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alpha-Terpineol

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alpha-Terpineol Basic information
alpha-Terpineol Chemical Properties
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alpha-Terpineol Usage And Synthesis
  • Description(-)-alpha terpineol is the alpha form of terpineol, a naturally monoterpene alcohol that can be isolated from various kinds of sources such as cajuput oil, pine oil, and petitgrain oil. The alpha form is the major constituent of terpineol. It is a common component in perfumes, cosmetic and flavors. It is also a kind of solvent used for extracting natural spices and as a kind of solvent of acetate fibers. Moreover, it exhibited strong and broad antimicrobial activity against fungi, bacteria and virus. Study has demonstrated that is antibacterial (bactericidal) effect originated from its destroying effect on the cell wall and cell membrane of bacteria. It also has certain anticonvulsant activity.
  • Referencesde Sousa, Damiao Pergentino, Lucindo Quintans Jr, and Reinaldo Nóbrega de Almeida. "Evolution of the anticonvulsant activity of α-terpineol."Pharmaceutical Biology 45.1 (2007): 69-70.
    Park, Soon-Nang, et al. "Antimicrobial effect of linalool and α- terpineol against periodontopathic and cariogenic bacteria." Anaerobe 18.3 (2012): 369-372.
    Dabbah, Roger, V. M. Edwards, and W. A. Moats. "Antimicrobial action of some citrus fruit oils on selected food-borne bacteria." Applied microbiology19.1 (1970): 27-31.
  • Chemical PropertiesClear colorless liquid after melting
  • Chemical Propertiesα-Terpineol is a colorless, crystalline solid, smelling of lilac. The most important commercial grade of terpineol consists of a liquid mixture of isomers that contains mainly α-terpineol and a considerable amount of ?γ-terpineol. This mixture has a stronger lilac odor than does pure crystalline α-terpineol.
    Hydrogenation of α-terpineol yields p-menthan-8-ol. Terpineol is readily dehydrated by acids, yielding a mixture of unsaturated cyclic terpene hydrocarbons. Under mildly acidic conditions, terpin hydrate is formed. The most important reaction for the fragrance industry is esterification, particularly acetylation to terpinyl acetate.
    Terpineol with its typical lilac odor is one of the most frequently used fragrance substances. It is stable and inexpensive and is used in soaps and cosmetics.
  • Chemical Propertiesα-Terpineol has a characteristic lilac odor with a sweet taste reminiscent of peach on dilution.
  • OccurrenceReported found in more than 150 derivatives from leaves, herbs and flowers; the d-, l- and dl-isomers are known: the d-form is found in the essential oils from Cupressaceae in general; also in the oils of Elettaria cardamomum, star anise, marjoram, clary sage, neroli and others. The l-form is found in Satureia montana, lavandin, cajeput, lime, lemon, cinnamon leaves and the distillates from Pinaceae (with exception of Pinus silvestris, which contains d-terpineol together with racemic form); likewise, Nectandra elaiophora (wood) and petitgrain bigarade. The racemic form is found in cajenne linalool, Thymus caespititius, cajeput, Eucalyptus globulus; mixed with the l-form it is found in petitgrain; a nondefined form of terpineol has been reported in the bitter orange. Reported found in over 260 natural sources including apple, apple juice, apricot, sweet and sour cherry, citrus peel oils and juices, orange, lemon, lime, grapefruit, tangerine, mandarin peels oils and juices, bergamot, cranberry, blueberry, black currant, raspberry, strawberry, guava, grapes, raisin, melon, papaya, peach, pear, pineapple, carrot, celery, peas, potato, bell pepper, tomato, anise, cinnamon, clove, cumin seed, ginger, Mentha oils, pepper, mace, parsley, nutmeg, thyme, Gruyere cheese, parmesan cheese, butter, cooked chicken and beef, hop oil, beer, cognac, rum, wines, tea, nuts, honey, avocado, passion fruit, prune, plums, beans, mushroom, sweet and wild marjoram, starfruit, mango, tamarind, parsnip root, cardamom, coriander seed, rice, quince, litchi, calamus, dill, licorice, lovage root, juniper berry, corn oil, laurel, sweet and bitter fennel, wort, elderberry, loquat, myrtle berry, rosemary, buchu oil, Bourbon vanilla, mountain papaya, turmeric, clary sage, lemon balm, nectarines, naranjilla fruit, cape gooseberry and sea buckthorn.
  • UsesShows antioxidant effects. Antiseptic. is present in many extracted oils of various plant species, acts as an antihypernociception and anti-inflammatory.
  • DefinitionChEBI: A terpineol that is propan-2-ol substituted by a 4-methylcyclohex-3-en-1-yl group at position 2.
  • PreparationAlthough α-terpineol occurs in many essential oils, only small quantities are isolated, for example, by fractional distillation of pine oils.
    A common industrial method of α-terpineol synthesis consists of the hydration of α-pinene or turpentine oil with aqueous mineral acids to give crystalline cis-terpin hydrate (mp 117 °C), followed by partial dehydration to α-terpineol. Suitable catalysts are weak acids or acid-activated silica gel.
    Selective conversion of pinene, 3-carene, and limonene or dipentene to terpineol, without terpin hydrate formation is also used. Addition of organic acids (weak acids require catalytic amounts of mineral acids) produces terpinyl esters, which are subsequently hydrolyzed to terpineol, sometimes in situ.
  • Aroma threshold valuesDetection: 280 to 350 ppb. Aroma characteristics in 1% ethanol: pine-like, woody and resinous with a slight cooling lemon and lime citrus nuance, and a floral dry out.
  • Taste threshold valuesTaste characteristics at 2 to 25 ppm: woody, terpy, lemon and lemon–lime-like with a slight herbal and floral nuance. Taste characteristics at 10 to 25 ppm: citrus woody with a lemon and lime nuance. It has a slight soapy mouthfeel.
  • Chemical SynthesisObtained from terpin hydrate by splitting off water; from pentane tricarboxylic acid by cyclization, followed by esterification to the hydroxy ester, then the unsaturated ester and Grignard to terpineol; also from isoprene and methyl vinyl ketone, using methyl magnesium iodide.
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