Trivial names of fatty acids-Part 2

Introduction

In 1930, Steger and Van Loon, encountered an unknown, heavily unsaturated fatty acid in the seeds of Couepia grandiflora and not surprisingly, they called it “Couepinezuur”, which can be translated into English as ‘couepinic acid’ (Rev. Trav. Chim., 50, 936 (1931) and 51, 345 (1932)). A few years later Brown and Farmer (Biochem. J., 29, 631 (1935)) isolated a fatty acid from oiticica oil (Licania rigida) and called it ‘α-Licanic acid’ (9Z,11E,13E)-4-Oxooctadeca-9,11,13-trienoic acid). Then they discovered that it was the same acid as described by Steger and Van Loon. In the list, both names are mentioned whereby the ‘couepinic acid’ refers to the ‘α-Licanic acid’.

This example, given by Boekenoogen (De Scheikunde der Oliën en Vetten, N.V. A. Oosthoek’s Uitgevers Mij, Utrecht, The Netherlands, 1948) clearly illustrates that the allocation of trivial names to fatty acid can be rather chaotic. Fatty acids may have a trivial name in one language and a quite different trivial name in another and in addition, things change. Boekenoogen (loc. cit.) advocates to scrap the name ‘carnaubic acid’ when this ‘acid’ turned out to be an impure sample of lignoceric acid. Accordingly, the entry ‘carnaubic acid’ refers to ‘lignoceric acid’. Fatty acids may have a trivial name in one language but not, or not yet in others since the need to use a trivial name in those other languages had not yet arisen. However, when an occasion to use such a trivial names arises, this can be met in three different ways. It can be ignored by using the systematic name. A new, local trivial name can be coined or the existing, foreign language (i.e. English) trivial name can be transcribed.

But take ‘fumaric acid’, ‘stearic’, and ‘margaric acid’. All three of them end on “…aric”, but their German translations are ‘Fumarsäure’, Stearinsäure and ‘Margarinsäure’. What is the rule and what is the exception? Should the rule be that ‘..aric acid’ becomes ‘..arsäure’ as in Fumarsäure or becomes ‘…arinsäure’ as in Stearinsäure and Margarinsäure? Well, it so happens that Stearinsäure and Margarinsäure are the only acids listed in Table 1 (Part 1) that have the ‘…arinsäure’ translation, so these acids become the exception and the translation to ‘…arsäure’ is the rule. In fact, the exceptions are not that exceptional since a general rule will be given that ‘…ic acid’ is transcribes as ‘…insäure”

After the description of the transcription rules, a table (Table 3) is given that has the same list of fatty acids as Table 1 (Part 1). This table lists the Russian and Japanese names and for ease of reference, I have also included the exceptions. So this table has four columns:

1. The trivial English name. Accordingly, this column is identical to the column of Table 1.
2. The exceptions and illustrations. For some fatty acids, this columns lists per language (DE, German; ES, Spanish; FR, French. IT, Italian; NL, Dutch; PT, Portuguese) the non-English trivial names that are exceptions to the transcription rules. For instance: According to the transcription rules from English to German, ‘butyric acid’ should be ‘Butyrinsäure’. Instead it is ‘Buttersäure’ so the latter is mentioned in this column. According to the transcription rules English to French, the same acid should be ‘acide butyrique’ in French; this is the correct translation so no mention is made in the exception column.
3. The Katakana transcription into Japanese, which column also contains some Japanese trivial names.
4. The Russian trivial names that have been retrieved from Russian literature. Consequently, this column has a fair number of blank cells. No attempt has been made so far to arrive at transcription rules from English to Russian that would allow to fill these blank cells

Transcription from English into French

The trivial names I managed to find in French can all be arrived at by changing the final ‘c’ in the English name by ‘que’. Accordingly, “lauric acid” is translated into “acide laurique”. The spelling of what comes before that final ‘c’ remains unchanged but may need one or more accents. In French, the ‘ai’ indicating a single trans bond like in elaidic acid, changes to ‘aï’, with a diaeresis mark on the ‘i’ to indicate that it is sounded separately as in ‘naïve’, acide élaïdique. In addition, the letter ‘e’ is given an acute accent because it occurs at the end of a syllable that is followed by one or more syllables. So the ‘e’ in ‘acide’ does not get an acute but in “acide cétoléique” both ‘e’s get an acute. Because the ‘e’ before the ‘i’ in ‘cétoléique’ has this acute accent that indicates that it is the end of a syllable, there is no need to put a diaeresis mark in the ‘i’.

There are several trivial names for fatty acids that refer to a person, for instance “Mead’s acid”. In French, this becomes “acide de Mead” (about 19,000 hits in Google). In fact, I made extensive use of Google to arrive at this and similar findings. I therefore advise readers to verify names in French and other languages by searching for them in Google. This also told me that the translation of ‘farnesenic acid’ into French is ‘acide farnesénique’ and not ‘acide farnésénique’ (with two acutes).

The French systematic names of fatty acids can also be easily be formed from the English names by changing the ending ‘oic’ to ‘oïque’, where the diaeresis mark indicates that the ‘o’ is the end of a syllable. Acute accents occur on the e’s in numeral parts like ‘tétra’ and déca’, and when unsaturation is indicated by an ‘e’ as in oleic acid: “acide octadécénoïque”. How to indicate the position of the double bond is as confusing in France as elsewhere. I have come across: “acide cis-9-octadécénoïque”, “acide cis-octadéc-9-énoïque” and “acide cis octadécène-9-oïque”, where the last version also shows a grave accent on the ‘e’.

Transcription from English into Spanish and Portuguese

Since I know neither Spanish nor Portuguese, I had to call on the local fatty acid experts mentioned in Part 1. I am most grateful to them both. It soon became clear to me that the transcription rules to Spanish and Portuguese would be far more complicated than those into French but that they would have a lot in common so I tried to combine these two sets of rules. For instance, in both languages the word for acid (ácido) is written in front of the name like in French and Italian, rather than behind like in English, German, etc. Both languages also indicate which syllable in a word has to be stressed if this is not the one but last.

1. As a rule, the English name can be translated into Spanish or Portuguese by adding the letter “o” to the name: “linoleic acid” → “ácido linoleico”.
2. In this example, the word ‘linoleico’ has no stress accent, which implies that the stress falls on the one but last (penultimate) syllable, which in this case is the ‘ei’. The vowels a, e, and o are strong in Spanish. They always form their own syllable wherever they appear. The vowels u and i are weak, and when a weak vowel is next to a strong vowel or another weak vowel, they AUTOMATICALLY form a diphthong, that is, just one syllable. An accent mark will also be placed over a weak vowel (u or i) in order to break an automatic diphthong. In this case the word would have an extra syllable. Fatty acids, which always end on the vowel ‘o’, have the stress nearly always on the second but last syllable, so this has to be indicated by an acute. Accordingly “caproic acid” becomes “ácido capróico” with an acute accent on the ‘o’. Fatty acids that end in English on ‘eic’ or ‘aic’ are stressed on these syllables in Spanish and Portuguese so they don’t need an accent: “ácido oleico”, “ácido azelaico”
   1. 2.1. In Portuguese, there is a different accent on the strong vowels ‘a’, the ‘e’ and the ‘o’ when they stand before an ‘n’ or an ‘m’. So “isanic acid” becomes “ácido isânico” in Portuguese”. In Spanish, this will be “ácido isánico”.
3. Names that in English start with an ‘s’ followed by a consonant such as “stearic acid” and “sterculic acid” get an ‘e’ in front of them when they are translated into Spanish or Portuguese, cf. Spain → España. So “stearic acid” becomes “ácido esteárico”. This also holds when the name starts with a prefix like ‘eleo’, ‘iso’, ‘neo’ or ‘subtilo’. For example “ácido isoesteárico” or “ácido demoespôngico”.
4. In both languages, the ‘k’ only exists in words like kilogram. I am willing to bet that Spanish and Portuguese Scrabble® games do not include a ‘k’. This is a fairly safe bet since I know that the French Scrabble® does not have a ’k’. On translation, the ‘k’ is changed. When followed by an ‘i’, it becomes ‘qu’ and when followed by an ‘e’ or an ‘o’, it becomes a ‘c’ So “bolekic acid” becomes “ácido boléquico” and “bolekolec acid” becomes “ácido bolecólico”.
5. With the ‘ch’ similar rules apply. When in front of an ‘i’ or ‘e’, it is changed into ‘qu’: “arachidic acid becomes “ácido araquídico”. When followed by another letter, it becomes a ‘c’; “selacholeic acid” becomes therefore “ácido selacoleico”.
6. Every ‘y’ in English names should be replaced by an ‘i’ in both languages: y → i. That holds for names such as “acrylic” (“acrílico”) or “isobutyric” (“isobutírico”) and for prefixes and postfixes. “hydroxy” becomes ‘hidroxi”, “…ynoic” becomes “…inóico”, etc.
7. The ‘h’ in the ‘th’ in English names should be scrapped in both languages: th → t. So “eranthic acid” is translates as “ácido erántico”(Spanish) or “ácido erântico” (Portuguese).
   1. 7.1. In Portuguese, the ‘h’, when between two vowels, such as in “behenic acid” is deleted as well: “ácido beénico” but in Spanish, the ‘h’ is maintained (“ácido behénico”).
   2. 7.2. The ‘gh’ in English names becomes ‘gu’ on translation: “gheddic acid’ translates into “ácido guédico”
   3. 7.3. The ‘sh’ in English names is translated to‘ch’: “goshuyic acid” becomes “ácido gochuico”
   4. 7.4. The ‘h’ in English names starting with ‘dehydro’ also disappears on translation into Portuguese and is replaced by an ‘s’: “dehydrocrepenynic acid” becomes “ácido desidrocrepenínico”, but in Spanish it is “ácido dehidrocrepenínico”.
   5. 7.5. In Portuguese, the ‘h’ is maintained when it is the first letter of the word. So in names like ‘ácido heptanóico’, the ‘h’ is not deleted and when names starting with an ‘h’ have a prefix that ends on a vowel, a hyphen is inserted between the prefix and the name: “ácido di-homolinoleico”, “ácido iso-heptanóico” or ”ácido docosa-hexenóico”; no such hyphens are inserted into Spanish names.
8. Similarly, the ‘h’ coming after an ‘r’ in English names should be dropped on transcribing: “rhodinic acid” → “ácido rodínico”
9. And again the ‘h’ after a ‘g’ is omitted on translation into Portuguese: “roughanic acid” → “ácido rugânico”
   1. 9.1. The name of this acid also shows that in Portuguese, the ‘ou’ has to be changed to an ‘u’ on translation. “Couepinic acid” is “ácido cuepínico” in Portuguese, but in Spanish, the ‘ou’ is kept: “ácido couepínico”.
10. If the ‘h’ in the English name is preceded by a ‘p’, this ‘ph’ is changed into an ‘f’ on translation: “ephedrenic acid” → “ácido efedrénico”.
11. Both Spanish and Portuguese have rules about double consonants like the two c’s in ‘vaccenic acid.
    1. 11.1. One of these c’s is deleted on translating into Spanish or Portuguese so that on translation, “vaccenic acid” becomes “ácido vacénico”; there is an exception though in that ‘succinic acid’ keeps its to c’s on translation: “ácido succínico” in both Spanish and Portuguese.
    2. 11.2. The double ‘d’ becomes a single ‘d’ after translation: “geddic acid” becomes “ácido gédico”
    3. 11.3. Double l’s also becomes a single ‘l’ on translation: “laballenic acid” becomes “ácido labalénico”.
    4. 11.4. This also holds for the double ‘n’: “thynnic acid” becomes “ácido tínico”, which translation also illustrates points 5 and 6 above.
    5. 11.5. Similarly for the double ‘r’: “kerrolic acid” becomes “ácido cerólico”, which translation illustrates point 4 above.
    6. 11.6. Finally the double ‘t’ is also changed into a single one: So “ambrettolic acid” becomes: “ácido ambretólico”.
    7. 11.7. In Portuguese, a single s is changed into a double one in “hydrosorbic acid”, which becomes “ácido hidrossorbico” and “physeteric acid”, which becomes “ácido fissetérico” when the ‘s’ is pronounced as an ‘s’. When the pronunciation is softer, more like a ‘z’ as in “petroselic acid”, a single ‘s’ is written: “ácido petrosélico”.

Transcription from English into Italian

Since I don’t know Italian either, I had to rely on expert advice that is hereby warmly acknowledged. Like the translation into Spanish and Portuguese, the translation from English into Italian can also be summarised in a number of consecutive rules.

1. As in the other Romanic languages, the word ‘acido’ (acid) is put in front of the trivial name, but unlike Spanish or Portuguese, it carries no accent.
2. The Italian trivial name can be arrived at by putting an ‘o’ behind the English trivial name: ‘cerotic acid’ becomes ‘acido cerotico’.
3. Change any ‘y’ in the English name to an ‘i’: ‘pyruvic acid’ translates into ‘acido piruvico’, and ‘acrylic acid’ becomes ‘acido acrilico’.
4. Like Spanish and Portuguese, Italian does not use the ‘ph’ either; it should be changed into an ‘f’: ‘phytanic acid’ becomes ‘acido fitanico’, which example also illustrates rule 3 (y → i).
5. Delete any ‘h’ from the English name if it starts with an ‘h’ or the ‘h’ follows a vowel: ‘homophytanic acid’ becomes ‘acido omofitanico’, which example also illustrates two previous rules (y → i and ph → f); ‘behenic acid’ becomes ‘acido beenico’ and ‘dihomolinoleic acid’ becomes ‘acido diomolinolenico’. However, after a consonant, the ‘h’ is retained: ‘shibic acid’ translates into ‘acido shibico’.
6. Change ‘x’ to ‘ss’: ‘taxoleic acid’ becomes ‘acido tassoleico’. However, this rule does not apply when the trivial name starts with an ‘x’: ‘ximenic acid’ retains its ‘x’ in ‘acido ximenico’.

Transcription from English into German and Dutch

As opposed to Spanish, Portuguese, Italian and French, the German and Dutch languages have coined quite a few trivial names of their own. Take acetic acid for instance. German and Dutch call this “vinegar acid” and that is what it is. Those trivial names and irregular names that are not to be translated according to the rules to be given below, have therefore been incorporated in Table 3 below after the English trivial name.

The author would be delighted to learn of additions or corrections to this list or to receive any general comments.