53912-30-4

Basic information

• Product Name: 13-methylberberrubine
• Synonyms: 13-methylberberrubine;5,6-Dihydro-9-hydroxy-10-methoxy-13-methylbenzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium
• CAS NO: 53912-30-4
• Molecular Formula: C20H18 N O4
• Molecular Weight: 0
• Mol File: 53912-30-4.mol

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• CAS DataBase Reference: 13-methylberberrubine(CAS DataBase Reference)
• NIST Chemistry Reference: 13-methylberberrubine(53912-30-4)
• EPA Substance Registry System: 13-methylberberrubine(53912-30-4)

Safety Data

• Hazardous Substances Data: 53912-30-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C20H17NO4/c1-11-13-3-4-16(23-2)20(22)15(13)9-21-6-5-12-7-17-18(25-10-24-17)8-14(12)19(11)21/h3-4,7-9H,5-6,10H2,1-2H3/p+1

Upstream product

• 38691-92-8 13-methylberberine 

Relevant articles and documents

Biotransformations of protoberberines in cell cultures of Dicentra spectablis

A liquid chromatography-atmospheric pressure chemical ionization mass spectrometry procedure was applied to biotransformation experiments in cultured cells of Dicentra, spectablis. Interconversions of tetrahydroberberine and berberine and those of cis- and trans-13-methyltetrahydroprotoberberines and 13-methylberberine were demonstrated. The corresponding α-N-metho salts having the B/C-cis ring-junction were produced from cis-and trans-13-methyltetrahydroprotoberberines. These findings show that the metabolism of protoberberines in D. spectablis proceeds analogously to that found in Cordyalis species.

Method for synthesizing benzophenanthridine and protoberberine alkaloids through modular diversity regulation and control

The invention discloses a method for synthesizing benzophenanthridine and protoberberine alkaloids through modular diversity regulation and control. The method comprises the following steps: improving a substituent group of a high-iodine salt leaving group, generating pyridine alkyne under the action of relatively mild potassium tert-butoxide, and carrying out [4 + 2] cycloaddition reaction on the pyridine alkyne and diene to obtain polysubstituted isoquinoline ring precursor compounds. Ring opening and aromatization of the isoquinoline ring precursor are realized by developing a novel iridium-catalyzed cross-coupling method, polysubstituted isoquinoline ring compounds with connecting capacity are efficiently synthesized, and then the polysubstituted isoquinoline ring compounds are coupled with a high-activity polysubstituted cyclic boric acid to obtain 3-aryl isoquinoline high-grade intermediates. Through application of two different chemical principles, regulation and control of the 3-aryl isoquinoline high-grade intermediates are realized, and benzophenanthridine and protoberberine alkaloids are modularly, diversely and efficiently synthesized.