반응 #1172416

ord-96992cd0460d4821a7e04f223c411f72

반응 방정식

O=S(=O)(O)O
sulphuric acid
C[C@H](O)[C@H](O)[C@@H](O)[C@@H](O)C=O
Rhamnose
C[C@@H]1O[C@@H](O[C@H]2[C@H](Oc3cc(O)c4c(c3)O[C@H](c3ccc(O)cc3)CC4=O)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O
Naringin
C[C@@H]1O[C@@H](O[C@H]2[C@H](Oc3cc(O)c4c(c3)O[C@H](c3ccc(O)cc3)CC4=O)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O
naringin
→
C[C@H](O)[C@H](O)[C@@H](O)[C@@H](O)C=O
L-rhamnose
O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO
Glucose
O=C1C[C@@H](c2ccc(O)cc2)Oc2cc(O)cc(O)c21
naringenin

반응물

O=S(=O)(O)O
sulphuric acid
C[C@H](O)[C@H](O)[C@@H](O)[C@@H](O)C=O
Rhamnose
C[C@@H]1O[C@@H](O[C@H]2[C@H](Oc3cc(O)c4c(c3)O[C@H](c3ccc(O)cc3)CC4=O)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O
Naringin
C[C@@H]1O[C@@H](O[C@H]2[C@H](Oc3cc(O)c4c(c3)O[C@H](c3ccc(O)cc3)CC4=O)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O
naringin

시약

없음

반응 조건

상세 조건
See reaction.notes.procedure_details.

실험 절차

Illustrative of a process for obtaining L-rhamnose from naringin is described by G. N. Pulley, et al., "Preparation of Rhamnose from Naringin", J. Amer. Chem. Soc., 61, p. 175 (1939), in which naringin is hydrolyzed by refluxing it with sulphuric acid (~3.7%). Glucose, L-rhamnose, naringenin and other reaction products are formed by the reaction. The reaction medium is cooled and naringenin, which is semi-solid, is separated from the cooled reaction medium. The remaining filtrate then is neutralized and heated to boiling in the presence of charcoal. The charcoal treated product is concentrated in vacuo and then is inoculated with yeast to ferment glucose. L-rhamnose is isolated from the fermented liquor by several steps of concentration in vacuo and washing.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US05008381uspto-grants-1991_04