3422-42-2

Basic information

• Product Name: (-)-Coclaurine Hydrochloride
• Synonyms: (-)-Coclaurine Hydrochloride
• CAS NO: 3422-42-2
• Molecular Formula: C₁₇H₁₉NO₃*ClH
• Molecular Weight: 321.7986
• Product Categories: Aromatics, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 3422-42-2.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• Storage Temp.: Refrigerator, Under Inert Atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• CAS DataBase Reference: (-)-Coclaurine Hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-Coclaurine Hydrochloride(3422-42-2)
• EPA Substance Registry System: (-)-Coclaurine Hydrochloride(3422-42-2)

Safety Data

• Hazardous Substances Data: 3422-42-2(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

Uses

(-)-Coclaurine Hydrochloride is a benzyltetrahydroisoquinoline alkaloid extracted from Magnolia salicifolia. (-)-Coclaurine hydrochloride was shown to block postsynaptic but not presynaptic dopamine receptors in the mouse striatum.

Upstream product

• 74-88-4 methyl iodide 
• 38474-19-0 7,12-O,O'-dibenzylcoclaurine 
• 132257-14-8 (+)-OO'-dibenzylcoclaurine hydrochloride 
• 38474-17-8 (-)-OO'-dibenzylcoclaurine 

Downstream Products

• 3423-07-2 (S)-N-methylcoclaurine 
• 5096-70-8 (-)-(R)-(N)-methylcoclaurine 

Relevant articles and documents

Organocatalytic Enantioselective Pictet-Spengler Approach to Biologically Relevant 1-Benzyl-1,2,3,4-Tetrahydroisoquinoline Alkaloids

(Figure Presented) A general procedure for the synthesis of 1-benzyl-1,2,3,4-tetrahydroisoquinolines was developed, based on organocatalytic, regio- and enantioselective Pictet-Spengler reactions (86-92% ee) of N-(o-nitrophenylsulfenyl)-2-arylethylamines with arylacetaldehydes. The presence of the o-nitrophenylsulfenyl group, together with the MOM-protection in the catechol part of the tetrahydroisoquinoline ring system, appeared to be a productive combination. To demonstrate the versatility of this approach, 10 biologically and pharmaceutically relevant alkaloids were prepared using (R)-TRIP as the chiral catalyst: (R)-norcoclaurine, (R)-coclaurine, (R)-norreticuline, (R)-reticuline, (R)-trimemetoquinol, (R)-armepavine, (R)-norprotosinomenine, (R)-protosinomenine, (R)-laudanosine, and (R)-5-methoxylaudanosine.

THE STRUCTURE, ABSOLUTE CONFIGURATION AND BIOSYNTHESIS OF NORTILIACORININE A

The incorporation of (+/-)-norcoclaurine, (+/-)-coclaurine, (+/-)-N-methylcoclaurine and dehydro-N-methylcoclaurine into nortiliacorinine A in Tilicora racemosa colebr has been studied and specific utilisation of the (+/-)-coclaurine demonstrated.The evidence supports oxidative dimerization of two coclaurine units to give nortiliacorinine A.Experiments with (+/-)-N-methylcoclaurine and (+/-)-N-methylcoclaurine established that only one N-methylcoclaurine unit is specifically utilised to constitute that the H atom at the asymmetric centre in the 1-benzylisoquinoline precursor is retained in the bioconversion into nortiliacorine A.Double labelling experiment with (+/-)-N-methylcoclaurine showed that O-Me function of the precursor is lost in the bioconversion into nortiliacorine A.Parallel feedings of (+)-(S)-, and (-)-(R)-N-methyl-coclaurines and (-)-(S)-, and (+)-(R)-coclaurines revealed that the stereo-specificity is maintained in the biosynthesis of nortiliacorinine A from 1-benzylisoquinoline precursors and established S,S'-configuration at the two asymmetric centres in nortiliacorinine A.