There are six pinene isomers , two each of α-pinene , two β-pinene and two known δ-pinene e; the latter are described in the literature as (+) - cis -δ-pinene and (-) - cis -δ-pinene.
In 1907 Otto Wallach assigned three pinene as α, β- and γ-pinene. Another representative was discovered in 1921 and consequently referred to as δ-pinene. The constitution of "γ-pinene" assigned by Wallach was rejected again by Harry Schmidt in 1947 because it contradicted Bredt's rule . The above-mentioned classic designations of the pinene (α, β, γ, δ) were retained because they had already become established in the literature at that time.
|Surname||(+) - α-pinene||(-) - α-pinene||(+) - β-pinene||(-) - β-pinene||(+) - cis -δ-pinene||(-) - cis -δ-pinene|
|other names||Pin-2 (3) -ene
|Pin-2 (10) -en
2 (10) -pinene
|Molecular formula||C 10 H 16|
|Molar mass||136.24 g mol −1|
|Brief description||colorless liquid with a turpentine odor|
|Melting point||−55 ° C||−61 ° C|
|boiling point||155 ° C||165-166 ° C|
|density||0.86 g cm −3 (15 ° C)||0.87 g cm −3 (20 ° C)|
|Vapor pressure||5 h Pa (25 ° C)||2.66 hPa|
|solubility||practically insoluble in water|
|Refractive index||1.4653 (20 ° C)||1.4768 (20 ° C)|
|Flash point||33 ° C||36 ° C|
|H and P phrases||---||---||----||see above||see above|
|no EUH phrases||no EUH phrases||no EUH phrases||see above||see above|
|--||--||----||see above||see above|
The α- and β-pinene occur, for example, in myrtle , spruce needles , dill , fennel , coriander and caraway , and in products such as paints, oils and waxes. δ-pinene in rosemary, for example . Oil of turpentine consists of about 60 percent α-pinene.
Pinene are not very volatile, flammable, clear liquids with a turpentine odor, less dense than water, and insoluble in water. Their melting and boiling temperatures and their densities differ only slightly. α-Pinene usually oxidizes to Verbenone , Myrtenol , Pinene Oxide and other products. When exposed to heat, β-pinene can be converted into myrcene . A secondary oxidation product of pinene is the allergenic ascaridol , which is why essential oils containing pinene can cause allergies after just a few days.
α-Pinene belongs to the monoterpenes and is used as a flavoring in the food industry.
α-pinene in higher doses is classified as harmful due to its irritative effects on the eyes, respiratory tract and skin, and possible neurotoxic and nephrotoxic effects. Β-pinene is also irritating. α-pinene may have an anti-inflammatory and at least in vitro anti-microbial effect . In low doses, α-pinene has a bronchospasmolytic effect .
For reliable qualitative and quantitative determination, after appropriate sample preparation, the coupling of gas chromatography and mass spectrometry is used. The use of olfactometry is also used for identification and characterization.
Pin-2 (10) -en was included by the EU in 2014 in accordance with Regulation (EC) No. 1907/2006 (REACH) in the context of substance evaluation in the Community's ongoing action plan ( CoRAP ). The effects of the substance on human health and the environment are re-evaluated and, if necessary, follow-up measures are initiated. The reasons for the uptake of Pin-2 (10) -en were concerns about consumer use , high (aggregated) tonnage and widespread use as well as the suspected dangers of sensitizing properties. The re-evaluation took place from 2014 and was carried out by Greece . A final report was then published.
- Dennis Hobuß: α- and β-Pinene: Versatile Chiral Carbon Scaffolds for Asymmetric Catalysis . WiKu-Wissenschaftsverlag Dr. Stein, Duisburg / Cologne 2007, ISBN 978-3-86553-225-1 .
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- O. Wallach: On the knowledge of the terpenes and the essential oils about Nopinon. In: Nachr. Ges. Wiss. Goettingen. 1907, p. 232.
- A. Blumann, O. Zeitschel: About verbena (dehydro-α-pinene) and some of its descendants. In: Chemical Reports . Volume 54, No. 5, 1921, p. 887.
- Harry Schmidt: On the spatial isomerism in the Pinanzeile, VI. Commun .: cis- and trans-δ-pinene. In: Chemical Reports. 80 (6), 1947, pp. 520-527. doi: 10.1002 / cber.19470800610
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- Data sheet (+) - β-Pinene from Sigma-Aldrich , accessed on August 30, 2018 ( PDF ).
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- European Chemicals Agency (ECHA): Substance Evaluation Conclusion and Evaluation Report .
- Community rolling action plan ( CoRAP ) of the European Chemicals Agency (ECHA): (-) - pin-2 (10) -ene , accessed on May 20, 2019.