Terpinen-4-ol

Structural formula
	Structural formula without stereochemistry
General
Surname	Terpinen-4-ol
other names	1- p -menthen-4-ol; 4-carvomenthenol; 4-TERPINEOL ( INCI ) ;
Molecular formula	C 10 H 18 O
Brief description	colorless liquid with a characteristic odor
External identifiers / databases
EC number	209-235-5
ECHA InfoCard	100.008.396
PubChem	11230
ChemSpider	10756
DrugBank	DB12816
Wikidata	Q416114
properties
Molar mass	154.25 g mol −1
Physical state	liquid
density	0.93 g cm −3
boiling point	211-213 ° C
Vapor pressure	5 h Pa (20 ° C)
solubility	soluble in ethanol
Refractive index	1.4785 (19 ° C)
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 302-315-319-335
	P: 261-305 + 351 + 338
	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

Terpinen-4-ol is a chemical compound that occurs naturally as a secondary plant substance. It is a colorless terpene - alcohol with characteristic floral and spicy smell.

Isomerism

The structure of terpinen-4-ol has a stereocenter, consequently the substance occurs in two stereoisomers or as a mixture thereof. Since only the racemic mixture is used in the perfume industry and the isomers hardly differ, we are only talking about the properties of the mixture here.

Terpinen-4-ol is found in the essential oil of pine trees

Occurrence

Terpinen-4-ol is a component of many essential oils , and occurs, for example, in pine ( pine oil ), eucalyptus ( eucalyptus oil ), lavender ( lavender oil ) and in the tea tree ( tea tree oil ).

Extraction and presentation

Terpinen-4-ol is a by-product in the manufacture of terpineol from terpin hydrate and is thus part of commercial terpineol mixtures.

Pure terpinen-4-ol ( 4 ) can be produced from terpinolene ( 1 ) by photooxidation, reduction of the hydroperoxide formed ( 2 ) and selective hydrogenation of the alcohol formed ( 3 ):

use

Terpinen-4-ol is used in artificial geranium or pepper oils and creates herbal and lavender scents in the perfume industry. It is also used in cosmetic care products ( tea tree oil ).

literature

H. Surburg and J. Panten: Common Fragrance and Flavor Materials: preparation, properties, and uses . Wiley-VCH, Weinheim 2006, ISBN 3-527-31315-X (English).

Individual evidence

↑ Entry on 4-TERPINEOL in the CosIng database of the EU Commission, accessed on May 11, 2020.
↑ ^a ^b ^c ^d data sheet (±) -Terpinen-4-ol (PDF) from Carl Roth , accessed on October 13, 2018.
↑ George A. Burdock: Fenaroli's Handbook of Flavor Ingredients . CRC Press, 2004, ISBN 1-4200-3787-0 , pp. 264 ( limited preview in Google Book search).
↑ 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. 3-358.
↑ ^a ^b Data sheet (-) - Terpinen-4-ol from Sigma-Aldrich , accessed on October 13, 2018 ( PDF ).
↑ R. Hegnauer: Chemotaxonomie der Pflanzen An overview of the distribution and the systematic importance of plant substances . Springer-Verlag, 2013, ISBN 978-3-0348-9389-3 , pp. 359 ( limited preview in Google Book Search).
↑ Rudolf Hänsel, Konstantin Keller, Horst Rimpler, Georg Schneider: Hager's handbook of pharmaceutical practice, drugs E-O . Springer-Verlag, 2013, ISBN 978-3-642-57993-6 , pp. 955 ( limited preview in Google Book Search).
↑ Ullmann's Encyclopedia of Technical Chemistry . Wiley, 1981, ISBN 3-527-20020-7 , pp. 201 ( limited preview in Google Book search).
↑ Peter Brandt: Reports on Food Safety 2008 Federal Monitoring Plan 2008 . Springer-Verlag, 2009, ISBN 978-3-0346-0254-9 , pp. 46 ( limited preview in Google Book search).

[CosIng-1] Entry on 4-TERPINEOL in the CosIng database of the EU Commission, accessed on May 11, 2020.

[Carl_Roth-2] ta sheet (±) -Terpinen-4-ol (PDF) from Carl Roth , accessed on October 13, 2018.

[George_A._Burdock-3] George A. Burdock: Fenaroli's Handbook of Flavor Ingredients . CRC Press, 2004, ISBN 1-4200-3787-0 , pp. 264 ( limited preview in Google Book search).

[CRC90_3_358-4] 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. 3-358.

[Sigma-5] Data sheet (-) - Terpinen-4-ol from Sigma-Aldrich , accessed on October 13, 2018 ( PDF ).

[R._Hegnauer-6] R. Hegnauer: Chemotaxonomie der Pflanzen An overview of the distribution and the systematic importance of plant substances . Springer-Verlag, 2013, ISBN 978-3-0348-9389-3 , pp. 359 ( limited preview in Google Book Search).

[Rudolf_Hänsel,_Konstantin_Keller,_Horst_Rimpler,_Georg_Schneider-7] Rudolf Hänsel, Konstantin Keller, Horst Rimpler, Georg Schneider: Hager's handbook of pharmaceutical practice, drugs E-O . Springer-Verlag, 2013, ISBN 978-3-642-57993-6 , pp. 955 ( limited preview in Google Book Search).

[8] Ullmann's Encyclopedia of Technical Chemistry . Wiley, 1981, ISBN 3-527-20020-7 , pp. 201 ( limited preview in Google Book search).

[Peter_Brandt-9] Peter Brandt: Reports on Food Safety 2008 Federal Monitoring Plan 2008 . Springer-Verlag, 2009, ISBN 978-3-0346-0254-9 , pp. 46 ( limited preview in Google Book search).