518-94-5

Basic information

• Product Name: CYCLEANINE
• Synonyms: 8,11:20,23-DIETHENO-1H,12H-[1,10]DIOXACYCLOOCTADECINO[2,3,4-IJ:11,12,13-I'J']DIISOQUINOLINE,2,3,12A,13,14,15,24,24A-OCTAHYDRO-5,6,17,18-TETRAMETHOXY-1,13-DIMETHYL-, [12AR-(12AR*,24AR*)]-;CYCLEANINE;CYCLEANINE: 8,11:20,23-DIETHENO-1H,12H-[1,10]DIOXACYCLOOCTADECINO[2,3,4-IJ:11,12,13-I'J']DIISOQUINOLINE,2,3,12A,13,14,15,24,24A-OCTAHYDRO-5,6,17,18-TETRAMETHOXY-1,13-DIMETHYL-, [12AR- (12AR*,24AR*)]-,;Cycleanin;(1R)-2,2'-Dimethyl-6,6',7,7'-tetramethoxy-7,18:11',18-diseco-8,18:12',18-dicyclotubocuraran;8,11:20,23-Dietheno-1H,12H-(1,10)dioxacyclooctadecino(2,3,4-ij:11,12,13-I'J')diisoquinoline, 2,3,12A,13,14,15,24,24A-octahydro-1,13-dimethyl-5,6,17,18-tetramethoxy-, (12ar-(12ar*,24ar*))-;Cycleanine (6ci,7ci,8ci);Dimethylisochondodendrine
• CAS NO: 518-94-5
• Molecular Formula: C₃₈H₄₂N₂O₆
• Molecular Weight: 622.75
• Mol File: 518-94-5.mol
• Article Data: 3

Chemical Properties

• Melting Point: 272-273 °C
• Boiling Point: 691.6°Cat760mmHg
• Flash Point: 169.8°C
• Appearance: /
• Density: 1.172g/cm³
• Refractive Index: 1.585
• PKA: 7.56±0.20(Predicted)
• CAS DataBase Reference: CYCLEANINE(CAS DataBase Reference)
• NIST Chemistry Reference: CYCLEANINE(518-94-5)
• EPA Substance Registry System: CYCLEANINE(518-94-5)

Safety Data

• Hazardous Substances Data: 518-94-5(Hazardous Substances Data)

Usage

Uses

Cycleanine is an alkaloid obtained from the Triclisia subcordata Oliv (Menispermeaceae) which is a medicinal plant used to treat various diseases in West Africa. Displays in-vitro anti-ovarian cancer activity.

InChI:InChI=1/C38H42N2O6/c1-39-16-14-25-21-32(42-4)36(44-6)38-33(25)29(39)19-23-10-12-27(13-11-23)45-37-34-26(22-31(41-3)35(37)43-5)15-17-40(2)30(34)20-24-8-7-9-28(18-24)46-38/h7-13,18,21-22,29-30H,14-17,19-20H2,1-6H3/t29-,30-/m1/s1

Upstream product

• 186581-53-3 diazomethane 
• 477-62-3 (R,R)-isochondodendrine 
• 50-00-0 formaldehyd 
• 64-18-6 formic acid 
• 68676-59-5 6,6',7'-trimethoxy-2'-methyl-cyclean-1-en-7-ol 
• 10438-13-8 1^5,6,9^4,5-tetramethoxy-2,10-dioxa-6,14-diaza-1,9(1,3),3,11(1,4)-tetrabenzena-cyclohexadecaphane-5,13-dione 
• 18110-78-6 {4-[5-(2-benzyloxycarbonylamino-ethyl)-2,3-dimethoxy-phenoxy]-phenyl}-acetic acid 

Downstream Products

• 477-62-3 (R,R)-isochondodendrine 
• 524-20-9 armepavine 

Relevant articles and documents

Synthesis of cycleanine mono-N-oxides

Oxidation of cycleanine (3) with m-chloroperbenzoic acid gave two diastereomeric N-oxides (1 and 2), and their stereochemistry was unambiguously determined on the basis of spectroscopic evidence. The NMR spectra of synthetic cycleanine mono-N-oxides 1 and 2 were significantly different from those of the natural product previously reported to be cycleanine N-oxide.

THE BIOSYNTHESIS OF THE ALKALOIDS OF CISSAMPELOS PAREIRA LINN

Tracer experimets show that the bisbenzylisoqunoline alkaloid,(S,R)-hayatidin (10) is stereospecifically biosynthesized in young Cissampelos pareira Linn plants by intermolecular oxidativ coupling of (S)-(5)-and (R)-(3)-N-methylcoclaurines whereas (R,R)-isochondrodendrine (14) and (R,R)-bebeerine (12) are formed in the plants by oxidative dimerization of (R)-N-methyl-coclaurine (3).