isoprenoid

 

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Class of organic compounds made up of two or more structural units derived from isoprene. Isoprene is a five-carbon hydrocarbon with a branched-chain structure, two double bonds (see bonding), and the molecular formula C₅H₈. In isoprenoids, isoprene units (with one or neither of their double bonds) are linked into larger molecules having from two to thousands of five-carbon units that can take the form of both linear structures and rings. Many of these molecules play a wide variety of roles in plant and animal physiological processes and as intermediates in the biological synthesis of other important molecules. They contribute greatly to the flavours and fragrances of essential oils and other plant-derived substances. Geraniol (a contributor to rose perfumes; from geranium oil), menthol (from peppermint oil), citral (from lemongrass oil), limonene (from lemon and orange oils), pinene (from turpentine), and camphor each have two isoprene units. Examples with more units include phytol, a precursor of chlorophyll; squalene, the precursor of cholesterol and other steroids; lycopene, the red pigment in tomatoes and an important phytochemical; and carotene, the pigment in carrots and a precursor of vitamin A. Natural rubber and the related gutta-percha are polyisoprenes comprising many thousands of isoprene units.