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(+)-alpha-Pinene is employed in the preparation of chiral hydroboration reagents. It is a bronchodilator in humans. α-Pinene is an anti-inflammatory and used as a broad-spectrum antibiotic.It exhibits activity as an acetylcholinesterase inhibitor, aiding memory. It is a biosynthetic base for CB2 ligands, such as HU-308.
G. B. Pitman. trans-Verbenol and Alpha-Pinene: Their Utility in Manipulation of the Mountain Pine Beetle.Journal of Economic Entomology.1971, 64 426 - 430.
Herbert C. Brown; Navalkishore N. Joshi. Hydroboration of terpenes. 9. A simple improved procedure for upgrading the optical purity of commercially available .alpha.- and .beta.-pinenes. Conversion of (+)-.alpha.-pinene to (+)-.beta.-pinene via hydroboration-isomerization.J. Org. Chem.1988, 53 (17), 4059-4062.
Forms a chiral adduct with diborane, useful for asymmetric hydroborations with high optical yields: J. Am. Chem. Soc., 99, 5514 (1977). Recrystallization of the borane adduct can be used to obtain a pure single diastereomer: J. Org. Chem., 49, 945 (1984). For reviews of the synthesis of pure enantiomers via chiral organoboranes, see: Acc. Chem. Res., 21, 287 (1988); and of asymmetric reduction with chiral organoboranes based on ɑ-pinene: Acc. Chem. Res., 25, 16 (1992).
Hazard Statements: H226-H315-H319-H317
Flammable liquid and vapour. Causes skin irritation. Causes serious eye irritation. May cause an allergic skin reaction.
Precautionary Statements: P210-P261-P280a-P303+P361+P353-P305+P351+P338-P501a
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves and eye/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Dispose of contents/container in accordance with local/regional/national/international regulations.