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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-08-13 19:29:25 UTC

Update Date

2022-03-07 02:49:21 UTC

HMDB ID

HMDB0004472

Secondary Accession Numbers

HMDB0002267
HMDB02267
HMDB04472

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 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0004472
     RDKit          3D
Eucalyptol
 29 30  0  0  0  0  0  0  0  0999 V2000
    1.6649    1.2995    1.2849 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1082    0.3888    0.1971 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2863   -0.1003   -0.6057 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2612    1.0635   -0.6533 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9670    0.3933   -0.7070 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9182    1.0549   -1.6743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5754    0.5035    0.6714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8193   -0.4257    1.5788 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4774   -0.7858    0.8863 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0953   -1.8134   -0.1858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8040   -1.0433   -1.1528 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7955    0.7604    2.2464 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0487    2.1901    1.4501 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6906    1.6586    1.0084 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6155   -1.1064   -0.3617 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367   -0.0914   -1.7053 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1628    0.5917   -0.4975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3624    1.9555   -1.2164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7757    0.3352   -1.8021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4753    1.2352   -2.6524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3412    1.5480    1.0250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6569    0.3854    0.6935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6908   -0.0653    2.5973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4327   -1.3695    1.6445 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1776   -1.1886    1.6177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4928   -2.6012    0.3487 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9594   -2.2574   -0.6697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7919   -1.4906   -1.2448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2764   -1.0247   -2.1215 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  6
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  9  2  1  0
 11  5  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
  3 16  1  0
  3 17  1  0
  6 18  1  0
  6 19  1  0
  6 20  1  0
  7 21  1  0
  7 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  1
 10 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
M  END

HMDB0004472
     RDKit          3D
Eucalyptol
 29 30  0  0  0  0  0  0  0  0999 V2000
    1.6649    1.2995    1.2849 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1082    0.3888    0.1971 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2863   -0.1003   -0.6057 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2612    1.0635   -0.6533 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9670    0.3933   -0.7070 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9182    1.0549   -1.6743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5754    0.5035    0.6714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8193   -0.4257    1.5788 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4774   -0.7858    0.8863 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0953   -1.8134   -0.1858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8040   -1.0433   -1.1528 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7955    0.7604    2.2464 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0487    2.1901    1.4501 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6906    1.6586    1.0084 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6155   -1.1064   -0.3617 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367   -0.0914   -1.7053 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1628    0.5917   -0.4975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3624    1.9555   -1.2164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7757    0.3352   -1.8021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4753    1.2352   -2.6524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3412    1.5480    1.0250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6569    0.3854    0.6935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6908   -0.0653    2.5973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4327   -1.3695    1.6445 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1776   -1.1886    1.6177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4928   -2.6012    0.3487 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9594   -2.2574   -0.6697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7919   -1.4906   -1.2448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2764   -1.0247   -2.1215 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  6
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  9  2  1  0
 11  5  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
  3 16  1  0
  3 17  1  0
  6 18  1  0
  6 19  1  0
  6 20  1  0
  7 21  1  0
  7 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  1
 10 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
M  END

COMPND    HMDB0004472
HETATM    1  C1  UNL     1       1.665   1.300   1.285  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.108   0.389   0.197  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.286  -0.100  -0.606  1.00  0.00           C  
HETATM    4  O1  UNL     1       0.261   1.063  -0.653  1.00  0.00           O  
HETATM    5  C4  UNL     1      -0.967   0.393  -0.707  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.918   1.055  -1.674  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.575   0.504   0.671  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.819  -0.426   1.579  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.477  -0.786   0.886  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.095  -1.813  -0.186  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.804  -1.043  -1.153  1.00  0.00           C  
HETATM   12  H1  UNL     1       1.796   0.760   2.246  1.00  0.00           H  
HETATM   13  H2  UNL     1       1.049   2.190   1.450  1.00  0.00           H  
HETATM   14  H3  UNL     1       2.691   1.659   1.008  1.00  0.00           H  
HETATM   15  H4  UNL     1       2.615  -1.106  -0.362  1.00  0.00           H  
HETATM   16  H5  UNL     1       2.037  -0.091  -1.705  1.00  0.00           H  
HETATM   17  H6  UNL     1       3.163   0.592  -0.497  1.00  0.00           H  
HETATM   18  H7  UNL     1      -2.362   1.955  -1.216  1.00  0.00           H  
HETATM   19  H8  UNL     1      -2.776   0.335  -1.802  1.00  0.00           H  
HETATM   20  H9  UNL     1      -1.475   1.235  -2.652  1.00  0.00           H  
HETATM   21  H10 UNL     1      -1.341   1.548   1.025  1.00  0.00           H  
HETATM   22  H11 UNL     1      -2.657   0.385   0.694  1.00  0.00           H  
HETATM   23  H12 UNL     1      -0.691  -0.065   2.597  1.00  0.00           H  
HETATM   24  H13 UNL     1      -1.433  -1.370   1.645  1.00  0.00           H  
HETATM   25  H14 UNL     1       1.178  -1.189   1.618  1.00  0.00           H  
HETATM   26  H15 UNL     1      -0.493  -2.601   0.349  1.00  0.00           H  
HETATM   27  H16 UNL     1       0.959  -2.257  -0.670  1.00  0.00           H  
HETATM   28  H17 UNL     1      -1.792  -1.491  -1.245  1.00  0.00           H  
HETATM   29  H18 UNL     1      -0.276  -1.025  -2.122  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    4    9
CONECT    3   15   16   17
CONECT    4    5
CONECT    5    6    7   11
CONECT    6   18   19   20
CONECT    7    8   21   22
CONECT    8    9   23   24
CONECT    9   10   25
CONECT   10   11   26   27
CONECT   11   28   29
END

HMDB0004472
     RDKit          3D
Eucalyptol
 29 30  0  0  0  0  0  0  0  0999 V2000
    1.6649    1.2995    1.2849 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1082    0.3888    0.1971 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2863   -0.1003   -0.6057 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2612    1.0635   -0.6533 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9670    0.3933   -0.7070 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9182    1.0549   -1.6743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5754    0.5035    0.6714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8193   -0.4257    1.5788 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4774   -0.7858    0.8863 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0953   -1.8134   -0.1858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8040   -1.0433   -1.1528 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7955    0.7604    2.2464 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0487    2.1901    1.4501 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6906    1.6586    1.0084 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6155   -1.1064   -0.3617 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367   -0.0914   -1.7053 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1628    0.5917   -0.4975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3624    1.9555   -1.2164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7757    0.3352   -1.8021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4753    1.2352   -2.6524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3412    1.5480    1.0250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6569    0.3854    0.6935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6908   -0.0653    2.5973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4327   -1.3695    1.6445 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1776   -1.1886    1.6177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4928   -2.6012    0.3487 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9594   -2.2574   -0.6697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7919   -1.4906   -1.2448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2764   -1.0247   -2.1215 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  6
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  9  2  1  0
 11  5  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
  3 16  1  0
  3 17  1  0
  6 18  1  0
  6 19  1  0
  6 20  1  0
  7 21  1  0
  7 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  1
 10 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,3,3-TRIMETHYL-2-oxabicyclo[2.2.2]octane	ChEBI
1,8-Cineol	ChEBI
1,8-Epoxy-p-menthane	ChEBI
1,8-Oxido-p-menthane	ChEBI
Cajeputol	ChEBI
Cineole	ChEBI
Zineol	ChEBI
1,8-Cineole	HMDB
1,8-Eucalyptol	HMDB
2-Oxa-1,3,3-trimethylbicyclo[2.2.2]octane	HMDB
Eucaliptol	HMDB
Eucalyptole	HMDB
Eucalytol	HMDB
Eukalyptol	HMDB
p-Cineole	HMDB
Eucalyptol	ChEBI
Cineol	PhytoBank
Eucapur	PhytoBank
Terpan	PhytoBank

Chemical Formula

C₁₀H₁₈O

Average Molecular Weight

154.2493

Monoisotopic Molecular Weight

154.135765198

IUPAC Name

(1s,4s)-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octane

Traditional Name

1,8-cineole

CAS Registry Number

470-82-6

SMILES

C[C@@]12CC[C@@H](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/t8-,10+

InChI Key

WEEGYLXZBRQIMU-WAAGHKOSSA-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

cineole (CHEBI:27961 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 8866111)
Saliva (PMID: 24421258)

Tissue

Epithelium

Epidermis (HMDB: HMDB0004472)

Excreta

Biofluid or Excreta

Feces (PMID: 23454028)

Cellular substructure

Membrane (HMDB: HMDB0004472)

Source

Exogenous

Exogenous (HMDB: HMDB0004472)

Herb and spice mixture

Curry powder (FooDB: FOOD00678)

Vegetable

Cabbage

Onion-family vegetable

Root vegetable

Shoot vegetable

Leaf vegetable

Common beet (FooDB: FOOD00025)
Endive (FooDB: FOOD00048)
Rocket salad (ssp.) (FooDB: FOOD00077)
Swamp cabbage (FooDB: FOOD00091)
Lettuce (FooDB: FOOD00095)
Garden cress (FooDB: FOOD00099)
Spinach (FooDB: FOOD00178)
Swiss chard (FooDB: FOOD00237)
Chicory leaves (FooDB: FOOD00250)
Garland chrysanthemum (FooDB: FOOD00333)
Corn salad (FooDB: FOOD00340)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
Malabar spinach (FooDB: FOOD00404)
New Zealand spinach (FooDB: FOOD00415)
Yautia (FooDB: FOOD00510)
Ostrich fern (FooDB: FOOD00556)
Romaine lettuce (FooDB: FOOD00888)
Iceberg lettuce (FooDB: FOOD00973)
Pea shoots (FooDB: FOOD00975)
Yau choy (FooDB: FOOD00976)
Water spinach (FooDB: FOOD00977)

Fruit vegetable

Pepper (FooDB: FOOD00040)
Olive (FooDB: FOOD00121)
Avocado (FooDB: FOOD00130)
Garden tomato (FooDB: FOOD00171)
Cherry tomato (FooDB: FOOD00172)
Garden tomato (var.) (FooDB: FOOD00173)
Eggplant (FooDB: FOOD00174)
Pepper (C. baccatum) (FooDB: FOOD00231)
Pepper (C. chinense) (FooDB: FOOD00232)
Pepper (Capsicum) (FooDB: FOOD00233)
Groundcherry (FooDB: FOOD00371)
Pepper (C. frutescens) (FooDB: FOOD00428)
Mexican groundcherry (FooDB: FOOD00491)
Pepper (C. pubescens) (FooDB: FOOD00849)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Orange bell pepper (FooDB: FOOD00879)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Jalapeno pepper (FooDB: FOOD00955)
Cubanelle pepper (FooDB: FOOD00971)

Tuber

Stalk vegetable

Other vegetable

Giant butterbur (FooDB: FOOD00314)
Carob (FooDB: FOOD00321)
Chinese water chestnut (FooDB: FOOD00332)
Horseradish tree (FooDB: FOOD00379)
Sacred lotus (FooDB: FOOD00402)
Nopal (FooDB: FOOD00416)
Okra (FooDB: FOOD00420)
Sesbania flower (FooDB: FOOD00469)
Agave (FooDB: FOOD00563)
Narrowleaf cattail (FooDB: FOOD00564)
Heart of palm (FooDB: FOOD00718)
Tree fern (FooDB: FOOD00797)

Mushroom

Castanospermum australe (FooDB: FOOD00893)
Gentiana lutea (FooDB: FOOD00894)
Juniperus communis (FooDB: FOOD00895)
Albizia gummifera (FooDB: FOOD00896)

Fruit

Tropical fruit

Citrus

Lime (FooDB: FOOD00053)
Lemon (FooDB: FOOD00054)
Pummelo (FooDB: FOOD00055)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Sweet orange (FooDB: FOOD00057)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Grapefruit (FooDB: FOOD00256)
Persian lime (FooDB: FOOD00543)
Sour orange (FooDB: FOOD00918)
Mikan (FooDB: FOOD00932)
Clementine (FooDB: FOOD00959)

Pome

Berry

Black crowberry (FooDB: FOOD00075)
Strawberry (FooDB: FOOD00083)
Black huckleberry (FooDB: FOOD00084)
Sea-buckthornberry (FooDB: FOOD00087)
Mulberry (FooDB: FOOD00116)
Black mulberry (FooDB: FOOD00117)
Black chokeberry (FooDB: FOOD00136)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Gooseberry (FooDB: FOOD00157)
Cloudberry (FooDB: FOOD00161)
Red raspberry (FooDB: FOOD00162)
Black raspberry (FooDB: FOOD00163)
Black elderberry (FooDB: FOOD00166)
Rowanberry (FooDB: FOOD00176)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
American cranberry (FooDB: FOOD00192)
Bilberry (FooDB: FOOD00193)
Lingonberry (FooDB: FOOD00194)
Muscadine grape (FooDB: FOOD00203)
Common grape (FooDB: FOOD00204)
Arctic blackberry (FooDB: FOOD00207)
Bayberry (FooDB: FOOD00209)
Elliott's blueberry (FooDB: FOOD00210)
Canada blueberry (FooDB: FOOD00211)
Bog bilberry (FooDB: FOOD00212)
Buffalo currant (FooDB: FOOD00213)
European cranberry (FooDB: FOOD00217)
Deerberry (FooDB: FOOD00218)
Cascade huckleberry (FooDB: FOOD00220)
Oval-leaf huckleberry (FooDB: FOOD00221)
Evergreen huckleberry (FooDB: FOOD00222)
Red huckleberry (FooDB: FOOD00223)
Summer grape (FooDB: FOOD00227)
Fox grape (FooDB: FOOD00228)
Half-highbush blueberry (FooDB: FOOD00248)
Jostaberry (FooDB: FOOD00257)
Sweet rowanberry (FooDB: FOOD00265)
Skunk currant (FooDB: FOOD00267)
Squashberry (FooDB: FOOD00344)
Elderberry (FooDB: FOOD00358)
Grape (FooDB: FOOD00369)
Alaska blueberry (FooDB: FOOD00380)
Loganberry (FooDB: FOOD00400)
Ohelo berry (FooDB: FOOD00419)
Salmonberry (FooDB: FOOD00456)
Strawberry guava (FooDB: FOOD00482)
Boysenberry (FooDB: FOOD00542)
Chinese bayberry (FooDB: FOOD00852)
Saskatoon berry (FooDB: FOOD00884)
Nanking cherry (FooDB: FOOD00885)
Rabbiteye blueberry (FooDB: FOOD00898)
Blackberry (FooDB: FOOD00906)
Partridge berry (FooDB: FOOD00931)
Green grape (FooDB: FOOD00964)
Red grape (FooDB: FOOD00965)
Black plum (FooDB: FOOD00966)
Black raisin (FooDB: FOOD00968)
Chinese plum (FooDB: FOOD00978)
Green plum (FooDB: FOOD00979)
Wampee (FooDB: FOOD00980)
Goji (FooDB: FOOD00982)
Monk fruit (FooDB: FOOD00983)
Hawthorn (FooDB: FOOD00985)
Lantern fruit (FooDB: FOOD00986)
Cape gooseberry (FooDB: FOOD00988)

Other fruit

Fig (FooDB: FOOD00081)
Date (FooDB: FOOD00135)
Jujube (FooDB: FOOD00388)

Drupe

Prunus (Cherry, Plum) (FooDB: FOOD00143)
Apricot (FooDB: FOOD00144)
Sweet cherry (FooDB: FOOD00145)
Sour cherry (FooDB: FOOD00146)
European plum (FooDB: FOOD00147)
Peach (FooDB: FOOD00149)
Nectarine (FooDB: FOOD00229)
Peach (var.) (FooDB: FOOD00230)
Common chokecherry (FooDB: FOOD00562)

Nut

Cashew nut (FooDB: FOOD00011)
Peanut (FooDB: FOOD00016)
Brazil nut (FooDB: FOOD00024)
Pecan nut (FooDB: FOOD00044)
Chestnut (FooDB: FOOD00045)
Common hazelnut (FooDB: FOOD00062)
Black walnut (FooDB: FOOD00093)
Common walnut (FooDB: FOOD00094)
Pine nut (FooDB: FOOD00138)
Pistachio (FooDB: FOOD00140)
Almond (FooDB: FOOD00148)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Japanese walnut (FooDB: FOOD00240)
Acorn (FooDB: FOOD00282)
Beech nut (FooDB: FOOD00299)
Butternut (FooDB: FOOD00316)
Chinese chestnut (FooDB: FOOD00331)
European chestnut (FooDB: FOOD00363)
Hazelnut (FooDB: FOOD00376)
Hickory nut (FooDB: FOOD00377)
Japanese chestnut (FooDB: FOOD00385)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Macadamia nut (FooDB: FOOD00525)
Walnut (FooDB: FOOD00608)

Cereal and cereal product

Cereal

Cereal product

Pasta (FooDB: FOOD00273)
Bulgur (FooDB: FOOD00741)
Semolina (FooDB: FOOD00745)
Flour (FooDB: FOOD00799)

Dough

Sourdough (FooDB: FOOD00275)

Leavened bread

Flat bread

Other bread

Potato bread (FooDB: FOOD00811)

Sweet bread

Raisin bread (FooDB: FOOD00817)

Pulse

Pea

Lentil

Lentils (FooDB: FOOD00098)

Other pulse

Lupine (FooDB: FOOD00104)
White lupine (FooDB: FOOD00403)

Bean

Green lentil (FooDB: FOOD00970)

Gourd

Watermelon (FooDB: FOOD00052)
Muskmelon (FooDB: FOOD00064)
Cucumber (FooDB: FOOD00065)
Cucurbita (FooDB: FOOD00066)
Bitter gourd (FooDB: FOOD00115)
Winter squash (FooDB: FOOD00283)
Butternut squash (FooDB: FOOD00317)
Calabash (FooDB: FOOD00318)
Chayote (FooDB: FOOD00325)
Towel gourd (FooDB: FOOD00492)
Wax gourd (FooDB: FOOD00499)
Tinda (FooDB: FOOD00559)
Horned melon (FooDB: FOOD00761)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Acorn squash (FooDB: FOOD00972)
Cantaloupe melon (FooDB: FOOD00984)

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Soy sauce (FooDB: FOOD00694)
Miso (FooDB: FOOD00695)
Tofu (FooDB: FOOD00696)
Soy milk (FooDB: FOOD00736)
Soy cream (FooDB: FOOD00784)

Tea

Herbal tea

Hibiscus tea (FooDB: FOOD00723)
Greenthread tea (FooDB: FOOD00820)

Baking good

Wrapper

Wonton wrapper (FooDB: FOOD00818)

Dish

Other dish

Tostada shell (FooDB: FOOD00992)
Taco shell (FooDB: FOOD00991)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Monoterpenoid Biosynthesis (PathBank: SMP0014204)

Role

Not Available

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	1.5 °C	Not Available
Boiling Point	176.00 to 177.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	3.5 mg/mL at 21 °C	Not Available
LogP	2.74	GRIFFIN,S ET AL. (1999)

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	173.004	30932474
DeepCCS	[M+Na]+	147.402	30932474
AllCCS	[M+H]+	131.5	32859911
AllCCS	[M+H-H2O]+	126.9	32859911
AllCCS	[M+NH4]+	135.7	32859911
AllCCS	[M+Na]+	136.9	32859911
AllCCS	[M-H]-	138.5	32859911
AllCCS	[M+Na-2H]-	139.8	32859911
AllCCS	[M+HCOO]-	141.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Eucalyptol	C[C@@]12CC[C@@H](CC1)C(C)(C)O2	1183.1	Standard polar	33892256
Eucalyptol	C[C@@]12CC[C@@H](CC1)C(C)(C)O2	1016.6	Standard non polar	33892256
Eucalyptol	C[C@@]12CC[C@@H](CC1)C(C)(C)O2	1023.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Eucalyptol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f79-3900000000-207d29106cfe3c54c018	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Eucalyptol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0536-9200000000-aa52695ff4a2c1313e0b	2015-03-01	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Eucalyptol Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-001i-9500000000-9dc534a13d795eb1b96c	2020-03-10	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Eucalyptol Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-001i-9000000000-c05885d0e60c65af2adf	2020-03-10	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Eucalyptol Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-003u-9000000000-217a9576a252e6456825	2020-03-10	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eucalyptol 10V, Positive-QTOF	splash10-0a4i-0900000000-87fbd679809c90a3eb19	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eucalyptol 20V, Positive-QTOF	splash10-0a4i-0900000000-aa8e8e9cd53dad3b120e	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eucalyptol 40V, Positive-QTOF	splash10-052r-0900000000-5296316e735fc49999bf	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eucalyptol 10V, Negative-QTOF	splash10-0udi-0900000000-99f5c9faaf8cf2b40394	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eucalyptol 20V, Negative-QTOF	splash10-0udi-0900000000-99f5c9faaf8cf2b40394	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eucalyptol 40V, Negative-QTOF	splash10-0f79-0900000000-da51d6a18dbcbda3b168	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eucalyptol 10V, Negative-QTOF	splash10-0udi-0900000000-d2363ae8d4dbdcccda80	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eucalyptol 20V, Negative-QTOF	splash10-0udi-0900000000-d2363ae8d4dbdcccda80	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eucalyptol 40V, Negative-QTOF	splash10-0udi-0900000000-9ea4da9bfdad90f3be7e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eucalyptol 10V, Positive-QTOF	splash10-0a4i-0900000000-085a10049717ea8e20df	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eucalyptol 20V, Positive-QTOF	splash10-0a4i-0900000000-085a10049717ea8e20df	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eucalyptol 40V, Positive-QTOF	splash10-0pbi-0900000000-5cb534f49edce4797f2c	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	2020-03-10	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Blood
Feces
Saliva

Tissue Locations

Epidermis

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	23454028	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	24421258	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	5.13 (2.98-7.36) uM	Adult (>18 years old)	Both	Eucalyptol exposure	8866111	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Nonalcoholic fatty liver disease (NAFLD)	23454028	details

Associated Disorders and Diseases

Disease References

Eucalyptol exposure
Jager W, Nasel B, Nasel C, Binder R, Stimpfl T, Vycudilik W, Buchbauer G: Pharmacokinetic studies of the fragrance compound 1,8-cineol in humans during inhalation. Chem Senses. 1996 Aug;21(4):477-80. [PubMed:8866111 ]
Nonalcoholic fatty liver disease
Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]

Associated OMIM IDs

None

External Links

DrugBank ID

DB03852

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

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

27961

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1056361

References

Synthesis Reference

Lana, Enio J. Leao; Rocha, Kelly A. da Silva; Kozhevnikov, Ivan V.; Gusevskaya, Elena V. Synthesis of 1,8-cineole and 1,4-cineole by isomerization of a-terpineol catalyzed by heteropoly acid. Journal of Molecular Catalysis A: Chemical (2006), 259(1-2), 99-102.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

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. [PubMed:12086718 ]
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. [PubMed:15653134 ]
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. Epub 2006 Jan 31. [PubMed:16451823 ]
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. [PubMed:7536240 ]
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. [PubMed:15477123 ]
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. [PubMed:9811155 ]
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 ]
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 ]
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. Epub 2005 Jan 17. [PubMed:15715982 ]
De Vincenzi M, Silano M, De Vincenzi A, Maialetti F, Scazzocchio B: Constituents of aromatic plants: eucalyptol. Fitoterapia. 2002 Jun;73(3):269-75. [PubMed:12048025 ]
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 ]

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

Reactions

Eucalyptol + NADPH + Oxygen → 2-exo-hydroxy-1,8-cineole + NADP + Water	details

Showing metabocard for Eucalyptol (HMDB0004472)

MOL for HMDB0004472 (Eucalyptol)

3D MOL for HMDB0004472 (Eucalyptol)

3D SDF for HMDB0004472 (Eucalyptol)

3D-SDF for HMDB0004472 (Eucalyptol)

PDB for HMDB0004472 (Eucalyptol)

3D PDB for HMDB0004472 (Eucalyptol)

SMILES for HMDB0004472 (Eucalyptol)

INCHI for HMDB0004472 (Eucalyptol)

Structure for HMDB0004472 (Eucalyptol)

3D Structure for HMDB0004472 (Eucalyptol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions