MiMeDB: Showing metabocard for Eucalyptol (MMDBc0053238)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-05-16 21:18:17 UTC

Update Date

2022-12-15 22:52:20 UTC

MiMeDB ID

MMDBc0053238

Metabolite Identification

Common Name

Eucalyptol

Description

Eucalyptol is an organic compound that is a colourless liquid. It is a cyclic ether and a monoterpene. Eucalyptol is a natural constituent of a number of aromatic plants and their essential oil fraction. Eucalyptol was given GRAS (Generally Recognized As Safe) status by the Flavor and Extract Manufacturer's Association FEMA, 1965 and is approved by the Food and Drug Administration for food use. 1,8-Dihydroxy-10-carboxy-p-menthane, 2-hydroxy-cineole, and 3-hydroxy-cineole are the main metabolites of eucalyptol. Toxicological data available on eucalyptol are rather limited. Following accidental exposure, death was reported in two cases after ingestion of 3.5-5 mL of essential eucalyptus oil, but a number of recoveries have also been described for much higher amounts of oil. In a 1994 report released by five top cigarette companies, eucalyptol was listed as one of the 599 additives to cigarettes. It is usually added to improve the flavour (PMID:12048025 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₁₀H₁₈O

Average Molecular Weight

154.253

Monoisotopic Molecular Weight

154.1357652

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

Not Available

InChI Identifier

InChI=1S/C10H18O/c1-9(2)8-4-6-10(3,11-9)7-5-8/h8H,4-7H2,1-3H3

InChI Key

WEEGYLXZBRQIMU-UHFFFAOYSA-N

Chemical Taxonomy

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Not Available

Spectra

Not Available

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Epidermis
Feces
Saliva

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Proteins

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Related Health Condition	Evidence Type	Measured in Matrix	Data Source	Reference

Microbial Sources

Kingdom	Phylum	Total species	Hosts and Body Sites
	Actinobacteria	1
	Proteobacteria	1
Fungi	Ascomycota	1	Human Feces
Fungi	Basidiomycota	1

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference	Details

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Min	Max	Age	Sex	Health Condition	Data Source	Reference
Human	Detected and Quantified	5.13	2.98	7.36	Adult (>18 years old)	Both	Eucalyptol exposure	HMDB	8866111	details
Human Epidermis	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597	details
Human Saliva	Detected but not Quantified				Adult (>18 years old)	Not Specified	Normal	HMDB	24421258	details
Human Feces	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	23454028	details

External Links

Not Available

References

Synthesis Reference

Not Available

General References

Kato T, Iijima H, Ishihara K, Kaneko T, Hirai K, Naito Y, Okuda K: Antibacterial effects of Listerine on oral bacteria. Bull Tokyo Dent Coll. 1990 Nov;31(4):301-7. [PubMed:2133450 ]
Cornwell PA, Barry BW, Stoddart CP, Bouwstra JA: Wide-angle X-ray diffraction of human stratum corneum: effects of hydration and terpene enhancer treatment. J Pharm Pharmacol. 1994 Dec;46(12):938-50. doi: 10.1111/j.2042-7158.1994.tb03248.x. [PubMed:7536240 ]
Moghimi HR, Williams AC, Barry BW: Enhancement by terpenes of 5-fluorouracil permeation through the stratum corneum: model solvent approach. J Pharm Pharmacol. 1998 Sep;50(9):955-64. doi: 10.1111/j.2042-7158.1998.tb06909.x. [PubMed:9811155 ]
Harper DS, Brogdon CL, Wu MM, Epelle U: A rapid method for evaluating microbicidal activity of dentifrice formulations against salivary bacteria ex vivo. J Clin Dent. 2000;11(4):89-93. [PubMed:11460277 ]
De Vincenzi M, Silano M, De Vincenzi A, Maialetti F, Scazzocchio B: Constituents of aromatic plants: eucalyptol. Fitoterapia. 2002 Jun;73(3):269-75. doi: 10.1016/s0367-326x(02)00062-x. [PubMed:12048025 ]
Giannakou SA, Dallas PP, Rekkas DM, Choulis NH: In vitro evaluation of nimodipine permeation through human epidermis using response surface methodology. Int J Pharm. 2002 Jul 8;241(1):27-34. doi: 10.1016/s0378-5173(02)00102-3. [PubMed:12086718 ]
Juergens UR, Engelen T, Racke K, Stober M, Gillissen A, Vetter H: Inhibitory activity of 1,8-cineol (eucalyptol) on cytokine production in cultured human lymphocytes and monocytes. Pulm Pharmacol Ther. 2004;17(5):281-7. doi: 10.1016/j.pupt.2004.06.002. [PubMed:15477123 ]
Narishetty ST, Panchagnula R: Effect of L-menthol and 1,8-cineole on phase behavior and molecular organization of SC lipids and skin permeation of zidovudine. J Control Release. 2005 Jan 20;102(1):59-70. doi: 10.1016/j.jconrel.2004.09.016. [PubMed:15653134 ]
Duisken M, Sandner F, Blomeke B, Hollender J: Metabolism of 1,8-cineole by human cytochrome P450 enzymes: identification of a new hydroxylated metabolite. Biochim Biophys Acta. 2005 Apr 15;1722(3):304-11. doi: 10.1016/j.bbagen.2004.12.019. Epub 2005 Jan 17. [PubMed:15715982 ]
Lim PF, Liu XY, Kang L, Ho PC, Chan YW, Chan SY: Limonene GP1/PG organogel as a vehicle in transdermal delivery of haloperidol. Int J Pharm. 2006 Mar 27;311(1-2):157-64. doi: 10.1016/j.ijpharm.2005.12.042. Epub 2006 Jan 31. [PubMed:16451823 ]
Bastos VP, Gomes AS, Lima FJ, Brito TS, Soares PM, Pinho JP, Silva CS, Santos AA, Souza MH, Magalhaes PJ: Inhaled 1,8-cineole reduces inflammatory parameters in airways of ovalbumin-challenged Guinea pigs. Basic Clin Pharmacol Toxicol. 2011 Jan;108(1):34-9. doi: 10.1111/j.1742-7843.2010.00622.x. Epub 2010 Aug 16. [PubMed:20722639 ]

Showing metabocard for Eucalyptol (MMDBc0053238)

MOL for #<Metabolite:0x000055b76dfb7758>

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Structure for #<Metabolite:0x000055b76dfb7758>

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