Terpinylacetate

Structural formula
	Simplified structural formula without stereochemistry
General
Surname	Terpinylacetate
other names	(±) -Terpinylacetate; (±) -2- (4-Methyl-3-cyclohexenyl) isopropyl acetate; ( RS ) terpinylacetate; ( RS ) -2- (4-methyl-3-cyclohexenyl) isopropyl acetate; α-terpinylacetate;
Molecular formula	C 12 H 20 O 2
Brief description	colorless liquid with a characteristic odor
External identifiers / databases
ECHA InfoCard	100.001.151
PubChem	111037
ChemSpider	99681
Wikidata	Q4456134
properties
Molar mass	196.29 g mol −1
Physical state	liquid
density	0.953 g cm −3 (25 ° C)
boiling point	220 ° C
solubility	practically insoluble in water; soluble in essential oils and most organic solvents;
Refractive index	1.465 (20 ° C)
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 315-319
	P: 305 + 351 + 338
Toxicological data	5075 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

Terpinylacetate is a chemical compound from the group of esters of terpineol .

Occurrence

Terpinylacetate occurs mainly in the α-, but also in the δ-form naturally in essential oils of cypress, cardamom, laurel, pine and others.

Extraction and presentation

Terpinylacetate can be obtained by acetylating terpineol or mixed isomeric terpineols using acetic anhydride and anhydrous sodium acetate . It can also be made from 1,8-cineole . The compound was first synthesized in 1888.

properties

Terpinylacetate is a colorless liquid with a characteristic odor that is soluble in essential oils and most organic solvents .

use

Terpinylacetate is used as a fragrance ( lavender and bergamot type) and as an intermediate in the manufacture of carvone .

Individual evidence

↑ ^a ^b ^c ^d ^e ^f George A. Burdock: Encyclopedia of Food and Color Additives . CRC Press, 1997, ISBN 978-0-8493-9414-0 , pp. 2995 ( limited preview in Google Book search).
↑ ^a ^b ^c ^d ^e ^f ^g data sheet α-Terpinyl acetate, FG from Sigma-Aldrich , accessed on November 8, 2018 ( PDF ).
↑ David R. Lide: CRC Handbook of Chemistry and Physics A Ready-reference Book of Chemical and Physical Data . CRC Press, 1995, ISBN 978-0-8493-0595-5 , pp. 510 ( limited preview in Google Book Search).
↑ Klaus Roth: Chemical delicacies . John Wiley & Sons, 2014, ISBN 978-3-527-33739-2 , pp. 199 ( limited preview in Google Book search).
^ Norbert A. Braun, Manfred Meier u. a .: δ-Terpinyl Acetate. A New Natural Component from the Essential Leaf Oil of L. (Lauraceae). In: Journal of Essential Oil Research. 13, 2001, p. 95, doi : 10.1080 / 10412905.2001.9699624 .
↑ Ean-Tun Liaw, Kuan-Ju Liu: Synthesis of terpinyl acetate by lipase-catalyzed esterification in supercritical carbon dioxide. In: Bioresource Technology. 101, 2010, p. 3320, doi : 10.1016 / j.biortech.2009.11.081 .
↑ Kurt Bauer, Dorothea Garbe, Horst Surburg: Common Fragrance and Flavor Materials Preparation, Properties and Uses . John Wiley & Sons, 2008, ISBN 3-527-61237-8 , pp. 69 ( limited preview in Google Book search).

[George_A._Burdock-1] ↑ ^a ^b ^c ^d ^e ^f George A. Burdock: Encyclopedia of Food and Color Additives . CRC Press, 1997, ISBN 978-0-8493-9414-0 , pp. 2995 ( limited preview in Google Book search).

[Sigma-2] ↑ ^a ^b ^c ^d ^e ^f ^g data sheet α-Terpinyl acetate, FG from Sigma-Aldrich , accessed on November 8, 2018 ( PDF ).

[David_R._Lide-3] David R. Lide: CRC Handbook of Chemistry and Physics A Ready-reference Book of Chemical and Physical Data . CRC Press, 1995, ISBN 978-0-8493-0595-5 , pp. 510 ( limited preview in Google Book Search).

[Klaus_Roth-4] Klaus Roth: Chemical delicacies . John Wiley & Sons, 2014, ISBN 978-3-527-33739-2 , pp. 199 ( limited preview in Google Book search).

[DOI10.1080/10412905.2001.9699624-5] Norbert A. Braun, Manfred Meier u. a .: δ-Terpinyl Acetate. A New Natural Component from the Essential Leaf Oil of L. (Lauraceae). In: Journal of Essential Oil Research. 13, 2001, p. 95, doi : 10.1080 / 10412905.2001.9699624 .

[DOI10.1016/j.biortech.2009.11.081-6] Ean-Tun Liaw, Kuan-Ju Liu: Synthesis of terpinyl acetate by lipase-catalyzed esterification in supercritical carbon dioxide. In: Bioresource Technology. 101, 2010, p. 3320, doi : 10.1016 / j.biortech.2009.11.081 .

[Kurt_Bauer,_Dorothea_Garbe,_Horst_Surburg-7] Kurt Bauer, Dorothea Garbe, Horst Surburg: Common Fragrance and Flavor Materials Preparation, Properties and Uses . John Wiley & Sons, 2008, ISBN 3-527-61237-8 , pp. 69 ( limited preview in Google Book search).