464-49-3 Usage
Description
(1R)-(+)-Camphor is a terpene that has been found in C. sativa, C. indica, and C. sativa/C. indica hybrid strains as well as the essential oils from a variety of herbs including rosemary, lavender, and sage and has diverse biological activities. It inhibits norepinephrine secretion and cytosolic calcium and sodium increases induced by the nicotinic acetylcholine receptor (nAChR) agonist 1,1-dimethyl-4-phenylpiperazinium iodide (DMPP) in chromaffin cells (IC50s = 70, 88, and 19 μM, respectively). (1R)-(+)-Camphor (65-260 μM) induces proliferation of and increases expression of collagen IA, collagen IIIA, collagen IVA, and elastin in human primary dermal fibroblasts. In vivo, (1R)-(+)-camphor increases expression of collagen IA, collagen IIIA, collagen IVA, and elastin in skin in UV-exposed mice when administered at doses of 26 and 55 mM in drinking water post UV-exposure. It reduces cough frequency in citric acid-challenged guinea pigs. (1R)-(+)-Camphor is insecticidal, reducing digging activity and inducing mortality of fire ant workers. It has also been used as a building block in the synthesis of cannabinergic ligands.
Chemical Properties
Different sources of media describe the Chemical Properties of 464-49-3 differently. You can refer to the following data:
1. d-Camphor has a warm, minty, almost ethereal diffusive aroma. For other details of description, see Camphor Tree.
2. white crystals
Occurrence
Frequently occurring in nature as the d- or l-form; the optically inactive form is seldom encountered. The
d-form has been reported found in Cinnamomum camphora Ness. (Laurus camphora L.) from China, Japan and the East Indies; in
Sassafras officinale, Lavandula spica and in other Labiatae. The l-form is reported found in the essential oils of Salvia grandiflora,
Matricaria parthenium, Artemisia herba alba; the optically inactive form is found in Chrysanthemum japonicum sinense. Also
reported found in orange peel oil, lemon peel oil, apricot, raspberry, anise, cinnamon root bark, ginger, pepper, coriander, calamus,
sweet fennel and rosemary.
Uses
Different sources of media describe the Uses of 464-49-3 differently. You can refer to the following data:
1. (1R)-(+)-Camphor is used as a chiral intermediate and auxiliary. It is also used as a skin antipruritic and as an anti-infective agent.
2. D-Camphor may be used as reference material for the quantification of the analyte in Saraca asoca and coriander using chromatography techniques.
3. (R)-(+)-Camphor is a terpenoid with a wide variety of use. (R)-(+)-Camphor has insecticidal activity and is also used as an antimicrobial agent. (R)-(+)-Camphor is used as a culinary flavouring agent in parts of asia.
4. analgesic, antiinfective, antipruritic
Definition
ChEBI: The (R)- enantiomer of camphor.
Aroma threshold values
Detection at 1 to 1.29 ppm
Taste threshold values
Taste characteristics at 20 ppm: medicinal, camphoraceous, mentholic and woody.
General Description
Colorless or white crystals. Sublimes. Flash point 149°F. Burns readily with a bright, smoky flame. Penetrating aromatic odor. Pungent, aromatic taste followed by a sensation of cold.
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%
Check Digit Verification of cas no
The CAS Registry Mumber 464-49-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,6 and 4 respectively; the second part has 2 digits, 4 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 464-49:
(5*4)+(4*6)+(3*4)+(2*4)+(1*9)=73
73 % 10 = 3
So 464-49-3 is a valid CAS Registry Number.
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
464-49-3Relevant articles and documents
Molybdenum(0)-Catalyzed Reductive Dehalogenation of α-Halo Ketones with Phenylsilane
Perez, Daniel,Greenspoon, Noam,Keinan, Ehud
, p. 5570 - 5574 (1987)
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.
carba Nicotinamide Adenine Dinucleotide Phosphate: Robust Cofactor for Redox Biocatalysis
D?ring, Manuel,Sieber, Volker,Simon, Robert C.,Tafertshofer, Georg,Zachos, Ioannis
supporting information, p. 14701 - 14706 (2021/05/13)
Here we report a new robust nicotinamide dinucleotide phosphate cofactor analog (carba-NADP+) and its acceptance by many enzymes in the class of oxidoreductases. Replacing one ribose oxygen with a methylene group of the natural NADP+ was found to enhance stability dramatically. Decomposition experiments at moderate and high temperatures with the cofactors showed a drastic increase in half-life time at elevated temperatures since it significantly disfavors hydrolysis of the pyridinium-N?glycoside bond. Overall, more than 27 different oxidoreductases were successfully tested, and a thorough analytical characterization and comparison is given. The cofactor carba-NADP+ opens up the field of redox-biocatalysis under harsh conditions.
A Structural View on the Stereospecificity of Plant Borneol-Type Dehydrogenases
Chánique, Andrea M.,Dimos, Nicole,Drienovská, Ivana,Calderini, Elia,Pantín, Mónica P.,Helmer, Carl P. O.,Hofer, Michael,Sieber, Volker,Parra, Loreto P.,Loll, Bernhard,Kourist, Robert
, p. 2262 - 2277 (2021/03/16)
The development of sustainable processes for the valorization of byproducts and other waste streams remains an ongoing challenge in the field of catalysis. Racemic borneol, isoborneol and camphor are currently produced from α-pinene, a side product from the production of cellulose. The pure enantiomers of these monoterpenoids have numerous applications in cosmetics and act as reagents for asymmetric synthesis, making an enzymatic route for their separation into optically pure enantiomers a desirable goal. Known short-chain borneol-type dehydrogenases (BDHs) from plants and bacteria lack the required specificity, stability or activity for industrial utilization. Prompted by reports on the presence of pure (?)-borneol and (?)-camphor in essential oils from rosemary, we set out to investigate dehydrogenases from the genus Salvia and discovered a dehydrogenase with high specificity (E>120) and high specific activity (>0.02 U mg?1) for borneol and isoborneol. Compared to other specific dehydrogenases, the one reported here shows remarkably higher stability, which was exploited to obtain the first three-dimensional structure of an enantiospecific borneol-type short-chain dehydrogenase. This, together with docking studies, led to the identification of a hydrophobic pocket in the enzyme that plays a crucial role in the stereo discrimination of bornane-type monoterpenoids. The kinetic resolution of borneol and isoborneol can be easily integrated into the existing synthetic route from α-pinene to camphor thereby allowing the facile synthesis of optically pure monoterpenols from an abundant renewable source.
Zwitterion-induced organic-metal hybrid catalysis in aerobic oxidation
Hu, Rong-Bin,Lam, Ying-Pong,Ng, Wing-Hin,Wong, Chun-Yuen,Yeung, Ying-Yeung
, p. 3498 - 3506 (2021/04/07)
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.
