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1,8-Cineole

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1,8-Cineole Basic information
1,8-Cineole Chemical Properties
  • Melting point:1-2 °C(lit.)
  • Boiling point:176-177 °C(lit.)
  • Density 0.9225
  • refractive index n20/D 1.457(lit.)
  • FEMA 2465 | EUCALYPTOL
  • Flash point:122 °F
  • storage temp. 2-8°C
  • solubility 3.5g/l
  • form Liquid
  • color Clear colorless to slightly yellow
  • Water Solubility Soluble in water(3500 mg/L (at 21°C). Miscible with ether, alcohol, chloroform, glacial acetic acid, oils. Soluble in ethanol, ethyl ether; slightly soluble in carbon tetrachloride.
  • Merck 14,3895
  • JECFA Number1234
  • BRN 105109
  • Stability:Stable. Flammable. Incompatible with acids, bases, strong oxidizing agents.
  • InChIKeyWEEGYLXZBRQIMU-WAAGHKOSSA-N
  • CAS DataBase Reference470-82-6(CAS DataBase Reference)
  • NIST Chemistry ReferenceEucalyptol(470-82-6)
  • EPA Substance Registry SystemEucalyptol (470-82-6)
Safety Information
MSDS
1,8-Cineole Usage And Synthesis
  • Chemical PropertiesColorless Liquid
  • Chemical Properties1,8-Cineole occurs in many terpene-containing essential oils, sometimes as the main component. For example, eucalyptus oils contain up to 85% 1,8-cineole and laurel leaf oil contains up to 70%. It is a colorless liquid with a characteristic odor, slightly reminiscent of camphor. 1,8-Cineole is one of the few fragrance materials that is obtained exclusively by isolation from essential oils, especially eucalyptus oils. Technical-grade 1,8- cineole with a purity of 99.6–99.8% is produced in large quantities by fractional distillation of Eucalyptus globulus oil. A product essentially free from other products can be obtained by crystallization of cineole-rich eucalyptus oil fractions
  • Chemical PropertiesEucalyptol has a characteristic camphoraceous odor and fresh, pungent, cooling taste.
  • OccurrenceIts name is derived from its presence in the essential oils of Eucalyptus globulus and Melaleuca leucadendron L. (essential oil of cajeput). It was originally identified in the essential oil of Artemisia maritime and subsequently in a large number (approx. 270) of other essential oils: rosemary, laurel leaves, clary sage, myrrh, cardamom, star anise, camphor, lavender, peppermint, Litsea guatemalensis, Luvunga scadens Roxb., Achillea micrantha and Salvia triloba. The essential oil of Eucalyptus polibrac tea has been reported to contain up to 91% eucalyptol. Also reported found in citrus oils and juices, guava, papaya, cinnamon bark, root and leaf, ginger, corn mint oil, spearmint, nutmeg, pepper, Thymus zygis, cardamom, cranberry, laurel, pepper, sweet marjoram, coriander, Spanish origanum, Ocimum basilicum, curcuma, sage, laurel, sweet and bitter fennel, myrtle leaf and berry, pimento and calamus.
  • Useseucalyptol is considered an antiseptic. This is a monoterpene compound that provides the fragrance associated with the essential oil of eucalyptus. eucalyptol is also used to fragrance cosmetic preparations.
  • Usesanthelminthic, antiseptic, expectorant
  • UsesLabelled 1,8-Cineol, the chief constituent of oil of eucalyptus. Used as pharmaceutic aid (flavor).
  • Uses1,8-Cineol is the chief constituent of oil of eucalyptus. Used as pharmaceutic aid (flavor).
  • UsesPharmaceutic aid (flavor).
  • PreparationBy fractional distillation (170 to 180°C) from those essential oils containing high levels of eucalyptol, such as Eucalyptus globulus (approx. 60%), and subsequent separation of the product by congealing the distillate.
  • Aroma threshold valuesDetection: 1 to 64 ppb. Aroma characteristics at 1.0%: sweet, cooling, fresh, chemical pine, slightly minty with a spicy cardamom nuance.
  • Taste threshold valuesTaste characteristics at 5 ppm: cooling, fresh, oily, green, spicy, pine-like.
  • General DescriptionColorless liquid with a camphor-like odor. Spicy cooling taste.
  • Air & Water ReactionsHighly flammable. Insoluble in water.
  • Reactivity ProfileCineole will react with acids and bases.
  • Fire HazardFlash point data for Cineole are not available but Cineole is probably combustible.
  • Anticancer ResearchA statistically significant reduction of cell proliferation was observed compared tothe control cells when tested on RKO cells and human colon cancer cell linesHCT116 injected into the SCID mice. The 1,8-cineole induced apoptosis by inactivatingsurviving and Akt, activating p38, inducing PARP, and cleaving caspase-3(Rodd et al. 2015).
  • MetabolismEucalyptol undergoes oxidation in vivo with the formation of hydroxy cineole, which is excreted as hydroxycineoleglucuronic acid (Williams, 1959).
  • Purification MethodsPurify 1,8-cineol by dilution with an equal volume of pet ether, then saturate with dry HBr. The precipitate is filtered off, washed with small volumes of pet ether, then cineole is regenerated by stirring the crystals with H2O. It can also be purified via its o-cresol or resorcinol addition compounds. Store it over Na until required. Purify it also by fractional distillation. It is insoluble in H2O but soluble in organic solvents. [IR: Kome et al. Nippon Kagaku Zasshi [J Chem Soc Japan (Pure Chem Sect)] 80 66 1959, Chem Abstr 603 1961, Beilstein 17 II 32, 17/1 V 273.]
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