TRITERPENES 383 



Soybean wax {Glycine soja), celery seed {ApiU7n graveolens L.), and sesame 

 seed {Sesamiim indicum L.) all contain waxes, which have been studied. 



a'. Jojoba Wax: The jojoba seeds or goat-nut {Simmondsia chinensis 

 (californica) Nutt.) are unique in having as their lipid component an oil 

 which has a composition closely resembling that of wax. The seeds are 

 produced by an evergreen shrub which grows in Western Mexico, Arizona, 

 and California. The jojoba nuts, which are also called "goat nuts," con- 

 tain more than 50% of oil.^«^ It has a density of 0.8642 at 25 °C., a refrac- 

 tive index at the same temperature of 1.4648, an iodine value (Hanus) of 

 81.7, and a saponification number of 92.2. ^ The chemical composition is 

 reported' as follows: saturated acids, 1.64%; palmitoleic acid, 0.24%,; 

 oleic acid, 0.66%; eicosenoic acid, 30.3%; docosenoic (erucic) acid, 14.2%; 

 eicosenol, 14.6%; docosenol, 33.7%; and hexacosenol, 2.0%. The chief 

 acid has been identified as 11-eicosenoic acid, by Green, Hilditch, and 

 Stainsby,*^ W'hile the principal alcohols are 11-eicosenol and 13-docosenol. 

 11,12-Dihydroxyeicosenoic acid has also been reported -as a constituent of 

 jojoba wax. 



(j) Flower Waxes. Wax-like extracts have been prepared from a 

 variety of flowers. Rogerson^^ was able to identify hentriacontane, 

 C31H64, incarnatyl alcohol, C34H69OH, a phytosterol "trifolianol," and pal- 

 mitic, stearic, oleic, linoleic, and isolinolenic acids from the wax of the crim- 

 son clo^'er flower {Trijolium incarnatum L.). The w-axes of roses, violets 

 {Viola odorata L.), acacia and silver-green w^attle flowers {Acacia cavenia 

 and A. decurrens var. dealhata), the grape hyacinth flow^er {Muscari 

 botryoides Mill.), the jasmine flower {Jasminum odoratissimum L.), and other 

 flowers have been investigated.' 



d. Waxes from Microorganisms. Tubercle bacilli contain a large 

 proportion of waxy materials, which have been extensively investigated. 

 In 1901 Kresling^^^ was the first to demonstrate the high proportion of 

 alcohols in the lipid extracts of tubercle bacilli. The principal acids are 

 mycolic and the forked-chain compounds tuberculostearic and phthioic^*^" 

 acids. The normal saturated fatty acids, palmitic, stearic, ^"^ and hexaco- 

 sanoic acids occur, as well as some unsaturated acids which yield hexaco- 

 sanoic acid on hydrogenation. For a discussion of these acids, see Chapter 

 II. All tubercle wax fractions contain an alcohol, phthiocerol, C35H72O3. 



2. Triterpenes 



The triterpenes are a group of plant constituents which contain 30 carbon 

 atoms. They may occur as the free triterpene or combined w^th sugars in 

 glucoside linkage to form a saponin. The aglycones formed on hydrolysis of 



'*' L. X. Markwood, U. S. Depl. Commerce, Domestic Commerce, SO, No. 11, 20-21 

 (Sept. 10, 1942). 



^ H. Rogerson, J. Chem. Soc, 97, 1004-1015 (1910); Proc. Chem. Soc.,26. 112 (1910). 

 «» H. Kresling, Zenlr. Bakl. Parasilenk., I, SO, 897-909 (1901). 



