Camphor sulfonic acid includes L-camphor sulfonic acid, D-camphor sulfonic acid and racemic camphor sulfonic acid these three isomers.
It is a kind of white columnar crystals with the melting point of 193°C (decomposition). [α]D20+24° (water). It is Slightly soluble in ethanol, insoluble in ether, soluble in sodium hydroxide and sodium carbonate solution. L-camphor sulfonic acid could be produced from reaction between camphor, sulfuric acid and acetic anhydride.It has a lot of functions such as exciting the respiratory center, the vascular movement center and myocardium. Its sodium salt plays pharmaceutical role in medicine.
Camphor sulfonic acid sodium salt is a kind of white crystalline powder. It is odorless and tastes bitter and then sweet. It is easily absorb moisture and easily dissolve in the water and hot ethanol. So it should be shading confined preservation. it can Directly excite the medulla oblongata respiratory center and vascular movement center, and quicken and deepen the breath, rise the blood pressure; it also can directly excite the myocardium and strength the contraction of cardiac muscle as well as could increase the output.
It is applied the treatment of infectious disease, as well as the disease like central inhibition of poisoning caused by respiratory depression, fatigue, high fever, poisoning, heat stroke and other acute heart failure.
(1) It is also used for the racemization of optical isomers.
(2) It can be applied to the resolution of intermediate or isomer in medicine.
(3) It also could play a role as organic synthesis intermediates and resolving agent.
Camphor sulfonic acid is obtained from camphor and sulfuric acid by irradiation.
This method involves:
1) Adding the camphor and acetic anhydride to the pot.
2) Mixing it and making it dissolved.
3) Dripping sulfuric acid after cooling. And the reaction should be maintained at 44-45 °C for 48 hours. Then cool it to 6-7 °C.
4) Crystallizing, filtrating, washing with a small amount of acetic acid crystals, and dry it to get camphor sulfonic acid.
(1R)-(-)-10-Camphorsulfonic acid is a kind of prismatic crystals and its melting point is 193-195 ° C (decompose). It is Insoluble in ether and slightly soluble in glacial acetic acid and ethyl acetate. And it is and moisture in wet air.
(1R)-(-)-Camphor-10-sulfonic acid, is used as a pharamaceutical intermediate and also used as a chiral derivative of Camp. It can also be used as resolving agents for chiral amines and other cations.
1R)-(-)-10-Camphorsulfonic acid is a chiral derivative of Camphor.It has the following uses:
(1)It is also used for the racemization of optical isomers.
(2) It can be applied to the resolution of intermediate or isomer in medicine.
(3) It also could play a role as organic synthesis intermediates and resolving agent.
ChEBI: The R enantiomer of camphorsulfonic acid.
(1R)-(-)-10-Camphorsulfonic acid is an HPLC derivatization reagent for UV/Vis detection. It is mainly employed for the resolution of bases.
Induced crystallization resolution of racemic camphorsulfonate to obtain enantiomers:
1. Formation of a racemic salt (e.g., ammonium salt).
2. To solutions of the racemic salt, a dextro- or levo- optically active inducer is added to induce crystallization of the corresponding enantiomeric salt.
3. The separated salt is acidified and crystallized from acetic acid to yield levo- or dextro-camphorsulfonic acid.
It forms prisms from AcOH or EtOAc, and is deliquescent in moist air. Store it in tightly stoppered bottles. The NH4 salt forms needles from H2O [] D ±20.5o (c 5, H2O). [Burgess & Lowry J Chem Soc 127 279 1925, Marsi et al. J Am Chem Soc [ 78 3063 1956.] The RS-acid recrystallises from AcOH. [60g of (±)-acid in 60mL of AcOH at 105o gave 40g of crystals has m 202-203o [Bartlett & Knox Org Synth 45 12 1965.] [Beilstein 11 IV 642.]
