The chemical compoundpinene is a bicyclic terpene known as a monoterpene. There are two variations: (−)-α-pinene and (−)-β-pinene. Both are used by many insects in their chemical communication system. A chemical compound is a chemical substance formed from two or more elements, with a fixed ratio determining the composition. ... Terpenes are a class of hydrocarbons, produced by many plants, particularly conifers. ...
Systematic names are (1S,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-2-ene and (1S,5S)-6,6-dimethyl-2-methylenebicyclo[3.1.1]heptane.
Molecular formula: C10H16 Molecular weight: 136.24 Boiling point: 155-156 deg C (alpha); 165-168 deg C (beta).
To the vigorously stirred pinene at 25°C is added the KAPA (0.1 mol) prepared in part A, using a double-ended needle, over 15 min.
The crude pinene is decanted from the calcium chloride through a plug of glass wool and distilled at reduced pressure from lithium aluminium hydride (Note 8) and (Note 9).
It was purified before use by distillation from lithium aluminium hydride; small increments of hydride were added to pinene stirred under nitrogen until an excess was present as determined by observing gas evolution on addition of a few drops of methanol to an aliquot of the slurry.
It is also important that the chemical structure of pinene has the same "handedness" as the taxol molecule, a feature that is crucial to developing a synthetic source of taxol with the same powerful anti-cancer effect.
In addition, pinene, a monoterpene, contains 10 of the carbons that are required in the 20-carbon skeleton of taxol, a diterpene.
So far, by building on pinene, the Stanford group has assembled the three rings of the core molecule of taxol and has put together all of the key functional groups on the first two of these three rings.
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