2752-64-9

Basic information

• Product Name: Mesaconitine
• Synonyms: (1-alpha,3-alpha,6-alpha,14-alpha,15-alpha,16-beta)-8-acetate14-benzoat;13,14,15-pentol,1,6,16-trimethoxy-4-(methoxymethyl)-20-methyl-aconitane-8;MESACONITINE;Aconitane-3,8,13,14,15-pentol, 1,6,16-trimethoxy-4-(methoxymethyl)-20-methyl-, 8-acetate 14-benzoate, (1alpha,3alpha,6alpha,14alpha,15alpha,16beta)-;MESACONITINE, 98% (PRIMARY STANDARD);Mesaaconitine;1α,6α,16β-Trimethoxy-4-methoxymethyl-20-methylaconitane-3α,8,13,14α,15α-pentol 8-acetate 14-benzoate;4-(Methoxymethyl)-20-methyl-1α,6α,16β-trimethoxyaconitane-3α,8,13,14α,15α-pentol 8-acetate 14-benzoate
• CAS NO: 2752-64-9
• Molecular Formula: C₃₃H₄₅NO₁₁
• Molecular Weight: 631.71
• EINECS: 220-397-6
• Product Categories: Miscellaneous Natural Products;Intermediates & Fine Chemicals;Pharmaceuticals;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 2752-64-9.mol
• Article Data: 1

Chemical Properties

• Melting Point: 208-209 °C
• Boiling Point: 695 °C at 760 mmHg
• Flash Point: 374.1 °C
• Appearance: /
• Density: 1.39 g/cm³
• Vapor Pressure: 4.45E-21mmHg at 25°C
• Refractive Index: 1.618
• Storage Temp.: 2-8°C(protect from light)
• PKA: 12.14±0.70(Predicted)
• CAS DataBase Reference: Mesaconitine(CAS DataBase Reference)
• NIST Chemistry Reference: Mesaconitine(2752-64-9)
• EPA Substance Registry System: Mesaconitine(2752-64-9)

Safety Data

• Safety Statements: 24/25
• RIDADR: 1544
• HazardClass: 6.1(a)
• PackingGroup: I
• Hazardous Substances Data: 2752-64-9(Hazardous Substances Data)

Usage

Description

The structure of this aconitine alkaloid has now been elucidated and shown to be that given above.

Chemical Properties

White Solid

References

Jacobs, Pelletier, Chern. & Ind., 591 (1960) Furner, Jeschka, Gibson,J. Arner. Chern. Soc., 82,5182 (1960)

InChI:InChI=1/C33H45NO11/c1-16(35)45-33-21-18(13-31(39,28(43-6)26(33)37)27(21)44-29(38)17-10-8-7-9-11-17)32-20(41-4)12-19(36)30(15-40-3)14-34(2)25(32)22(33)23(42-5)24(30)32/h7-11,18-28,36-37,39H,12-15H2,1-6H3/t18-,19-,20+,21-,22+,23+,24-,25?,26+,27-,28+,30+,31-,32+,33-/m1/s1

Upstream product

• 302-27-2 indaconitine 
• 3327-35-3 N-desethylaconitine 
• 74-88-4 methyl iodide 

Downstream Products

• 86500-43-8 hokbusine A 
• 101247-25-0 C₃₃H₄₇NO₁₀ 
• 86817-64-3 anhydromesaconitine trifluoromethanesulfonate 
• 121236-31-5 3-O-(imidazolylthiocarbonyl)-mesaconitine 
• 81941-16-4 8-linoleate mesaconitine 
• 86817-65-4 C₃₃H₄₃NO₉ 
• 69787-30-0 3,13,15-trideoxymesaconitine 
• 6900-87-4 hypaconitine 
• 545-57-3 oxonitine 
• 139617-14-4 3,13,15-tri-O-(S-methyl)thiocarbonylmesaconitine 
• 139617-06-4 3,13-di-O-(S-methyl)thiocarbonylmesaconitine 
• 139617-07-5 3-O-(S-methyl)thiocarbonylmesaconitine 
• 545-57-3 oxonitine 

Relevant articles and documents

DEOXYGENATION REACTIONS OF C19-DITERPENOID ALKALOIDS

Efficient methods for deoxygenation of secondary and tertiary alcohols of some C19-diterpenoid alkaloids are presented.Delphisine (12) was converted to 1-deoxydelphisine (19) via either 1,2-pyrodelphisine (17) or phenyl thionocarbonate 20.The following alkaloids were deoxygenated via their thiocarbonylimidazolyl derivatives: 14-acetyldelcosine (13) to 14-acetyl-1-deoxydelcosine (22); alkaline hydrolysis of 22 gave 1-deoxydelcosine (23); aconitine (24) to 3-deoxyaconitine (27); yunaconitine (25) to crassicauline A (28).Deoxygenation of 14-acetyldictyocarpine (30) via the chloro-derivate 31 gave 14-acetyl-10-deoxydictiocarpine (34).Reduction of 31 with LiAlH4 gave the unusual elimination product 32.An improved partial synthesis of hypaconitine (35) from aconitine (24) is also presented.