Eucalyptol
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Names | |||
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IUPAC name
1,3,3-Trimethyl-2-oxabicyclo[2.2.2]octane
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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 ) |
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105109 5239941 | |||
ChEBI | |||
ChEMBL | |||
ChemSpider | |||
DrugBank | |||
ECHA InfoCard
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100.006.757 | ||
EC Number |
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131076 | |||
IUPHAR/BPS |
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KEGG | |||
PubChem CID
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UNII | |||
CompTox Dashboard (EPA)
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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: | |||
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).
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Eucalyptol (also called cineole) is a
In 1870, F. S. Cloez identified and ascribed the name "eucalyptol" to the dominant portion of Eucalyptus globulus oil.[2]
Uses
Because of its pleasant, spicy aroma and taste, eucalyptol is used in flavorings, fragrances, and cosmetics.
Eucalyptol is an ingredient in commercial
Other
Eucalyptol exhibits insecticidal and insect repellent properties.[8][9]
In contrast, eucalyptol is one of many compounds that are attractive to males of various species of
Toxicology
Eucalyptol has a toxicity (
Biosynthesis
Eucalyptol is generated from geranyl pyrophosphate (GPP) which isomerizes to (S)-linalyl diphosphate (LPP). Ionization of the pyrophosphate, catalyzed by cineole synthase, produces eucalyptol. The process involves the intermediacy of alpha-terpinyl cation.[12][13][14]
Plants containing eucalyptol
- Aframomum corrorima[15]
- Artemisia tridentata[16]
- Cannabis[17]
- Cinnamomum camphora, camphor laurel (50%)[18]
- Eucalyptus globulus[19]
- Eucalyptus largiflorens[20]
- Eucalyptus salmonophloia[21]
- Eucalyptus staigeriana[22]
- Eucalyptus wandoo[23]
- Hedychium coronarium, butterfly lily[24][25]
- Helichrysum gymnocephalum[26]
- Kaempferia galanga, galangal, (5.7%)[27]
- Salvia lavandulifolia, Spanish sage (13%)[28]
- Turnera diffusa, damiana[29]
- Umbellularia californica, pepperwood (22.0%)[30]
- Zingiber officinale, ginger[31]
See also
References
- ^ a b c d e f g h i "Eucalyptol". PubChem, US National Library of Medicine. 22 April 2023. Retrieved 28 April 2023.
- ^ ISBN 0-909605-69-6.
- ^ "GCMS – Gas Chromatography Mass Spectrometry Analysis" (PDF). New Direction Aromatics. Archived (PDF) from the original on 28 October 2020. Retrieved 7 December 2022.
- ISBN 978-3527306732.
- ISBN 0-471-49226-4.
- ^ "Cigarette Ingredients – Chemicals in Cigarettes". New York State Department of Health. Retrieved 28 July 2014.
- ^ "Tea tree oil". Drugs.com. 17 June 2019. Retrieved 31 July 2019.
- S2CID 23271137.
- S2CID 23452066.
- S2CID 2845587.
- S2CID 54411184.
- PMID 28144299.
- ISSN 0021-9258.
- ISSN 0003-9861.
- .
The chemical composition of … Aframomum corrorima (l, 8-cineole 41.9%) … is also presented.
- .
- . Retrieved 20 September 2013.
- S2CID 85418932.
- S2CID 7665066.
- ^ Zhang J, An M, Wu H, Stanton R, Lemerle D (2010). "Chemistry and bioactivity of Eucalyptus essential oils" (PDF). Allelopathy Journal. 25 (2): 313–330.
- Charles Austin Gardner (1 August 1952). "Trees of Western Australia - salmon gum and scarlet pear gum". Journal of the Department of Agriculture Western Australia Series 3. 1 (4). Department of Primary Industries and Regional Development. Retrieved 23 January 2023.
- .
- PMID 34384412.
- S2CID 95463805.
- S2CID 27756399.
- .
- .
- S2CID 34457692.
- ISBN 978-1-58333-143-9.
- .
- S2CID 20981360.