Camphor 275978 218459677 2008-06-10T19:17:37Z 71.210.88.247 /* Uses */ {{Chembox new | Reference=<ref>''The Merck Index'', 7th edition, Merk & Co, Rahway, New Jersey, USA, 1960</ref><ref>''Handbook of Chemistry and Physics'', CRC Press, Ann Arbor, Michigan</ref> | Name = Camphor | ImageFile = camphor structure.png | ImageSize = 80px | ImageName = Structure of camphor | IUPACName = 1,7,7-trimethylbicyclo<br /><nowiki>[2.2.1]heptan-2-one</nowiki> | OtherNames = 2-bornanone, 2-camphanone<br />bornan-2-one, Formosa | Section1 = {{Chembox Identifiers | SMILES = O=C1CC2CCC1(C)C2(C)(C) | CASOther = [76-22-2] (unspecified)<br />[464-49-3] ((1''R'')-Camphor)<br />[464-48-2] ((1''S'')-Camphor} | RTECS = EX1260000 (''R'')<br />EX1250000 (''S'') }} | Section2 = {{Chembox Properties | Formula = C<sub>10</sub>H<sub>16</sub>O | MolarMass = 152.23 | Appearance = White or colorless crystals | Density = 0.990 (solid) | Solubility = 0.12 [[gram|g]] in 100 ml | SolubilityOther = ~200 g in 100 ml | Solvent = acetic acid | SolubilityOther = ~100 g in 100 ml | Solvent = ethanol | SolubilityOther = ~250 g in 100 ml | Solvent = acetone | Solvent = [[Diethyl ether|ether]] | SolubleOther = ~100 g in 100 ml | SolubilityOther = ~200 g in 100 ml | Solvent = chloroform | MeltingPt = 179.75 °C (452.9 K) | BoilingPt = 204 °C (477 K) | pKa = | SpecRotation = +44.1°|(1''R'')-Camphor }} | Section7 = {{Chembox Hazards | MainHazards = flammable | EUClass = | NFPA-H = 2 | NFPA-F = 2 | NFPA-R = 0 | RPhrases = 11-20/21/22-36/37/38 | SPhrases = 16-26-36 }} | Section8 = {{Chembox Related | Function = ketone | OtherFunctn = [[fenchone]],[[thujone]] | OtherCmpds = [[camphene]], [[pinene]]<br />[[borneol]], [[isoborneol]]<br />[[10-Camphorsulfonic acid]] }} }} '''Camphor''' is a waxy, white or transparent solid with a strong, aromatic odor.<ref>J. Mann, R. S. Davidson, J. B. Hobbs, D. V. Banthorpe, J. B. Harborne, ''Natural Products'', pp. 309-311, Addison Wesley Longman Ltd., Harlow, UK, 1994. ISBN 0-582-06009-5</ref> It is a [[terpenoid]] with the [[chemical formula]] [[carbon|C]]<sub>10</sub>[[hydrogen|H]]<sub>16</sub>[[oxygen|O]]. It is found in wood of the '''camphor laurel''' (''[[Cinnamomum camphora]]''), a large [[evergreen]] tree found in Asia (particularly in [[Borneo]] and [[Taiwan]], hence its alternate name). It also occurs in some other related trees in the laurel family, notably ''[[Ocotea usambarensis]]''. It can also be synthetically produced from oil of [[turpentine]]. It is used for its scent, as an ingredient in cooking (mainly in India), as an embalming fluid, in religious ceremonies and for medicinal purposes. A major source of camphor in Asia is [[Ocimum kilimandscharicum|camphor basil]]. ==History== The word camphor derives from the French word ''camphre'', itself from Medieval Latin ''camfora'', from Arabic ''kafur'', from Malay ''kapur Barus'' meaning "Barus chalk". In fact Malay traders from whom Indian and Middle East merchants would buy camphor called it ''kapur'', "chalk" because of its white colour [http://www.etymonline.com/index.php?search=camphor&searchmode=none]. Barus was the port on the western coast of the [[Indonesia|Indonesian]] island of [[Sumatra]] where foreign traders would call to buy camphor. In the Indian language Sanskrit, the word ''karpoor'' is used to denote Camphore. A South-Indian adaptation of this word, ''karpooram'', has been used for camphor in many South-Indian/[[Dravidian languages]] (like [[Telugu language|Telugu]], [[Tamil language|Tamil]], [[Kannada language|Kannada]] and [[Malayalam language|Malayalam]]). Camphor was first synthesized by [[Gustaf Komppa]] in 1903. Previously, some organic compounds (such as [[urea]]) had been synthesized in the laboratory as a [[proof of concept]], but camphor was a scarce natural product with a worldwide demand. The synthesis was the first industrial [[total synthesis]], when Komppa began industrial production in [[Tainionkoski]], [[Finland]], in 1907. '''Norcamphor''' is a camphor derivative with the three [[methyl]] groups replaced by hydrogen. Other substances deriving from trees are sometimes wrongly sold as camphor. ==Uses== Modern uses include as a plasticizer for [[Nitrocellulose]], as a [[mothball|moth repellent]], as an antimicrobial substance, in embalming, and in [[fireworks]]. Solid camphor releases fumes that form a [[rust]]-preventative coating and is therefore stored in tool chests to protect tools against rust.<ref>[http://www.cabinetshoptips.com/ Tips for Cabinet Making Shops]</ref> Camphor crystals are also used to prevent damage to [[insect collecting|insect collections]] by other small insects. It is also used in [[medicine]]. Camphor is readily absorbed through the skin and produces a feeling of cooling similar to that of [[menthol]] and acts as slight local [[anesthetic]] and [[antimicrobial]] substance. A form of [[antipruritic|anti-itch gel]] currently on the market uses camphor as its [[active ingredient]]. Camphor is an active ingredient (along with menthol) in vapor-steam products, such as [[Vicks]] VapoRub, and it is effective as a cough suppressant. It may also be administered orally in small quantities (50 mg) for minor heart symptoms and fatigue.<ref>[http://spc.nam.fi/indox/english/html/nam/humspc/1/90151.shtml National Agency for Medicines]</ref> In the 18th Century, it was used by [[Leopold_Auenbrugger|Auenbrugger]] in the treatment of [[mania]].{{Fact|date=March 2007}} It is also believed that camphor will deter snakes and other reptiles due to its strong odor. Similarly, camphor is believed to be toxic to insects and is thus sometimes used as a repellent.{{Fact|date=March 2007}} Camphor is also used in the Mahashivratri celebrations of Shiva, the Hindu god of destruction of (re)creation. As a natural pitch substance it burns cool without leaving an ash residue, which symbolizes consciousness. It is also found in clarifying masks used for skin. Recently, [[carbon nanotubes]] were successfully synthesized using camphor in [[chemical vapor deposition]] process.<ref>Mukul Kumar, Yoshinori Ando, ''Carbon Nanotubes from Camphor: An Environment-Friendly Nanotechnology'', Journal of Physics: Conference Series 61 (2007) 643–646</ref> ===Culinary=== Currently, camphor is mostly used as a flavoring for sweets in Asia. In ancient and medieval Europe it was widely used as ingredient for sweets but it is now mainly used for medicinal purposes. Camphor was used as a flavoring in confections resembling [[ice cream]] in [[China]] during the [[Tang dynasty]] (A.D. 618-907).{{Fact|date=June 2007}} Camphor is widely used in cooking (mainly for dessert dishes) in India where it is known as ''Pachha Karpooram'' (literally meaning "green camphor" though "Pachha" in Tamil can also be translated to mean "raw" which is "Pachha Karpooram's" intended meaning). It is widely available at Indian grocery stores and is labeled as "Edible Camphor." In Hindu [[pooja]]s and ceremonies, camphor is burned in a ceremonial spoon for performing [[aarti]]. This type of camphor is also sold at Indian grocery stores but it is not suitable for cooking. The only type that should be used for food are those which are labeled as "Edible Camphor." ==Toxicology== In larger quantities, it is [[toxic|poisonous]] when ingested and can cause seizures, confusion, irritability, and [[neuromuscular]] [[hyperactivity]]. In 1980, the [[United States]] [[Food and Drug Administration]] set a limit of 11% allowable camphor in consumer products and totally banned products labeled as camphorated oil, camphor oil, camphor [[liniment]], and camphorated liniment (but "white camphor [[essential oil]]" contains no significant amount of camphor). Since alternative treatments exist, medicinal use of camphor is discouraged by the FDA, except for skin-related uses, such as medicated powders, which contain only small amounts of camphor. Lethal doses in adults are in the range 50–500 mg/kg (orally). Generally, 2 g causes serious toxicity and 4 g is potentially lethal. ==Reactions== Typical camphor reactions are: * [[bromination]] :[[Image:Camphor-3-Brominecampher.png|500px]] * [[oxidation]] with [[nitric acid]] :[[Image:Camphor-Camphor_acid.png]] * conversion to isonitrosocamphor :[[Image:Camphor-Isonitrosocamphor.png|550px]] Camphor can also be reduced to [[isoborneol]] using [[sodium borohydride]]. ==Biosynthesis== In [[biosynthesis]] camphor is produced from [[geranyl pyrophosphate]], via cyclisation of [[linalool|linaloyl]] pyrophosphate to [[Borneol|bornyl]] pyrophosphate, followed by hydrolysis to [[borneol]] and oxidation to camphor. [[Image:CamphorBiosynthesis.png|700px|center|Biosynthesis of camphor from geranyl pyrophosphate]] ==References== <references/> ==External links== *[http://www.naturaldatabase.com/ce/ceNDMono.aspx?mono_id=709&view=m Camphor Evidence-based Monograph] from ''Natural Medicines Comprehensive Database'' [[Category:Pyrotechnic chemicals]] [[Category:flavors]] [[Category:Ketones]] [[Category:Terpenes and terpenoids]] [[Category:Materials involved in Hinduism]] [[ca:Càmfora]] [[cs:Kafr]] [[de:Campher]] [[dv:ކާފޫރު]] [[es:Alcanfor]] [[eo:Kamforo]] [[fa:کافور]] [[fr:Camphre]] [[it:Canfora]] [[hu:Kámfor]] [[nl:Kamfer]] [[ja:樟脳]] [[no:Kamfer]] [[pl:Kamfora]] [[ru:Камфора]] [[sk:Gáfor]] [[fi:Kamferi]] [[sv:Kamfer]] [[te:కర్పూరం]] [[vi:Long não]] [[tg:Каҳрабо]] [[zh:樟腦]]