464-49-3

Basic information

• Product Name: D-CAMPHOR
• Synonyms: 7,7-trimethyl-(1r)-bicyclo(2.2.1)heptan-2-on;7,7-trimethyl-(1theta)-bicyclo[2.2.1]heptan-2-on;Bicyclo[2.2.1]heptan-2-one, 1,7,7-trimethyl-, (1R)-;bicyclo[2.2.1]heptan-2-one,1,7,7-trimethyl-,(1R)-;Camphor usp;CAMPHOR, (1R,4R)-(+)-;camphorusp;d-2-Bornanone
• CAS NO: 464-49-3
• Molecular Formula: C₁₀H₁₆O
• Molecular Weight: 152.23
• EINECS: 207-355-2
• Product Categories: Food and Feed Additive;Bicyclic Monoterpenes;Biochemistry;Camphor, etc. (Plasticizer);Functional Materials;Plasticizer;Terpenes;Alphabetical Listings;C-D;Flavors and Fragrances;Inhibitors
• Mol File: 464-49-3.mol
• Article Data: 94

Chemical Properties

• Melting Point: 179-181 °C(lit.)
• Boiling Point: 204 °C
• Flash Point: 148 °F
• Appearance: White/Crystals
• Density: 0,99 g/cm3
• Vapor Density: 5.24 (vs air)
• Vapor Pressure: 4 mm Hg ( 70 °C)
• Refractive Index: 44.5 ° (C=20, EtOH)
• Storage Temp.: 2-8°C
• Solubility: Slightly soluble in water, very soluble in alcohol and in light petroleum, freely soluble in fatty oils, very slightly soluble in glycerol.
• Explosive Limit: 3.5%
• Water Solubility: Soluble in water (0.1 g/L at 20°C).
• Stability: Stable. Incompatible with strong reducing agents, strong oxidizing agents, chlorinated solvents. Protect from direct sunlight.
• Merck: 14,1732
• BRN: 2042745
• CAS DataBase Reference: D-CAMPHOR(CAS DataBase Reference)
• NIST Chemistry Reference: D-CAMPHOR(464-49-3)
• EPA Substance Registry System: D-CAMPHOR(464-49-3)

Safety Data

• Hazard Codes: F,Xn,Xi
• Statements: 11-22-36/37/38-20/21/22-36
• Safety Statements: 16-26-36-37/39
• RIDADR: UN 2717 4.1/PG 3
• WGK Germany: 1
• RTECS: EX1260000
• TSCA: Yes
• HazardClass: 4.1
• PackingGroup: III
• Hazardous Substances Data: 464-49-3(Hazardous Substances Data)

Usage

Description

D-CAMPHOR, also known as (1R)-(+)-Camphor, is a terpene compound that occurs naturally in various plants and herbs. It is characterized by its colorless or white crystalline appearance, sublimation properties, and a penetrating aromatic odor with a pungent, aromatic taste followed by a sensation of cold. D-CAMPHOR has been found to possess a wide range of biological activities, including insecticidal, anti-infective, and antipruritic properties.

Uses

1. Chiral Intermediate and Auxiliary:
D-CAMPHOR is used as a chiral intermediate and auxiliary in the synthesis of various compounds, contributing to its importance in the chemical industry.
2. Skin Antipruritic:
D-CAMPHOR serves as a skin antipruritic, helping to relieve itching and irritation on the skin.
3. Anti-infective Agent:
Due to its anti-infective properties, D-CAMPHOR is used as an anti-infective agent, providing protection against various infections.
4. Culinary Flavoring Agent:
In some parts of Asia, D-CAMPHOR is used as a culinary flavoring agent, adding a unique taste to certain dishes.
5. Insecticidal Activity:
D-CAMPHOR exhibits insecticidal activity, making it useful in controlling and reducing insect populations, particularly in agricultural settings.
6. Building Block in Synthesis:
D-CAMPHOR has been used as a building block in the synthesis of cannabinergic ligands, highlighting its versatility in chemical applications.
7. Quantification of Analytes:
D-CAMPHOR may be used as a reference material for the quantification of analytes in Saraca asoca and coriander using chromatography techniques, aiding in the analysis and quality control of these plants.
8. Aroma and Taste:
D-CAMPHOR's warm, minty, and almost ethereal aroma, along with its medicinal, camphoraceous, mentholic, and woody taste characteristics, make it a valuable component in the fragrance and flavor industries.
Occurrence:
D-CAMPHOR is frequently found in nature as the dor l-form, with the optically inactive form being seldom encountered. The d-form has been reported in various plants, including Cinnamomum camphora, Sassafras officinale, Lavandula spica, and other Labiatae. The l-form is found in the essential oils of Salvia grandiflora, Matricaria parthenium, and Artemisia herba alba. Additionally, D-CAMPHOR is reported in orange peel oil, lemon peel oil, apricot, raspberry, anise, cinnamon root bark, ginger, pepper, coriander, calamus, sweet fennel, and rosemary.

Air & Water Reactions

Flammable. Insoluble in water.

Reactivity Profile

D-CAMPHOR is incompatible with strong oxidizing agents, strong reducing agents and chlorinated solvents.

Fire Hazard

D-CAMPHOR is combustible.

Flammability and Explosibility

Flammable

Synthesis

Natural camphor is obtained by distillation from the plants of Cinnamomum or Laurus camphora from China and Japan, together with the corresponding essential oils; the raw camphor contains several impurities. It is separated from the water and the essential oil by pressure or by centrifugation and subsequently purified by sublimation or crystallization. Synthetic camphor is prepared from pinene isolated by fractional distillation of turpentine oil; pinene is reacted to bornyl chloride with gaseous HCl under pressure and then to camphene. The distilled and purified camphene is then oxidized to camphor with Na+ or K+ bichromate in the presence of H2SO4.

Purification Methods

Crystallise it from EtOH, 50% EtOH/water, MeOH, or pet ether or from glacial acetic acid by addition of water. It can be sublimed (50o/14mm) and also fractionally crystallised from its own melt. It is steam volatile. It should be stored in tight containers as it is appreciably volatile at room temperature. The solubility is 0.1% (H2O), 100% (EtOH), 173% (Et2O) and 300%

InChI:InChI=1/C10H16O/c1-9(2)7-4-5-10(9,3)8(11)6-7/h7H,4-6H2,1-3H3/t7?,10-/m0/s1

Upstream product

• 14487-70-8 3-diazocamphor 
• 15099-93-1 (1R)-bornen-⁽²⁾-one-⁽⁶⁾ 
• 109-72-8 n-butyllithium 
• 465500-08-7 (1R)-2-endo-[(1R)-4-methylcyclohex-3-en-1-ylcarbonyl]-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol 
• 363152-44-7 (S)-4-Nitro-3-phenyl-1-((1R,2R,4R)-1,7,7-trimethyl-2-trimethylsilanyloxy-bicyclo[2.2.1]hept-2-yl)-butan-1-one 
• 126015-18-7 [2-(4-Methoxy-phenyl)-1-naphthalen-1-yl-ethyl]-[(1R,4R)-1,7,7-trimethyl-bicyclo[2.2.1]hept-(2E)-ylidene]-amine 
• 53402-10-1 thiocamphor 
• 68330-43-8 (+)-R-methylisoborneol 
• 1075216-42-0 2-ethinyl-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol 
• 204577-66-2 1-(2-hydroxy-1,7,7-trimethylbicyclo[2.2.1]hept-endo-2-yl)ethanone 
• 204577-67-3 (1R)-2-endo-acetyl-2-exo-(trimethylsilyloxy)-1,7,7-trimethylbicyclo[2.2.1]heptane 
• 271600-09-0 [(S)-1-Ethyl-3-oxo-3-((1R,2R,4R)-1,7,7-trimethyl-2-trimethylsilanyloxy-bicyclo[2.2.1]hept-2-yl)-propyl]-carbamic acid benzyl ester 
• 450371-16-1 {(S)-1-[(S)-1-Ethyl-3-oxo-3-((1R,2R,4R)-1,7,7-trimethyl-2-trimethylsilanyloxy-bicyclo[2.2.1]hept-2-yl)-propylcarbamoyl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester 
• 450371-20-7 [(S)-1-((S)-1-{[(S)-1-Ethyl-3-oxo-3-((1R,2R,4R)-1,7,7-trimethyl-2-trimethylsilanyloxy-bicyclo[2.2.1]hept-2-yl)-propylcarbamoyl]-methyl}-propylcarbamoyl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester 

Downstream Products

• 124-76-5 isoborneol 
• 464-43-7 d-borneol 
• 478011-87-9 2-(2-Bornylamino)ethanol 
• 826-36-8 2,2,6,6-Tetramethyl-4-piperidone 
• 41720-04-1 Camphor-3-carbonyl chloride 
• 129502-23-4 C-Phenyl-N-[1,7,7-trimethyl-bicyclo[2.2.1]hept-(2E)-ylidene]-methanesulfonamide 
• 129368-88-3 (2-Methylsulfanyl-phenyl)-[(1R,4R)-1,7,7-trimethyl-bicyclo[2.2.1]hept-(2E)-ylidene]-amine 
• 15229-07-9 dichloro-2',4' benzylidene-3 bornanone-2 
• 136206-67-2 4-Methyl-N-(1R)-(1,7,7-trimethylbicyclo<2.2.1>hept-2-ylidene)benzesulphonamide 
• 63765-03-7 N-(benzyl)-(D)-camphorimine 
• 499-75-2 carvacrol 
• 1585-40-6 benzenepentacarboxylic acid 
• 6627-72-1 rac-endo-borneol 
• 507-70-0 1,7,7-trimethyl bicyclo[2.2.1]heptan-2-ol 

Relevant articles and documents

Molybdenum(0)-Catalyzed Reductive Dehalogenation of α-Halo Ketones with Phenylsilane

Reductive dehalogenation of α-halo ketones and esters is effectively achieved by using a novel reducing system comprised of phenylsilane and catalytic amounts of molybdenum hexacarbonyl and triphenylphosphine.Reactions are carried out at 60-80 deg C in variety of solvents, including THF, benzene, toluene, and diglyme.With respect to α-halo carbonyl reduction, this combination of Mo(0) and phenylsilane is superior to our previously described palladium (0)/diphenylsilane system and produces higher yields and cleaner products.

Dysprosium-doped zinc tungstate nanospheres as highly efficient heterogeneous catalysts in green oxidation of terpenic alcohols with hydrogen peroxide

A green route to oxidize terpenic alcohols (nerol and geraniol) with H2O2over a solid catalyst was developed. The Dy-doped ZnWO4catalyst was synthesized by coprecipitation and microwave-assisted hydrothermal heating, containing different dysprosium loads. All the catalysts were characterized through infrared spectroscopy, powder X-ray diffraction, surface area and porosimetry, transmission electronic microscopy image, andn-butylamine potentiometric titration analyses. The influence of main reaction parameters such as temperature, the stoichiometry of reactants, loads, and catalyst nature was assessed. ZnWO42.0 mol% Dy was the most active catalyst achieving the highest conversion (98%) and epoxide selectivity (78%) in nerol oxidation. The reaction scope was extended to other terpenic alcohols (i.e., geraniol, borneol, and α-terpineol). The highest activity of ZnWO42.0 mol% Dy was assigned to the lower crystallite size, higher surface area and pore volume, higher acidity strength and the greatest dysprosium load.

Borneol dehydrogenase from Pseudomonas sp. TCU-HL1 possesses novel quinuclidinone reductase activities

Borneol dehydrogenase (BDH) catalyses the last step of the camphor biosynthetic pathway in plants and the first reaction in the borneol degradation pathway in soil microorganisms. Native or engineered BDH can be used to produce optically pure borneol and camphor. The recently reported apo-form crystal structure of BDH (PDB ID: 6M5N) from Pseudomonas sp. TCU-HL1 superimposes well with that of 3-quinuclidinone reductase (QR) (PDB ID: 3AK4) from Agrobacterium tumefaciens. QR catalyses the conversion of 3-quinuclidinone into (R)-3-(?)-quinuclidinol, an important chiral synthone for several drugs. However, the kinetic parameter, kcat, of QR was not determined in the previous reports even though both BDH and QR have various potential industrial applications. Here, we aimed to further characterise their structural and functional relationship. Recombinant QR with the native sequence was cloned, expressed in E. coli, and purified. We found that 3-quinuclidinone can be used as an alternative substrate for BDH. Only (R)-3-(?)-quinuclidinol was detected in this BDH-catalysed reaction. The results of 3 D molecular docking simulation show that 3-quinuclidinone and (+)-/(-)- borneol were docked to two different parts of the QR active site. In contrast, all three compounds are docked uniformly to the alpha-1 helix of BDH. There results explain why BDH can turnover 3-quinuclidinone, while QR can not act on (+)-/(-)-borneol.

Zwitterion-induced organic-metal hybrid catalysis in aerobic oxidation

In many metal catalyses, the traditional strategy of removing chloride ions is to add silver salts via anion exchange to obtain highly active catalysts. Herein, we reported an alternative strategy of removing chloride anions from ruthenium trichloride using an organic [P+-N-] zwitterionic compound via multiple hydrogen bond interactions. The resultant organic-metal hybrid catalytic system has successfully been applied to the aerobic oxidation of alcohols, tetrahydroquinolines, and indolines under mild conditions. The performance of zwitterion is far superior to that of many other common Lewis bases or Br?nsted bases. Mechanistic studies revealed that the zwitterion triggers the dissociation of chloride from ruthenium trichloride via nonclassical hydrogen bond interaction. Preliminary studies show that the zwitterion is applicable to catalytic transfer semi-hydrogenation.