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Eucalyptol

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**Uses of Eucalyptol**:
– Used in flavorings, fragrances, cosmetics, and commercial mouthwashes.
– Cineole-based eucalyptus oil is utilized in baked goods, confectionery, meat products, and beverages.
– Listed as an additive in cigarettes for flavor enhancement.
– Traditional medicinal use as a cough suppressant.

**Properties and Effects of Eucalyptol**:
– Exhibits insecticidal and insect repellent properties.
– Attracts orchid bees for pheromone synthesis and territorial behavior.
– Used as bait for studying orchid bees.
– Forms crystalline adducts with various compounds for purification.

**Toxicology of Eucalyptol**:
– LD50 toxicity of 2.48 grams per kg (rat).
– Ingestion in significant quantities can cause headache and gastric distress.
– Low viscosity may lead to lung entry if swallowed or vomited.
– Presence in lungs can cause severe injury or death.
– Can result in delirium and convulsions.

**Biosynthesis of Eucalyptol**:
– Generated from geranyl pyrophosphate (GPP).
– Isomerizes to ()-linalyl diphosphate (LPP).
– Ionization of pyrophosphate by cineole synthase produces eucalyptol.
– Involves the intermediacy of alpha-terpinyl cation.
– Found in various plant species like ginger and eucalyptus.

**Essential Oils and Their Medicinal Properties**:
– Eucalyptol is a natural organic compound found in plants like eucalyptus.
– Essential oils possess antimicrobial activity against bacteria and fungi.
– Used in traditional medicine for anti-inflammatory purposes.
– Aromatherapy and skincare products utilize essential oils for therapeutic benefits.
– Research explores the medicinal potential of essential oils for various health conditions.

Eucalyptol (Wikipedia)

Eucalyptol (also called cineole) is a monoterpenoid colorless liquid, and a bicyclic ether. It has a fresh camphor-like odor and a spicy, cooling taste. It is insoluble in water, but miscible with organic solvents. Eucalyptol makes up about 70–90% of eucalyptus oil. Eucalyptol forms crystalline adducts with hydrohalic acids, o-cresol, resorcinol, and phosphoric acid. Formation of these adducts is useful for purification.

Eucalyptol
Names
IUPAC name
1,3,3-Trimethyl-2-oxabicyclo[2.2.2]octane
Other names
1,8-Cineole
1,8-Epoxy-p-menthane
cajeputol
1,8-epoxy-p-menthane, 1,8-oxido-p-menthane
eucalyptole
1,3,3-trimethyl-2-oxabicyclo[2.2.2]octane
cineol
cineole.
Identifiers
3D model (JSmol)
105109 5239941
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.006.757 Edit this at Wikidata
EC Number
  • 207-431-5
131076
KEGG
UNII
  • InChI=1S/C10H18O/c1-9(2)8-4-6-10(3,11-9)7-5-8/h8H,4-7H2,1-3H3 checkY
    Key: WEEGYLXZBRQIMU-UHFFFAOYSA-N checkY
  • InChI=1/C10H18O/c1-9(2)8-4-6-10(3,11-9)7-5-8/h8H,4-7H2,1-3H3
    Key: WEEGYLXZBRQIMU-UHFFFAOYAY
  • O2C1(CCC(CC1)C2(C)C)C
Properties
C10H18O
Molar mass 154.249 g/mol
Density 0.9225 g/cm3
Melting point 2.9 °C (37.2 °F; 276.0 K)
Boiling point 176–177 °C (349–351 °F; 449–450 K)
−116.3×10−6 cm3/mol
Pharmacology
R05CA13 (WHO)
Hazards
GHS labelling:
GHS02: FlammableGHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
Danger
H226, H304, H315, H317, H319, H411
P210, P233, P240, P241, P242, P243, P261, P264, P272, P273, P280, P301+P310, P302+P352, P303+P361+P353, P305+P351+P338, P321, P331, P332+P313, P333+P313, P337+P313, P362, P363, P370+P378, P391, P403+P235, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

In 1870, F. S. Cloez identified and ascribed the name "eucalyptol" to the dominant portion of Eucalyptus globulus oil.

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