1,8-Cineol






Names

    • SMR000471853
    • Eucalyptol, United States Pharmacopeia (USP) Reference Standard
    • NSC-6171
    • InChI=1/C10H18O/c1-9(2)8-4-6-10(3,11-9)7-5-8/h8H,4-7H2,1-3H
    • p-Menthane,8-epoxy-
    • Eucalyptol 1000 ug/mL in Methanol
    • cineoles
    • Eucalyptol (cineole), Pharmaceutical Secondary Standard; Certified Reference Material
    • 1_8_cineole
    • NCGC00091666-01
    • NSC6171
    • MLS001066338
    • 1,8-Cineole, primary pharmaceutical reference standard
    • KBioGR_002194
    • CHEBI:27961
    • 4,7,7-trimethyl-8-oxabicyclo[2.2.2]octane
    • NCI60_005108
    • NCGC00091666-03
    • NSC-760388
    • UNII-RV6J6604TK
    • bmse000523
    • DB03852
    • Eucapur
    • MFCD00167977
    • EUCALYPTOL (USP MONOGRAPH)
    • (1s,4s)-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octane
    • D04115
    • NSC 6171
    • RV6J6604TK
    • 2-Oxa-1,3,3-trimethylbicyclo[2.2.2]octane
    • 1,3,3-TRIMETHYL-2-OXABICYCLO(2.2.2.)OCTANE
    • DTXSID4020616
    • 470-82-6
    • 1,8 Cineol
    • 1,8-Cineol
    • cineole
    • HSDB 991
    • CS-8146
    • Cajeputol
    • P-METHANE, 1,8-EPOXY-
    • EUCALYPTOL [USP MONOGRAPH]
    • 1,8-Oxido-p-menthane
    • 1,8-Epoxy-p-menthane
    • NCGC00091666-02
    • NCGC00178671-01
    • CHEMBL485259
    • LMPR0102090019
    • CCRIS 3727
    • Eucalyptol,(S)
    • CNL
    • EUCALYPTOL [HSDB]
    • Tox21_111161
    • Spectrum4_001747
    • Eucalyptol
    • Cucalyptol
    • 1,8-Oxido-p-methane
    • 1,3,3-Trimethyl-2-oxabicyclo[2.2.2]octane
    • CINEOLE [EP MONOGRAPH]
    • 1,8-Cineole
    • GTPL2464
    • SCHEMBL13554591
    • EUCALYPTOL [USP-RS]
    • 2-Oxa-1,3-trimethylbicyclo[2.2.2]octane
    • F0001-1260
    • HMS501A15
    • NCI-C56575
    • Tox21_302902
    • BDBM50459887
    • Soledum
    • EUCALYPTOL [FHFI]
    • AKOS037514637
    • NSC760388
    • CINEOLE (EP MONOGRAPH)
    • Eucalyptole
    • Eukalyptol
    • EINECS 207-431-5
    • EUCALYPTOL [HPUS]
    • CHEMBL1231862
    • p-Menthane, 1,8-epoxy-
    • 2-Oxabicyclo(2.2.2)octane, 1,3,3-trimethyl-
    • EUCALYPTOL [FCC]
    • Eucalyptol 1000 microg/mL in Methanol
    • Pharmakon1600-01500294
    • AKOS015903223
    • NS00002794
    • W-106080
    • Spectrum5_000704
    • Cineole (VAN)
    • KBio3_001625
    • EUCALYPTOL [VANDF]
    • HY-N0066
    • Tox21_202090
    • SCHEMBL23876132
    • HMS2271P04
    • Spectrum2_000221
    • Spectrum3_000683
    • EUCALYPTOL [USP IMPURITY]
    • Eukalyptol [Czech]
    • Rosatra
    • 2-Oxabicyclo[2.2.2]octane,3,3-trimethyl-
    • SR-01000763816
    • Eucalyptol [USAN:USP]
    • Cineole, European Pharmacopoeia (EP) Reference Standard
    • SR-01000763816-2
    • EUCALYPTOL (USP-RS)
    • CAS-470-82-6
    • Cineole (Eucalyptol)
    • Terpan
    • Eucaly
    • AI3-00578
    • SCHEMBL17836873
    • BRD-K15671046-001-03-6
    • FEMA No. 2465
    • 1.8-cineole
    • Eucalyptol (natural)
    • EUCALYPTOL (USP IMPURITY)
    • SCHEMBL19622
    • SPBio_000261
    • 1,3,3-Trimethyl-2-oxabicyclo(2.2.2)octane
    • Eucalyptol, 99%
    • IDI1_000333
    • Eucalyptol, Ph Helv
    • NCGC00091666-05
    • SCHEMBL41020
    • CINEOL
    • AKOS016034339
    • Zineol
    • EUCALYPTOL [II]
    • AC-20234
    • Eucalyptol (USP)
    • Eucalyptol, tested according to Ph.Eur.
    • DTXCID60616
    • CHEMBL1397305
    • NCGC00095774-01
    • 2,2,4-trimethyl-3-oxabicyclo[2.2.2]octane
    • CINEOLE (MART.)
    • DivK1c_000333
    • p-Cineole
    • BRD-K29996876-001-09-3
    • Rosatra Synergyfor treatment of Acne Rosacea
    • WLN: T66 A B AOTJ B1 B1 F1
    • BIDD:ER0481
    • Q161572
    • NCGC00091666-04
    • CINEOLE [WHO-DD]
    • 1,8 Epoxy p menthane
    • MLS001050089
    • CCG-266254
    • 2-Oxa-1,3,3-trimethylbicyclo(2.2.2)octane
    • NCGC00259639-01
    • BSPBio_002405
    • SPECTRUM1500294
    • NCGC00256479-01
    • EUCALYPTOL (II)
    • NINDS_000333
    • Eucalyptol, analytical standard
    • Eucalyptol, certified reference material, TraceCERT(R)
    • CINEOLE [MART.]
    • 1,3-Trimethyl-2-oxabicyclo[2.2.2]octane
    • CCG-36080
    • AB01563262_01
    • Tox21_111161_1
    • NCGC00389703-01
    • 2-Oxabicyclo[2.2.2]octane, 1,3,3-trimethyl-
    • Eucalyptol [USAN]
    • 1,8 Cineole
    • KBio1_000333
    • DB-070775
    • CHEBI:23243
    • EC 207-431-5
    • Germ Free ARIA
    • LS-13868
    • Eucalyptol, natural, >=99%, FCC, FG
    • EUCALYPTOL [MI]
    • C09844

Attributes

  • Canonical SMILES

    CC1(C2CCC(O1)(CC2)C)C

  • InChI

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

  • Molecule Class: Terpenoids
  • TPSA: 9.23
  • #RotBonds: 0
  • MW: 154.25300000000001
  • HBD: 0
  • HBA: 1
  • logP: 2.7441000000000013
  • Chemical Formula: C10H18O


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. catharinensis Brazil 403124 UEC117862

External Databases


References

  • Chemical composition and antioxidant activity of the essential oil of Tabernaemontana catharinensis A. DC. leaves. Nat Prod Res, 2013 (PMID 22273350).

Compound-Protein Relationships

Compound Activities

    • Antioxidant

Predicted NMR Spectral Data


Predicted MS Fragmentation Pattern

    N.B.: It is recommended to zoom in on a specific area of an MS plot before hovering on a peak.


Predicted ADMET Properties

    Property Model Name Predicted Value

    Absorption Caco-2 (logPaap) -4.64
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -3.94
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Non-Substrate
    Skin Permeability -2.31

    Distribution Blood-Brain Barrier (Central Nervous System) -3.02
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.27
    Plasma Protein Binding 10.53
    Steady State Volume of Distribution 2.31

    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Non-Inhibitor
    CYP 1A2 substrate Non-Substrate
    CYP 2C19 Inhibitor Inhibitor
    CYP 2C19 substrate Non-Substrate
    CYP 2C9 Inhibitor Inhibitor
    CYP 2C9 Substrate Substrate
    CYP 2D6 Inhibitor Non-Inhibitor
    CYP 2D6 Substrate Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Non-Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor

    Excretion Clearance 12.53
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs

    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 1.22
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Safe
    Liver Injury I Safe
    Eye Corrosion Toxic
    Eye irritation Toxic
    Maximum Tolerated Dose 0.49
    Liver Injury II Safe
    hERG Blockers Safe
    Daphnia Maga 3.15
    Micronucleos Safe
    NR-AhR Safe
    NR-AR Safe
    NR-AR-LBD Safe
    NR-Aromatase Safe
    NR-ER Safe
    NR-ER-LBD Safe
    NR-GR Safe
    NR-PPAR-gamma Safe
    NR-TR Safe
    T. Pyriformis 3.2
    Rat (Acute) 1.69
    Rat (Chronic Oral) 1.18
    Fathead Minnow 3.32
    Respiratory Disease Safe
    Skin Sensitisation Toxic
    SR-ATAD5 Safe
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe

    General Properties Boiling Point 170.73
    Hydration Free Energy -2.66
    Log(D) at pH=7.4 1.82
    Log(P) 2.7
    Log S -1.83
    Log(Vapor Pressure) 0.23
    Melting Point 9.48
    pKa Acid 13.75
    pKa Basic 8.88