Eugenol

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Structural formula
Structural formula of eugenol
General
Surname Eugenol
other names
  • 4-allyl-2-methoxyphenol
  • 4-prop-2-enyl-2-methoxyphenol
  • 4-allyl catechol 2-methyl ether
  • 5-allyl guaiacol
  • EUGENOL ( INCI )
Molecular formula C 10 H 12 O 2
Brief description

yellow, oily liquid with an intense odor of cloves

External identifiers / databases
CAS number 97-53-0
EC number 202-589-1
ECHA InfoCard 100.002.355
PubChem 3314
ChemSpider 13876103
DrugBank DB09086
Wikidata Q423357
Drug information
ATC code

A01 AB29

properties
Molar mass 164.20 g mol −1
Physical state

liquid

density

1.07 g cm −3 (20 ° C)

Melting point

−9 ° C

boiling point

253 ° C

Vapor pressure

<0.1 h Pa (20 ° C)

solubility

poor in water (2.46 g l −1 at 25 ° C)

Refractive index

1.5410

safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 302-315-317-319
P: 261-280-305 + 351 + 338-362-301 + 312-501
Toxicological data

1930 mg kg −1 ( LD 50 ,  rat ,  oral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Eugenol is a phenylpropanoid with an intense clove odor .

Occurrence

Basil ( Ocimum basilicum )

Eugenol occurs naturally in clove oil (70–95%), in allspice and allspice leaf oil (60–90%), in bay oil (50–60%) and cinnamon oils (cinnamon bark oil: 5–10%, cinnamon leaf oil over 90%). It is also found in laurel , basil , banana, cherry and nutmeg .

Extraction and presentation

Eugenol is obtained by shaking out clove oil with 5% potassium hydroxide solution .

properties

Eugenol (1 ) is oxidized (via isoeugenol , 2) to vanillin (3) by potassium permanganate or ozone . It gradually turns brown and gummy in the air.

Synthesis of vanillin from eugenol

Analytics

The reliable qualitative and quantitative detection of eugenol can be carried out after sufficient sample preparation by coupling gas chromatography or HPLC with mass spectrometry . Eugenol can also be detected in the smoke from water pipes .

use

Eugenol is used in large quantities in the perfume industry for spicy notes, especially for carnation types and oriental smells. Eugenol is the next in the papermaking resulting lignosulfonate a main raw material ( starting material ) for the production of synthetic vanillin .

In dentistry , eugenol is used as an analgesic (only superficial ), antibacterial and anti-inflammatory agent. It is used for the prophylaxis of pulpitis , for the treatment of acute pulpitis or acute periodontitis . Eugenol is also used in temporary cements and filling materials (zinc oxide-eugenol cement) together with eugenol ether, eugenol benzoate, eugenol cinnamate and eugenol acetate.

In fish farming, research and industry, eugenol is used as an anesthetic and sedative under the name Aqui-S®.

In agriculture, eugenol is approved as an antioxidant and as a germ inhibitor .

Biological importance and activity

A phytochemical database lists 68 areas of biological activity of eugenol. In the zoological / microbiological field, it has an antibacterial effect ( e.g. against salmonella and staphylococci ); antifungal (against candida ); against nematodes and trichomonads ; acaricidal (i.e., against mites and ticks), insecticidal and insectifugal , also larvicidal ; apifugal (driving away bees); as well as against termites . Some species of insects are attracted to eugenol ( Euglossa , Maladera ).

In humans it has analgesic and anti-inflammatory effects. In the laboratory, it inhibits tumor necrosis factor and the enzymes thromboxane , COX-1, COX-2 and cytochrome P450 . Many other individual effects were found. Clinical studies on this are unknown. During the metabolism of eugenol mainly phase II conjugates with glucuronic acid , sulfate and glutathione are formed . The harmful quinone methide can be formed during the radical conversion.

Eugenol can also be used as an anesthetic for fish.

toxicity

Eugenol is cytotoxic and genotoxic ; the genotoxic effects are dependent on activation by the enzyme cytochrome P450 . It is both an antioxidant and a prooxidant ; Its (mucus) skin-irritating, allergy-promoting effect is probably based on the latter.

See also

Individual evidence

  1. ↑ Entry on EUGENOL in the CosIng database of the EU Commission, accessed on May 17, 2020.
  2. ↑ a b c d e Entry on eugenol in the GESTIS substance database of the IFA , accessed on January 10, 2017(JavaScript required) .
  3. ↑ a b c Entry on eugenol. In: Römpp Online . Georg Thieme Verlag, accessed on November 10, 2014.
  4. ↑ DIMDI : ATC classification Germany
  5. ↑ Eugenol data sheet (PDF) from Merck , accessed on February 19, 2010.
  6. ↑ Patent WO2005074965 : Applications of natural and synthetic eugenol and essential oils from cloves, pimentos and cinnamon leaves for the prevention and treatment of animal deseases caused by bacteria, fungi and parasites. Published on August 18, 2005 , inventor: Vojin Gligovic. ‌
  7. ↑ Entry on eugenol in the ChemIDplus database of the United States National Library of Medicine (NLM) .
  8. ↑ M. Iwasa, S. Nakaya, Y. Maki, S. Marumoto, A. Usami, M. Miyazawa: Identification of Aroma-active Compounds in Essential Oil from Uncaria Hook by Gas Chromatography- Mass Spectrometry and Gas Chromatography-Olfactometry. In: J Oleo Sci. 64 (8), 2015, pp. 825-833. PMID 26179003
  9. ↑ C. Ke, Q. Liu, L. Li, J. Chen, X. Wang, K. Huang: Simultaneous determination of eugenol, isoeugenol and methyleugenol in fish fillet using gas chromatography coupled to tandem mass spectrometry. In: J Chromatogr B Analyt Technol Biomed Life Sci. 1031, Sep 15, 2016, pp. 189-194. PMID 27497157
  10. ^ J. Schubert, A. Luch, TG Schulz: Waterpipe smoking: analysis of the aroma profile of flavored waterpipe tobaccos. In: Talanta . 115, Oct 15, 2013, pp. 665-674. PMID 24054646
  11. ↑ xeda international: BIOX-C
  12. ↑ a b Eugenol at Dr Duke's Phytochemical Databases ( Memento from November 26, 2015 in the Internet Archive ).
  13. ↑ El-Sayed AM 2005: The Pherobase: Database of Insect Pheromones and Semiochemicals.
  14. ^ Joint FAO / WHO Expert Committee on Food Additives (JECFA), Monograph for Eugenol and related Hydroxyallylbenzene Derivatives , accessed September 15, 2015.
  15. ↑ Federico Baici: Fair fish - stunning methods in comparison. Possibilities for the detection of a head blow stunning and alternatives for the anesthesia of edible fish. ( Memento of March 5, 2016 in the Internet Archive ) (PDF; 1.8 MB). 2004, p. 5.
  16. ↑ A. Prashar, IC Locke, CS Evans: Cytotoxicity of clove (Syzygium aromaticum) oil and its major components to human skin cells. In: Cell Prolif. 39 (4), 2006, pp. 241-248. PMID 16872360 .
  17. ↑ MC Munerato, M. Sinigaglia, ML Reguly, HH de Andrade: Genotoxic effects of eugenol, isoeugenol and safrole in the wing spot test of Drosophila melanogaster. In: Mutation Research . 582 (1-2), 2005, pp. 87-94. PMID 15781214 .
  18. ↑ T. Atsumi, S. Fujisawa, K. Tonosaki: A comparative study of the antioxidant / prooxidant activities of eugenol and isoeugenol with various concentrations and oxidation conditions. In: Toxicol Vitro . 19 (8), 2005, pp. 1025-1033. PMID 15964168 .