Difference between revisions of "Camphor" - New World Encyclopedia

Revision as of 13:34, 11 June 2008

Camphor^[1]^[2]

IUPAC name

1,7,7-trimethylbicyclo
[2.2.1]heptan-2-one

Other names

2-bornanone, 2-camphanone
bornan-2-one, Formosa

Identifiers

CAS number

[76-22-2] (unspecified)
[464-49-3] ((1R)-Camphor)
[464-48-2] ((1S)-Camphor}

RTECS number

EX1260000 (R)
EX1250000 (S)

SMILES

O=C1CC2CCC1(C)C2(C)(C)

Properties

Molecular formula

C₁₀H₁₆O

Molar mass

152.23

Appearance

White or colorless crystals

Density

0.990 (solid)

Melting point

179.75 °C (452.9 K)

Boiling point

204 °C (477 K)

Solubility in water

0.12 g in 100 ml

Solubility in chloroform

~100 g in 100 ml

Chiral rotation [α]_D

+44.1°

Hazards

Main hazards

flammable

NFPA 704

2

0

R-phrases

11-20/21/22-36/37/38

S-phrases

16-26-36

Related Compounds

Related ketone

fenchone,thujone

Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Camphor is a waxy, white or transparent solid with a strong, aromatic odor.^[3] It is a terpenoid with the chemical formula C₁₀H₁₆O. 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 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 [1]. Barus was the port on the western coast of the 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, Tamil, Kannada and 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 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.^[4] Camphor crystals are also used to prevent damage to 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 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.^[5]

In the 18th Century, it was used by Auenbrugger in the treatment of mania.^{[citation needed]}

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.^{[citation needed]}

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.^[6]

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).^{[citation needed]} 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 poojas 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 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

oxidation with nitric acid

conversion to isonitrosocamphor

Camphor can also be reduced to isoborneol using sodium borohydride.

Biosynthesis

In biosynthesis camphor is produced from geranyl pyrophosphate, via cyclisation of linaloyl pyrophosphate to bornyl pyrophosphate, followed by hydrolysis to borneol and oxidation to camphor.

References
ISBN links support NWE through referral fees

↑ The Merck Index, 7th edition, Merk & Co, Rahway, New Jersey, USA, 1960
↑ Handbook of Chemistry and Physics, CRC Press, Ann Arbor, Michigan
↑ 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
↑ Tips for Cabinet Making Shops
↑ National Agency for Medicines
↑ Mukul Kumar, Yoshinori Ando, Carbon Nanotubes from Camphor: An Environment-Friendly Nanotechnology, Journal of Physics: Conference Series 61 (2007) 643–646

External links

Camphor Evidence-based Monograph from Natural Medicines Comprehensive Database

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

[1] The Merck Index, 7th edition, Merk & Co, Rahway, New Jersey, USA, 1960

[2] Handbook of Chemistry and Physics, CRC Press, Ann Arbor, Michigan

[3] 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

[4] Tips for Cabinet Making Shops

[5] National Agency for Medicines

[6] Mukul Kumar, Yoshinori Ando, Carbon Nanotubes from Camphor: An Environment-Friendly Nanotechnology, Journal of Physics: Conference Series 61 (2007) 643–646

[1]

[2]

[3]

[4]

[5]

[6]

@@ Line 1: / Line 1: @@
-{{Ready}}
 {{Chembox new
-|  Reference=<ref>''The Merck index: an encyclopedia of chemicals, drugs, and biologicals'', Whitehouse Station, N.J.: Merck, 2001. ISBN 0911910131.</ref><ref>''Handbook of Chemistry and Physics'', Cleveland, Chemical Rubber Pub. Co. ISSN 0363-3055.</ref>
+|  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
@@ Line 11: / Line 10: @@
 |  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)''
+|  RTECS = EX1260000 (''R'')<br />EX1250000 (''S'')
    }}
 | Section2 = {{Chembox Properties
@@ Line 37: / Line 36: @@
 |  MainHazards = flammable
 |  EUClass =
-|  NFPA-H = 0
+|  NFPA-H = 2
 |  NFPA-F = 2
 |  NFPA-R = 0
@@ Line 50: / Line 49: @@
 }}
-'''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'' (Addison Wesley Longman Ltd., Harlow, UK, 1994. ISBN 0582060095) 309-311.</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]].
+'''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]]n 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]]).
+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.
@@ Line 61: / Line 60: @@
 Other substances deriving from trees are sometimes wrongly sold as camphor.
-Camphor Trees are widely found in very deep jungles of Western Ghats of Tamil Nadu and Kerala states in South India.
 ==Uses==
-Modern uses include as a plasticizer for [[cellulose nitrate]], as a [[mothball|moth repellent]], as an antimicrobial substance, in embalming, and in [[fireworks]]. Camphor crystals are also used to prevent damage to [[insect collecting|insect collections]] by other small insects. A form of [[antipruritic|anti-itch gel]] currently on the market uses camphor as its [[active ingredient]]. 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. 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 Summaries of Product Characteristics (SPC) for Human medicinal products], National Agency for Medicines. In English and Finish. Retrieved December 15, 2007.</ref>
+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.
-In the 17th Century, it was used by Auenbrugger in the treatment of [[mania]].{{Fact|date=March 2007}}
+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 Mahashiva ratri celebrations of Shiva, the Hindu god of destruction of evil. Its natural pitch substance burns cool without leaving an ash residue, which symbolizes the consciousness.
+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>
+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 desert 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."
+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.
+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==
@@ Line 85: / Line 87: @@
 :[[Image:Camphor-3-Brominecampher.png|500px]]
 * [[oxidation]] with [[nitric acid]]
-:[[Image:Camphor-Camphor acid.png|500px]]
+:[[Image:Camphor-Camphor_acid.png]]
 * conversion to isonitrosocamphor
 :[[Image:Camphor-Isonitrosocamphor.png|550px]]
@@ Line 92: / Line 94: @@
 ==Biosynthesis==
-In [[biosynthesis]] camphor is produced from [[geraniol|geranyl]] [[pyrophosphate]], via cyclisation of [[linalool|linaloyl]] pyrophosphate to [[Borneol|bornyl]] pyrophosphate, followed by hydrolysis to borneol and oxidation to camphor.
+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]]
-==Notes==
+==References==
 <references/>
-==External Links==
+==External links==
-*[http://www.naturaldatabase.com/ce/ceNDMono.aspx?mono_id=709&view=m Camphor Evidence-based Monograph], Natural Medicines Comprehensive Database. Retrieved December 15, 2007.
+*[http://www.naturaldatabase.com/ce/ceNDMono.aspx?mono_id=709&view=m Camphor Evidence-based Monograph] from ''Natural Medicines Comprehensive Database''
-[[Category:Chemistry]]
+[[Category:Pyrotechnic chemicals]]
+[[Category:flavors]]
+[[Category:Ketones]]
+[[Category:Terpenes and terpenoids]]
+[[Category:Materials involved in Hinduism]]
-{{credits|172229401}}
+[[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]]