Eucalyptol

Base Information

• Chemical Name: Eucalyptol
• CAS No.: 470-82-6
• Deprecated CAS: 10458-11-4,8024-52-0,8024-53-1,855347-23-8,8024-53-1,855347-23-8
• Molecular Formula: C10H18O
• Molecular Weight: 154.252
• Hs Code.: 2932 99 00
• European Community (EC) Number: 207-431-5
• NSC Number: 760388,6171
• UN Number: 1993
• UNII: RV6J6604TK
• DSSTox Substance ID: DTXSID4020616
• Nikkaji Number: J3.281F
• Wikipedia: Eucalyptol
• Wikidata: Q161572,Q105302939
• NCI Thesaurus Code: C76772
• RXCUI: 21116
• Pharos Ligand ID: VRPTF2RTTDKH
• Metabolomics Workbench ID: 28107
• ChEMBL ID: CHEMBL485259,CHEMBL1231862,CHEMBL1397305
• Mol file: 470-82-6.mol

Synonyms:1,8 Cineol;1,8 Cineole;1,8 Epoxy p menthane;1,8-cineol;1,8-cineole;1,8-Epoxy-p-menthane;cineole;eucalyptol;Soledum

Chemical Property of Eucalyptol

Chemical Property:

• Appearance/Colour: colorless liquid with a fresh camphor-like smell and a spicy, cooling taste
• Vapor Pressure: 1.65mmHg at 25°C
• Melting Point: 1-2 °C(lit.)
• Refractive Index: n20/D 1.457(lit.)
• Boiling Point: 174.012 °C at 760 mmHg
• Flash Point: 50.868 °C
• PSA: 9.23000
• Density: 0.923 g/cm³
• LogP: 2.74410
• Storage Temp.: 2-8°C
• Solubility.: 3.5g/l
• Water Solubility.: Soluble in water(3500 mg/L (at 21°C). Miscible with ether, alcohol, chloroform, glacial acetic acid, oils. Soluble in ethanol, ethyl ether; slightly soluble in carbon tetrachloride.
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 154.135765193
• Heavy Atom Count: 11
• Complexity: 164
• Transport DOT Label: Flammable Liquid

Purity/Quality:

99% ^*data from raw suppliers

Eucalyptol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,F
• Hazard Codes: Xi:Irritant
• Statements: R10:; R37/38:; R41:
• Safety Statements: S26:; S39:

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Plant Oils and Extracts
• Canonical SMILES: CC1(C2CCC(O1)(CC2)C)C
• Recent ClinicalTrials: Sinolpan? Pharmacy Non-interventional Study - Quality of Live
• Recent EU Clinical Trials: The effect of early administered cineole on the course of a common cold
• Description: Eucalyptol is a bicyclic monoterpene that has been found in Eucalyptus and other plants, including C. sativa and has diverse biological activities, including anti-inflammatory, decongestant, antinociceptive, and insect repellent properties. Eucalyptol (10 μM) inhibits TNF-α, IL-1β, IL-4, and IL-5 production by primary human lymphocytes stimulated by ionomycin and phorbol 12-myristate 13-acetate (PMA; ). It also decreases LPS-induced mucus production by primary human nasal turbinate slices when used at a concentration of 10 μM. Eucalyptol (400 mg/kg) decreases carrageenan-induced hind paw edema in rats and reduces the time spent licking the hind paw in a formalin-induced nociception test in mice. It inhibits A. aegypti mosquitoes from feeding on anesthetized gerbils when applied topically at a concentration of 10% and from laying eggs in an ovipositional bioassay when used at a concentration of 1% in standing water. Formulations containing eucalyptol have been used in mouthwash and cough suppressants.
• Uses: Labelled 1,8-Cineol, the chief constituent of oil of eucalyptus. Used as pharmaceutic aid (flavor). 1,8-Cineol is the chief constituent of oil of eucalyptus. Used as pharmaceutic aid (flavor). eucalyptol is considered an antiseptic. This is a monoterpene compound that provides the fragrance associated with the essential oil of eucalyptus. eucalyptol is also used to fragrance cosmetic preparations.

Technology Process of Eucalyptol

There total 52 articles about Eucalyptol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

3,7-dimethylocta-1,6-dien-3-ol (78-70-6) → 1,8-Cineole (470-82-6) + Terpinolene (586-62-9,69073-38-7) + 1-methyl-4-isopropyl-1,3-cyclohexadiene (99-86-5) + terpineol (98-55-5,2438-12-2)

Guidance literature:

With C-undecylcalix[4]resorcinarene; In decane; chloroform-d1; at 30 ℃;

DOI:10.1021/jacs.7b04480

Reference yield:

(Z)-geranyl 4-methoxybenzoate → 1,8-Cineole (470-82-6) + Terpinolene (586-62-9,69073-38-7) + 1-methyl-4-isopropyl-1,3-cyclohexadiene (99-86-5) + crithmene (99-85-4) + isoterpinolene (586-63-0)

Guidance literature:

With C-undecylcalix[4]resorcinarene; In decane; chloroform-d1; at 30 ℃;

DOI:10.1021/jacs.7b04480

Reference yield:

1-(tert-butyldimethylsiloxy)-3,7-dimethyl-2,6-octadiene (80873-76-3) → 1,8-Cineole (470-82-6) + Terpinolene (586-62-9,69073-38-7) + 1-methyl-4-isopropyl-1,3-cyclohexadiene (99-86-5) + crithmene (99-85-4) + isoterpinolene (586-63-0)

Guidance literature:

With C-undecylcalix[4]resorcinarene; In decane; chloroform-d1; at 30 ℃;

DOI:10.1021/jacs.7b04480

upstream raw materials:

terpineol

rac-α-pinene

cis-4-hydroxy-α,α,4-trimethyl-cyclohexanemethanol, monohydrate

methanol

Downstream raw materials:

1,3,3-trimethyl-2-oxabicyclo<2.2.2>octan-5-one

exo-1,3,3-trimethyl-2-oxabicyclo<2.2.2>octan-5-ol acetate

1,3,3-trimethyl-2-oxabicyclo<2.2.2>octane-5,8-dione

1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-6-one

Refernces

• 1、 Nakano, Chiaki,Kim, Hyo-Kyoung,Ohnishi, Yasuo. "Identification of the first bacterial monoterpene cyclase, a 1,8-cineole synthase, that catalyzes the direct conversion of geranyl diphosphate". . p. 1988 - 1991. Retrieved 2011.
• 2、 Nemat, Suren J.,Tiefenbacher, Konrad. "Thioderivatives of Resorcin[4]arene and Pyrogallol[4]arene: Are Thiols Tolerated in the Self-Assembly Process?". supporting information. p. 6861 - 6865. Retrieved 2021/09/14.
• 3、 -. "Method for synthetizing 1,8-eudesmin from alpha-terpilenol". Paragraph 0018-0046. . Retrieved 2019/06/08.