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

2024-10-06 23:40:35 UTC

Metabolite 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

Value	Source
1,8-Cineol	Kegg
1,3,3-Trimethyl-2-oxabicyclo[2.2.2]octane	Kegg
Cineole	Kegg
1,8-Cineole	HMDB
Soledum	HMDB
1,8-Epoxy-p-menthane	HMDB
1,8-Oxido-p-menthane	HMDB
2-Oxa-1,3,3-trimethylbicyclo[2.2.2]octane	HMDB
Cajeputol	HMDB
CINEOL	HMDB
CNL	HMDB
Cucalyptol	HMDB
Eucalyptole	HMDB
Eucapur	HMDB
Eukalyptol	HMDB
Limonene oxide	HMDB
p-Cineole	HMDB
Terpan	HMDB
Zedoary oil	HMDB
Zineol	HMDB
1,8 Epoxy p menthane	MeSH
1,8 Cineol	MeSH
1,8 Cineole	MeSH

Molecular Formula

C₁₀H₁₈O

Average Mass

154.253

Monoisotopic Mass

154.1357652

IUPAC Name

1,3,3-trimethyl-2-oxabicyclo[2.2.2]octane

Traditional Name

eucalyptol

CAS Registry Number

Not Available

SMILES

CC12CCC(CC1)C(C)(C)O2

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

Description

Belongs to the class of organic compounds known as oxanes. Oxanes are compounds containing an oxane (tetrahydropyran) ring, which is a six-member saturated aliphatic heterocycle with one oxygen atom and five carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxanes

Sub Class

Not Available

Direct Parent

Oxanes

Alternative Parents

Substituents

Oxane
Oxacycle
Ether
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Menthane monoterpenoids (C09844 )
Cyclic monoterpenes (C09844 )
Menthane monoterpenoids (LMPR0102090019 )
a monoterpenoid (CPD-4261 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.022 g/L	ALOGPS
logP	3.36	ALOGPS
logP	2.35	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	9.23 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	45.86 m³·mol⁻¹	ChemAxon
Polarizability	18.54 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-EI-Q (Non-derivatized)	splash10-000x-9200000000-f7ec56dac2ebea83be0e	2020-07-08	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f79-3900000000-207d29106cfe3c54c018	2017-07-27	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-001i-9500000000-9dc534a13d795eb1b96c	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-001i-9000000000-c05885d0e60c65af2adf	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-003u-9000000000-217a9576a252e6456825	2012-07-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0900000000-87fbd679809c90a3eb19	2017-06-28	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0900000000-aa8e8e9cd53dad3b120e	2017-06-28	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052r-0900000000-5296316e735fc49999bf	2017-06-28	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-99f5c9faaf8cf2b40394	2017-06-28	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0900000000-99f5c9faaf8cf2b40394	2017-06-28	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0f79-0900000000-da51d6a18dbcbda3b168	2017-06-28	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, experimental)		2012-12-05	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)		2012-12-05	View Spectrum

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

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites
Bacteria	Actinobacteria	1
Bacteria	Proteobacteria	1
Eukaryota/Fungi	Ascomycota	1	Human feces
Eukaryota/Fungi	Basidiomycota	1

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

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

External Links

HMDB ID

HMDB0004472

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Eucalyptol

METLIN ID

7060

PubChem Compound

2758

PDB ID

Not Available

ChEBI ID

584235

Food Biomarker Ontology

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:0x00007f46ec647690>

3D MOL for #<Metabolite:0x00007f46ec647690>

3D SDF for #<Metabolite:0x00007f46ec647690>

3D-SDF for #<Metabolite:0x00007f46ec647690>

PDB for #<Metabolite:0x00007f46ec647690>

3D PDB for #<Metabolite:0x00007f46ec647690>

SMILES for #<Metabolite:0x00007f46ec647690>

INCHI for #<Metabolite:0x00007f46ec647690>

Structure for #<Metabolite:0x00007f46ec647690>

3D Structure for #<Metabolite:0x00007f46ec647690>