List of chemical compounds with unusual names
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Chemical nomenclature, replete as it is with compounds with very complex names, is a repository for some names that may be considered unusual. A browse through the Physical Constants of Organic Compounds in the CRC Handbook of Chemistry and Physics (a fundamental resource) will reveal not just the whimsical work of chemists, but the sometimes peculiar compound names that occur as the consequence of simple juxtaposition
. Some names derive legitimately from their chemical makeup, from the geographic region where they may be found, the plant or animal species from which they are isolated or the name of the discoverer.
Some are given intentionally unusual trivial names based on their structure, a notable property or at the whim of those who first isolate them. However, many trivial names predate formal naming conventions. Trivial names can also be ambiguous or carry different meanings in different industries, geographic regions and languages.
Godly noted that "Trivial names having the status of
INN or ISO are carefully tailor-made for their field of use and are internationally accepted".[1] In his preface to Chemical Nomenclature, Thurlow wrote that "Chemical names do not have to be deadly serious".[2] A website in existence since 1997[3] and maintained at the University of Bristol lists a selection of "molecules with silly or unusual names" strictly for entertainment. These so-called silly or funny trivial names (depending on culture) can also serve an educational purpose. In an article in the Journal of Chemical Education, Dennis Ryan argues that students of organic nomenclature (considered a "dry and boring" subject) may actually take an interest in it when tasked with the job of converting funny-sounding chemical trivial names to their proper systematic names.[4]
The collection listed below presents a sample of trivial names and gives an idea how chemists are inspired when they coin a brand new name for a chemical compound outside of systematic naming. It also includes some examples of systematic names and acronyms that accidentally resemble English words.
Elements
Glenn Seaborg told his students that he proposed the chemical symbol Pu (from P U) instead of the conventional "Pl" for plutonium as a joke, only to find it officially adopted.[5]
Unununium (Uuu) was the former temporary name of the chemical element number 111, a synthetic transuranium element. This element was named roentgenium (Rg) in November 2004.
Compounds
Name based on shape
| Barrelene |  |
| Basketane |  |
Bowtiediene |
 |
| Churchane |  |
| Cubane |  |
| Dodecahedrane |  |
| Fenestrane (Windowpane) | carbocycles centred on a quaternary carbon resulting in a twice-over spiro compound. The illustration at right shows a generic fenestrane as well as the specific example [4,4,4,4]fenestrane. Fenestranes are of considerable interest in theoretical chemistry though comparatively few have actually been synthesised.
|
| Housane |  |
| Ladderane |  |
| Nanokid | lilliputian, a fictional race of humans in the novel Gulliver's Travels by Jonathan Swift .
There are no chemical or practical uses for the NanoKid molecule or any of its known derivatives. However, James Tour has turned the NanoKid into a lifelike character to educate children in the sciences. It was found that 82% of students found that NanoKids made learning science more interesting and led to a 10–59% increase in understanding of the material presented.[10] |
| Olympiadane | Olympic rings .
|
| Olympicene | Olympic Flag.[11]
|
| Paddlanes |  |
| Penguinone |  |
| Pterodactylane | Pterodactyl.[12]
|
| Prismane |  |
| Propellanes | ![[1.1.1]Propellane](/File:1.1.1-propellane.svg) |
Quadratic acid |
 |
| Sulflower | sunflower .
|
| Volleyballene |  |
Named after people
| Buckminsterfullerene (Fullerene) | |
| Bullvalene | organic chemist Maitland Jones Jr. for William "Bull" Doering who predicted its properties in 1963.[15][16] Within a specific temperature range the molecule is subject to rapid degenerate Cope rearrangements with the result that all carbon atoms and hydrogen atoms are equivalent and that none of the carbon–carbon bonds is permanent.
|
| Dickite | ( Allan Brugh Dick.[17]
|
| Josiphos ligands | A well-known catalyst, named after Josi Puleo, the technician who first prepared it.[18] Mandyphos and Taniaphos also exist. |
| Welshite |
A mineral named after the US amateur mineralogist Wilfred R. Welsh. Its formula is Ca2SbMg4FeBe2Si4O20. |
Named after fictional characters
| Alcindoromycine | An La Bohème.[19]
|
Bohemamine |
An anti- La Bohème.[19]
|
Collinemycin |
An La Bohème.[19]
|
| Ranasmurfin | A blue protein from the foam nests of a tropical frog, named after the Smurfs .
|
Mimimycin |
An La Bohème.[19]
|
Musettamycin |
An La Bohème.[19]
|
Marcellomycin |
An La Bohème.[19]
|
| Pikachurin | A retinal protein named after Pokémon character / species Pikachu |
Rudolphomycin |
An |
Sonic hedgehog |
A protein named after Sonic the Hedgehog |
Related to sex
| Arsole | benzene ring is fused to arsole — typically on the carbon atoms 3 and 4 — is known as benzarsole.[3]
|
| Cumene | (C9H12), an aromatic hydrocarbon used in the production of phenol and acetone. |
| Cummingtonite | ((Mg,Fe2+)2(Mg,Fe2+)5Si8O22(OH)2), a magnesium-iron silicate hydroxide, first identified in Cummington, Massachusetts.[3] |
| FAP | Tris(pentafluoroethyl)trifluorophosphate, an anion used in some ionic liquids.[23] |
| Fornacite | A rare |
| Fucitol | optical isomers are also called D-fuc-ol and L-fuc-ol.[3]
|
| FucK | The name of the L-fuculokinase, an enzyme that catalyzes a chemical reaction between L-fuculose, ADP, and L-fuculose-1-phosphate.[3]
|
| Fukalite | (Ca4Si2O6(CO3)(OH, F))2, a rare form of calcium silicocarbonate discovered in the Fuka Mine of Takahashi, Japan.[3] |
| Orotic acid |  |
| Pizda |  |
| Rhamnetin | buckthorn (rhamnus).[24]
|
| SEX |  |
| Spermine, Spermidine |
  |
Related to bodily functions
| BARF |  |
| catP | The name of the enzyme responsible for chloramphenicol resistance in various species of bacteria. |
| Constipatic acid | |
| Crapinon | An |
| Diurea |  |
dUMP |
 |
| Earthcide, or Fartox |
Some of the many names for pentachloronitrobenzene, a fungicide.[28] |
| Nonanal |  |
| PoO | Chemical formula of polonium monoxide. |
| Uranate | The chemical term for an oxyanion of the element uranium.[3] |
| Vomitoxin |  |
Related to death and decay
| Cadaverine |  |
| DEAD, DEADCAT |  |
| Earthcide, or Fartox |
Some of the many names for pentachloronitrobenzene, a fungicide.[31] |
| Putrescine |  |
Related to religion or legend
| Angelic acid |  |
| DAMN |  |
Diabolic acid |
A series of long-chain dicarboxylic acids with chains of different lengths. Named after the Greek word diabollo meaning to mislead.[32] |
| Draculin | An anticoagulant found in the saliva of vampire bats.[33] |
| Vitamin C (Godnose) | Albert Szent-Gyorgyi coined the term "ignose" to describe ascorbic acid, which he isolated and published. When the journal's editor refused to accept ignose as a plausible name, Szent-Gyorgyi suggested 'Godnose' (a joke meaning that only God could know the real identity of the molecule). The editor suggested that the name be changed to something more formal.[34] |
| Luciferase | A generic term for the class of oxidative enzymes that produce bioluminescence. |
| Lucifer yellow | Lucifer Yellow is a food coloring that is commonly found in hot sauces such as salsa pickle. Because it fluoresces under ultraviolet light and stains certain regions between plant cells, it's also used in plant microscopy anatomy studies. |
| Miraculin | A glycoprotein found in miracle fruit that makes sour foods taste sweet after contact with taste buds.[35]
|
Sounds like a name (person, brand or organization)
| Adamantane |  |
| Irene | Hantzsch-Widman nomenclature for a monocyclic, heterocyclic compound with three ring atoms.[38]
|
| Naftazone | (C11H9N3O2), a vasoprotective drug. The NAFTA free-trade zone is the area covered by the North American Free Trade Agreement.[39] |
| PEPPSI | Pyridine-Enhanced Precatalyst Preparation Stabilization and Initiation.[40] |
A part sounds like an English word
| Antipain | Antipain works as a protease inhibitor, preventing proteins from being degraded. It is a highly toxic compound that, ironically, causes severe itching or pain when it comes into contact with the skin. Because it inhibits the action of papain, an enzyme found in papayas, its name is actually an abbreviation of anti-papain. |
| Bongkrek acid | lysergic acid diethylamide .
|
| Constipatic Acid | Some Australian lichens, like Parmelia constipata, have this as a component. Protoconstipatic acid, dehydroconstipatic acid, and methyl constipatate are all constipatic acid derivatives. |
| DiNOsar | Common shortening of di-nitro sarcophagine. Used due to shorter length compared to the IUPAC name of 1,8-dinitro-3,6,10,13,16,19-hexaazabicyclo[6.6.6]icosane. Sounds similar to the word dinosaur |
| Gardenin | Gardenins, which are flavones extracted from the Indian plant Gardenia lucida, come in a variety of forms. |
| Hirsutene |  |
| Magic acid | A superacid consisting of a mixture, most commonly in a 1:1 molar ratio, of fluorosulfuric acid (HSO3F) and antimony pentafluoride (SbF5). |
| Megaphone | A ketone derived from the root of Aniba megaphylla.[43] |
| Melon | A compound consisting mostly of linked heptazine units with an undetermined composition. |
| Mispickel | An older name for the mineral arsenopyrite, an iron arsenic sulfide and major source of the element arsenic, sounds like 'miss pickle'. From German.[44] |
| Moronic acid |  |
| Noggin | A signalling protein involved in embryonic development. |
| Performic acid | A strongly oxidizing acid related to formic acid. |
| Periodic acid |  |
| Picket Fence Porphyrin | (5,10,15,20-tetrakis(alpha,alpha,alpha-2-pivalamidophenyl)porphyrin), used to model heme enzyme active sites. |
| Piranha solution | A strongly oxidizing mixture of hydrogen peroxide and sulfuric acid used to remove organic residues from substrates and glassware. The name refers to the voracious appetite of the Amazonian piranha fish. |
Rednose |
A sugar derived from the degradation of rudolphomycin.[19]
|
| Rhamnose | buckthorn (rhamnus).
|
| Ru(Tris)BiPy-on-a-stick | Shorthand form of (trans-1,4-bis[(4-pyridyl)ethenyl]benzene)(2,2'-bipyridine)ruthenium(II).[45] |
| Traumatic acid |  |
Other
| Bastardane | A close relative to tetramantane (a higher homologue of adamantane), its proper name is nonacyclo[11.7.1.112,18.03,16.04,13.05,10.06,14.07,11.015,20]docosane. Because its unusual ethano-bridge was a deviation from the standard hydrocarbon caged rearrangements, it came to be known as bastardane—the unwanted child.[3][46] |
| Dinocap | miticide and contact fungicide used to control powdery mildew in crops.
|
| DuPhos | asymmetric synthesis. The name DuPhos is derived from the chemical company that developed this type of ligand (DuP, DuPont) and the compound class of phospholanes (Phos) it belongs to.
|
| FOOF |  |
| Furfuryl furfurate | The name of the molecule is difficult to say fast. It has a strong odor and can be used as a polymerization inhibitor in the vapor phase. Its name is derived from the Latin word "furfur," which means "bran" (the source of the compound). Furfural alcohol, a related molecule, is reportedly used in the fabrication of the Reinforced Carbon-Carbon (RCC) sections used in the space shuttle. |
| Gossypol | male oral contraceptive.[3]
|
| Methionylthreonylthreonylglutaminylarginyl...isoleucine | The |
| Periplanone B |  |
Thebacon |
 |
See also
- International Union of Pure and Applied Chemistry
- IUPAC nomenclature
- List of places with unusual names
- List of unusual biological names
- List of places used in the names of chemical elements
References
- ISBN 978-0-7514-0475-3.
- ISBN 978-0-7514-0475-3.
- ^ a b c d e f g h i j k l m n o p q r s t u v May, Paul (28 May 2013). "Molecules with Silly or Unusual Names". Bristol University. Retrieved 1 November 2013.
- ]
- ^ Glenn T. Seaborg, Citizen-Scholar Archived 2020-11-14 at the Wayback Machine, By Peggy House, Reprinted from The Seaborg Center Bulletin, April 1999
- .
- ^ "Elusive bowtie pinned down - synthesis of spiropentadiene, a carbonaceous compound nicknamed bowtiediene because it is shaped like a bowtie". Science News. July 13, 1991.
- ^ Verbrugge, P. A. (1977). "Unusual organic compounds. XXIV. Compounds with the formula (CH)n. (d). Synthesis of cubane, (CH)8; homocubanes". Chemie en Techniek (Amsterdam). 32 (4): 120–123.
- ^ Pubchem. "Dodecahedrane". pubchem.ncbi.nlm.nih.gov. Retrieved 2018-07-28.
- ^ "NanoKids - Mission". 2007. Archived from the original on 2016-08-19. Retrieved February 21, 2023.
- ^ "'Olympic rings' molecule olympicene in striking image". BBC Online. 27 May 2012. Retrieved 28 May 2012.
- ISSN 0002-7863.
- S2CID 4314237.
- .
- ]
- .
- ^ Ross, C.; Kerr, P.F. (1931). "Dickite, a Kaolin Mineral" (PDF). American Mineralogist. 15: 34–39.
- S2CID 95738043.
- ^ a b c d e f g h Nettleton DE Jr, Balitz DM, Doyle TW, Bradner WT, Johnson DL, O'Herron FA, Schreiber RH, Coon AB, Moseley JE, Myllymaki RW, J Nat Prod. 1980 Mar–Apr;43(2):242–258. DOI: 10.1021/np50008a003
- ^ "Canadian Patents Database CA 1110562: Anthracycline antibiotic designated RUDOLPHOMYCIN". Archived from the original on 2007-11-14. Retrieved 2007-08-16.
- .
- ^ Mikael P. Johansson & Jonas Jusélius (2005). "Arsole Aromaticity Revisited". Lett. Org. Chem. (3): 469–474.
- .
- ^ Uri J, Csoban G, Viragh E., Acta Physiol Hung. 1951;2(2):223-8.
- S2CID 23948075.
- ^ "BARF". ChemSpider. Royal Society of Chemistry. 2013. Retrieved 4 November 2013.
- .
- ^ "NIST Standard Reference Database 69, June 2005 Release: NIST Chemistry WebBook – Pentachloronitrobenzene". Retrieved 2007-08-16.
- ^ May also be considered to be related to sex.
- PMID 14856760.
- ^ "NIST Standard Reference Database 69, June 2005 Release: NIST Chemistry WebBook – Pentachloronitrobenzene". Retrieved 2007-08-16.
- ^ R A Klein, G P Hazlewood, P Kemp, and R M Dawson, Biochem J. 1979 December 1; 183(3): 691–700.
- S2CID 25989455.
- PMID 22116694.
- PMID 3403544.
- doi:10.1002/cber.19410741109.)
{{cite journal}}: CS1 maint: multiple names: authors list (link - ^ Not to be confused with the fictional material adamantium
- ^ Parent Hydride Names and Substantive Nomenclature (PDF). IUPAC. March 2004. p. 16.
- PMID 4562066.
- ^ "PEPPSI Catalysts". Retrieved 2009-04-01.
- .
- .
- ^ SM Kupchan, KL Stevens, EA Rohlfing, BR Sickles, AT Sneden, RW Miller, RF Bryan, J. Org. Chem., 43(4) (1978) 586
- ISBN 0706404084.
- PMID 15154817.
- . Retrieved 2007-08-15.
- ^ Derek, Lowe (2010-02-23). "Things I Won't Work With: Dioxygen Difluoride". In the Pipeline. Retrieved 2019-04-02.
- ISBN 9781446437650
Bibliography
- E.C. Alyea, "Metal Complexes of Ditertiary Arsines. Chapter in Transition Metal Complexes of Phosphorus, Arsenic and Antimony Ligands", MacMillan, 1973. Chapter: "Some amusing names of arsine ligands: edas, vdias, dam, ffars etc"
- J. Andraos, "Glossary of Coined Names & Terms Used in Science", York University, 2004.
- Giles, P.M. (1999). "Revised Section F: Natural products and related compounds". Pure Appl. Chem. 71 (4): 587–643. S2CID 94379874. Retrieved 2007-08-16.
- Aronson, Jeff (1999). "That's show business". British Medical Journal. 319 (7215): 972. PMID 10514162.
- Browne, Malcolm W. (April 22, 1986). "Chemists dabble in whimsy". International New York Times. Retrieved 3 October 2013.
- Paul May, "Molecules with Silly or Unusual Names," Imperial College Press, July 2008, ISBN 978-1-84816-207-5.
- Metanomski, W. V. (1987). "Unusual Names Assigned to chemical substances". Chem. Int. 9: 211–215.
- Monk, Felonious (13 April 2006). "Chemical Cock-ups: A Story of How Not to Name a Chemical Compound". h2g2: The guide to life, the universe and everything. Not Panicking Ltd. Retrieved 30 October 2013.
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- Randall, David (February 1, 2004). "Storyville: Molecular scientists have a word for it". The Independent on Sunday. London, England.(subscription required)
- Wallechinsky, David; Wallace, Amy (2005). "24. Molecules and amoebas with funny names". The new book of lists : the original compendium of curious information. New York, N.Y.: Canongate. pp. 203–205. ISBN 9781841957197.