Isoeugenol

Structural formula
General
Surname	Isoeugenol
other names	2-methoxy-4- (1-propenyl) phenol; ISOEUGENOL ( INCI ) ;
Molecular formula	C 10 H 12 O 2
Brief description	yellowish viscous liquid with a characteristic odor
External identifiers / databases
EC number	202-590-7
ECHA InfoCard	100.002.356
PubChem	7338
ChemSpider	7061
Wikidata	Q420043
properties
Molar mass	164.20 g mol −1
Physical state	liquid
density	1.077 g cm −3 (20 ° C)
Melting point	19-23 ° C
boiling point	266-268 ° C
solubility	poorly soluble in water
Refractive index	1.5739 (19 ° C)
safety instructions
GHS hazard labeling from Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary Caution
H and P phrases	H: 302-315-317-319
	P: 280-301 + 330 + 331-312-302 + 352-305 + 351 + 338-337 + 313
Toxicological data	1560 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

Isoeugenol belongs to the phenylpropanoid group and is a yellowish liquid with a characteristic clove odor. It occurs naturally as a mixture of cis and trans isomers, with the proportion of the trans isomer predominating. Isoeugenol comes in a. in ylang-ylang oil , nutmeg oil , cloves and dill.

properties

Vanillin can be obtained industrially by isomerizing eugenol (1) to isoeugenol (2) using alkalis and subsequent oxidation with potassium permanganate or ozone .

The flash point of isoeugenol is> 150 ° C.

toxicity

Isoeugenol is not genotoxic , but causes hepatocellular carcinoma and adenoma after oral administration in male mice. It is both an antioxidant and a prooxidant ; Its (mucus) skin-irritating, allergy-promoting effect is probably based on the latter.

Legal

Because of its (skin) sensitizing and allergenic potential, isoeugenol is subject to labeling (Appendix 2 of the Cosmetics Ordinance ) if it is more than 0.001% in products that remain on the skin or more than 0.01% in products that are rinsed off again will be included.

Trivia

Otto Hahn , who later won the Nobel Prize for Chemistry , received his doctorate for a thesis on the bromine derivatives of isoeugenol.

Individual evidence

↑ Entry on ISOEUGENOL in the CosIng database of the EU Commission, accessed on May 18, 2020.

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Entry on isoeugenol in the GESTIS substance database of the IFA , accessed on December 30, 2019(JavaScript required) .

↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-312.

↑ Entry on Isoeugenol in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on December 30, 2019. Manufacturers or distributors can expand the harmonized classification and labeling .

↑ Li, YH; Sun, ZH; Zheng, P., Determination of Vanillin, Eugenol and Isoeugenol by RP-HPLC , in: Chromatographia , 2004 , 60 , pp. 709-713 ( doi : 10.1365 / s10337-004-0440-4 ).

^ Gary M. Lampman, Jennifer Andrews, Wayne Bratz, Otto Hanssen, Kenneth Kelley, Dana Perry, Anthony Ridgeway: The Preparation of Vanillin from Eugenol and Sawdust , in: Journal of Chemical Education , 1977 , 54 (12), p. 776 -778 ( doi : 10.1021 / ed054p776 ).

^ Beyer / Walter : Textbook of Organic Chemistry , 19th edition, S. Hirzel Verlag, Stuttgart 1981, ISBN 3-7776-0356-2 , p. 504.

↑ 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 , 2005 , 582 (1–2), pp. 87– 94 ( PMID 15781214 ).

↑ Natl Toxicol Program, Tech Rep Ser. 2010 Sep; (551): 1-178. Toxicology and carcinogenesis studies of isoeugenol (CAS No. 97-54-1) in F344 / N rats and B6C3F1 mice (gavage studies) ( PDF ( Memento of the original from October 10, 2012 in the Internet Archive ) Info: The archive link was inserted automatically and not yet checked. Please check the original and archive link according to the instructions and then remove this note. ). @1@ 2

↑ 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 , 2005 , 19 (8), pp. 1025-1033 ( PMID 15964168 ).

[CosIng-1] Entry on ISOEUGENOL in the CosIng database of the EU Commission, accessed on May 18, 2020.

[GESTIS-2] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Entry on isoeugenol in the GESTIS substance database of the IFA , accessed on December 30, 2019(JavaScript required) .

[CRC90_3_312-3] David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-312.

[CLP_100.002.356-4] Entry on Isoeugenol in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on December 30, 2019. Manufacturers or distributors can expand the harmonized classification and labeling .

[5] Li, YH; Sun, ZH; Zheng, P., Determination of Vanillin, Eugenol and Isoeugenol by RP-HPLC , in: Chromatographia , 2004 , 60 , pp. 709-713 ( doi : 10.1365 / s10337-004-0440-4 ).

[LAMPMAN-6] Gary M. Lampman, Jennifer Andrews, Wayne Bratz, Otto Hanssen, Kenneth Kelley, Dana Perry, Anthony Ridgeway: The Preparation of Vanillin from Eugenol and Sawdust , in: Journal of Chemical Education , 1977 , 54 (12), p. 776 -778 ( doi : 10.1021 / ed054p776 ).

[BEYER_WALTER_504-7] Beyer / Walter : Textbook of Organic Chemistry , 19th edition, S. Hirzel Verlag, Stuttgart 1981, ISBN 3-7776-0356-2 , p. 504.

[8] 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 , 2005 , 582 (1–2), pp. 87– 94 ( PMID 15781214 ).