Terpinoles

Structural formula
General
Surname	Terpinoles
other names	1-methyl-4-propan-2-ylidenecyclohexene; δ-terpinene;
Molecular formula	C 10 H 16
Brief description	colorless liquid
External identifiers / databases
EC number	209-578-0
ECHA InfoCard	100.008.709
PubChem	11463
Wikidata	Q2405051
properties
Molar mass	136.23 g mol −1
density	0.86 g cm −3 (20 ° C)
Melting point	<25 ° C
boiling point	186 ° C
solubility	almost insoluble in water (9.5 mg l −1 at 23 ° C)
Refractive index	1.4888
safety instructions
H and P phrases	H: 304-317-410
	P: 273-280-301 + 310-331-302 + 352-333 + 313-501
Toxicological data	4390 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

Terpinolene belongs to the naturally occurring group of menthadienes , that is, terpenes with a p-menthane structure and two double bonds . These occur in numerous isomeric forms in essential oils . Terpinolene is found in traces in Vitis vinifera , parsley roots and in a few other plants. Here it is produced via a (-) - α- terpineol synthase ( terpene synthase ). Parsnip oil is particularly rich in terpinol, which contains between 40 and 70 percent. Terpinolene is also a termite alarm pheromone .

The α-terpinolene is also known inconsistently as δ-terpinene and is therefore one of the isomeric terpinenes .

properties

Terpinolene is a colorless liquid that, like all menthadienes, is sensitive to light, air and heat. According to Antoine, the vapor pressure function results from log ₁₀ (P) = A− (B / (T + C)) (P in bar, T in K) with A = 2.95742, B = 934.936 and C = −146.641 in the temperature range from 313.6 K to 452 K.

The compound forms flammable vapor-air mixtures above the flash point. The flash point is around 53 ° C.

use

Terpinolene is used as an additive in furniture polishes and shoe care products.

Individual evidence

↑ Terpinolen data sheet (PDF) from Carl Roth , accessed on December 14, 2010.

^ ^A ^b R. T. O'Connor, LA Goldblatt: Correlation of Ultraviolet and Infrared Spectra of Terpene Hydrocarbons , in: Anal. Chem. , 1954 , 26 , pp. 1726-1737; doi : 10.1021 / ac60095a014 .

↑ ^a ^b ^c ^d Entry on terpinolene in the ChemIDplus database of the United States National Library of Medicine (NLM) .

↑ ^a ^b Entry on p-Mentha-1,4 (8) -diene in the GESTIS substance database of the IFA , accessed on January 10, 2017(JavaScript required) .

↑ The chemistry of parsley (Bernhard Peter and Stephanie Brach)

↑ Liber Herbarum Minor

↑ ^a ^b ^c Entry on p-menthadiene. In: Römpp Online . Georg Thieme Verlag, accessed on June 13, 2014.

↑ Pickett, OA; Peterson, JM: Terpenes and Terpene Alcohols. I. Vapor Pressure-Temperature Relationships , in: Ind. Eng. Chem. , 1929 , 21 , pp. 325-326.

^ E. Brandes, W. Möller: Safety-related parameters - Volume 1: Flammable liquids and gases , Wirtschaftsverlag NW - Verlag für neue Wissenschaft GmbH, Bremerhaven 2003.

[roth-1] Terpinolen data sheet (PDF) from Carl Roth , accessed on December 14, 2010.

[oc-2] A ^b R. T. O'Connor, LA Goldblatt: Correlation of Ultraviolet and Infrared Spectra of Terpene Hydrocarbons , in: Anal. Chem. , 1954 , 26 , pp. 1726-1737; doi : 10.1021 / ac60095a014 .

[ChemIDplus-3] Entry on terpinolene in the ChemIDplus database of the United States National Library of Medicine (NLM) .

[GESTIS-4] Entry on p-Mentha-1,4 (8) -diene in the GESTIS substance database of the IFA , accessed on January 10, 2017(JavaScript required) .

[5] The chemistry of parsley (Bernhard Peter and Stephanie Brach)

[6] Liber Herbarum Minor

[Römpp-7] Entry on p-menthadiene. In: Römpp Online . Georg Thieme Verlag, accessed on June 13, 2014.

[8] Pickett, OA; Peterson, JM: Terpenes and Terpene Alcohols. I. Vapor Pressure-Temperature Relationships , in: Ind. Eng. Chem. , 1929 , 21 , pp. 325-326.

[9] E. Brandes, W. Möller: Safety-related parameters - Volume 1: Flammable liquids and gases , Wirtschaftsverlag NW - Verlag für neue Wissenschaft GmbH, Bremerhaven 2003.