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1,8-Cineol

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1,8-Cineol

EINECS 207-431-5
CAS No. 470-82-6 Density 0.923 g/cm3
PSA 9.23000 LogP 2.74410
Solubility Insoluble in water, miscible with ethanol, chloroform, glacial acetic acid, and volatile oil or fixed oil Melting Point 1-2 °C(lit.)
Formula C10H18O Boiling Point 174.012 °C at 760 mmHg
Molecular Weight 154.252 Flash Point 50.868 °C
Transport Information UN 1993 3/PG 3 Appearance colorless liquid with a fresh camphor-like smell and a spicy, cooling taste
Safety 26-39-16 Risk Codes 10-41-36/37/38
Molecular Structure Molecular Structure of 470-82-6 (Cineole) Hazard Symbols IrritantXi,FlammableF
Synonyms

p-Menthane,1,8-epoxy- (8CI);1,3,3-Trimethyl-2-oxabicyclo[2.2.2]octane;1,8-Cineol;1,8-Cineole;1,8-Epoxy-p-menthane;2-Oxa-1,3,3-trimethylbicyclo[2.2.2]octane;Cajeputol;Cineol;2-Oxabicyclo[2.2.2]octane,1,3,3-trimethyl-;Eucalyptole;Eucapur;NSC 6171;Terpan;p-Cineole;

Article Data 39

1,8-Cineol Consensus Reports

Reported in EPA TSCA Inventory.

1,8-Cineol Specification

The 1,8-Cineol, with the CAS registry number 470-82-6, is also known as 1,8-Oxido-p-menthane. It belongs to the product categories of Miscellaneous Natural Products; Heterocycles; Heterocyclic Compounds; Bicyclic Monoterpenes; Biochemistry; Terpenes; Intermediates & Fine Chemicals; Isotope Labeled Compounds; Pharmaceuticals; Isotope Labelled Compounds. Its EINECS number is 207-431-5. This chemical's molecular formula is C10H18O and molecular weight is 154.25. What's more, its systematic name is 1,3,3-Trimethyl-2-oxabicyclo[2.2.2]octane. Its classification codes are: (1)Anti-Infective Agents; (2)Mutation data; (3)Reproductive Effect; (4)Solvents. This chemical should be sealed and stored in a ventilated and dry place. Moreover, it should be protected from oxides. Its storage temperature is 2 - 8°C. This chemical is a permanent component of lavender oil and spike lavender oil. It is used in flavorings, fragrances, and cosmetics. It is an ingredient in many brands of mouthwash and cough suppressant.

Physical properties of 1,8-Cineol are: (1)ACD/LogP: 2.795; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.80; (4)ACD/LogD (pH 7.4): 2.80; (5)ACD/BCF (pH 5.5): 78.43; (6)ACD/BCF (pH 7.4): 78.43; (7)ACD/KOC (pH 5.5): 790.07; (8)ACD/KOC (pH 7.4): 790.07; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 9.23 Å2; (13)Index of Refraction: 1.461; (14)Molar Refractivity: 45.87 cm3; (15)Molar Volume: 167.159 cm3; (16)Polarizability: 18.184×10-24cm3; (17)Surface Tension: 32.49 dyne/cm; (18)Density: 0.923 g/cm3; (19)Flash Point: 50.868 °C; (20)Enthalpy of Vaporization: 39.351 kJ/mol; (21)Boiling Point: 174.012 °C at 760 mmHg; (22)Vapour Pressure: 1.65 mmHg at 25°C.

Preparation: this chemical can be prepared by methylmagnesium iodide and C9H15O(1+)·F6Sb(1-). This reaction will need solvent diethyl ether with the reaction time of 10 min. The yield is about 51%.

1,8-Cineol can be prepared by methylmagnesium iodide and C9H15O(1+)·F6Sb(1-)

Uses of 1,8-Cineol: it can be used to produce (+-)-2,6,6-trimethyl-tetrahydro-pyran-2r,5c-dicarboxylic acid by heating. It will need reagents KMnO4, aq. NaOH with the reaction time of 7 hours. The yield is about 41.5%.

1,8-Cineol can be used to produce (+-)-2,6,6-trimethyl-tetrahydro-pyran-2r,5c-dicarboxylic acid by heating

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. It is flammable, so you should keep it away from sources of ignition - No smoking. This substance has a risk of serious damage to eyes. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need to wear eye/face protection.

You can still convert the following datas into molecular structure:
(1)SMILES: O2C1(CCC(CC1)C2(C)C)C
(2)Std. InChI: InChI=1S/C10H18O/c1-9(2)8-4-6-10(3,11-9)7-5-8/h8H,4-7H2,1-3H3
(3)Std. InChIKey: WEEGYLXZBRQIMU-UHFFFAOYSA-N

The toxicity data is as follows:  

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LDLo subcutaneous 1500mg/kg (1500mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" Trudy Instituta Fiziologii, Akademiya Nauk Kazakhshoi SSR. Transactions of the Institute of Physiology, Academy of Sciences of the Kazakh. SSR. Vol. 1, Pg. 134, 1955.
guinea pig LDLo intramuscular 2250mg/kg (2250mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION
Trudy Instituta Fiziologii, Akademiya Nauk Kazakhshoi SSR. Transactions of the Institute of Physiology, Academy of Sciences of the Kazakh. SSR. Vol. 1, Pg. 134, 1955.
mouse LD50 intramuscular 1gm/kg (1000mg/kg)   Journal of Scientific and Industrial Research, Section C: Biological Sciences. Vol. 21, Pg. 342, 1962.
mouse LD50 subcutaneous 1070mg/kg (1070mg/kg) PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Sapporo Igaku Zasshi. Sapporo Medical Journal. Vol. 3, Pg. 73, 1952.
rat LD50 oral 2480mg/kg (2480mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: COMA
Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964.

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