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Camphor[1][2]
IUPAC name 1,7,7-Trimethylbicyclo[2.2.1]heptan-2-one
Systematic name 1,7,7-Trimethylbicyclo[2.2.1]heptan-2-one
Other names 2-Bornanone; Bornan-2-one; 2-Camphanone; Formosa
Identifiers
CAS number	76-22-2 Y, 464-49-3 (R) Y, 464-48-2 (S) Y
PubChem	2537, 9543187 (R), 10050 (S)
ChemSpider	2441 Y, 7822160 (R) Y, 9655 (S) Y
UNII	5TJD82A1ET Y
EC number	200-945-0
UN number	2717
DrugBank	DB01744
KEGG	D00098 Y
MeSH	Camphor
ChEBI	CHEBI:36773 Y
ChEMBL	CHEMBL15768 Y
IUPHAR ligand	2422
RTECS number	EX1225000
ATC code	C01EB02
Beilstein Reference	1907611
Gmelin Reference	83275
3DMet	B04729
Jmol-3D images	Image 1 Image 2
SMILES CC1(C)C2CCC1(C)C(=O)C2 O=C1CC2CCC1(C)C2(C)C
InChI InChI=1S/C10H16O/c1-9(2)7-4-5-10(9,3)8(11)6-7/h7H,4-6H2,1-3H3 Y Key: DSSYKIVIOFKYAU-UHFFFAOYSA-N Y InChI=1/C10H16O/c1-9(2)7-4-5-10(9,3)8(11)6-7/h7H,4-6H2,1-3H3 Key: DSSYKIVIOFKYAU-UHFFFAOYAK
Properties
Molecular formula	C10H16O
Molar mass	152.23 g mol−1
Appearance	White, translucent crystals
Density	0.990 g cm−3
Melting point	175-177 °C, 448-450 K, 347-351 °F
Boiling point	204 °C, 477 K, 399 °F
Solubility in water	1.2 g dm−3
Solubility in acetone	~2500 g dm−3
Solubility in acetic acid	~2000 g dm−3
Solubility in diethyl ether	~2000 g dm−3
Solubility in chloroform	~1000 g dm−3
Solubility in ethanol	~1000 g dm−3
log P	2.089
Vapor pressure	4 mmHg (at 70 °C)
Chiral rotation [α]D	+44.1°
Hazards
EU classification	F Xn
R-phrases	R11 R22 R36/37/38
S-phrases	S16 S26
NFPA 704	2 2 0
Flash point	64 °C
Explosive limits	3.5%
Related compounds
Related Ketones	Fenchone, Thujone
Related compounds	Camphene, Pinene, Borneol, Isoborneol, Camphorsulfonic acid
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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) and also of Dryobalanops aromatica, a giant of the Bornean forests. It also occurs in some other related trees in the laurel family, notably Ocotea usambarensis. Dried rosemary leaves (Rosmarinus officinalis), in the mint family, contain up to 20% camphor. 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, for medicinal purposes, and in religious ceremonies. A major source of camphor in Asia is camphor basil.

Norcamphor is a camphor derivative with the three methyl groups replaced by hydrogen.

History[link]

The word camphor derives from the French word camphre, itself from Medieval Latin camfora, from Arabic kafur, from Sanskrit, karpuura.^[4] Barus was the name of an early port on a city named "Sibolga" (located in the western coast of Sumatra island - North Sumatra Province, Republic of Indonesia]. At that time, this city was initially built prior to the Indian - Bataknese trade of camphor and spices. Foreign traders such as Indian, East Asian and Middle east traders would call "kapur barus" to buy the extract/dried ooze of camphor tree from the local tribesman (Bataknese), in proto malay-austronesian language (Sanskrit adapted-Bataknese alphabets it also known as kapur Barus. Until now, the local tribesman and Indonesian in general refer to naphthalene balls and moth balls as kapur Barus. For the local tribesman the use of camphor are ranging from deodorant, wood - cloth finishing veneer coat, traditional ritual and non edible preservatives as the camphor tree itself natively found in that region. The tree itself in Indonesian language called as "Kamfer" (Which also known for its resistance towards tropical termites).

A sample of sublimed camphor

The sublimate capabilities of camphor is quite similar to alcohol of which in early international trade has made camphor widely known in Arabia in pre-Islamic times, as it is mentioned in the Quran 76:5 as a flavoring for drinks. In the 9th century, the Arab chemist, Al-Kindi (known as Alkindus in Europe), provided the earliest "publicity" for the production of camphor in his Kitab Kimiya' al-'Itr (Book of the Chemistry of Perfume).^{[citation needed]} By the 13th century, it was used in recipes everywhere in the Muslim world, ranging from main dishes such as tharid and stew to desserts.^[5]

Already in the 19th century, it was known that with nitric acid, camphor could be oxidized into camphoric acid. Haller and Blanc published a semisynthesis of camphor from camphoric acid, which, although demonstrating its structure, would not prove it. The first complete total synthesis for camphoric acid was published by Gustaf Komppa in 1903. Its starting materials were diethyl oxalate and 3,3-dimethylpentanoic acid, which reacted by Claisen condensation to give diketocamphoric acid. Methylation with methyl iodide and a complicated reduction procedure produced camphoric acid. William Perkin published another synthesis a short time later. 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. Komppa realized this and began industrial production of camphor in Tainionkoski, Finland, in 1907.

Production[link]

Camphor can be 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 acid as the solvent and with catalysis by a strong acid, alpha-pinene readily rearranges into camphene, which in turn undergoes Wagner-Meerwein rearrangement into the isobornyl cation, which is captured by acetate to give isobornyl acetate. Hydrolysis into isoborneol followed by oxidation gives camphor.

Biosynthesis[link]

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.

Reactions[link]

Typical camphor reactions are

• bromination,

• oxidation with nitric acid,

• conversion to isonitrosocamphor.

Camphor can also be reduced to isoborneol using sodium borohydride.

In 2007, carbon nanotubes were successfully synthesized using camphor in chemical vapor deposition process.^[6]

Uses[link]

Modern uses include camphor as a plasticizer for nitrocellulose (see Celluloid), 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.^[7]

Camphor crystals are also used to prevent damage to insect collections by other small insects, also as a cough suppressant. Some folk remedies state 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.^[8]

Culinary[link]

In ancient and medieval Europe, camphor was used as an ingredient in sweets. It was also used as a flavoring in confections resembling ice cream in China during the Tang dynasty (AD 618–907).^{[citation needed]} It was used in a wide variety of both savory and sweet dishes in medieval Arabic language cookbooks, such as al-Kitab al-Ṭabikh compiled by ibn Sayyâr al-Warrâq in the 10th century,^[9] and an anonymous Andalusian cookbook of the 13th century.^[10] It also appears in sweet and savory dishes in a book written in the late 15th century for the sultans of Mandu, the Ni'matnama.^[11]

Currently, camphor is used as a flavoring, mostly for sweets, in Asia. It is widely used in cooking, mainly for dessert dishes, in India where it is known as kachha karpooram or "pachha karpoora" ("crude/raw camphor"), in (Telugu:పచ్చ కర్పూర), (Tamil:பச்சைக் கற்பூரம்), (Kannada:ಪಚ್ಚ ಕರ್ಪೂರ), and is available in Indian grocery stores where it is labeled as "Edible Camphor". But in Tamil, rasak karpooram is entirely different and toxic.

Medicinal[link]

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. There are anti-itch gels and cooling gels with camphor as the active ingredient. Camphor is an active ingredient (along with menthol) in vapor-steam products, such as Vicks VapoRub. Although touted as a cough suppressant, it has no effects on respiratory tract function.

Camphor may also be administered orally in small quantities (50 mg) for minor heart symptoms and fatigue.^[12] Through much of the 1900s this was sold under the trade name Musterole; production ceased in the 1990s.

In the 18th century, camphor was used by Auenbrugger in the treatment of mania.^[13]

Alternative medicine[link]

Camphor is available as an essential oil for aromatherapy or topical application.

Hindu religious ceremonies[link]

Camphor is widely used in Hindu religious ceremonies. Hindus worship a holy flame by burning camphor, which forms an important part of many religious ceremonies. Camphor is used in the Mahashivratri celebrations of Shiva, the Hindu god of destruction and (re)creation. As a natural pitch substance, it burns cool without leaving an ash residue, which symbolizes consciousness. Of late^[when?], most temples in southern India have stopped lighting camphor in the main Sanctum Sanctorum because of the heavy carbon deposits it produces; however, open areas still burn it.

In Hindu pujas and ceremonies, camphor is burned in a ceremonial spoon for performing aarti. This type of camphor, the processed white crystalline kind, is also sold at Indian grocery stores. It is not suitable for cooking, however, and is hazardous to health if eaten.

Toxicology[link]

In larger quantities, camphor is poisonous when ingested and can cause seizures, confusion, irritability, and neuromuscular hyperactivity. In extreme cases, even topical application of camphor may lead to hepatotoxicity.^{[14] [15]} Lethal doses in adults are in the range 50–500 mg/kg (orally). Generally, two grams cause serious toxicity and four grams are potentially lethal.^[16]

In 1980, the U.S. 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 (except "white camphor essential oil", which 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.

See also[link]

• 1,4-Dichlorobenzene
• Citral
• Eucalyptol
• Lavender
• Vaporizer

References[link]

Notes

External links[link]

Wikimedia Commons has media related to: Camphor

• Camphor Evidence-based Monograph from Natural Medicines Comprehensive Database
• INCHEM at IPCS (International Programme on Chemical Safety)

MF DOOM
MF Doom at the Hultsfred Festival 2011 in Sweden
Background information
Also known as	DOOM, King Geedorah, Metal Face, Metal Fingers, Viktor Vaughn, Zev Love X, Madvillain
Born	(1971-01-09) January 9, 1971 (age 41) London, United Kingdom
Origin	Long Island, New York
Genres	East Coast hip hop
Occupations	Rapper, hip hop producer
Instruments	Vocals, sampler, synthesizer, drum machine, Pro Tools
Years active	1988–1993 1997–present
Labels	Elektra (1988–1993) Sub Verse (1997–2003) Fondle 'Em (1997–2001) Metal Face (1997–present) Big Dada (2003) Naturesounds (2003–present) Rhymesayers (2004) Stones Throw (2004–present) Lex (2005–present)
Associated acts	KMD, Madvillain, Danger Doom, Madlib, MF Grimm, Ghostface Killah, J Dilla, Count Bass D, Aesop Rock, Jneiro Jarel, Gorillaz, Masta Ace, De La Soul
Website	Official website

Daniel Dumile (pronounced /ˈduːmɨleɪ/ DOO-mə-lay; born January 9, 1971) is a hip hop artist who has taken on several stage names in his career, most notably MF Doom, often stylized as MF DOOM, where the "MF" stands for metal face, but metal fingers when using his producing name. He has appeared in several collaborative projects such as Danger Doom (with Danger Mouse) and Madvillain (with Madlib).

History[link]

Early years with KMD[link]

Dumile was born on January 9, 1971, in London, England, the son of a Trinidadian mother and Zimbabwean father.^[1] He then moved with his family to New York and was raised in the city of Long Beach, New York on Long Island.

As Zev Love X, he formed the group KMD in 1988 with his younger brother DJ Subroc and another MC called Rodan. When Rodan left the group, Zev found another MC to replace Rodan named Onyx the Birthstone Kid.^[1] A&R rep Dante Ross learned of KMD through the hip hop group 3rd Bass, and signed the group to Elektra Records.^[2]

Dumile and KMD's recorded debut came on 3rd Bass's song "The Gas Face" from The Cactus Album,^[1] followed in 1991 with KMD's album Mr. Hood, which became a minor hit through its singles "Peachfuzz", "Who Me?" and heavy video play on cable TV's Yo! MTV Raps and Rap City.

Subroc was struck and killed by a car in 1993 while attempting to cross the Long Island Expressway before the release of a second KMD album, titled Black Bastards.^[1] The group was subsequently dropped from Elektra Records that same week. Before the release of the album, it was shelved due to controversy over its cover art,^[2] which featured a cartoon of a stereotypical pickaninny or sambo character being hung from the gallows.

With the loss of his brother, Dumile retreated from the hip hop scene from 1994 to 1997. He testifies to disillusionment and depression, living "damn near homeless, walking the streets of Manhattan, sleeping on benches.^[1][3]" In the late 1990s, he left New York City and settled in Atlanta. According to interviews with Dumile, he was also "recovering from his wounds" and swearing revenge "against the industry that so badly deformed him."^[1] Black Bastards had become bootlegged at the time, leading to Doom's rise in the underground hip hop scene.

Birth of MF DOOM[link]

In 1997, Dumile began freestyling incognito at open-mic events at the Nuyorican Poets Café in Manhattan, obscuring his face by putting a stocking over his head. He meanwhile had taken on a new identity, MF Doom, patterned after and wearing a mask similar to that of Marvel Comics super-villain Doctor Doom, who is depicted rapping on the cover of the 1999 album Operation: Doomsday. He wears this mask while performing and isn't photographed without it, except for very short glimpses in videos such as Viktor Vaughn's "Mr. Clean", "?", and in earlier photos with KMD.^[1] MF Doom's mask has undergone at least one design revision since its adoption (it is now an altered version of the mask worn by the character Maximus Decimus Meridius in the film Gladiator).

Early career[link]

Dumile released three singles on "Bobbito" García's Fondle 'Em Records, "Dead Bent", and "Greenbacks" (1997), and "The M.I.C." (1998). In 1999 Fondle 'Em released MF Doom's first full-length LP, Operation: Doomsday, which included these singles and their b-sides, and additional tracks. Dumile had used the spelling variant "M.F. DOOM" for the singles releases, but thereafter changed this to "MF DOOM".

Among the collaborators on these tracks were fellow members of the Monsta Island Czars collective (The M.I.C.), for which each artist took on the persona of a monster from the Godzilla mythos. Dumile went by the alias "King Geedorah," a three-headed golden dragon space monster, modeled after King Ghidorah, the Toho movie monster who was a three-headed dragon that often battled Godzilla. Some of his appearances on the LP are as, and are credited to this persona, instead of that of MF Doom. Dumile would revisit this character later under various name-spellings.

Guest appearances, production, and instrumental work[link]

In the years intervening before his next full-length solo release, and continually since, Dumile has appeared on several tracks on other artists' LPs and remixes, contributed one-off tracks to compilations, and done various guest production work.^[4]

In 2002, he appeared on the Sound-Ink's Colapsus collection,on a very hard to find track titled "Monday Nite at Fluid" featuring Kurious with production by King Honey, who also produced some tracks for Dumile's album Vaudeville Villain. DOOM also made an appearance in "November Has Come", a track on Gorillaz's 2005 album Demon Days, which reached #6 on the Billboard 200.^[5]

Besides the Viktor Vaughn album Dumile produces all the instrumentation tracks for his solo releases with very few exceptions.^[4]

Beginning in 2001, under the "Metal Fingers" moniker, Dumile began releasing his Special Herbs instrumentals series. Many of these beats can be heard as the instrumentation tracks throughout his body of work. A separate website catalogs for which tracks each instrumental has been used.^[6]

Ongoing career[link]

In 2003, Dumile released the King Geedorah album Take Me to Your Leader. Geedorah is credited as producer, but only appears as an MC on four tracks. The majority of vocal tracks feature guest MCs, and the album features several instrumental montages of sampled vocals from old movies and TV shows—a technique employed on most of Dumile's albums. Both Venomous Villain and Take Me to Your Leader feature appearances by MF Doom.

Also in 2003, Dumile released the LP Vaudeville Villain under the moniker Viktor Vaughn (another play on Doctor Doom, whose "real name" is Victor von Doom). In 2004 he released a follow-up LP, Venomous Villain (also called VV2).

And, in 2004, the second MF Doom album MM.. Food was released by the Minnesota-based label Rhymesayers Entertainment.

Mainstream recognition[link]

DOOM's first commercial breakthrough came in 2004, with the album Madvillainy, created with producer Madlib under the group name Madvillain. Released by Stones Throw Records, the album was a critical and commercial success. MF DOOM was seen by mainstream audiences for the first time as Madvillain received publicity and acclaim in publications such as Rolling Stone, The Washington Post, The New York Times, The New Yorker, and Spin. A video for "All Caps" and a four-date U.S. tour followed the release of Madvillainy. Additional videos for "Rhinestone Cowboy" and "Accordion", both directed by Andrew Gura, were released on the DVDs Stones Throw 101 and Stones Throw 102: In Living the True Gods, respectively.

MF Doom collaborated with Danger Mouse who together are known as DANGERDOOM.

Though still an independent artist, MF DOOM took a bigger step towards the mainstream in 2005 with The Mouse and the Mask, a collaboration with producer DJ Danger Mouse under the group name Danger Doom. The album, released on October 11, 2005 by Epitaph, was done in collaboration with Cartoon Network's Adult Swim and featured voice-actors and characters from its programs (mostly Aqua Teen Hunger Force). Danger Doom reached #41 on the Billboard 200.^[7] In 2006 DOOM hosted the Adult Swim Christmas special and he could be seen in between shows, usually talking about what was up next, and making jokes.

2006–2009[link]

MF Doom produced tracks for both of Ghostface Killah's 2006 albums Fishscale and More Fish, and the two are currently at work on a collaboration album titled Swift & Changeable. So far only track released from the album is "Angels", which appeared on a Nature Sounds compilation in late 2006, and later re-released in a different fashion on Doom's 2009 album Born Like This. Doom has also revealed plans for a second Madvillain album with producer Madlib, with one song, "Monkey Suite", first appearing on the Adult Swim/Stones Throw Records album Chrome Children, later it appeared on Madvillainy 2 - The Madlib Remix. Other potential projects mentioned by Doom include new albums from Danger Doom,^[8] KMD, as well as further albums under both his Viktor Vaughn and King Geedorah aliases. However, many such Doom projects have been rumored in recent years without materializing.

Despite no new Doom releases in 2006, Kidrobot and Stones Throw released an 8" tall Madvillain toy available to coincide with the release of the Chrome Children CD/DVD (hosted by Peanut Butter Wolf) which featured a DVD performance of Madvillain and several other Stones Throw artists. Doom also continued to work with Adult Swim doing voice-over work as Sherman the Giraffe on Perfect Hair Forever, being the voice for The Boondocks ads and previews and hosting their Christmas Eve 2006 programming.

In late January 2009, Lex records confirmed Doom's new album title to be Born Like This, and that the "MF" would be dropped from his name, now just "DOOM".^[9] The album was released worldwide on March 24, 2009.^[10] As a teaser, the track "Ballskin" was posted on Doom's Myspace page on January 13, 2009.^[11] Snippets of the entire album were made available for streaming on Doom's Myspace on the album's release date. The title for the album was inspired by the poem "Dinosauria, We" by poet and writer Charles Bukowski. Doom samples a performance of the poem by Bukowski on the track "Cellz". Previously, Doom used a Bukowski sample for a vocal interlude on 2004's "All Outta Ale.^[12] "Thom Yorke of Radiohead remixed the track "Gazillion Ear" which is available as an iTunes-only bonus track.^[13] June 26, 2009 Kurious released II which featured Doom on the song "Benetton".^[14]

2009-2012[link]

On May 26, 2010, the second single for the next Madvillain album "Paper Mill" was released through Adult Swim.^[15] Expektoration, a live Doom album, was released on September 14, 2010 through Gold Dust Media. In mid 2010, DOOM released the mix-tape "DOOM!", a collection of greatest hits, B-sides and rareties, including the theme for the video game Grand Theft Auto: Chinatown Wars featuring Ghostface Killah, and Biochemical Equation, featuring the RZA.

On July 27, 2011 DOOM and Ghostface Killah released the track "Victory Laps" from their long awaited collaboration project Swift & Changeable on the Nature Sounds label.

DOOM was chosen by Portishead to perform at the ATP I'll Be Your Mirror festival that they curated in July 2011 at London's Alexandra Palace.^[16]

DOOM will be the guest curator for Chapter 48 of Frank151's quarterly magazine. Chapter 48 will be released Summer 2012 and will feature a candid interview with DOOM on a variety of topics.^[17]

In September DOOM will be performing live as part of Bestival 2012 on the Isle Of Wight.^[18]

Live show controversy[link]

Dumile has become infamous for allegedly sending imposters to perform on his behalf.^[19] Doom initially countered such accusations by claiming that he lost weight and thus looked - and sounded - different,^[20] before his road manager described the move as an intentional choice made by Dumile.^[21] For his 2011 UK tour, a promoter for the Glasgow show - fearing reduced attendance from a cautious public - guaranteed on Twitter that Dumile would be appearing in person.

Discography[link]

Solo[link]

• 1999: Operation: Doomsday
• 2003: Take Me to Your Leader (as King Geedorah)
• 2003: Vaudeville Villain (as Viktor Vaughn)
• 2004: Venomous Villain (as Viktor Vaughn)
• 2004: Mm.. Food
• 2009: Born Like This (as DOOM)

Compilation Albums[link]

• 2009: Unexpected Guests

Collaboration Albums[link]

• 1991: Mr. Hood (as Zev Love X with KMD)
• 2001: Black Bastards (as Zev Love X with KMD)
• 2003: Escape from Monsta Island! (as King Geedorah with Monsta Island Czars)
• 2004: Madvillainy (with Madlib as Madvillain)
• 2005: The Mouse and the Mask (with Danger Mouse as DANGERDOOM)
• 2006: Occult Hymn (with Danger Mouse as DANGERDOOM)
• 2012: Son of Yvonne (with Masta Ace as MA DOOM)
• 2012: Key to the Kuffs (with Jneiro Jarel as JJ DOOM) ^[22]
• TBA: Swift & Changeable (with Ghostface Killah as DOOMSTARKS)

References[link]

External links[link]

Wikiquote has a collection of quotations related to: Daniel Dumile

• MF Doom on Myspace
• Official website