5872-08-2 Usage
Uses
Used in Pharmaceutical Industry:
DL-10-CAMPHORSULFONIC ACID is used as a pharmaceutical intermediate for the production of various drugs, such as intestinal disorder inhibitors and HIV improving agents. It serves as an optical split agent, playing a crucial role in the separation of optical isomers for racemisation.
DL-10-CAMPHORSULFONIC ACID is also used as a resolving agent for optically active amino acids, such as phenylpropanolamine, metoprolol, propranolol, epinephrine, salbutamol, and atenolol. These substances have various applications, including receptor-blocking action, cardiac inhibition, and local anesthetic effects.
Used in Chiral Asymmetric Synthesis:
DL-10-CAMPHORSULFONIC ACID is employed as a chiral ion-pairing reagent in the preparation of active pharmaceutical ingredients, such as trimetaphan camsilate, which is used to reduce bleeding during neurosurgery.
Used in Veterinary Medicine:
Camphor sulfonate, derived from camphorsulfonic acid, is used as a veterinary central stimulant. It stimulates the respiratory center, causing respiratory excitement, and is utilized for the treatment of respiratory and circulatory acute disorders, as well as for resisting central nervous system poisoning.
Used in Drug Delivery Systems:
Camphor ammonium sulfonate, another derivative, acts as a chiral ion pair reagent added to the mobile phase to separate the aromatic alcohol amine drug enantiomers, enhancing the delivery, bioavailability, and therapeutic outcomes of various drugs.
Used in Polymer Doping:
DL-10-CAMPHORSULFONIC ACID is involved in the doping of polyaniline to prepare nano-scale conductive polymer materials, which have potential applications in the development of advanced materials for various industries.
Used in Enantiomer Separation:
(+)-Camphor-10-sulfonic acid is used as a resolving agent for chiral amines and other cations, playing a vital role in the transglucosidation of methyl and ethyl D-glucopyranosides by alcoholysis.
Preparation
natural camphor is mainly extracted from camphor plants, ginger plants and sage seeds, and with optical activity; synthetic camphor is generally prepared by the isomerization of turpentine to obtain camphene, then by esterification, hydrolysis and dehydrogenation reaction process; synthetic camphor is racemic, almost lacking optical activity. Through the reaction of camphor powder and concentrated sulfuric acid sulfonation, racemic camphorsulfonic acid is obtained, and then by the resolution, left and right handed camphorsulfonic acid is made. The optimum conditions for the synthesis of camphorsulfonic acid are as follows: the molar ratio of camphor powder, concentrated sulfuric acid and acetic anhydride is 1.0: 1.4: 3.0; reaction temperature is10 ℃; standing time is 5 days, and camphorsulfonic acid is vacuum dried. Utilizing sopropyl alcohol as solvent, camphor sulfonate is obtained by neutralization of camphorsulfonic acid and a resolving agent made by alcohol amine; camphorsulfonic acid is obtained by purification.
Figure 2: Preparation principle
Resolution
Kinetic resolution is the selective chiral reduction of racemic camphor, so that one of the enantiomers of racemates is selectively reducted, leaving the required isomers, and then purifying. It is also possible to add optically active amino acids, phenylglycine, phenylalanine, hydroxyphenylglycine, o-chlorophenylglycine and resolving agents of its derivatives. Subjecting racemic camphorsulfonic acid to salting treatment, separating the left and right camphorsulfonic acid ammonium salt solution by chromatography, film evaporation, crystallization and filtration; drying to get white crystals, the left and right handed camphorsulfonic acid is made.
Market
The domestic demand for camphorsulfonic acid is high; camphorsulfonic acid is basically dependent on imports, and the price of it is also very expensive, especially for L-camphorsulfonic acid.
References
[1] KE Chunlan, LIU Xiaohong, XU Chunxiao etc. Synthesis and Resolution of Camphor Sulfonic Acid [J]. Journal of Nanchang University Engineering, 2010, 32 (4): 381-384.
[2] KE Chunlan, LIU Xiaohong, XU Chunxiao etc. Synthesis and latest application of chiral camphorsulfonic acid and its salts [J] .Jiangxi Chemical Industry, 2010 (2): 1-4.
Check Digit Verification of cas no
The CAS Registry Mumber 5872-08-2 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,8,7 and 2 respectively; the second part has 2 digits, 0 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 5872-08:
(6*5)+(5*8)+(4*7)+(3*2)+(2*0)+(1*8)=112
112 % 10 = 2
So 5872-08-2 is a valid CAS Registry Number.
InChI:InChI=1/C10H16O4S/c1-9(2)7-3-4-10(9,8(11)5-7)6-15(12,13)14/h7H,3-6H2,1-2H3,(H,12,13,14)
5872-08-2Relevant articles and documents
Identification of small molecule sulfonic acids as ecto-5'-nucleotidase inhibitors
Raza, Rabia,Saeed, Aamer,Lecka, Joanna,Sévigny, Jean,Iqbal, Jamshed
, p. 1133 - 1139 (2013/01/15)
Ecto-5'-Nucleotidase inhibitors have great potential as anti-tumor agents. We have investigated biochemical properties of human and rat ecto-5'-Nucleotidases and characterized 19 small molecule sulfonic acid derivatives as potential inhibitors of ecto-5'-Nucleotidases. We identified 11 potent inhibitors of human and rat ecto-5'-Nucleotidases and checked their selectivity. Compound 10 (Sodium 2,4-dinitrobenzenesulfonate) with Ki value of 0.66 μM and 19 (N-(4- sulfamoylphenylcarbamothioyl) pivalamide) with Ki value of 0.78 μM were identified as the most potent inhibitors for human and rat ecto-5'-Nucleotidase, respectively. The present compounds have low molecular weights, water solubility and equal potency as compared to the reported inhibitors.
Polymorphic clopidogrel hydrogenesulphate form
-
, (2008/06/13)
Novel orthorombic polymorph of clopidogrel hydrogen sulfate or hydrogen sulfate of methyl (+)-(S)-α-(2-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-5-acetate and a process for its preparation.
Dibenzonaphthyrones
-
, (2008/06/13)
Dibenzonaphthyrone of formula (I) wherein A1and A2independently of each other are unsubstituted or mono- to tetra-substituted o-C6-C18arylene, with the proviso that formula (I) does not represent a dibenzonaphthyrone of the formula The invention further relates to processes for the preparation thereof, to the use thereof for colouring/pigmenting high-molecular-weight organic material and to substance compositions comprising dibenzonaphthyrones.
Action of Red Light on Solid (+)-10-Bromo-2-chloro-2-nitrosocamphane: (i) Nuclear and Electron Paramagnetic Resonance Studies; (ii) Reaction Products; (iii) Solid-state Photolysis Reaction Mechanisms
Majeed, Nesreen N.,Porte, Andrew L.
, p. 1139 - 1146 (2007/10/02)
Photolysis of blue, solid (+)-10-bromo-2-chloro-2-nitrosocamphane (1) with red light produces two nitroxide radicals (2) and (3), 10-bromocamphor (4), a 10-bromo-2-chloro-2-nitrocamphane (5), a 2-chloro-5,5-dimethyl-1,2-dinitrobicyclooctane (6a), and a corresponding 1-nitrato-analogue (6b).E.p.r. spectra of (2) and (3) are described and interpreted.Analyses of the 1H n.m.r. spectra of compounds (1) and (5) show that n.m.r. method can be used to determine configurations at active XCCl (X = NO or NO2) centres of gem-chloronitroso and gem-chloronitro derivatives of the terpenes.The combination of chemical and spectroscopic evidence enables some of the steps involved in the solid-state red photolysis reaction of (1) to be unravelled.
Process for the preparation of D(-)αphenylglycine
-
, (2008/06/13)
The invention provides a process for the preparation of D(-)αphenylglycine by resolution of DLαphenylglycine by means of D(+)camphorsulfonic acid. The present process enables the preparation of D(-)αphenylglycine at a minimum loss of the very expensive starting materials, such as DLαphenylglycine and D(+)camphorsulfonic acid. The salts produced in this process are precipitated from the resolution filtrate and the filtrate may be discarded as effluent water without any danger to the environment.
