3-carene

Structural formula
	Structure without showing the stereochemical configuration
General
Surname	3-carene
other names	3-Karen; Δ 3 -carene; 3,7,7-Trimethylbicyclo [4.1.0] hept-3-en; 3-CARENE ( INCI ) ;
Molecular formula	C 10 H 16
Brief description	colorless liquid with a turpentine odor
External identifiers / databases
EC number	236-719-3
ECHA InfoCard	100.033.367
PubChem	26049
Wikidata	Q19414
properties
Molar mass	136.24 g mol −1
Physical state	liquid
density	0.86 g cm −3
boiling point	170-172 ° C
Vapor pressure	2.7 h Pa (20 ° C)
solubility	practically insoluble in water
Refractive index	1.4722
safety instructions
H and P phrases	H: 226-304-315-317-412
	P: 210-262-273-280-301 + 310-302 + 352-331
	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

3-Carene (stress on the final syllable: Car e n ) is an organic - chemical compound and belongs to the Carenen , bicyclic mono terpenes . Furthermore, it is shared the group of unsaturated hydrocarbons to be, as it is a compound having a carbon -Kohlenstoff- double bond is.

Isomers

3-Carene occurs in two stereoisomeric forms, (+) - 3-Carene and (-) - 3-Carene.

3-carene isomers
Surname	(+) - 3-carene	(-) - 3-carene
other names	(1 S , 6 R ) - (+) - 3-carene	(1 R , 6 S ) - (-) - 3-carene
Structural formula
CAS number	498-15-7	20296-50-8
	13466-78-9 (unspec.)
EC number	207-856-6	-
	236-719-3 (unspec.)
ECHA info card	100.007.143	-
	100.033.367 (unspec.)
PubChem	443156	442461
	26049 (unspec.)
Wikidata	Q15222640	Q15222645
	Q19414 (unspec.)

Occurrence

Scots pine ( Pinus sylvestris )

(+) - 3-Carene occurs with up to 60% in the tropical pine ( Pinus longifolia ), (-) - 3-Carene with up to 19% in the Scots pine ( Pinus sylvestris , Pinaceae).

Oil of turpentine contains different amounts of 3-carene, depending on its provenance: it is not contained in the American , Greek and Portuguese varieties , in Soviet oil of turpentine the content is up to 24%. It can also be found in pepper oil , in citrus plants , various pine trees , cypresses and juniper species, in the resin of frankincense trees , in essential hemp oil and in nutmeg .

properties

The colorless liquid is flammable, has a flash point of approx. 43 ° C and has a pleasant, sweet odor. 3-Caren is considered to be allergenic and can cause skin eczema ( painter's scratches ).

use

3- Carene can be converted into fragrances by ozonolysis . For the menthol - synthesis can be selected as the starting material.

Furthermore, pyrethroids (chrysanthemum and norchrysanthemic acid esters) can be synthesized enantioselectively from 3-carene .

Monomer components ( camphor lactam and caranlactam ) for polyamides can be produced from 3-carene .

Individual evidence

^ Entry on 3-CARENE in the CosIng database of the EU Commission, accessed on February 16, 2020.
↑ ^a ^b ^c ^d ^e ^f ^g Entry on 3-Carene in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .
^ RT O'Connor, LA Goldblatt: Correlation of Ultraviolet and Infrared Spectra of Terpene Hydrocarbons. In: Anal. Chem. 26, 1954, pp. 1726-1737, doi: 10.1021 / ac60095a014 .
↑ entry to Carene. In: Römpp Online . Georg Thieme Verlag, accessed on April 15, 2017.
↑ Entry on turpentine oil. In: Römpp Online . Georg Thieme Verlag, accessed on April 15, 2017.
^ Robert Tisserand, Rodney Young: Essential Oil Safety. 2nd Edition. Churchill Livingstone / Elsevier, 2014, ISBN 978-0-443-06241-4 , pp. 288, 367, 516, limited preview in the Google book search.
↑ Data sheet δ-3-CAREN (PDF) from Carl Roth , accessed on April 16, 2017.
^ Armin Radünz: Construction products and building-related diseases. Springer, 1998, ISBN 3-642-63717-5 , p. 109.
↑ N. Matsuo, T. Mori, K. Ujihara: Recent Advances of Pyrethroids for Household Use. In: Pyrethroids. From Chrysanthemum to Modern Industrial Insecticide. Springer, 2012, ISBN 978-3-642-27345-2 , p. 31 ff.
↑ Polyamides from wood waste. on: fraunhofer.de , October 7, 2016, accessed April 15, 2017.
↑ Transparent and heat-stable polyamide - 100 percent bio-based. In: fraunhofer.de , August 29, 2018, accessed on July 31, 2020.

[CosIng-1] Entry on 3-CARENE in the CosIng database of the EU Commission, accessed on February 16, 2020.

[GESTIS-2] ↑ ^a ^b ^c ^d ^e ^f ^g Entry on 3-Carene in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .

[3] RT O'Connor, LA Goldblatt: Correlation of Ultraviolet and Infrared Spectra of Terpene Hydrocarbons. In: Anal. Chem. 26, 1954, pp. 1726-1737, doi: 10.1021 / ac60095a014 .

[4] try to Carene. In: Römpp Online . Georg Thieme Verlag, accessed on April 15, 2017.

[5] Entry on turpentine oil. In: Römpp Online . Georg Thieme Verlag, accessed on April 15, 2017.

[6] Robert Tisserand, Rodney Young: Essential Oil Safety. 2nd Edition. Churchill Livingstone / Elsevier, 2014, ISBN 978-0-443-06241-4 , pp. 288, 367, 516, limited preview in the Google book search.

[7] Data sheet δ-3-CAREN (PDF) from Carl Roth , accessed on April 16, 2017.

[8] Armin Radünz: Construction products and building-related diseases. Springer, 1998, ISBN 3-642-63717-5 , p. 109.

[9] N. Matsuo, T. Mori, K. Ujihara: Recent Advances of Pyrethroids for Household Use. In: Pyrethroids. From Chrysanthemum to Modern Industrial Insecticide. Springer, 2012, ISBN 978-3-642-27345-2 , p. 31 ff.

[10] Polyamides from wood waste. on: fraunhofer.de , October 7, 2016, accessed April 15, 2017.

[11] Transparent and heat-stable polyamide - 100 percent bio-based. In: fraunhofer.de , August 29, 2018, accessed on July 31, 2020.