Phenolic Monoterpenoids

Vilkas, M. Vilkas, D. Joniaux, and C. Pascard-Billy, J.C.S. Chem. Comm., 1978, 125. 

Begley, L. Crombie, D. A. Slack, and D. A. Whiting, J.C.S. Chem. Comm., 1976, 140 J.C.S. Perkin 1,1977,2402. In the latter there is a discrepancy between the crystallographic models and the formulae which are used the absolute configuration was not determined, however. 

---

This chapter is organized similarly to the previous ones, although there are some differences within the sections. It does not include topics discussed elsewhere in these volumes (such as ionones, phenolic monoterpenoids, and pheromones that are not directly monoteipenoid). 

The phenolic hydroxy-group in THC s is important to their pharmacological activity,357 and analgesic properties may be due to metabolism to 7-hydroxy-derivatives (using normal monoterpenoid numbering).358 l-Nor-lj8-hydroxyhexahydrocannabinol is a potent analgesic.359 Cannabinol is a rapidly formed metabolite of A -THC and A6-THC in rats.360 The activity of A6-THC- and cannabidiol-containing polymers is reported.361... 

There are abundant and diverse flavonoids with carbohydrates and lipids, alkaloids (betalain alkaloids and other alkaloids), phenols (chromones, cou-marins, lignans, quinines, and other phenolics), terpenoids (monoterpenoids, sesquiterpene lactones, triperpenoid saponins, carotenoids, and other terpenoids), and minerals as micronutritional phytochemicals in fruits and vegetables of our daily diets. Among these phytochemicals, the flavonoids have specific functionality in relation to age-related diseases such as hypertension, diabetes, cardiac infarction, cataracts, and cancer. The authors of each chapter in the first section have presented their evidence in relation to the mechanism of the preventative and therapeutic ability of the compounds. 

Cyclohexane monoterpenes are a chemically diverse group of monoterpenoids that occur in the plant kingdom mainly as hydrocarbons, alcohols, ketones, aromatic hydrocarbons, and phenols (Fig. 5). The saturated hydrocarbon trans-p-menthme (El) is a constituent of the oil of turpentine and the resin of pine (Pinaceae) trees. Its unsaturated analogs, namely (i )-(- -)-limonene (E2) [present in oil of orange (Citrus aurantium) and mandarin (Citrus reticulata, Rutaceae) peel oil] a-terpinene (E3) and terpinolene (E4) in some Citrus, Juniperus, Mentha and Pinus species (i )-(-)-a-phellandrene (E5) in Eucalyptus phellandra (Myrtaceae) and (5)-(- -)-3-phellandrene (E6) in water feimel (Phel-landrium aquaticum, Umbelliferae), are components of many plant volatile oils. The rich chemical diversity of cyclohexane monoterpene alcohols is apparent from the natural occurrence of all four pairs of / -menthan-3-ol enantiomers, for... 

Chiang LC, Ng LT, Chiang W, Chang MY, Lin CC (2003) Immunomodulatory activities of flavonoids, monoterpenoids, triterpenoids, iridoid glycosides and phenolic compounds of Plantago species. Planta Med 69 600-604... 

Pure a-terpineol has a delicate sweet floral, lilac-type odor (though only present at very low levels, if at all, in lilac). Its odor qualities are greatly affected by impurities, and many fragrance houses buy cheap grades and redistill it to their perfumery quality. The monoterpenoid hydrocarbons tend to give a pine character, the other alcohols and the phenols give a medicinal quality. Low-cost, ready availability and stability to air, soap and household products make it a very useful ingredient. 

---