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Camphor
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Camphor

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Camphor

Camphor (/ˈkæmfər/) is a waxy, colorless solid with a strong aroma. It is classified as a terpenoid and a cyclic ketone. It is found in the wood of the camphor laurel (Cinnamomum camphora), a large evergreen tree found in East Asia; and in the kapur tree (Dryobalanops sp.), a tall timber tree from South East Asia. It also occurs in some other related trees in the laurel family, notably Ocotea usambarensis. Rosemary leaves (Rosmarinus officinalis) contain 0.05 to 0.5% camphor, while camphorweed (Heterotheca) contains some 5%. A major source of camphor in Asia is camphor basil (the parent of African blue basil). Camphor can also be synthetically produced from oil of turpentine.

The compound is chiral, existing in two possible enantiomers as shown in the structural diagrams. The structure on the left is the naturally occurring (+)-camphor ((1R,4R)-bornan-2-one), while its mirror image shown on the right is the (−)-camphor ((1S,4S)-bornan-2-one). Camphor has few uses but is of historic significance as a compound that is readily purified from natural sources.

The word camphor derived in the 14th century from Old French: camphre, itself from Medieval Latin: camfora, from Arabic: كافور, romanizedkāfūr, perhaps through Sanskrit: कर्पूर, romanizedkarpūra, from Tamil: கற்பூரம், romanized: karpooram apparently from Austronesian Malay: kapur 'lime' (chalk).

In Old Malay, camphor was called kapur barus, meaning "the chalk of Barus", referring to Barus, an ancient port near modern Sibolga on the western coast of Sumatra. This port traded in camphor extracted from the Borneo camphor trees (Dryobalanops aromatica) that were abundant in the region.

(+)-camphor has been produced as a forest product for centuries, condensed from the vapor given off by the roasting of wood chips cut from Camphora officinarum, and later by passing steam through the pulverized wood and condensing the vapors. By the early 19th century most camphor tree reserves had been depleted with the remaining large stands in Japan and Taiwan, with Taiwanese production greatly exceeding Japanese. Camphor was one of the primary resources extracted by Taiwan's colonial powers as well as one of the most lucrative. First the Chinese and then the Japanese established monopolies on Taiwanese camphor. In 1868, a British naval force sailed into Anping harbor and the local British representative demanded the end of the Chinese camphor monopoly. After the local imperial representative refused, the British bombarded the town and took the harbor. The "camphor regulations" negotiated between the two sides subsequently saw a brief end to the camphor monopoly.

(-)-camphor occurs naturally in the essential oil of Matricaria plants. As a result, it's much rarer.

Camphor is produced from alpha-pinene, which is abundant in the oils of coniferous trees and can be distilled from turpentine produced as a side product of chemical pulping. With acetic anhydride as the solvent and with catalysis by a strong acid, alpha-pinene is converted to isobornyl acetate. Hydrolysis of this ester gives isoborneol which can be oxidized to give racemic camphor.

A biological enzyme has been proposed for producing only the rare (-) or L-camphor. This EstB esterase from Burkholderia gladioli hydrolyzes only (+)-isobornyl acetate.

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