Creosol

Structural formula
General
Surname	Creosol
other names	Homocatechol methyl ether; Homoguajacol; Dimethyl catechol; 2-methoxy-4-methylphenol; 4-methylguaiacol; 2-methoxy-p-cresol; Creosol; FEMA 2671 ; 2-METHOXY-P-CRESOL ( INCI ) ; Valspice;
Molecular formula	C 8 H 10 O 2
Brief description	colorless to yellowish liquid, sweet, spicy, with a slight vanilla odor
External identifiers / databases
EC number	202-252-9
ECHA InfoCard	100.002.049
PubChem	7144
ChemSpider	21105936
Wikidata	Q403037
properties
Molar mass	138.16 g mol −1
Physical state	liquid
density	1.092 g cm −3 (25 ° C)
Melting point	5 ° C
boiling point	221-222 ° C
Vapor pressure	3.2 Pa (25 ° C)
pK s value	10.28
solubility	Slightly soluble in water; Miscible with ethanol, ether, benzene, chloroform, acetic acid;
Refractive index	1.537
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 302-315-319
	P: 301 + 312 + 330-305 + 351 + 338
Toxicological data	76 mg kg −1 ( LD 50 , mouse , iv ) ; 740 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

Creosol ( not to be confused with cresol ) is an aromatic compound . It can be seen as a methyl derivative of guaiacol or as a methoxy derivative of p -cresol. It is an isomer to isocreosol , from which it differs only in the position of the methoxy group.

Occurrence

Creosol found mainly in Holzteerkreosot and in Holzteeren , the largest content has Buchholz, but it is also produced in addition to guaiacol in the dry distillation of the guaiacum resin and forms a the guaiacol-like liquid, as well as in pinoresinol . It is also found in vanilla beans , as well as prickly juniper Juniperus oxycedrus and tobacco, as well as many other foods and plants.

presentation

Creosol can be reduced from vanillin with zinc powder and hydrochloric acid . It is also created by the thermal breakdown of ferulic acid . The cleavage of ethers produces 3,4-dihydroxytoluene .

properties

Kreosol is a colorless to yellowish liquid with a sweet, spicy smell that smells slightly of vanilla.

The pK _s value of 10.28 is virtually indistinguishable from p -cresol with 10.26; the additional methoxy group has practically no influence.

use

Kreosol is a repellent against tsetse flies . It is used in hair growth preparations and eye lotions, it is an antiseptic and disinfectant. It is also used as a herbicide , in detergents and as a textile abrasive.

Individual evidence

^ Entry on FEMA 2671 in the database of the Flavor and Extract Manufacturers Association of the United States .
↑ Entry on 2-METHOXY-P-CRESOL in the CosIng database of the EU Commission, accessed on July 10, 2020.
↑ entry to cresol in the ChemSpider database of the Royal Society of Chemistry , accessed on 29 July 2016th
↑ ^a ^b ^c ^d ^e ^f ^g data sheet 2-methoxy-4-methylphenol from Sigma-Aldrich , accessed on August 7, 2017 ( PDF ).
↑ ^a ^b ^c ^d ^e Entry on Creosol in the ChemIDplus database of the United States National Library of Medicine (NLM), accessed on July 29, 2016.
↑ George A. Burdock: Encyclopedia of Food and Color Additives . CRC Press, 1997, ISBN 978-0-8493-9412-6 , pp. 1697 ( limited preview in Google Book search).
↑ ^a ^b George A. Burdock: Fenaroli's Handbook of Flavor Ingredients. Sixth Edition. CRC Press, Boca Raton 2010, ISBN 978-1-420-09086-4 , p. 1198.
↑ External identifiers or database links for pinoresinol : CAS number: 487-36-5, PubChem : 73399 , Wikidata : Q3388802 .
↑ Emil Abderhalden : Biochemisches Handlexikon. 1st volume, 1st half, Springer-Verlag, 1911, ISBN 978-3-642-51328-2 , p. 645.
^ Hermann von Fehling, Carl Hell, Carl Haeussermann, Karl Hugo Bauer (eds.): New Concise Dictionary of Chemistry: based on the Concise Dictionary of Pure and Applied Chemistry published by Liebig, Poggendorf and Wöhler, Kolbe and Fehling . tape 3 . Vieweg, Braunschweig 1878, DNB 560549326 .
↑ Daphna Havkin-Frenkel, Faith C. Belanger: Handbook of Vanilla Science and Technology. John Wiley & Sons, 2010, ISBN 978-1-4443-2937-7 .
↑ Marina Bährle-Rapp: Springer Lexicon Cosmetics and Body Care. Springer-Verlag, 2007, ISBN 978-3-540-71095-0 , p. 293.
↑ Alan Rodgman, Thomas A. Perfetti: The Chemical Components of Tobacco and Tobacco Smoke. CRC Press, 2013, ISBN 978-1-4200-7884-8 , p. 556.
^ R. Schwarz, H. Hering: Creosol In: Organic Syntheses . 33, 1953, p. 17, doi : 10.15227 / orgsyn.033.0017 ; Coll. Vol. 4, 1963, p. 203 ( PDF ).
↑ Hans-Dieter Belitz, Werner Grosch: Textbook of food chemistry. Springer-Verlag, 1987, ISBN 978-3-662-08308-6 , p. 297.
↑ CRC Handbook of Tables for Organic Compound Identification . Third Edition, 1984, ISBN 0-8493-0303-6 .
↑ Wolfgang Legrum: Fragrances, between stench and fragrance. 2nd Edition. Springer-Verlag, Wiesbaden 2015, ISBN 978-3-658-07310-7 , p. 67.
↑ Ruth Winter: A Consumer's Dictionary of Household, Yard and Office Chemicals. iUniverse, 2007, ISBN 978-0-595-44948-4 , p. 118.

[FEMA2671-1] Entry on FEMA 2671 in the database of the Flavor and Extract Manufacturers Association of the United States .

[CosIng-2] Entry on 2-METHOXY-P-CRESOL in the CosIng database of the EU Commission, accessed on July 10, 2020.

[3] try to cresol in the ChemSpider database of the Royal Society of Chemistry , accessed on 29 July 2016th

[sigma-4] ↑ ^a ^b ^c ^d ^e ^f ^g data sheet 2-methoxy-4-methylphenol from Sigma-Aldrich , accessed on August 7, 2017 ( PDF ).

[Creo-5] Entry on Creosol in the ChemIDplus database of the United States National Library of Medicine (NLM), accessed on July 29, 2016.

[George_A._Burdock-6] George A. Burdock: Encyclopedia of Food and Color Additives . CRC Press, 1997, ISBN 978-0-8493-9412-6 , pp. 1697 ( limited preview in Google Book search).

[Fenaroli-7] George A. Burdock: Fenaroli's Handbook of Flavor Ingredients. Sixth Edition. CRC Press, Boca Raton 2010, ISBN 978-1-420-09086-4 , p. 1198.

[8] External identifiers or database links for pinoresinol : CAS number: 487-36-5, PubChem : 73399 , Wikidata : Q3388802 .

[9] Emil Abderhalden : Biochemisches Handlexikon. 1st volume, 1st half, Springer-Verlag, 1911, ISBN 978-3-642-51328-2 , p. 645.

[10] Hermann von Fehling, Carl Hell, Carl Haeussermann, Karl Hugo Bauer (eds.): New Concise Dictionary of Chemistry: based on the Concise Dictionary of Pure and Applied Chemistry published by Liebig, Poggendorf and Wöhler, Kolbe and Fehling . tape 3 . Vieweg, Braunschweig 1878, DNB 560549326 .

[11] Daphna Havkin-Frenkel, Faith C. Belanger: Handbook of Vanilla Science and Technology. John Wiley & Sons, 2010, ISBN 978-1-4443-2937-7 .

[12] Marina Bährle-Rapp: Springer Lexicon Cosmetics and Body Care. Springer-Verlag, 2007, ISBN 978-3-540-71095-0 , p. 293.

[13] Alan Rodgman, Thomas A. Perfetti: The Chemical Components of Tobacco and Tobacco Smoke. CRC Press, 2013, ISBN 978-1-4200-7884-8 , p. 556.

[14] R. Schwarz, H. Hering: Creosol In: Organic Syntheses . 33, 1953, p. 17, doi : 10.15227 / orgsyn.033.0017 ; Coll. Vol. 4, 1963, p. 203 ( PDF ).

[15] Hans-Dieter Belitz, Werner Grosch: Textbook of food chemistry. Springer-Verlag, 1987, ISBN 978-3-662-08308-6 , p. 297.

[CRC-16] CRC Handbook of Tables for Organic Compound Identification . Third Edition, 1984, ISBN 0-8493-0303-6 .

[17] Wolfgang Legrum: Fragrances, between stench and fragrance. 2nd Edition. Springer-Verlag, Wiesbaden 2015, ISBN 978-3-658-07310-7 , p. 67.

[18] Ruth Winter: A Consumer's Dictionary of Household, Yard and Office Chemicals. iUniverse, 2007, ISBN 978-0-595-44948-4 , p. 118.