Eukaliptol (1,8-cineol)

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Uzorak

Eukaliptol (1,8-cineol) kao sirovina za parfeme — Gornje note

Prirodni izolat

Definicija

Eucalyptol (1,8-cineole) is a monoterpenoid colorless liquid and a bicyclic ether. It has a fresh camphor-like odor.

cineole, cineol, cajeputol, eucalyptole

Type: Sirovina
Olfactive family: Aromatični
Source: eucalyptus leaves
Chemical class: monoterpenoid, bicyclic ether

Instrumenti

Piramida

GGornje note

SSrednje note

BBazne note

Zemlje proizvođači

China South Africa Portugal Spain Brazil Australia Chile Eswatini

Miris

The odor of eucalyptol is camphor-like, and a fresh smell is also reported. Its aroma is described as pleasant and spicy.

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Detaljno

Eucalyptol has the IUPAC name 1,3,3-trimethyl-2-oxabicyclo[2.2.2]octane. It is insoluble in water, but miscible with organic solvents. It has a spicy, cooling taste.

Eucalyptol makes up about 70-90% of eucalyptus oil. Eucalyptus oil contains 1,4-cineole as well, a compound of similar structure. Global production is dominated by oil from Eucalyptus globulus. The oil yield of Eucalyptus globulus ranges from 1.0 to 2.4% (fresh weight), with cineole being the major isolate. Eucalyptus kochii and Eucalyptus polybractea have the highest cineole content, ranging from 80 to 95%. The British Pharmacopoeia states that pharmaceutical-grade oil must have a minimum cineole content of 70%. In 1991, global annual production was estimated at 3,000 tonnes of medicinal eucalyptus oil. China produces about 75% of the world's eucalyptus oil output, but most of it comes from the cineole fractions of camphor laurel rather than from true eucalyptus oil. The most abundant component of laurel essential oil is 1,8-cineole, also called eucalyptol. The leaves of bay laurel contain about 1.3% essential oil, and eucalyptol makes up 45% of that oil. Cardamom seed oil is typically 2% 1,8-cineol. In the seeds of round cardamom from Java, the oil contains mainly 1,8-cineol, up to 70%.

Eucalyptol elicits a cooling sensation when ingested or applied to the skin. It acts as an agonist of the TRPM8 channel, with lower efficacy and potency than menthol. It activates the human TRPM8 channel but inhibits human TRPA1 activated by several agonists. Its known analgesic and anti-inflammatory actions are suggested to arise from its TRPM8-activating and TRPA1-inhibiting abilities. It inhibits the chemical nociception produced by several irritants and has an anti-inflammatory efficacy in patients with severe asthma. Eucalyptol also exhibits insecticidal and insect repellent properties.

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Related: 4 Methylanisole · Almaciga · Arnica · Assam Tea · Calycanthus · Camphor · Canvas · Carvone

Istorija

In 1852 Joseph Bosisto, a Melbourne pharmacist, started the commercial eucalyptus oil industry near Dandenong, Victoria, Australia, by setting up a distillation plant to extract the essential oil from the cineole chemotype of Eucalyptus radiata. The cineole chemotype thus became the generic oil of eucalyptus. By the 1870s oil from Eucalyptus globulus, the Tasmanian blue gum, was being exported worldwide, and it eventually dominated world trade. Surgeons were using eucalyptus oil as an antiseptic during surgery by the 1880s. Eucalyptus oil was in particularly big demand during the global influenza pandemic of 1918-19. The Australian eucalyptus oil industry peaked in the 1940s. By the 1950s the cost of producing eucalyptus oil in Australia had risen so much that it could not compete against cheaper Spanish and Portuguese oils.

Zanimljivosti

The abundant eucalyptus trees of the Blue Mountains in New South Wales emit volatile terpenoids in large quantities, which may scatter light and so produce the blue haze that gave the mountains their name.

Dobijanje i hemija

Način dobijanja

Eucalyptus oil is obtained by steam distillation of the leaves of selected Eucalyptus species. Rectification brings lower grade oils up to the high cineole standard required. Batch vacuum fractional distillation of Eucalyptus camaldulensis oil at 60 mmHg, through a 500 mm Hempel column packed with small metal helixes, raised the 1,8-cineole content from 47.9% to 74.6%. That distillation reached 97% recovery and a yield of over 60%. The conditions tested covered operating pressures from 60 to 160 mmHg, Vigreux and Hempel columns, and column heights of 300 to 600 mm. Eucalyptol forms crystalline adducts with hydrohalic acids, o-cresol, resorcinol and phosphoric acid, and forming them is useful for purification.

Formula: C₁₀H₁₈O
CAS: 470-82-6
Izgled: Colorless liquid
Sinonimi: cineole, cineol, cajeputol, eucalyptole

Status prema standardima IFRA

Pogledajte napomenu

No IFRA Standard for the material itself (51st Amendment)

Fizička svojstva

Tačka ključanja: 176-177 °C
Tačka topljenja: 1.5 °C
Tačka paljenja: 49 °C (120 °F), closed cup
Relativna gustina: 0.921-0.923 at 25 °C/25 °C
Indeks prelamanja: 1.455-1.460 at 20 °C/D

U parfemima

Eucalyptol is used in flavorings, fragrances and cosmetics for its pleasant, spicy aroma and taste. Eucalyptus oil based on cineole serves as a flavoring at a low level of 0.002% in products such as baked goods, confectionery, meat products and beverages. Eucalyptol is a natural cooling agent. Eucalyptol is an ingredient in commercial mouthwashes and cough suppressants.

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