6451-73-6

Basic information

• Product Name: SCOULERIN
• Synonyms: SCOULERIN;(-)-scoulerine;3,10-dimethoxy-13a-alpha-berbine-2,9-diol;3,10-dimethoxy-13a-alpha-berbine-9-diol;g)quinolizine-2,9-diol,5,8,13,13a-tetrahydro-3,10-dimethoxy-6h-dibenzo((;l-scoulerine;l-skoulerine;2,9-DIOXY-3,10-DIMETHOXYBERBINE
• CAS NO: 6451-73-6
• Molecular Formula: C₁₉H₂₁NO₄
• Molecular Weight: 327.37
• EINECS: 200-258-5
• Product Categories: Alkaloids;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 6451-73-6.mol
• Article Data: 5

Chemical Properties

• Melting Point: 192°C
• Boiling Point: 503.3oC at 760 mmHg
• Flash Point: 258.2oC
• Appearance: /
• Density: 1.37g/cm3
• Vapor Pressure: 9.39E-11mmHg at 25°C
• Refractive Index: 1.679
• PKA: 9.88±0.20(Predicted)
• CAS DataBase Reference: SCOULERIN(CAS DataBase Reference)
• NIST Chemistry Reference: SCOULERIN(6451-73-6)
• EPA Substance Registry System: SCOULERIN(6451-73-6)

Safety Data

• Hazardous Substances Data: 6451-73-6(Hazardous Substances Data)

Usage

Description

This form of the alkaloid is more widespread than the d-form, occurring in Corydalis caseana, C. micrantha, C. montana, C. scouleri, C. sibirica and Papaver somniferum. It has [α]26D - 318° (c 0.41, MeOH) or - 289° (c 0.62, MeOH). It forms pale grey needles when crystallized from MeOH. The hydrochloride has m.p. 268-9°C; the picrate, m.p. 206°C (dec.) and the diethyl ether, m.p. 155°C. The oxidation products are the same as for the preceding base.

Chemical Properties

Off-White to Pale Pink Solid

Uses

Different sources of media describe the Uses of 6451-73-6 differently. You can refer to the following data:
1. The S-(+)-enantiomer of Scoulerine, an alkaloid found in the opium poppy.
2. (S)-Scoulerine is an alkaloid found in the opium poppy. (S)-Scoulerine acts as an antagonist at the α2-adrenoceptor, α1D-adrenoceptor and 5-HT receptor.

Definition

ChEBI: A berberine alkaloid isolated from Corydalis saxicola.

References

Manske., Can. J. Res., 14B, 347, 354 (1936) Manske., ibid, 17B, 57 (1939) Manske., ibid, 18B, 414 (1940) Manske., ibid, 20B, 49 (1942) Brochmann-Hanssen, Nielsen., Tetrahedron Lett., 2261 (1966) Synthesis: Kametani., Japanese Patent, 70, 37,976, 10 December 1970

InChI:InChI=1/C19H21NO4/c1-23-17-4-3-11-7-15-13-9-16(21)18(24-2)8-12(13)5-6-20(15)10-14(11)19(17)22/h3-4,8-9,15,21-22H,5-7,10H2,1-2H3/t15-/m0/s1

Upstream product

• 1699-46-3 reticuline 
• 483-14-7 tetrahydropalmatine 
• 485-19-8 (+)-(S)-reticuline 
• 6346-05-0 3-benzyloxy-4-methoxybenzaldehyde 
• 121-33-5 vanillin 
• 70614-67-4 1-(3-benzyloxy-4-methoxybenzyl)-7-benzyloxy-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline 
• 38171-33-4 2-(4-(benzyloxy)-3-methoxyphenyl)-N-methylethanamine 
• 1700-33-0 N-ethoxycarbonyl-4-benzyloxy-3-methoxyphenethylamine 
• 54313-33-6 2-(3-(benzyloxy)-4-methoxyphenyl)acetyl chloride 
• 63909-38-6 3-methoxy-4-benzyloxy-ω-nitrostyrolene 
• 5487-33-2 O-benzylhomoisovanillic acid 
• 22231-61-4 2-[4-(benzyloxy)-3-methoxyphenyl]ethylamine 
• 2426-87-1 3-methoxy-4-(phenylmethoxy)benzaldehyde 
• 1316258-95-3 2-(3-benzyloxy-4-methoxyphenyl)-N-(4-benzyloxy-3-methoxyphenethyl)-N-methylacetamide 

Downstream Products

• 3621-36-1 columbamine 
• 572-76-9 tetrahydroberberrubine 
• 84-39-9 (S)-stylopine 
• 6487-33-8 (-)-isocorypalmine 

Relevant articles and documents

Inverting the regioselectivity of the berberine bridge enzyme by employing customized fluorine-containing substrates

Fluorine is commonly applied in pharmaceuticals to block the degradation of bioactive compounds at a specific site of the molecule. Blocking of the reaction center of the enzyme-catalyzed ring closure of 1,2,3,4- tetrahydrobenzylisoquinolines by a fluoro moiety allowed redirecting the berberine bridge enzyme (BBE)-catalyzed transformation of these compounds to give the formation of an alternative regioisomeric product namely 11-hydroxy-functionalized tetrahydroprotoberberines instead of the commonly formed 9-hydroxy-functionalized products. Alternative strategies to change the regioselectivity of the enzyme, such as protein engineering, were not applicable in this special case due to missing substrate-enzyme interactions. Medium engineering, as another possible strategy, had clear influence on the regioselectivity of the reaction pathway, but did not lead to perfect selectivity. Thus, only substrate tuning by introducing a fluoro moiety at one potential reactive carbon center switched the reaction to the formation of exclusively one regioisomer with perfect enantioselectivity. Custom-made substrates: Employing customized substrates with a fluoro atom at the normally preferred reaction site switched the regioselectivity of the berberine-bridged enzyme. With this strategy, it was possible to get access to (S)-11-hydroxy-functionalized berbines in an asymmetric fashion by using the wild-type enzyme (see scheme). Copyright

Characterization of two methylenedioxy bridge-forming cytochrome P450-dependent enzymes of alkaloid formation in the Mexican prickly poppy Argemone mexicana

Formation of the methylenedioxy bridge is an integral step in the biosynthesis of benzo[c]phenanthridine and protoberberine alkaloids in the Papaveraceae family of plants. This reaction in plants is catalyzed by cytochrome P450-dependent enzymes. Two cDNAs that encode cytochrome P450 enzymes belonging to the CYP719 family were identified upon interrogation of an EST dataset prepared from 2-month-old plantlets of the Mexican prickly poppy Argemone mexicana that accumulated the benzo[c]phenanthridine alkaloid sanguinarine and the protoberberine alkaloid berberine. CYP719A13 and CYP719A14 are 58% identical to each other and 77% and 60% identical, respectively, to stylopine synthase CYP719A2 of benzo[c]phenanthridine biosynthesis in Eschscholzia californica. Functional heterologous expression of CYP719A14 and CYP719A13 in Spodoptera frugiperda Sf9 cells produced recombinant enzymes that catalyzed the formation of the methylenedioxy bridge of (S)-cheilanthifoline from (S)-scoulerine and of (S)-stylopine from (S)-cheilanthifoline, respectively. Twenty-seven potential substrates were tested with each enzyme. Whereas CYP719A14 transformed only (S)-scoulerine to (S)-cheilanthifoline (Km 1.9 ± 0.3; kcat/Km 1.7), CYP719A13 converted (S)-tetrahydrocolumbamine to (S)-canadine (Km 2.7 ± 1.3; kcat/Km 12.8), (S)-cheilanthifoline to (S)-stylopine (Km 5.2 ± 3.0; kcat/Km 2.6) and (S)-scoulerine to (S)-nandinine (Km 8.1 ± 1.9; k cat/Km 0.7). These results indicate that although CYP719A14 participates in only sanguinarine biosynthesis, CYP719A13 can be involved in both sanguinarine and berberine formation in A. mexicana.

BIOTRANSFORMATION OF ISOQUINOLINE ALKALOIDS WITH RAT LIVER MICROSOMES

Optically active (+)-reticuline (1) was biotransformed into (-)-coreximine (2), (-)-scoulerine (3), (+)-isoboldine (4) and (-)-pallidine (5) with retention of the chirality by the incubation with rat liver microsomes.On the other hand, the racemate of reticuline formed the racemates of the above alkaloids on the some treatment.The S-adenosylmethionine was partially incorporated into the berberine bridge during the biotransformation of reticuline into the protoberberines.