1,8-Cineole

  • GreenMolBD CID : 44
  • Molecular Formula : C10H18O
  • Molecular Weight : 154.253
  • Exact Molecular Mass : 154.136
  • IUPAC Name : 2,2,4-trimethyl-3-oxabicyclo[2.2.2]octane
  • InChI : 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
  • Canonical SMILES : CC1(C2CCC(O1)(CC2)C)C
  • Isomeric SMILES : CC1(C2CCC(O1)(CC2)C)C
  • Cross Reference  Pubchem

1. Classification

1.1. Description

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

1.2. Taxonomy Tree

1.3. Alternative Parent

Oxacyclic compounds; Dialkyl ethers; Hydrocarbon derivatives;

1.4. Molecular Framework

Aliphatic heteropolycyclic compounds

1.5. Substituents

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

2. Physical Properties

SlogP TPSA HBD HBA nHA nRB nAA nAB SMR vdw_vol vdw_area Density
2.7441 9.23 0 1 11 0 0 0 4.5527 241.057 170.329 0.639902

3. Quantum Information

Heat of Formation Dipole Moment Electronegativity Homo Lumo Hardness
-106.218504 1.32 -3.725 -10.32045 2.87078 6.596

4. Compound Reactivity

DLP nRFG nLMR
5 0 1

5. Topkat Properties

WOE Prediction Ames Prediction DTP Prediction Rat Oral LD50 (g/kg body weight) Rat Inhalational LC50 (mg/m3/h) Chronic LOAEL (g/kg body weight) Skin Irritancy Skin Sensitization Ocular Irritancy Aerobic Biodegradability Prediction Fathead Minnow LC50 (g/l) Daphnia EC50 (mg/l)
Carcinogen Non-Mutagen Non-Toxic 4.11047 25053.9 0.0233248 Moderate Weak None Degradable 0.0336051 14.0624

6. Drug-Likeliness Test

Lipinski's rule of five Jorgensen's rule of three Goshe filter Veber filter PAINS1 PAINS2 PAINS3
Yes Yes No Yes Yes Yes Yes

7. Synonyms

Name
Eucalyptol
cineole
1,8-Cineole
1,8-Cineol
Cajeputol
1,8-Epoxy-p-menthane
470-82-6
Eucalyptole
Zineol
Eucapur
Terpan
p-Cineole
1,8-Oxido-p-menthane
1,3,3-Trimethyl-2-oxabicyclo[2.2.2]octane
Eukalyptol
CINEOL
Cucalyptol
Eukalyptol [Czech]
Soledum
Eucalyptol (natural)
Zedoary oil
p-Menthane, 1,8-epoxy-
Cineole (VAN)
EUCALYPTUS OIL
2-Oxabicyclo[2.2.2]octane, 1,3,3-trimethyl-
Eucalyptol [USAN]
NCI-C56575
UNII-RV6J6604TK
FEMA No. 2465
NSC 6171
1,3,3-Trimethyl-2-oxabicyclo(2.2.2)octane
2-Oxa-1,3,3-trimethylbicyclo(2.2.2)octane
Eucalyptol (USAN)
2-Oxabicyclo(2.2.2)octane, 1,3,3-trimethyl-
CCRIS 3727
HSDB 991
Cineole (Eucalyptol)
NSC6171
2,2,4-trimethyl-3-oxabicyclo[2.2.2]octane
2-Oxa-1,3,3-trimethylbicyclo[2.2.2]octane
EINECS 207-431-5
Cineolum
BIDD:ER0481
AI3-00578
RV6J6604TK
CNL
4,7,7-trimethyl-8-oxabicyclo[2.2.2]octane
CHEBI:27961
WEEGYLXZBRQIMU-UHFFFAOYSA-N
MFCD00167977
8000-48-4
NCGC00091666-01
NCGC00091666-04
WLN: T66 A B AOTJ B1 B1 F1
DSSTox_CID_616
DSSTox_RID_75692
DSSTox_GSID_20616
W-106080
CAS-470-82-6
SMR000471853
Eucalyptol [USAN:USP]
eucaliptol
eucalytol
Eucalyptusoil
1.8-cineole
Eucalyptol, 99%
Eucalyptol, Ph Helv
p-Menthane,8-epoxy-
OILS EUCALYPTUS
AC1L1EEE
Spectrum2_000221
Spectrum3_000683
Spectrum4_001747
Spectrum5_000704
1,8-cineol (eucalyptol)
bmse000523
D05YAR
EC 207-431-5
Ambap470-82-6
Casella-med brand of cineole
SCHEMBL19622
SCHEMBL41020
BSPBio_002405
KBioGR_002194
MLS001050089
MLS001066338
DivK1c_000333
SPECTRUM1500294
SPBio_000261
Eucalyptol, analytical standard
CHEMBL485259
GTPL2464
CHEMBL1231862
CHEMBL1397305
DTXSID4020616
SCHEMBL13554591
SCHEMBL17836873
CTK6B3326
HMS501A15
KBio1_000333
KBio3_001625
MolPort-003-929-343
MolPort-039-339-173
NINDS_000333
HMS2271P04
Pharmakon1600-01500294
ZINC967566
p-Menthane, 1,8-epoxy- (VAN)
HY-N0066
NSC-6171
Tox21_111161
Tox21_202090
Tox21_302902
5750AF
CCG-36080
LS-128
NSC760388
SBB057535
Acylated oxime isatin derivative, 19
AKOS015903223
AKOS016034339
Tox21_111161_1
CS-8146
DB03852
FCH1679459
LMPR0102090019
NSC-760388
IDI1_000333
Eucalyptol, tested according to Ph.Eur.
NCGC00091666-02
NCGC00091666-03
NCGC00091666-05
NCGC00095774-01
NCGC00178671-01
NCGC00256479-01
NCGC00259639-01
AC-20234
AN-23469
BT000181
Eucalyptol, natural, >=99%, FCC, FG
HE033340
HE083136
HE344413
KB-51836
NCI60_005108
SC-47256
ST096004
1,3-Trimethyl-2-oxabicyclo[2.2.2]octane
2-Oxa-1,3-trimethylbicyclo[2.2.2]octane
TR-017465
2-Oxabicyclo[2.2.2]octane,3,3-trimethyl-
FT-0607033
FT-0626369
ST50308096
1,3,3-Trimethyl-2-oxabicyclo[2,2,2]octan
1,3,3-trimethyl-2-oxabicyclo[2,2,2]octane
1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan
A19469
C09844
D04115
{1,3,3-Trimethyl-2-oxabicyclo[2.2.2]octane}
{2-Oxa-1,3,3-trimethylbicyclo[2.2.2]octane}
AB01563262_01
SR-01000763816
{2-Oxabicyclo[2.2.2]octane,} 1,3,3-trimethyl-
SR-01000763816-2
1,8-Cineole, primary pharmaceutical reference standard
I14-18994
3B1-005465
Cineole, European Pharmacopoeia (EP) Reference Standard
Eucalyptol, certified reference material, TraceCERT(R)
F0001-1260
Eucalyptol Solution, 1000 mg/L, (RM, ISO GUIDE 34)
1,3,3-trimethyl-2-oxabicyclo[2.2.2]octane (ACD/Name 4.0)
Eucalyptol, United States Pharmacopeia (USP) Reference Standard
Eucalyptol (cineole), pharmaceutical secondary standard
traceable to USP, PhEur
InChI=1/C10H18O/c1-9(2)8-4-6-10(3,11-9)7-5-8/h8H,4-7H2,1-3H
10458-11-4
8024-52-0
8024-53-1
855347-23-8
1,8 Cineole

8. Compound in Different Plants

Compound Name Plant Name Compound in Plant Parts Ref
1,8-Cineole
Abelmoschus esculentus (L.) Moench Pod 3
Abelmoschus moschatus (L.) Medic. Seed 5
Ageratum conyzoides L Leaf; Aerial 1 , 2
Amoora rohituka (Roxb.) Wight & Arn. Leaf; Fruit 1
Anisomeles indica (L.) Kuntze. Flower 11
Aquilaria malaccensis Wood 7
Coriandrum sativum Linn. Seed; Leaf; Fruit; Root 1 , 3 , 6 , 7 , 12 , 13 , 27 , 32
Curcuma amada Rhizome 1 , 4 , 5 , 7 , 8 , 9 , 15
Curcuma aromatica Salisb. Rhizome; Leaf; Petiole 1 , 8 , 9
Curcuma caesia Roxb. Rhizome 1
Cuscuta reflexa Whole Plant 2
Cymbopogon citrates Leaf 11
Cyperus rotundus L Rhizome; Tuber 9 , 6 , 2
Helianthus annuus Flower 8
Hemidesmus indicus br. Root 6
Jatropha curcas L. Leaf 11
Juglans regia Leaf 13 , 14
Kaempferia parviflora Rhizome 5
Kalanchoe pinnata Leaf 11
Lantana camara L Aerial; Seed 2 , 4
Lepidium sativum Seed 5
Luffa acutangula Flower 3
Luvunga scandens Fruit 2
Magnolia grandiflora Flower 11
Mangifera indica Fruit Pulp 6
Mentha arvensis Leaf; Shoot Stem; Shoot Leaf; Stolon Stem; Stolon Leaf; Stolon; Rhizome 1 , 2 , 3 , 8 , 11 , 15 , 16 , 17 , 18 , 19
Olea europea 6
Ricinus communis Leaf; Aerial 15 , 4 , 5 , 29
Rosa damascena Petal 6
Tamarindus indica Fruit 9
Viola odorata Leaf 3

9. Targets

ID Target Name Gene Symbol Organism Protein Crystal Complex Activity Values Reference
Potency (nM) Ki (nM) IC50 (nM) Kd (nM) EC50 (nM) kon (M-1-s-1) koff (s-1) Biological Assay DOI Article PMID PubChem AID
68 activating transcription factor 6 ATF6 Homo sapiens 60.8462 1159516
56 androgen receptor AR Homo sapiens 19.9526 588516
24 aryl hydrocarbon receptor AHR Homo sapiens 49.7911 743122
24 aryl hydrocarbon receptor AHR Homo sapiens 60.3233 743085
41 chromobox 1 CBX1 Homo sapiens 89.1251 540317
57 estrogen receptor 1 ESR1 Homo sapiens 9.77 743069
57 estrogen receptor 1 ESR1 Homo sapiens 54.2292 743069
25 estrogen related receptor alpha ESRRA Homo sapiens 6.0323 1224848
25 estrogen related receptor alpha ESRRA Homo sapiens 6.0323 1224849
84 geminin, DNA replication inhibitor GMNN Homo sapiens 5.8048 624296
85 Jun proto-oncogene, AP-1 transcription factor subunit JUN Homo sapiens 0.6085 1159526
28 lamin A/C LMNA Homo sapiens 35.4813 1487
16 microtubule associated protein tau MAPT Homo sapiens 4.4668 1460
86 mitogen-activated protein kinase 1 MAPK1 Homo sapiens 0.0316 995
55 nuclear receptor subfamily 3 group C member 1 NR3C1 Homo sapiens 2.3914 720691
53 peroxisome proliferator activated receptor delta PPARD Homo sapiens 21.589 743215
50 RAR-related orphan receptor gamma Rorc Mus musculus 0.1933 1159521
87 streptokinase A precursor Streptococcus pyogenes M1 GAS 150000 1914
87 streptokinase A precursor ska Streptococcus pyogenes M1 GAS 150 1902
87 streptokinase A precursor ska Streptococcus pyogenes M1 GAS 150 1914
47 thyroid hormone receptor beta Thrb Rattus norvegicus 30.2333 743066
32 thyroid stimulating hormone receptor TSHR Homo sapiens 15.8489 926
32 thyroid stimulating hormone receptor TSHR Homo sapiens 15.8489 938
67 tyrosyl-DNA phosphodiesterase 1 TDP1 Homo sapiens 2.6609 686979
88 Ubiquitin carboxyl-terminal hydrolase isozyme L1 (UCH-L1) Mus musculus 1.80E+4 14522054

10. Chemical Vendors

SID Source Name Source URL Source Detail Registry ID Source Record URL
162240160Chembase.cnSource URLSource Detail145960Source Record URL
160966932Chembase.cnSource URLSource Detail3493Source Record URL
354300570iChemical Technology USA IncSource URLSource DetailEBD2184890Source Record URL
163246870ChemTikSource URLSource DetailCTK6B3326Source Record URL
252491597AK Scientific, Inc. (AKSCI)Source URLSource Detail5750AFSource Record URL
164792194Finetech Industry LimitedSource URLSource DetailFT-0607033Source Record URL
164810326Finetech Industry LimitedSource URLSource DetailFT-0626369Source Record URL
342422325Wubei-BiochemSource URLSource DetailWB024502SUSource Record URL
329746991Sigma-AldrichSource URLSource Detail00020590_SIALSource Record URL
329749821Sigma-AldrichSource URLSource Detail1268900_USPSource Record URL
329753321Sigma-AldrichSource URLSource Detail29210_SIALSource Record URL
329757077Sigma-AldrichSource URLSource Detail46128_SIALSource Record URL
329758001Sigma-AldrichSource URLSource Detail53801_SIALSource Record URL
329770472Sigma-AldrichSource URLSource Detail95656_SIALSource Record URL
24893017Sigma-AldrichSource URLSource DetailC80601_ALDRICHSource Record URL
329823628Sigma-AldrichSource URLSource DetailPHR1828_SIALSource Record URL
24901113Sigma-AldrichSource URLSource DetailW246506_ALDRICHSource Record URL
329830872Sigma-AldrichSource URLSource DetailY0000176_SIALSource Record URL
92718056Hangzhou APIChem TechnologySource URLSource DetailAC-20234Source Record URL
29204125R&D ChemicalsSource URLSource Detail5009Source Record URL
57321439NovoSeekSource URLSource Detail2758Source Record URL
310110461Aurora Fine Chemicals LLCSource URLSource DetailA17.882.744Source Record URL
252392763AHH Chemical co.,ltdSource URLSource DetailMT-02664Source Record URL
252393146AHH Chemical co.,ltdSource URLSource DetailMT-03047Source Record URL
87565652TCI (Tokyo Chemical Industry)Source URLSource DetailC0542Source Record URL
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126621763ChemMolSource URLSource Detail30107844Source Record URL
126677610ChemMolSource URLSource Detail49416259Source Record URL
241078951ChemMolSource URLSource Detail99088055Source Record URL
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350089378DC ChemicalsSource URLSource DetailDCA-003Source Record URL
346694990LabNetwork, a WuXi AppTec CompanySource URLSource DetailLN00195816Source Record URL
340511677LGC StandardsSource URLSource DetailDRE-GA09010075IPSource Record URL
340521228LGC StandardsSource URLSource DetailMM1763.00Source Record URL
143432027TimTecSource URLSource DetailSBB057535Source Record URL
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