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

• ChemBase ID: 3493
• Molecular Formular: C10H18O
• Molecular Mass: 154.24932
• Monoisotopic Mass: 154.1357652
• SMILES: O1C2(CCC(C1(C)C)CC2)C
• Canonical SMILES: CC12CCC(CC1)C(O2)(C)C
• InChI: InChI=1S/C10H18O/c1-9(2)8-4-6-10(3,11-9)7-5-8/h8H,4-7H2,1-3H3
• InChIKey: WEEGYLXZBRQIMU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,3,3-trimethyl-2-oxabicyclo[2.2.2]octane
• IUPAC Traditional name: eucalyptol
• Synonyms: 1,8-Cineole; 1,8-cineol; limonene oxide; cajeputol; 1,8-epoxy-p-menthane; 1,8-oxido-p-menthane; eucalyptole; cineole; cineol; 1,3,3-Trimethyl-2-oxabicyclo(2.2.2)octane; 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]octane (ACD/Name 4.0); 1,8-cineol (eucalyptol); 2-Oxa-1,3,3-trimethylbicyclo(2.2.2)octane; 2-Oxa-1,3,3-trimethylbicyclo[2.2.2]octane; 2-Oxabicyclo(2.2.2)octane, 1,3,3-trimethyl-; 2-Oxabicyclo[2.2.2]octane, 1,3,3-trimethyl-; 4,7,7-trimethyl-8-oxabicyclo[2.2.2]octane; BIDD:ER0481; CNL; Casella-med brand of cineole; Cineolum; Cucalyptol; Eucalyptol (natural); Eucalyptol (usan); Eucalyptol [usan]; Eucalyptus oil; Eucapur; Eukalyptol; Eukalyptol [czech]; FEMA No. 2465; P-cineole; Soledum; Terpan; UNII-RV6J6604TK; WLN: T66 A B AOTJ B1 B1 F1; Zedoary oil; Zineol; p-Menthane, 1,8-epoxy-; p-Menthane, 1,8-epoxy- (VAN); {1,3,3-Trimethyl-2-oxabicyclo[2.2.2]octane}; {2-Oxa-1,3,3-trimethylbicyclo[2.2.2]octane}; {2-Oxabicyclo[2.2.2]octane,} 1,3,3-trimethyl-; Eucalyptol; Eucalyptol; CINEOLE; 1,8-Cineole; 1,8-桉树脑

Database IDs

• CAS Number: 470-82-6
• EC Number: 207-431-5
• MDL Number: MFCD00167977
• Beilstein Number: 105109
• Merck Index: 143895
• PubChem SID: 160966932
• PubChem CID: 2758
• CHEMBL: 485259
• Chemspider ID: 2656
• DrugBank ID: DB03852
• KEGG ID: D04115
• Unique Ingredient Identifier: RV6J6604TK
• Wikipedia Title: Eucalyptol

CALCULATED PROPERTIES

JChem

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 2.3484197
• LogD (pH = 7.4): 2.3484197
• Log P: 2.3484197
• Molar Refractivity: 45.8609 cm^3
• Polarizability: 18.385763 Å^3
• Polar Surface Area: 9.23 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.36
• LOG S: -3.84
• Solubility (Water): 2.25e-02 g/l

PROPERTIES

Physical Property

• Solubility: 3.5 mg/mL at 21 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]
• Melting Point: 1.0°C; 1.5 °C (274.6 K); 1.5°C
• Boiling Point: 174-177°C; 176–177 °C (449–450 K); 176-177°C
• Flash Point: 49°C(120°F); 50°C
• Density: 0.921-0.924 g/ml; 0.9225 g/cm^3; 0.923
• Refractive Index: 1.4575
• Hydrophobicity(logP): 2.74 [GRIFFIN,S ET AL. (1999)]

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• RTECS: OS9275000
• European Hazard Symbols: Flammable (F)
• UN Number: 1993; UN3271
• Hazard Class: 3
• Packing Group: III
• Australian Hazchem: 3Y
• Risk Statements: 10; R:10
• Safety Statements: S:9-16-29
• EU Classification: F1
• EU Hazard Identification Number: 3B
• Emergency Response Guidebook(ERG) Number: 128
• TSCA Listed: 是
• GHS Pictograms: GHS02
• GHS Hazard statements: H226-H303
• GHS Precautionary statements: P210-P241-P280-P303+P361+P353-P403+P235-P501A

Product Information

• Purity: ~99%; 99%

DETAILS

MP Biomedicals - 02150689

Purity: ~99%
1 ml = approx. 0.92 g

DrugBank - DB03852

• Drug Groups: nutraceutical
• Description: Eucalyptol is a natural organic compound which is a colorless liquid. It is a cyclic ether and a monoterpenoid. Eucalyptol is an ingredient in many brands of mouthwash and cough suppressant. It controls airway mucus hypersecretion and asthma via anti-inflammatory cytokine inhibition. Eucalyptol is an effective treatment for nonpurulent rhinosinusitis. Eucalyptol reduces inflammation and pain when applied topically. It kills leukaemia cells in vitro.
• Toxicity: Oral, rat LD50: 2480 mg/kg
• Affected Organisms: Humans and other mammals
• References: 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. 2010 Aug 16. [Pubmed]
• External Links: Wikipedia

REFERENCES

• 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. 2010 Aug 16. Pubmed