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List of chemical compounds with unusual names

(Redirected from Molecules with silly or unusual names)

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

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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

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Name based on shape

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Barrelene
 
Barrelene
C8H8, the name derives from the resemblance to a barrel.[6]
Basketane
 
Basketane
pentacyclo[4.4.0.02,5.03,8.04,7]decane (C10H12), a polycyclic alkane with a structure similar to a basket.[3]
Bowtiediene
 
Bowtiediene
Spiropentadiene, a polycyclic alkene with a 2D projection similar to a bowtie.[7]
Churchane
 
Churchane
A polycyclic alkane named "churchane" because it looks superficially like a church.
Cubane
 
Cubane
A hydrocarbon whose eight carbon atoms occupy the vertices of a cube.[8]
Dodecahedrane
 
Dodecahedrane
A Platonic hydrocarbon shaped like a dodecahedron.[9]
Fenestrane (Windowpane)
 
Fenestranes
A class of compounds with astructural formula that resembles a "window pane motif" (the name fenestrane derives from the Latin word fenestra, meaning window), comprising four fused 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
 
A polycyclic alkane named "housane" because it looks superficially like a house.[3]
Ladderane
 
Pentacycloanammoxic Acid
An organic molecule that looks like a ladder because it contains two or more fused rings of cyclobutane.
Nanokid
 
Nanokids belongs to a series of NanoPutians, a series of organic molecules whose structural formula resemble human forms. "NanoPutian" is a portmanteau of nano-, a unit prefix meaning one billionth, and 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
 
Olympiadane
A mechanically-interlocked compound based on the topology for the Olympic rings.
Olympicene
 
Olympicene
Refers to the fused 5-benzene rings (C19H12), which is reminiscent of the Olympic Flag.[11]
Paddlanes
 
Paddlane
Paddlanes are bicyclic molecules that resemble the paddles on steamboats.
Pagodane
 
An organic compound which resembles a pagoda.
Penguinone
 
Penguinone
3,4,4,5-tetramethylcyclohexa-2,5-dienone; a two-dimensional representation of its structure resembles a penguin.
Pterodactylane
 
Pterodactylane
[4]-ladderanes with substituents on the central rung. So named for their resemblance to a Pterodactyl.[12]
Prismane
 
Prismane
An isomer of benzene with the carbon atoms arranged in the shape of a triangular prism.
Propellanes
 
[1.1.1]Propellane
Propellanes are bicyclic molecules that resemble propellers.
Quadratic acid
 
Squaric acid
A square-shaped organic compound, also called squaric acid.
Sulflower
 
Sulflower
A stable heterocyclic octacirculene based on thiophene, named as a portmanteau of sulfur and sunflower.
Volleyballene
 
Molecule composed of 60 carbon and 20 scandium atoms, which has an appearance similar to that of a volleyball.

Named after people

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Buckminsterfullerene (Fullerene)
 
Fullerene
Also called the buckyball, this is an allotrope of carbon named after Richard Buckminster Fuller due to its resemblance to Fuller's geodesic domes. The term was coined by Harold Kroto.[13] The alternative name footballene was coined by A.D.J. Haymet[14] because the molecule also resembles a football;[3] the 70-atom version is said to resemble a rugby ball from its own oval shape.
Bullvalene
 
Bullvalene C10H10
(tricyclo[3.3.2.02,8]deca-3,6,9-triene) (C10H10), was named by 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 (Al2Si2O5(OH)4), a clay-like material with a number of manufacturing uses, one of which is as a coating for high-quality bond paper. It is named after its discoverer, 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

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Alcindoromycine An anthracycline antibiotic agent named after the character Alcindoro in La Bohème.[19]
Bohemamine An anti-tumour agent named after the Puccini opera La Bohème.[19]
Collinemycin An anthracycline antibiotic agent named after the character Colline in La Bohème.[19]
Ranasmurfin A blue protein from the foam nests of a tropical frog, named after the Smurfs.
Mimimycin An anthracycline antibiotic agent named after the character Mimì in La Bohème.[19]
Musettamycin An anthracycline antibiotic agent named after the character Musetta in La Bohème.[19]
Marcellomycin An anthracycline antibiotic agent named after the character Marcello in La Bohème.[19]
Pikachurin A retinal protein named after Pokémon character / species Pikachu
Rudolphomycin An anthracycline antibiotic agent named after the character Rodolfo (Rudolph) in La Bohème.[19][20]
Sonic hedgehog A protein named after Sonic the Hedgehog
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Arsole
 
Arsole
(C4H5As), an analogue of pyrrole in which an arsenic atom replaces the nitrogen atom.[21] The aromaticity of arsoles has been debated for many years.[22] The compound in which a 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 lead, copper chromate arsenate hydroxide mineral (Pb2CuCrO4AsO4OH), named after its discoverer, Lucien Lewis Forneau.[3]
Fucitol
 
L-Fucitol
(C6H14O5), an alcohol derived from Fucus vesiculosus, a North Atlantic seaweed. Its optical isomers are also called D-fuc-ol and L-fuc-ol.[3]
FucK The name of the gene that encodes 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
 
Orotic acid
Pyrimidinecarboxylic acid has been referred to as vitamin B13. Often misspelled "erotic acid".[3]
Pizda
 
Pizda
Abbreviated ligand name of a substance 1-(2’’-hydroxyl cyclohexyl)-3-[aminopropyl]-4-[3’-aminopropyl] piperazine, first synthesized by a group of Australian chemists. In Romanian and some Slavic languages, the word pizda is a vulgarism for "vagina" (see Reconstruction:Proto-Slavic/pizda).
Rhamnetin
 
Rhamnetin
A flavonol dye derived from buckthorn (rhamnus).[24]
SEX
 
SEX
An abbreviation of sodium ethyl xanthate,[25] a flotation agent used in the mining industry.
Spermine,
Spermidine
 
Spermine
 
Spermidine
growth factors involved in cellular metabolism.[3]
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BARF
 
BARF
(tetrakis[3,5-bis(trifluoromethyl)phenyl]borate), a fluoroaryl borate B(Ar(CF3)2)4−, used as a non-coordinating anion[26]
catP The name of the enzyme responsible for chloramphenicol resistance in various species of bacteria.
Constipatic acid
 
Constipatic acid
[2-(14-hydroxypentadecyl)-4-methyl-5-oxo-2,5-dihydrofuran-3-carboxylic acid], an aliphatic acid derived from the Australian Xanthoparmelia lichen.[3][27]
Crapinon An anticholinergic drug, one side effect of which is constipation.[3]
Diurea
 
Methylene diurea
Organic compounds containing two urea moieties. Specific examples include methylene diurea and ethylene diurea.
dUMP
 
dUMP
Deoxyuridine monophosphate, an intermediate in nucleotide metabolism
Earthcide,
or Fartox		 Some of the many names for pentachloronitrobenzene, a fungicide.[28]
Nonanal
 
Nonanal
(C9H18O), an aldehyde derived from nonane.[29]
PoO Chemical formula of polonium monoxide.
Uranate The chemical term for an oxyanion of the element uranium.[3]
Vomitoxin
 
Vomitoxin
A mycotoxin occurring in grains.[3]
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Cadaverine
 
Cadaverine
A foul-smelling diamine produced by putrefaction of dead animal tissue.[3][30]
DEAD, DEADCAT
 
DEAD
Diethyl azodicarboxylate: An apt acronym, given that diethyl azodicarboxylate is explosive; shock sensitive; carcinogenic; and an eye, skin, and respiratory irritant.[3]
Earthcide,
or Fartox		 Some of the many names for pentachloronitrobenzene, a fungicide.[31]
Putrescine
 
Putrescine
A foul-smelling diamine produced by the putrefaction of dead animal tissue.[3]
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Angelic acid
 
Angelic acid
An organic acid found in garden angelica (Angelica archangelica), Umbelliferae, and many other plants.
DAMN
 
Diaminomaleonitrile, a cyanocarbon that contains two amine groups and two nitrile groups bound to an ethylene backbone.
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)

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Adamantane
 
Adamantane
(tricyclo[3.3.1.13,7]decane), a crystalline cycloalkane,[36][37] an isomer of twistane. Name resembles that of English pop star Adam Ant.[3]
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

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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
 
Bongkrek acid
Name sounds like a combination of English words related to recreational drugs: bong; crack, a preparation of cocaine; and acid, a street name for 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
 
Hirsutene
[41][42] Is also named after an animal, a goat (Hircus).
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.
 
Melon
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
 
Moronic acid
[3-oxoolean-18-en-28-oic acid], a natural triterpene
Performic acid A strongly oxidizing acid related to formic acid.
Noggin A signalling protein involved in embryonic development.
Nonose A monosaccharide with nine carbons. An example is sialic acid.
Periodic acid
 
Periodic acid
Or per-iodic acid, is pronounced /ˌpɜːraɪˈɒdɪk/ PURR-eye-OD-ik and not */ˌpɪəriˈɒdɪk/ PEER-ee-OD-ik. It refers to one of two interconvertible species: HIO4 (metaperiodic acid), or H5IO6 (orthoperiodic acid – illustrated at right). The per- prefix in the name denotes that iodine is present in its highest possible (+VII) oxidation state.
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
 
Rhamnose
A sugar naturally occurring in 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
 
Traumatic acid
A substance occurring in plants, with a role in healing damaged tissue.

Other

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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
 
Dinocap
(C18H24N2O6), a miticide and contact fungicide used to control powdery mildew in crops.
DuPhos
 
DuPhos
A class of asymmetric ligands for 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
 
Dioxygen difluoride, O2F2, an extremely unstable compound which reacts explosively with most other substances – the nickname "FOOF" is a play on its formula.[47]
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
 
Gossypol
A toxin found in cottonseed used as a male oral contraceptive.[3]
Methionylthreonylthreonylglutaminylarginyl...isoleucine The IUPAC name for Titin. This is the largest known protein and so has the longest chemical name. Written in full, it contains 189,819 letters.[48]
Periplanone B
 
Periplanone B
A pheromone of the female American cockroach.
Thebacon
 
Thebacon
Dihydrocodeinone enol acetate, an opioid analgesic or antitussive. [citation needed]

See also

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References

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  1. ^ Godly, E.W. (1998). Chemical Nomenclature. Kluwer Academic Publishers. p. 20. ISBN 978-0-7514-0475-3.
  2. ^ Thurlow, Kevin (1998). Chemical Nomenclature. Kluwer Academic Publishers. xii. ISBN 978-0-7514-0475-3.
  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.
  4. ^ Ryan, Dennis (1997). "Old MacDonald Named a Compound: Branched Enynenynols" (PDF). Journal of Chemical Education. 74 (7): 782. Bibcode:1997JChEd..74..782R. doi:10.1021/ed074p782. Retrieved 2007-08-16.[permanent dead link‍]
  5. ^ Glenn T. Seaborg, Citizen-Scholar Archived 2020-11-14 at the Wayback Machine, By Peggy House, Reprinted from The Seaborg Center Bulletin, April 1999
  6. ^ Zimmerman, Howard E.; Robert M. Paufler (1960). "Bicyclo [2.2.2]octa-2,5,7-triene (barrelene), a unique cyclic six electron pi system". Journal of the American Chemical Society. 82 (6): 1514–1515. doi:10.1021/ja01491a071.
  7. ^ "Elusive bowtie pinned down - synthesis of spiropentadiene, a carbonaceous compound nicknamed bowtiediene because it is shaped like a bowtie". Science News. July 13, 1991.
  8. ^ 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.
  9. ^ Pubchem. "Dodecahedrane". pubchem.ncbi.nlm.nih.gov. Retrieved 2018-07-28.
  10. ^ "NanoKids - Mission". 2007. Archived from the original on 2016-08-19. Retrieved February 21, 2023.
  11. ^ "'Olympic rings' molecule olympicene in striking image". BBC Online. 27 May 2012. Retrieved 28 May 2012.
  12. ^ Horst, Matías; Meisner, Jan; Yang, Jinghui; Kouznetsova, Tatiana B.; Craig, Stephen L.; Martínez, Todd J.; Xia, Yan (2024-01-10). "Mechanochemistry of Pterodactylane". Journal of the American Chemical Society. 146 (1): 884–891. doi:10.1021/jacs.3c11293. ISSN 0002-7863. PMID 38131266.
  13. ^ Kroto, H.W.; Heath, J.R.; O'Brien, S.C.; Curl, R.F.; Smalley, R.E. (1985). "C60: Buckminsterfullerene". Nature. 318 (6042): 162. Bibcode:1985Natur.318..162K. doi:10.1038/318162a0. S2CID 4314237.
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  16. ^ Ault, Addison (2001). "The Bullvalene Story. The Conception of Bullvalene, a Molecule That Has No Permanent Structure". J. Chem. Educ. 78 (7): 924. Bibcode:2001JChEd..78..924A. doi:10.1021/ed078p924.
  17. ^ Ross, C.; Kerr, P.F. (1931). "Dickite, a Kaolin Mineral" (PDF). American Mineralogist. 15: 34–39.
  18. ^ Blaser, Hans-Ulrich; Brieden, Walter; Pugin, Benoit; Spindler, Felix; Studer, Martin; Togni, Antonio (2002). "Solvias Josiphos ligands: from discovery to technical applications". Topics in Catalysis. 19 (1): 3–16. doi:10.1023/A:1013832630565. S2CID 95738043.
  19. ^ 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
  20. ^ "Canadian Patents Database CA 1110562: Anthracycline antibiotic designated RUDOLPHOMYCIN". Archived from the original on 2007-11-14. Retrieved 2007-08-16.
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  22. ^ Mikael P. Johansson & Jonas Jusélius (2005). "Arsole Aromaticity Revisited". Lett. Org. Chem. (3): 469–474.
  23. ^ Ignat’ev, N.V.; Welz-Biermann, U.; Kucheryna, A.; Bissky, G.; Willner, H. (2005). "New ionic liquids with tris(perfluoroalkyl)trifluorophosphate (FAP) anions". Journal of Fluorine Chemistry. 126 (8): 1150–1159. Bibcode:2005JFluC.126.1150I. doi:10.1016/j.jfluchem.2005.04.017.
  24. ^ Uri J, Csoban G, Viragh E., Acta Physiol Hung. 1951;2(2):223-8.
  25. ^ See, for example, Okibe, N; Johnson, DB (2004). "Toxicity of flotation reagents to moderately thermophilic bioleaching microorganisms". Biotechnology Letters. 24 (23): 2011–2016. doi:10.1023/A:1021118915720. S2CID 23948075.
  26. ^ "BARF". ChemSpider. Royal Society of Chemistry. 2013. Retrieved 4 November 2013.
  27. ^ Chester, DO (1979). "Three New Aliphatic Acids from Lichens of Genus Parmelia (Subgenus Xanthoparmelia )". Australian Journal of Chemistry. 32 (11): 2565. doi:10.1071/CH9792565.
  28. ^ "NIST Standard Reference Database 69, June 2005 Release: NIST Chemistry WebBook – Pentachloronitrobenzene". Retrieved 2007-08-16.
  29. ^ May also be considered to be related to sex.
  30. ^ Nordenström, Björn E. W. (1951). "Effect of cadaverine and lysine on the urinary excretion of piperidine in rabbits". Acta Pharmacologica et Toxicologica. 7 (3): 287–296. doi:10.1111/j.1600-0773.1951.tb02870.x. PMID 14856760.
  31. ^ "NIST Standard Reference Database 69, June 2005 Release: NIST Chemistry WebBook – Pentachloronitrobenzene". Retrieved 2007-08-16.
  32. ^ R A Klein, G P Hazlewood, P Kemp, and R M Dawson, Biochem J. 1979 December 1; 183(3): 691–700.
  33. ^ Apitz-Castro R, Béguin S, Tablante A, Bartoli F, Holt JC, Hemker HC (1995). "Purification and partial characterization of draculin, the anticoagulant factor present in the saliva of vampire bats (Desmodus rotundus)". Thromb. Haemost. 73 (1): 94–100. doi:10.1055/s-0038-1653731. PMID 7740503. S2CID 25989455.
  34. ^ De Tullio, Mario C. (2012). "Beyond the Antioxidant: The Double Life of Vitamin C". Water Soluble Vitamins. Subcellular Biochemistry. Vol. 56. pp. 49–65. doi:10.1007/978-94-007-2199-9_4. ISBN 978-94-007-2198-2. ISSN 0306-0225. PMID 22116694.
  35. ^ Theerasilp S, Kurihara Y (August 1988). "Complete purification and characterization of the taste-modifying protein, miraculin, from miracle fruit". J. Biol. Chem. 263 (23): 11536–11539. doi:10.1016/S0021-9258(18)37991-2. PMID 3403544.
  36. ^ Prelog, V., Seiwerth, R. (1941). "Über eine neue, ergiebigere Darstellung des Adamantans". Berichte. 74 (11): 1769–1772. doi:10.1002/cber.19410741109.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  37. ^ Not to be confused with the fictional material adamantium
  38. ^ Parent Hydride Names and Substantive Nomenclature (PDF). IUPAC. March 2004. p. 16.
  39. ^ Charles O, Coolsaet B (1972). "[Prevention of hemorrhage in prostatic surgery. Apropos of the study of the hemostatic activity in prostatectomy of a new molecule: beta-naphthoquinone monosemicarbazone (Naftazone)]". Annales d'Urologie (in French). 6 (3): 209–212. PMID 4562066.
  40. ^ "PEPPSI Catalysts". Retrieved 2009-04-01.
  41. ^ Curran, Dennis P. (1985). "Tandem radical approach to linear condensed cyclopentanoids. Total synthesis of (.+-.)-hirsutene". Journal of the American Chemical Society. 107 (5): 1448–1449. doi:10.1021/ja00291a077.
  42. ^ Nozoe, Shigeo (1976). "Isolation, structure and synthesis of hirsutene, a precursor hydrocarbon of coriolin biosynthesis". Tetrahedron Letters. 17 (3): 195–198. doi:10.1016/0040-4039(76)80013-5.
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  44. ^ Kouřimský, Jiří (1974). A Colour Guide to Familiar Minerals and Rocks. Translated by Náglová, Zdenka. Octopus Books. p. 94. ISBN 0706404084.
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Bibliography

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