3-carene
Structural formula | ||||||||||||||||
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Structure without showing the stereochemical configuration | ||||||||||||||||
General | ||||||||||||||||
Surname | 3-carene | |||||||||||||||
other names |
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Molecular formula | C 10 H 16 | |||||||||||||||
Brief description |
colorless liquid with a turpentine odor |
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External identifiers / databases | ||||||||||||||||
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properties | ||||||||||||||||
Molar mass | 136.24 g mol −1 | |||||||||||||||
Physical state |
liquid |
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density |
0.86 g cm −3 |
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boiling point |
170-172 ° C |
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Vapor pressure |
2.7 h Pa (20 ° C) |
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solubility |
practically insoluble in water |
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Refractive index |
1.4722 |
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safety instructions | ||||||||||||||||
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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
(+) - 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.