid that is found in Pistacia resin, and is therefore of interest to people studying archaelogical relics, shipwrecks and the contents of ancient Egyptian jars. But why it's called moronic acid is still unknown... Derivatives of this are called moronates.
Ref: P.L. Majumdar, R.N. Maity, S.K. Panda, D. Mal, M.S. Raju and E. Wenkert, J.Org.Chem. (1979) 44, 2811.
Thanks to Dr Ben Stern of Bradford University for supplying this one.

Curious Chloride and Titanic Chloride
The trivial name for some curium compounds is 'curious', so curium trichloride becomes curious chloride. However the only curious property it has is that it's sufficiently radioactive that a solution, if concentrated enough, will boil spontaneously after a while. In a similar way, titanium compounds can be 'titanic', so we get the wonderfully named titanic chloride, TiCl4. It's also interesting to know that in the titanium industry, TiCl4 is known as 'tickle'.
Thanks to Beveridge and Dr Justin E. Rigden for supplying these two.

Traumatic Acid
This is an organic acid with two carboxylic acid groups, one at each end. I don't know where the name came from, or much about it...anyone know?
Thanks to Dr Neil Edwards of Sussex University for supplying this one.

Arabitol
No, this has nothing to do with rabbits - it's an organic alcohol that's one constituent of wine. It's also known as pentahydric alcohol.
Thanks to David Brady for supplying this one.

Fucitol
Although this sounds like what an undergraduate chemist might exclaim when their synthesis goes wrong, it's actually an alcohol, whose other names are L-fuc-ol or 1-deoxy-D-galactitol. It gets its wonderful trivial name from the fact that it is derived from the sugar fucose, which comes from a seaweed found in the North Atlantic called Bladderwrack whose latin name is Fucus vesiculosis.
Thanks to David Brady for supplying this one.

Erotic Acid
No, this isn't the world's best aphrodisiac. Its correct name is orotic acid, but it has been misspelt so often in the chemical literature that it is also known as erotic acid! Another name for it is vitamin B13. Apparently, if you add another carbon to it, it becomes homo-erotic acid...
Thanks to Gerard J. Kleywegt of Uppsala University for info on this molecule.

There are some molecules that I've heard of but don't have information about or I don't know the structure. I'm not even sure if they are genuine molecules. If you can help with any of these, please let me know. They are: Penguinone, Windowpane, Homo-Erotic acid (is the above info about this molecule true?)...