Isoprene in the context of "India rubber"

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⭐ Core Definition: Isoprene

Isoprene, or 2-methyl-1,3-butadiene, is a common volatile organic compound with the formula CH2=C(CH3)−CH=CH2. In its pure form it is a colorless volatile liquid. It is produced by many plants and animals (including humans) and its polymers are the main component of natural rubber.

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Isoprene in the context of Lipids

Lipids are a broad group of organic compounds that include fats, waxes, sterols, fat-soluble vitamins (such as vitamins A, D, E and K), monoglycerides, diglycerides, phospholipids, and others. The functions of lipids include storing energy, signaling, and acting as structural components of cell membranes. Lipids have applications in the cosmetic and food industries, and in nanotechnology.

Lipids are broadly defined as hydrophobic or amphiphilic small molecules; the amphiphilic nature of some lipids allows them to form structures such as vesicles, multilamellar/unilamellar liposomes, or membranes in an aqueous environment. Biological lipids originate entirely or in part from two distinct types of biochemical subunits or "building-blocks": ketoacyl and isoprene groups. Using this approach, lipids may be divided into eight categories: fatty acyls, glycerolipids, glycerophospholipids, sphingolipids, saccharolipids, and polyketides (derived from condensation of ketoacyl subunits); and sterol lipids and prenol lipids (derived from condensation of isoprene subunits).

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Isoprene in the context of Carotenoid

Carotenoids (/kəˈrɒtɪnɔɪd/) are yellow, orange, and red organic pigments that are produced by plants and algae, as well as several bacteria, archaea, and fungi. Carotenoids give the characteristic color to pumpkins, carrots, parsnips, corn, tomatoes, canaries, flamingos, salmon, lobster, shrimp, and daffodils. Over 1,100 identified carotenoids can be further categorized into two classes – xanthophylls (which contain oxygen) and carotenes (which are purely hydrocarbons and contain no oxygen).

All are derivatives of tetraterpenes, meaning that they are produced from 8 isoprene units and contain 40 carbon atoms. In general, carotenoids absorb wavelengths ranging from 400 to 550 nanometers (violet to green light). This causes the compounds to be deeply colored yellow, orange, or red. Carotenoids are the dominant pigment in autumn leaf coloration of about 15-30% of tree species, but many plant colors, especially reds and purples, are due to polyphenols.

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Isoprene in the context of Biopolymer

Biopolymers are natural polymers produced by the cells of living organisms. Like other polymers, biopolymers consist of monomeric units that are covalently bonded in chains to form larger molecules. There are three main classes of biopolymers, classified according to the monomers used and the structure of the biopolymer formed: polynucleotides, polypeptides, and polysaccharides. The polynucleotides, RNA and DNA, are long polymers of nucleotides. Polypeptides include proteins and shorter polymers of amino acids; some major examples include collagen, actin, and fibrin. Polysaccharides are linear or branched chains of sugar carbohydrates; examples include starch, cellulose, and alginate. Other examples of biopolymers include natural rubbers (polymers of isoprene), suberin and lignin (complex polyphenolic polymers), cutin and cutan (complex polymers of long-chain fatty acids), melanin, and polyhydroxyalkanoates (PHAs).

In addition to their many essential roles in living organisms, biopolymers have applications in many fields including the food industry, manufacturing, packaging, and biomedical engineering.

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Isoprene in the context of Rubber

Rubber, also called India rubber, latex, Amazonian rubber, caucho, or caoutchouc, as initially produced, consists of polymers of the organic compound isoprene, with minor impurities of other organic compounds.

Types of polyisoprene that are used as natural rubbers are classified as elastomers. Currently, rubber is harvested mainly in the form of the latex from the Pará rubber tree (Hevea brasiliensis) or others. The latex is a sticky, milky and white colloid drawn off by making incisions in the bark and collecting the fluid in vessels in a process called "tapping". Manufacturers refine this latex into the rubber that is ready for commercial processing.

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Isoprene in the context of Polyisoprene

Polyisoprene is, strictly speaking, a collective name for polymers that are produced by polymerization of isoprene. In practice polyisoprene is commonly used to refer to synthetic cis-1,4-polyisoprene, made by the industrial polymerisation of isoprene. Natural forms of polyisoprene are also used in substantial quantities, the most important being "natural rubber" (99.99% cis-1,4-polyisoprene), which is derived from the sap of trees. Both synthetic polyisoprene and natural rubber are highly elastic and consequently used in a variety of applications, such as making tires.

The trans isomer, which is much harder than the cis isomer, has also seen significant use in the past. It too has been synthesised and extracted from plant sap, the latter resin being known as gutta-percha. These were widely used as an electrical insulator and as components of golf balls. Annual worldwide production of synthetic polyisoprene was 13 million tons in 2007 and 16 million tons in 2020.

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Isoprene in the context of Isoprenoids

The terpenoids, also known as isoprenoids, are a class of naturally occurring organic chemicals derived from the 5-carbon compound isoprene and its derivatives called terpenes, diterpenes, etc. While sometimes used interchangeably with "terpenes", terpenoids contain additional functional groups, usually containing oxygen. When combined with the hydrocarbon terpenes, terpenoids comprise about 80,000 compounds. They are the largest class of plant secondary metabolites, representing about 60% of known natural products. Many terpenoids have substantial pharmacological bioactivity and are therefore of interest to medicinal chemists.

Plant terpenoids are used for their aromatic qualities and play a role in traditional herbal remedies. Terpenoids contribute to the scent of eucalyptus, the flavors of cinnamon, cloves, and ginger, the yellow color in sunflowers, and the red color in tomatoes. Well-known terpenoids include citral, menthol, camphor, salvinorin A in the plant Salvia divinorum, ginkgolide and bilobalide found in Ginkgo biloba and the cannabinoids found in cannabis. The provitamin beta carotene is a terpene derivative called a carotenoid.

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