Trivial and Systematic Names

D-Talose o-Galactose D-ldose o-Gulose D-Mannose o-Glucose 

FIGURE 2.6 The acyclic forms, trivial names and abbreviations of D-aldoses drawn as their Fischer projections. 

2-Amino-3-bromo-D-erj/f/7ro-butanoic acid 2,4-Dibromo-L-fhreo-pentanoic acid 

EIGURE 2.9 Systematic names of carbohydrates with more than four stereogenic centers. 

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American practice is to use the terminations -ane for saturated and ene for unsaturated compounds in both the hydrocarbon and the heterocyclic series. British usage is essentially the same for hydrocarbons, but for heterocyclic molecules the final e is omitted in fact, a terminal e is used in general only for hydrocarbons, bases, and the five-membered ring ending ole. This leads in particular to some differences in the spelling of both trivial and systematic names for one-ring heterocycles e.g., thiophen, oxiren, dioxaphospholan (British) thiophene, oxirene, dioxaphospholane (American). 

But we do need to be able to communicate by speech and by writing as well. In principle we could do this by using systematic names. In practice, though, the full systematic names of anything but the simplest molecules are far too clumsy for use in everyday chemical speech. There are several alternatives, mostly based on a mixture of trivial and systematic names. 

Table 1. Trivial and Systematic Names of Purine Derivatives...

Electron-donor properties of systems 72, 75, and their derivatives are shown in the formation of complexes with electron acceptors such as tetra-cyanoethylene or chloranil. We shall designate the constituents of the complexes studied here by the most commonly used abbreviations which are summarized in Table V along with the corresponding trivial and systematic names. 

Rules of the Fischer Projection Trivial and Systematic Names Absolute and Relative Configuration... 

The utility of the systematic name of a compound lies in the information that it provides about the parent compound, the position of bond unsaturation, and the nature, position, and orientation of substituents. The trivial name, as the term suggests, conveys little or no information about the chemical origin and characteristics of a compound (e.g., cortisol, progesterone, and testosterone). The trivial and systematic names of some of the important steroid hormones are given in Table 51-2. 

In view of the many alternative trivial and systematic names for chemical compounds, the indexes should be searched under any alternative names which may be indicated in the main body of the text. Only a limited amount of cross-referencing has been carried out, where it is considered that it would be helpful to the user. 

In a similar manner to the fatty acids, monohydric, dihydric and phenolic members invariably exists as a mixture of saturated, monoene, diene and triene constituents and rarely in the pure form as one of these four. In the nomenclature of this series a comprehensive system which takes account of the chain length, double bond position and its stereochemistry has not been widely agreed and accepted. Trivial and systematic names thus both abound and because of their dual functional nature as aromatic and acyclic these compounds have remained relatively unclassified. For example, cardanol is a well-known member consisting of saturated, monoene, diene... 

It should be pointed out that currently both trivial and systematic names are commonly used for naming the heterocyclic compounds. For example, an organic chemist will recognize without any difficulty the structures connected to names such as furane, pyrrole, pyrrolidine, pyrazole, imidazole, pyridine, or piperidine, despite the fact that all these names are trivial. On the other hand, the complex heterocycles require more sophisticated approaches in order to avoid ambiguity and correctly translate the chemical strucmre into the name. For these, compound names are often made using either trivial name (e.g., indazole for benzopyrazole, benzimidazole, indole, and isoindole) or the Hantzsch-Widman nomenclature, for example, 1,2,3- or 1,2,5-oxadiazoles, 1,3-dioxolane, 1,2- or 1,3-dithiolane, and 1,3- or 1,4-dioxane. It should be noted that the Hantzsch-Widman nomenclature treats the unsaturated heterocycle with maximum number of conjugated double bonds as parent compound. This adds another layer of complexity, giving rise to names such as... 

Table 6.4.4. Trivial and systematic names of -aliphatic acids found in suberin...

Table 2.1 Trivial and systematic names of proteinogenic amino acids and their codes.

Table 3.38 Overview of trivial and systematic names of selected steroids.

Commonly used and recommended trivial and systematic names of key vitamins D and related steroids are listed in Table 5.3. 

A number of bicyclic hydrocarbons are present in turpentine, and also as components of fruits, vegetables and spices (8-6). A frequently occurring compound is sabinene, also known as thujene or 4(10)-thujene (which is found in higher concentrations in the essential oil of black pepper), car-3-ene (A -carene), a-pinene (2-pinene), P-pinene, also known as 2(10)-pinene, nopinene or pseudopinene and camphene. Trivial and systematic names of the main compounds are Ksted in Table 8.2. 

P-Caryophyllene is a common component of many essential oils. For example, the essential oil of black pepper (see Table 8.32, later) contains about 20% of P-caryophyllene. Its a-isomer humulene (also known as a-caryophyllene) occurs in the hops essential oil Humulus lupulus, Cannabaceae) both compounds are often present in the mixture. Common components of essential oils are also bisabolenes. Higher quantities of P-bisabolene (10-15%) and also a-zingiberene (22-30%), ar-curcumene (20%), a-selinene and p-farnesene are found in ginger essential oil. The essential oil of white sandalwood Santalum album, Santalaceae) contains, in addition to sesquiterpenic alcohols as major components, many sesquiterpenic hydrocarbons, including a-bergamotene or-curcumene, P-bisabolene and many others. Trivial and systematic names of the main sesquiterpenic hydrocarbons are listed in Table 8.3. 

Table 8.6 Trivial and systematic names of monoterpenic alcohols. ...

An important precursor of (-)-perrillyl aldehyde (periUal) is (-)-perillyl alcohol. Fenchol (also known as a-fenchyl alcohol or fenchan-2-ol, 8-20) is a bicyclic monoterpenic alcohol occurring as a minor component in citrus, fennel and sage essential oils. Another common compound is the bicyclic alcohol thujan-4-ol (sabinene hydrate), which occurs at a high level in the marjoram essential oil (see Table 8.32, later). Borneol (bornan-2-ol) is a component of camphor oils Cinnamomum camphora, Lauraceae). Trivial and systematic names of selected monoterpenic alcohols are listed in Table 8.6. 

An example of monocyclic sesquiterpenic alcohols is (-l-)-o(-bisabolol (8-24). It occurs in citrus essential oils along with other sesquiterpenic alcohols, and represents the major component of the essential oil of chamomile flowers (Matricaria chamomilla, Asteraceae). a-Bisabolol (0.26%) and other sesquiterpenoids, such as monocyclic sesquiterpenic alcohol (Z)-lanceol (1.7%), bicyclic sesquiterpenic alcohol (Z)-a-essential components of white sandalwood oil (Santalum album, Santa-laceae) used in perfumery, cosmetics and aromatherapy. (Z)-Lanceol is also a component of sage species (Salvia spp., Lamiaceae) essential oil. Sesquiterpenic bicyclic alcohol (-F)-P-nootkatol is the precursor of ketone (-F)-nootkatone, an important component of grapefruit essential oil. Trivial and systematic names of the main sesquiterpenic alcohols are listed in Table 8.7. 

An example of terpenic 1,2-epoxides is -caryophyllene oxide, also known as (-)-epoxycaryophyllene (8-31), which occurs in many essential oils. An example of terpenic 1,4-epoxides is the so-called (-l-)-dill ether, (3J ,4S,8S)-3,9-epoxy-p-menth-l-ene (8-31), which is a typical component of the essential oil of caraway (30%) and dill. An example of unsaturated 1,4-epoxides is (-l-)-menthofuran (8-31), the metabolite of ketone (-l-)-pulegone. Both compounds are components of peppermint oil (see Table 8.32, later) and are hepatotoxic. Monoterpenoid compound (- -)-l,8-cineole (also known as limonene oxide, eucalyptol or 1,8-epoxy-p-menthane 8-31) is an example of more complex structures. It is present in essential oils of many types of spices, and higher quantities are found in the essential oil of trees of the genus Eucalyptus (Myrtaceae). Trivial and systematic names of selected ethers are given in Table 8.8. 

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