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D-2-CAMPHANONE

d-2-camphanone is a white, waxy organic compound that is incorporated in lotions, ointments, and creams.
d-2-camphanone is also an active ingredient that is integrated into a majority of over-the-counter medications for cold and cough relief.
d-2-camphanone is obtained from d-2-camphanone tree wood, where the extract is processed through steam distillation.

CAS Number: 76-22-2
EC Number: 200-945-0
Molecular Formula: C10H16O
Molecular Weight: 152.23

Synonyms: camphor, DL-Camphor, 76-22-2, 2-Camphanone, 2-Bornanone, (+/-)-Camphor, Bornan-2-one, 1,7,7-Trimethylbicyclo[2.2.1]heptan-2-one, (+)-Camphor, 21368-68-3, Alphanon, Kampfer, D-CAMPHOR, Formosa camphor, Laurel camphor, Matricaria camphor, Camphor, synthetic, Bornane, 2-oxo-, 1,7,7-Trimethylnorcamphor, 464-48-2, Japan camphor, 2-Camphonone, Huile de camphre, 2-Kamfanon, l-(-)-Camphor, DL-Bornan-2-one, 2-Keto-1,7,7-trimethylnorcamphane, Caswell No. 155, D-(+)-Camphor, Norcamphor, 1,7,7-trimethyl-, Zang Qi, Kampfer [German], 1,7,7-Trimethylbicyclo[2.2.1]-2-heptanone, HSDB 37, 2-Kamfanon [Czech], DTXSID5030955, CHEBI:36773, Camphor, (1R,4R)-(+)-, 4,7,7-trimethylbicyclo[2.2.1]heptan-3-one, (1R)-(+)-amphor, Camphor (synthetic), Camphor, (+/-)-, EINECS 200-945-0, EINECS 244-350-4, Huile de camphre [French], UNII-5TJD82A1ET, EPA Pesticide Chemical Code 015602, BRN 1907611, BRN 3196099, Alcanfor, SYNTHETIC CAMPHOR, AI3-18783, Japanese camphor, DTXCID3010955, Camphor USP, 1,7,7-Trimethylbicyclo(2.2.1)-2-heptanone, 1,7,7-Trimethylbicyclo(2.2.1)heptan-2-one, d-2-Camphanone, d-2-Bornanone, Bicyclo(2.2.1)heptan-2-one, 1,7,7-trimethyl-, Bicyclo[2.2.1]heptan-2-one, 1,7,7-trimethyl-, Camphor (USP), Camphor [USP], (-)-Alcanfor, (1R)-Camphor, camphor, (synthetic), EC 200-945-0, 0-07-00-00135 (Beilstein Handbook Reference), 4-07-00-00213 (Beilstein Handbook Reference), Camphor Powder, (1RS,4RS)-1,7,7-trimethylbicyclo(2.2.1)heptan-2-one, Bicyclo(2.2.1)heptan-2-one, 1,7,7-trimethyl-, (1R)-, Bicyclo[2.2.1]heptan-2-one, 1,7,7-trimethyl-, (1R)-, Bicyclo[2.2.1]heptan-2-one, 1,7,7-trimethyl-, (1S)-, Formosa, Bicyclo[2.2.1]heptan-2-one, 1,7,7-trimethyl-, (.+/-.)-, EINECS 207-355-2, UN2717, (+-)-Camphor, AI3-01698, Camphor, (1R)-Isomer, Camphor, (+-)-Isomer, (+) - bornan - 2 - one, Bicyclo(2.2.1)heptan-2-one, 1,7,7-trimethyl-, (1S)-, racemic camphor, NSC26351, DisperseYellow3, EINECS 207-354-7, NA2717, NSC 26351, Camphor, natural, bornan-2-on, DL-2-Bornanone, Kamfer (syntetisk), ()-Camphor, Heet (Salt/Mix), dextro,laevo-camphor, Sarna (Salt/Mix), Camphor - Synthetic, (?)-Camphor, bornan - 2 - one, dl-Camphor (JP17), CPO (CHRIS Code), (.+/-.)-Camphor, D0H1QY, UNII-SV6B76DK9N, Camphor Powder - Synthetic, SCHEMBL16068, Camphor, (.+/-.)-, Bicyclo(2.2.1)heptan-2-one, 1,7,7-trimethyl-, (1theta)-, MLS001055495, CHEMBL15768, DivK1c_000724, CAMPHOR, (+-)-, GTPL2422, HMS502E06, KBio1_000724, NINDS_000724, HMS2268A06, HMS3885J06, 8008-51-3, HY-N0808, Tox21_200237, BBL012963, LS-126, MFCD00074738, s3851, s4516, STK803534, ( inverted exclamation markA)-Camphor, AKOS000118728, AKOS022060577, AC-5284, CCG-266237, CCG-266238, DB14156, LMPR0102120001, LS-1691, UN 2717, CAS-76-22-2, IDI1_000724, USEPA/OPP Pesticide Code: 015602, NCGC00090681-05, NCGC00090730-01, NCGC00090730-02, NCGC00090730-05, NCGC00257791-01, AC-15523, LS-48718, SMR000386909, VS-03622, (1R,4R)-1,7,7-trimethylnorbornan-2-one, C1251, CS-0009813, FT-0607017, FT-0607018, FT-0608303, 4,7,7-trimethyl-3-bicyclo[2.2.1]heptanone, EN300-19186, 1,7,7-trimethyl-bicyclo[2.2.1]heptan-6-one, C00809, C18369, D00098, E75814, 1,7,7-Trimethyl-bicyclo[2.2.1]heptan-2-one, Camphor, synthetic [UN2717] [Flammable solid], A838646, Q181559, Biciclo [2.2.1] heptan-2-ona, 1,7,7-trimetil-, Q-200784, W-109539, W-110530, (+/-)-1,7,7-trimethyl-bicyclo[2,2,1]heptane-2-one, F0001-0763, Z104473074, CAMPHOR (SEE ALSO DL-CAMPHOR (21368-68-3) AND D-CAMPHOR (464-49-3)), DL-CAMPHOR (SEE ALSO D-CAMPHOR (464-49-3) AND DL-CAMPHOR (21368-68-3)), CAMPHOR SQUARES SYNTHETIC TECHNICAL, CAMPHOR SYNTHETIC FLAKES, CAMPHOR SYNTHETIC POWDER, CAMPHOR TECH. GRADE, 1,7,7-trimethyl-bicyclo(2.2.1)heptan-2-on, 1,7,7-trimethylbicyclo[2.2.1]-2-heptanone (camphor), 1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-on, 1,7,7-trimethyl-norcampho, 2-Bornanone, 2-Camphanonoe, 2-Camphonone, 2-Kamfanon, 2-Keto-1,7,7-trimethylnorcamphane, 2-oxo-bornan, 2-oxobornane, Bicyclo[2,2,1]heptan-2-one,1,7,7-trimethyl-, Bicyclo[2.2.1]heptan-2-one, 1,7,7-trimethyl-, Camphor Ep5, METHYLBENZYLIDENE, CHINESENASALOIL, 1,7,7-Trimethylbicyclo[2.2.1]-2-heptanone, 1,7,7-Trimethylbicyclo[2.2.1]heptan-2-one, 1,7,7-Trimethylnorcamphor, 2-CAMPHOR, 2-Camphanone, Bornan-2-one, Caladryl, Camphor, Radian B, DL-CAMPHOR USP, CAMPHOR SPIRITS USP, (±)-Camphor, 1,7,7-Trimethylbicyclo[2.2.1]heptan-2-one, DL-Camphor,98%, DL-Camphor,96%, Ordinary camphor 1,7,7-Trimethyl bicyclo(2,2,1)-2-heptanone, Camphor,(±)-Camphor, 1,7,7-Trimethylbicyclo[2.2.1]heptan-2-one, (à)-Camphor, DL-CaMphor, 96% 1KG, (+/-)-CaMphor puruM, synthetic, >=95.0% (GC), (+/-)-Camphor meets analytical specification of Ph.Eur., BP, >=95% (GC), racemic, Synthetic camphor powder, refined camphor powder, DL-Camphor for synthesis, Alphanon, Camphor (8CI), CAMPHORATEDMETACRESOL, bicyclo[2.2.1]heptan-2-one,1,7,7,-trimethyl-,(±)-, bicyclo[2.2.1]heptan-2-one,1,7,7-trimethyl-, Bicyclo[2.2.1]heptane-2-one, 1,7,7-trimethyl-, Bornane, 2-oxo-, camphanone, camphor,natural, camphor--natural, camphre, component of Campho-phenique, component of Campho-phenique cold sore gel, component of Campho-phenique liquid, component of Heet,

d-2-camphanone has a pungent odor and a strong taste, and d-2-camphanone can be absorbed into the skin easily.
Currently, synthetic d-2-camphanone is extracted from turpentine, and d-2-camphanone is considered safe for use as long as appropriate indications are upheld.

d-2-camphanone was recorded in the ancient books of traditional Chinese medicine, such as Pin Hui Jing Yao, Ben Cao Gang Mu, and Sheng Lian Fang.
There has been a long history for traditional Chinese medicine to use d-2-camphanone.

d-2-camphanone is a ketone occurring naturally in the wood of the cam- phor tree (Cinnamomum d-2-camphanonea).
d-2-camphanone is a naturally- occurring white organic compound with a characteristic penetrating odor.
d-2-camphanone is a cyclic compound and a ketone, formerly obtained from the wood of the d-2-camphanone tree but now made synthetically.

d-2-camphanone is used as a platicizer for celluloid and as an insecticide against clothes moths.
d-2-camphanone is a white crystalline cyclicketone.

d-2-camphanone was formerly obtainedfrom the wood of the Formosand-2-camphanone tree, but can now besynthesized.
d-2-camphanone has acharacteristic odour associated withits use in mothballs.

d-2-camphanone is a plasticizerin celluloid.
d-2-camphanone is a colorless or white colored crystalline powder with a strong mothball-like odor.

d-2-camphanone is about the same density as water.
d-2-camphanone is emits flammable vapors above 150°F.
d-2-camphanone is used to make moth proofings, pharmaceuticals, and flavorings.

d-2-camphanone is a waxy, colorless solid with a strong aroma.
d-2-camphanone is classified as a terpenoid and a cyclic ketone.

d-2-camphanone is found in the wood of the d-2-camphanone laurel (Cinnamomum d-2-camphanonea), a large evergreen tree found in East Asia; and in the kapur tree (Dryobalanops sp.), a tall timber tree from South East Asia.
d-2-camphanone also occurs in some other related trees in the laurel family, notably Ocotea usambarensis.

Rosemary leaves (Rosmarinus officinalis) contain 0.05 to 0.5% d-2-camphanone, while d-2-camphanoneweed (Heterotheca) contains some 5%.
A major source of d-2-camphanone in Asia is d-2-camphanone basil (the parent of African blue basil).
d-2-camphanone can also be synthetically produced from oil of turpentine.

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

Both optical isomers are found widely in nature, with (+)-d-2-camphanone being the more abundant.
d-2-camphanone is, for example, the main component of oils obtained from the d-2-camphanone tree C. d-2-camphanonea.

d-2-camphanone is produced by fractional distillation and crystallization of d-2-camphanone oil or, synthetically, by dehydrogenation of isoborneol over a copper catalyst.
Due to d-2-camphanone characteristic penetrating, slightly minty odor, d-2-camphanone is only used in perfuming industrial products.

d-2-camphanone is far more important as a plasticizer.
d-2-camphanone, C1oH160, also known as Camphor, Japan d-2-camphanone, laurel d-2-camphanone, Formosa d-2-camphanone and gumd-2-camphanone is a terpene ketone.

d-2-camphanone is colourless solid with a characteristic odour that is obtained from the wood and bark of the d-2-camphanone tree and is soluble in water and alcohol.
d-2-camphanone has two optically active forms (dextro and levo) and an optically inactive mixture (racemic) of these two forms.

d-2-camphanone is used in pharmaceuticals,in disinfectants, in explosives,and to harden nitrocellulose plastics.
d-2-camphanone is colorless to white, flammable granules, crystals or waxy semi-solid with a strong, penetrating, fragrant or aromatic odor.
d-2-camphanone is odor threshold concentration is 0.27 ppm.

d-2-camphanone oil is obtained from d-2-camphanone tree wood, where the extract is processed through steam distillation.
d-2-camphanone has a pungent odor and a strong taste, and d-2-camphanone can be absorbed into the skin easily.
Currently, synthetic d-2-camphanone is extracted from turpentine, and d-2-camphanone is considered safe for use as long as appropriate indications are upheld.

d-2-camphanone is a waxy, flammable, transparent solid with a strong aroma.
d-2-camphanone is a terpenoid with the chemical formula C10H16O.

d-2-camphanone is found in the wood of the d-2-camphanone laurel (Cinnamomum d-2-camphanonea), a large evergreen tree found in East Asia; and in the related kapur tree (Dryobalanops sp.), a tall timber tree from South East Asia.
d-2-camphanone also occurs in some other related trees in the laurel family, notably Ocotea usambarensis.

The molecule has two possible enantiomers as shown in the structural diagrams.
The structure on the left is the naturally occurring (+)-d-2-camphanone ((1R,4R)-bornan-2-one), while d-2-camphanone mirror image shown on the right is the (−)-d-2-camphanone ((1S,4S)-bornan-2-one).

d-2-camphanone is used for its scent, as an embalming fluid, as topical medication, as a manufacturing chemical, and in religious ceremonies.

Uses of d-2-camphanone:
d-2-camphanone has a wide range of uses based on d-2-camphanone anti-inflammatory, anti-fungal, and anti-bacterial properties.
d-2-camphanone can be used for the treatment of certain skin conditions, enhance respiratory function and as a pain reliever.

d-2-camphanone may also be indicated for the treatment of low libido, muscle spasms, anxiety, depression, flatulence, and poor blood circulation, corns, symptoms of heart disease, cold sores, earaches, acne, and hair loss.
d-2-camphanone is considered effective for coughs, pain, skin irritation or itching relief, and osteoarthritis.
However, there is insufficient evidence that reinforces d-2-camphanone effectiveness as a treatment for hemorrhoids, warts, and low blood pressure and as a remedy for insect bites.

d-2-camphanone is used as a plasticizer for celluloseesters and ethers; in the manufacture ofplastics and cymene; in cosmetics, lacquers, medicine, explosives, and pyrotechnics; andas a moth repellent.

Physical uses:
The sublimating capability of d-2-camphanone gives d-2-camphanone several uses.

Plastics:
The first significant manmade plastics were low-nitrogen (or "soluble") nitrocellulose (pyroxylin) plastics.
In the early decades of the plastics industry, d-2-camphanone was used in immense quantities as the plasticizer that creates celluloid from nitrocellulose, in nitrocellulose lacquers and other plastics and lacquers.

Pest deterrent and preservative:
d-2-camphanone is believed to be toxic to insects and is thus sometimes used as a repellent.
d-2-camphanone is used as an alternative to mothballs.
d-2-camphanone crystals are sometimes used to prevent damage to insect collections by other small insects.

d-2-camphanone is kept in clothes used on special occasions and festivals, and also in cupboard corners as a cockroach repellent.
The smoke of d-2-camphanone crystal or d-2-camphanone incense sticks can be used as an environmentally-friendly mosquito repellent.

Recent studies have indicated that d-2-camphanone essential oil can be used as an effective fumigant against red fire ants, as d-2-camphanone affects the attacking, climbing, and feeding behavior of major and minor workers.

d-2-camphanone is also used as an antimicrobial substance.
In embalming, d-2-camphanone oil was one of the ingredients used by ancient Egyptians for mummification.

Solid d-2-camphanone releases fumes that form a rust-preventative coating and is therefore stored in tool chests to protect tools against rust.

Perfume:
In the ancient Arab world, d-2-camphanone was a common perfume ingredient.
The Chinese referred to the best d-2-camphanone as "dragon's brain perfume," due to d-2-camphanone "pungent and portentous aroma" and "centuries of uncertainty over d-2-camphanone provenance and mode of origin."

Culinary uses:
One of the earliest known recipes for ice cream dating to the Tang dynasty includes d-2-camphanone as an ingredient.
d-2-camphanone was used to flavor leavened bread in ancient Egypt.

In ancient and medieval Europe, d-2-camphanone was used as an ingredient in sweets.
d-2-camphanone was used in a wide variety of both savory and sweet dishes in medieval Arabic language cookbooks, such as al-Kitab al-abikh compiled by ibn Sayyâr al-Warrâq in the 10th century.
d-2-camphanone also was used in sweet and savory dishes in the Ni'matnama, according to a book written in the late 15th century for the sultans of Mandu.

Medicinal uses:
d-2-camphanone is commonly applied as a topical medication as a skin cream or ointment to relieve itching from insect bites, minor skin irritation, or joint pain.
d-2-camphanone is absorbed in the skin epidermis, where d-2-camphanone stimulates nerve endings sensitive to heat and cold, producing a warm sensation when vigorously applied, or a cool sensation when applied gently.
The action on nerve endings also induces a slight local analgesia.

d-2-camphanone is also used as an aerosol, typically by steam inhalation, to inhibd-2-camphanone coughing and relieve upper airway congestion due to the common cold.

In high doses, d-2-camphanone produces symptoms of irritability, disorientation, lethargy, muscle spasms, vomiting, abdominal cramps, convulsions, and seizures.
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.

d-2-camphanone has limited use in veterinary medicine as a respiratory stimulant for horses.
d-2-camphanone was used by Ladislas J. Meduna to induce seizures in schizophrenic patients.

Traditional medicine:
d-2-camphanone has been used in traditional medicine over centuries, probably most commonly as a decongestant.
d-2-camphanone was used in ancient Sumatra to treat sprains, swellings, and inflammation.

d-2-camphanone also was used for centuries in traditional Chinese medicine for various purposes.
d-2-camphanone has also been used in India since ancient times.

Consumer Uses:
Air care products
Cleaning and furnishing care products
Laundry and dishwashing products
Non-TSCA use
Paper products
Personal care products
Plastic and rubber products not covered elsewhere

Uses Areas of d-2-camphanone:
Agent for soaking up liquid
Adhesion of molecules to a surface
Relating to agricultural, including the raising and farming of animals and growing of crops
Related to animals (but non-veterinary) e.g., animal husbandry, farming of animals/animal production, raising of animals for food or fur, animal feed, products for household pets
Products used on crops, or related to the growing of crops
Air cleaners and anti-odor agents, air purifiers, air conditioners, air filters, general air care products
Antifreezing agents, or de-icing products
Related to food and beverage service activities
Modifier used for chemical, when chemical is used in a laboratory
Related to all forms of cleaning/washing, including cleaning products used in the home, laundry detergents, soaps, de-greasers, spot removers, etc; modifiers included when specific information is known, such as drycleaning, laundry, soap, window/floor, etc
Drug product, or related to the manufacturing of drugs
Related to carpets/rugs, the manufacturing of carpets, carpet detergents
Flooring materials (carpets, wood, vinyl flooring), or related to flooring such as wax or polish for floors
Pharmaceutical related
Stain and spot removers
Term used for colorants, dyes, or pigments; includes colorants for drugs, textiles, personal care products (cosmetics, tatoo inks, hair dye), food colorants, and inks for printing
Veterinary activities or veterinary drugs
Explosives and pyrotechnics
Laundry products (such as cleaning/washing agents), or laundry facilities
Includes spices, extracts, colorings, flavors, etc added to food for human consumption
Includes antifoaming agents, coagulating agents, dispersion agents, emulsifiers, flotation agents, foaming agents, viscosity adjustors, etc
General flavoring agents used in foods, including condiments and seasonings
Includes food packaging, paper plates, cutlery, small appliances such as roasters, etc.; does not include facilities that manufacture food
Residues found in food, typically from drugs or pesticides
Fragrances or odor agents, can be used in home products (cleaners, laundry products, air fresheners) or similar industrial products
Related to the activity of hunting
Home air fresheners
Generic lubricants, lubricants for engines, brake fluids, oils, etc
Non-metallic mineral products and their manufacture
Personal care products, including cosmetics, shampoos, perfumes, soaps, lotions, toothpastes, etc
Fragrance used as a personal care product

Properties of d-2-camphanone:

Chemical Properties:
Both optical isomers are found widely in nature, with (+)-d-2-camphanone being the more abundant.
d-2-camphanone is, for example, the main component of oils obtained from the d-2-camphanone tree C. d-2-camphanonea.

d-2-camphanone, C1oH160, also known as Camphor, Japan d-2-camphanone, laurel d-2-camphanone,Formosa d-2-camphanone,and gumd-2-camphanone,is a terpene ketone.
d-2-camphanone is colourless solid with a characteristic odour that is obtained from the wood and bark of the d-2-camphanone tree and is soluble in water and alcohol.

d-2-camphanone has two optically active forms (dextro and levo) and an optically inactive mixture (racemic) of these two forms.
d-2-camphanone is used in pharmaceuticals,in disinfectants, in explosives,and to harden nitrocellulose plastics.
d-2-camphanone is a colorless glassy solid.

Physical properties:
Colorless to white, flammable granules, crystals or waxy semi-solid with a strong, penetrating, fragrant or aromatic odor.
Odor threshold concentration is 0.27 ppm (quoted, Amoore and Hautala, 1983).

Pharmacology of d-2-camphanone:
d-2-camphanone is a parasympatholytic agent which acts as a non-competitive nicotinic antagonist at nAChRs.

d-2-camphanone is toxic to human.
Overdose of d-2-camphanone can cause irritability, drowsiness, muscle spasms, vomiting, convulsions, epilepsy, and other symptoms.

The lethal dose of d-2-camphanone is 50–500 mg/kg (oral administration).
In general, 2 g of d-2-camphanone can cause serious toxicity, and 4 g of d-2-camphanone will produce fatal toxicity.

d-2-camphanone can cause a cold sensation similar to mint when applied to human skin.

In addition, d-2-camphanone has a slightly local anesthetic effect.
d-2-camphanone can act on the gastrointestinal mucosa to produce a certain degree of stimulating effect.

An appropriate dose of d-2-camphanone can make people feel warm and comfortable in the stomach, but high dose of d-2-camphanone will cause nausea and vomiting reaction.
The effect of d-2-camphanone on the central nervous system is obvious.

d-2-camphanone can act on the motor area of cerebral cortex and brain stem to produce the epilepsy-like seizures.
d-2-camphanone is generally believed that d-2-camphanone may have some therapeutic effects on patients with acute heart failure or recurrent collapse.

A low dose (50 mg) may treat mild heart fatigue and other illnesses.
The oxidized d-2-camphanone metabolite has a more obvious cardiotonic, hypertensive, and respiratory excitement effects.

d-2-camphanone can be absorbed by the body after oral administration easily through the mucous, subcutaneous, and muscle.
The in vivo metabolism of d-2-camphanone occurs mainly in the liver.

d-2-camphanone is firstly oxidized into d-2-camphanoneol and then goes through phase II metabolism to produce glucuronide conjugate with glucuronic acid.
Finally, the vast majority of glucuronide conjugate is excreted from the urine.

Dosage:
The topical dose of d-2-camphanone is 3-11% as an ointment.
For skin irritation, itching and pain, 3-11% of the ointment should be applied to the skin 3-4times per day.

For coughs and cold relief, a dense layer of 4.7-5.3% of d-2-camphanone ointment can be spread evenly onto the chest.
For Osteoarthritis, a topical combination comprising 32mg/g of d-2-camphanone, 50mg/g of chondroitin sulfate, and 30mg/g of glucosamine sulfate can be applied based on one’s requirements for about 8 weeks.

To relieve respiratory congestion through inhalation, 1 tablespoon of d-2-camphanone for every quart of water should be placed in a vaporizer 3 times per day.
The American Academy of Pediatrics suggests that d-2-camphanone should not exceed 11% for topical products and disqualifies the oral use of d-2-camphanone in children as d-2-camphanone may result in toxicity and death.

dl-d-2-camphanone is used as a plasticizer for celluloseesters and ethers; in the manufacture ofplastics and cymene; in cosmetics, lacquers,medicine, explosives, and pyrotechnics; andas a moth repellent.
d-2-camphanone is credited with anesthetic, antiinflammatory, antiseptic, astringent, cooling, and refreshing properties, and thought to be slightly stimulating to blood circulation and function.

Once absorbed by the subcutaneous tissue, d-2-camphanone combines in the body with glucoronic acid and is released through the urine.
d-2-camphanone is effective for oily and acne skin treatment, and has a scent similar to eucalyptus.

In high concentrations, d-2-camphanone can be an irritant and numb the peripheral sensory nerves.
Natural d-2-camphanone is derived from an evergreen tree indigenous to Asia, although now d-2-camphanone synthetic substitute is often used.

Manufacturing Methods of d-2-camphanone:
Steam distillation of d-2-camphanone-tree wood and crystallization.
d-2-camphanone is called natural d-2-camphanone and is dextrorotatory.
Synthetic d-2-camphanone, most of which is optically inactive, may be made from pinene, which is converted into camphene; by treatment with acetic acid and nitrobenzene d-2-camphanone becomes d-2-camphanone, turpentine oil is also used.

Natural d-2-camphanone is obtained by distillation from the plants of Cinnamomum or Laurus d-2-camphanonea from China and Japan, together with corresponding essential oils; the raw d-2-camphanone contains several impurities.
d-2-camphanone is separated from the water and the essential oil by pressure or by centrifugation and subsequently purified by sublimation or crystallization.

Production of d-2-camphanone:

Natural d-2-camphanone:
d-2-camphanone has been produced as a forest product for centuries, condensed from the vapor given off by the roasting of wood chips cut from the relevant trees, and later by passing steam through the pulverized wood and condensing the vapors.
By the early 19th century most d-2-camphanone tree reserves had been depleted with the remaining large stands in Japan and Taiwan, with Taiwanese production greatly exceeding Japanese.
d-2-camphanone 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 d-2-camphanone.
In 1868, a British naval force sailed into Anping harbor and the local British representative demanded the end of the Chinese d-2-camphanone monopoly.

After the local imperial representative refused, the British bombarded the town and took the harbor.
The "d-2-camphanone regulations" negotiated between the two sides subsequently saw a brief end to the d-2-camphanone monopoly.

Synthetic d-2-camphanone:
d-2-camphanone 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 acid 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 d-2-camphanone.
By contrast, d-2-camphanone occurs naturally as D-d-2-camphanone, the (R)-enantiomer.

Etymology of d-2-camphanone:
The word d-2-camphanone derives from the French word camphre, itself from Latin: camfora, from Arabic: كافور‎, romanized: kafur, from Malay: kapur, perhaps via Sanskrit: कर्पुरम्, romanized: karpuram.

d-2-camphanone has been in burnt as an offering to Hindu deities as since ancient times and is known in India as "karpoora aarathi".

In Old Malay d-2-camphanone is known as kapur Barus, which means "the chalk of Barus".
Barus was an ancient port located near modern Sibolga on the western coast of Sumatra.

This port traded in d-2-camphanone extracted from the d-2-camphanone trees (Cinnamonum d-2-camphanonea) that were abundant in the region.
Even now Indonesians refer to aromatic naphthalene balls and moth balls as kapur Barus.

History of d-2-camphanone:
The research and development process of d-2-camphanone has gone through from the natural product extraction to the modern chemical drug synthesis.
For a long time, the Chinese extracted d-2-camphanone mainly from d-2-camphanone tree (Cinnamomum d-2-camphanonea), root bark of bodinier cinnamon, and Yunnan d-2-camphanone tree.

With the development of chemical industry, human beings started to use chemical synthesis methods to obtain a large amount of d-2-camphanone.
At present, the chemical synthesis process of d-2-camphanone in China has been well developed.

The synthetic d-2-camphanone is divided into industrial and pharmaceutical grades.
The industrial grade d-2-camphanone has a content of up to 96% or higher, and the pharmaceutical grade d-2-camphanone with high purity can meet the standard of pharmacopeia.

Production History:
d-2-camphanone has been produced as a forest product for centuries, condensed from the vapor given off by the roasting of wood chips cut from the relevant trees, and later by passing steam through the pulverized wood and condensing the vapors.
By the early 19th century most d-2-camphanone tree reserves had been depleted with the remaining large stands in Japan and Taiwan with Taiwanese production greatly exceeding Japanese.

d-2-camphanone 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 d-2-camphanone.

In 1868 a British naval force sailed into Anping harbor and the local British representative demanded the end of the Chinese d-2-camphanone monopoly, after the local Qing representative refused the British bombarded the town and took the harbor.
The "d-2-camphanone regulations” negotiated between the two sides subsequently saw a brief end to the d-2-camphanone monopoly.

When d-2-camphanone use in the nascent chemical industries (discussed below) greatly increased the volume of demand in the late 19th century, potential for changes in supply and in price followed.
In 1911 Robert Kennedy Duncan, an industrial chemist and educator, related that the Imperial Japanese government had recently (1907–1908) tried to monopolize the production of natural d-2-camphanone as a forest product in Asia but that the monopoly was prevented by the development of the total synthesis alternatives, which began in "purely academic and wholly uncommercial" form with Gustav Komppa's first report "but d-2-camphanone sealed the fate of the Japanese monopoly.

For no sooner was d-2-camphanone accomplished than d-2-camphanone excited the attention of a new army of investigators—the industrial chemists.
The patent offices of the world were soon crowded with alleged commercial syntheses of d-2-camphanone, and of the favored processes companies were formed to explod-2-camphanone them, factories resulted, and in the incredibly short time of two years after d-2-camphanone academic synthesis artificial d-2-camphanone, every whd-2-camphanone as good as the natural product, entered the markets of the world.

And yet artificial d-2-camphanone does not—and cannot—displace the natural product to an extent sufficient to ruin the d-2-camphanone-growing industry.
d-2-camphanone sole present and probable future function is to act as a permanent check to monopolization, to act as a balance-wheel to regulate prices within reasonable limits."

This ongoing check on price growth was confirmed in 1942 in a monograph on DuPont's history, where William S. Dutton said, "Indispensable in the manufacture of pyroxylin plastics, natural d-2-camphanone imported from Formosa and selling normally for about 50 cents a pound, reached the high price of $3.75 in 1918 [amid the global trade disruption and high explosives demand that World War I created].
The organic chemists at DuPont replied by synthesizing d-2-camphanone from the turpentine of Southern pine stumps, with the result that the price of industrial d-2-camphanone sold in carload lots in 1939 was between 32 cents and 35 cents a pound."

The background of Gustaf Komppa's synthesis was as follows.
In the 19th century, d-2-camphanone was known that nitric acid oxidizes d-2-camphanone into d-2-camphanoneic acid.

Haller and Blanc published a semisynthesis of d-2-camphanone from d-2-camphanoneic acid.
Although they demonstrated d-2-camphanone structure, they were unable to prove d-2-camphanone.

The first complete total synthesis of d-2-camphanoneic acid was published by Komppa in 1903.
d-2-camphanone inputs were diethyl oxalate and 3,3-dimethylpentanoic acid, which reacted by Claisen condensation to yield diketod-2-camphanoneic acid.

Methylation with methyl iodide and a complicated reduction procedure produced d-2-camphanoneic 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 d-2-camphanone was a scarce natural product with a worldwide demand.

Komppa realized this.
He began industrial production of d-2-camphanone in Tainionkoski, Finland, in 1907 (with plenty of competition, as Kennedy Duncan reported).

d-2-camphanone 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 racemic d-2-camphanone.
By contrast, d-2-camphanone occurs naturally as D-d-2-camphanone, the (R)-enantiomer.

Fire Hazard of d-2-camphanone:
d-2-camphanone is flammable/combustible material.
d-2-camphanone may be ignited by friction, heat, sparks or flames.

d-2-camphanone is some may burn rapidly with flare burning effect.
d-2-camphanone is powders, dusts, shavings, borings, turnings or cuttings may explode or burn with explosive violence.

d-2-camphanone may be transported in a molten form at a temperature that may be above d-2-camphanone flash point.
d-2-camphanone may re-ignite after fire is extinguished.

Identifiers of d-2-camphanone:
CAS Number:
76-22-2
464-49-3 (R)
464-48-2 (S)

3DMet: B04902
Beilstein Reference: 1907611
ChEBI: CHEBI:36773
ChEMBL: ChEMBL504760

ChemSpider:
2441
7822160 (R)
9655 (S)

DrugBank: DB01744
ECHA InfoCard: 100.000.860
EC Number: 200-945-0
Gmelin Reference: 83275
IUPHAR/BPS: 2422
KEGG: D00098
MeSH: Camphor

PubChem CID:
2537
9543187 (R)
10050 (S)

RTECS number: EX1225000

UNII:
5TJD82A1ET
N20HL7Q941 (R)
213N3S8275 (S)

UN number: 2717
CompTox Dashboard (EPA): DTXSID5030955
InChI: InChI=1S/C10H16O/c1-9(2)7-4-5-10(9,3)8(11)6-7/h7H,4-6H2,1-3H3
Key: DSSYKIVIOFKYAU-UHFFFAOYSA-N
InChI=1/C10H16O/c1-9(2)7-4-5-10(9,3)8(11)6-7/h7H,4-6H2,1-3H3
Key: DSSYKIVIOFKYAU-UHFFFAOYAK

SMILES:
CC1(C)C2CCC1(C)C(=O)C2
O=C1CC2CCC1(C)C2(C)C

Properties of d-2-camphanone:
Melting point: 175-177 °C(lit.)
Boiling point: 204 °C(lit.)
Density: 0.992
Vapor density: 5.2 (vs air)
Vapor pressure: 4 mm Hg ( 70 °C)
Refractive index: 1.5462 (estimate)
FEMA: 4513 | dl-CAMPHOR
Fp: 148 °F
Storage temp.: Store below +30°C.
Solubility: Soluble in acetone, ethanol, diethylether, chloroform and acetic acid.
Form: neat
Color: White or Colorless
Odor: at 10.00 % in dipropylene glycol. camphoreous
Odor Type: camphoreous
Optical activity: [α]20/D +0.15 to -0.15°, c = 10% in ethanol
Explosive limit: 0.6-4.5%(V)
Water Solubility: 0.12 g/100 mL (25 ºC)
Merck: 14,1732
JECFA Number: 2199
BRN: 1907611
Henry's Law Constant: (x 10-5 atm?m3/mol): 3.00 at 20 °C (approximate - calculated from water solubility and vapor pressure)
Exposure limits: TLV-TWA 12 mg/m3 (2 ppm), STEL 18 mg/m3 (3 ppm) (ACGIH); IDLH 200 mg/m3 (NIOSH).
Stability: Stable. Combustible. Incompatible with strong oxidizing agents, metallic salts, combustible materials, organics.
InChIKey: DSSYKIVIOFKYAU-MHPPCMCBSA-N
LogP: 2.38
CAS DataBase Reference: 76-22-2
NIST Chemistry Reference: d-2-camphanone(76-22-2)
EPA Substance Registry System: d-2-camphanone (76-22-2)

Names of d-2-camphanone:

IUPAC Names:
(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one
-bornan-2-one
1,7,7-TRIMETHYL-BICYCLO[2.2.1]HEPTAN-2-ONE
1,7,7-Trimethyl-Bicyclo[2.2.1]Heptan-2-one
1,7,7-trimethylbicyclo [2.2.1]heptan-2-one
1,7,7-trimethylbicyclo(2.2.1)-2 heptanone
1,7,7-Trimethylbicyclo[2.2.1]heptan-2-one
1,7,7-trimethylbicyclo[2.2.1]heptan-2-one
1,7,7-trimethylbicyclo[2.2.1]heptan-2-one, 1,7,7-trimethylbicyclo[2.2.1]heptan-6-one
1,7,7-Trimethyll-bicyclo[2.2.1]heptan-2-one
1,7.7-Trimethylbicyclo[2.2.1]heptan-2-one
4,7,7-trimethylbicyclo[2.2.1]heptan-3-one
4.7.7-trimethylbicyclo[2.2.1]heptane-3-one
Bicyclo[2.2.1]Heptan-2-One, 1,7,7-Trimethyl-
Bicyclo[2.2.1]heptan-2-one, 1,7,7-trimethyl-
Bornan-2-one
bornan-2-one
CAMPHOR
Camphor
camphor
Camphor
DL-bornan-2-one
Kampfer