Eugenol (4-allyl-2-methoxyphenol) C 10 H 12 O 2 ( formula I ) is a substance of the phenol class, it belongs to aromatic substances .
The name comes from the tropical and subtropical shrubs Eugene ( lat. Eugenia ) - a large genus of plants of the Myrtle family , the aerial parts of which contain a large amount of essential oils , which contain eugenol.
Eugenol | |
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General | |
| Chem. formula | C₁₀H₁₂O₂ |
Classification | |
| CAS Number | |
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| ChemSpider | |
| EINECS Number | 202-589-1 |
| Chebi | 4917 |
| Drugbank | |
Smiles | |
COC1 = C (C = CC (= C1) CC = C) O | |
Inchi | |
1S / C10H12O2 / c1-3-4-8-5-6-9 (11) 10 (7-8) 12-2 / h3.5-7.111H, 1.4H2.2H3 | |
| Data is provided for standard conditions (25 ℃, 100 kPa) , unless otherwise indicated. | |
Content
- 1 Properties
- 2 Distribution in nature
- 3 Getting
- 4 Application
- 5 Literature
Properties
Eugenol is a colorless, yellowing in the air liquid with a strong smell of cloves. It is soluble in propylene glycol and essential oils , soluble in 50% ethanol in a ratio of 1: 5 ÷ 1: 6, insoluble in water.
- M.m. 164.2
- T bale = 252.7 about With
- d 4 22 = 1.0664
- n D 20 = 1.5410
- T pop = 110 about
- Threshold odor concentration 2.38⋅10 −8 g / l
- LD 50 2.68 g / kg (for rats, oral).
When interacting with aqueous solutions of alkali, it forms soluble salts (eugenolates). It forms vanillin during oxidation. When heated with alkalis, with platinum on coal, it isomerized into isoeugenol ( formula II ).
Propagation in nature
Eugenol is the main component of a number of essential oils: clove oil (up to 85%), eugenolic basil oil (70-80%), colouri oil (70-80%), as well as citronella , ylang-ylang , airy , sassafras and some others.
Getting
Eugenol is isolated from essential oils (in particular, via eugenolates) or from guaiacol by allyl alcohol or allyl chloride .
Application
Eugenol is used:
- for the preparation of perfume compositions,
- like perfumes for tobacco
- in the synthesis of isoeugenol .
As an integral part, it is part of painkillers , biocidal drugs and antiseptics .
It has widespread (and long-standing) application in orthopedic and therapeutic dentistry (mixed with zinc oxide ) under the name zinc oxide eugenol cement. It is used as a material for insulating and medical gaskets, impression material, temporary filling material, as well as sealer in endodontics . Among dentists, it is more often used in the composition and under the name of clove oil .
Literature
- Eugenol // Chemical Encyclopedia in 5 volumes. - M.: Big Russian Encyclopedia, 1998. - V. 5. - 784 p.
- Kremlev A.M. ,. Eigenol // Encyclopedic Dictionary of Brockhaus and Efron : in 86 volumes (82 volumes and 4 additional). - SPb. , 1890-1907.