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When reviewing the citric acid cycle, I find names like glutarate and succinate to be helpful in thinking about the structure of the molecules because I was taught about the sequential dicarboxylic acid naming scheme: oxalic (2 carbon), malonic (3C), succinic (4C), glutaric (5C) etc.

But I often struggle with fumarate and malate because I have not learned the numbering or nomenclature system that these names are derived from. Can someone point me in the right direction so that I can learn the background behind these names?

Knowing that will be helpful to my recall of the molecular structure. Then I can stop memorizing and start understanding.

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  • $\begingroup$ As per the OED, the etymology of maleic is related to that of malate. Loss of water from the latter gives the cis-form of the former. $\endgroup$
    – user55119
    Nov 8 '20 at 19:49
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    $\begingroup$ malic, maleic, and malonic acids have all the same origin : malus = apple in latin $\endgroup$
    – Maurice
    Nov 8 '20 at 20:23
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Unfortunately, you will have to memorize the structures and the names because there is no chemical structure hidden in those names.

From Elsevier's Dictionary of Chemoetymology

fumaric acid $\ce{C4H4O4}$, derived from the genus name Fumaria (fumitory), from fumus (Latin: smoke)

Fumaria plant enter image description here

malic acid $\ce{C4H6O5}$, derived from malum (Latin: apple)

The same goes for all other common names like oxalic acid, acetic acid etc.

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  • $\begingroup$ "Dictionary of Chemoetymology" Price is a bit steep, but would you otherwise recommend it? $\endgroup$
    – Karl
    Nov 8 '20 at 19:52
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    $\begingroup$ My favorite source of historical word origins is the unabridged version of the Oxford English Dictionary. It is also subscription based. OED will most likely have 99% of the words contained in Chemoetymology. $\endgroup$
    – M. Farooq
    Nov 8 '20 at 19:56
  • $\begingroup$ How is Chemoetymology stuctured? Just A-Z? $\endgroup$
    – Karl
    Nov 8 '20 at 19:59
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    $\begingroup$ Yes, A-Z just like a dictionary. If you want more "stories" and the names which are not present in OED is Alex Nikon's "Organic Chemistry- The Name Game" is worth it. $\endgroup$
    – M. Farooq
    Nov 8 '20 at 20:02
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    $\begingroup$ Yea, I'd want a good enlightening read, not a dictionary. Unfortunately, that one is also from Elsevier and therefore equally overpriced, for a Christmas or graduation present. ;-) $\endgroup$
    – Karl
    Nov 8 '20 at 20:32

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