(1a,14a,16b)-20-Ethyl-1,14,16-trimethoxyaconitane-4,8,9-triol 4-(2-acetylamino)benzoate)

Base Information

• Chemical Name: (1a,14a,16b)-20-Ethyl-1,14,16-trimethoxyaconitane-4,8,9-triol 4-(2-acetylamino)benzoate)
• CAS No.: 32854-75-4
• Molecular Formula: C32H44N2O8
• Molecular Weight: 584.71
• Hs Code.: PRICE
• Mol file: 32854-75-4.mol

Synonyms:Lappaconitine(7CI,8CI);(+)-Lappaconitine;Acetyl-10-deoxysepaconitine;(1a,14a,16b)-20-Ethyl-1,14,16-trimethoxyaconitane-4,8,9-triol 4-(2-acetylamino)benzoate);

Chemical Property of (1a,14a,16b)-20-Ethyl-1,14,16-trimethoxyaconitane-4,8,9-triol 4-(2-acetylamino)benzoate)

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 8.44E-22mmHg at 25°C
• Melting Point: 217-218oC
• Refractive Index: 1.623
• Boiling Point: 720.699 °C at 760 mmHg
• PKA: 12.55±0.70(Predicted)
• Flash Point: 389.665 °C
• PSA: 126.79000
• Density: 1.353 g/cm³
• LogP: 2.23250

Purity/Quality:

99% ^*data from raw suppliers

Lappaconitine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: A highly toxic aconitine alkaloid present in Aconitum leucostomum and A. septentrionale Koelle, lappaconitine crystallizes in hexagonal tablets for whichtwo melting points have been recorded. It has [α]D + 22.3° (C6H6) or [α]18D + 27.0° (CHC1 3). The early view that a methylimino group is present has been shown to be erroneous. No crystalline salts are known but the diacetyl derivative forms colourless crystals, m.p. l25-7°C. The base is only sparingly soluble in H20 and most organic solvents, but dissolves readily in CHC1 3.Boiling the alkaloid with dilute H2S04 in a stream of H2 yields acetic acid and anthranoyllappaconine, C30H4207N2, which forms colourless rhombic tablets, m.p. 146-9°C;[α]25D + 22.07° (C6H6), giving a platinichloride tetrahydrate as brown needles, m.p. 300-31 O°C (dec.). When hydrolyzed with HCl, the base furnishes acetic and anthranilic acids and lappaconine, m.p. 96°C; [α]25D + 22.41°, giving a crystalline hydrochloride, m.p. 246-7°C and the aurichloride monohydrate, m.p. l26-7°C. Alkaline hydrolysis, on the other hand, furnishes lappaconine and lappaconitic acid (acetylanthranilic acid). From these observations, it is clear that only one hydroxyl group is associated with an acyl group in the molecule.Pharmacologically, lappaconitine is toxic although its action is less pronounced than that of aconitine (q.v.). Toxic doses produce respiratory paralysis and have a direct action upon the heart often terminating in ventricular fibrillation.

Technology Process of (1a,14a,16b)-20-Ethyl-1,14,16-trimethoxyaconitane-4,8,9-triol 4-(2-acetylamino)benzoate)

There total 1 articles about (1a,14a,16b)-20-Ethyl-1,14,16-trimethoxyaconitane-4,8,9-triol 4-(2-acetylamino)benzoate) which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 70.0%

4β-(2-acetylaminobenzoyloxy)-1α,14α,16β-trimethoxyaconitane-8,9-diol (433717-26-1) + ethyl bromide (74-96-4) → (1α,14α,16β)-20-ethyl-1,14,16-trimethoxy-aconitane-4,8,9-triol 4-[2-(acetylamino)benzoate] (32854-75-4)

Guidance literature:

at 20 ℃; for 96h;

DOI:10.1023/B:RUCB.0000012375.59390.38

Reference yield: 96.6%

lappaconitine (32854-75-4) → N-deethyllappaconitine

Guidance literature:

With N-Bromosuccinimide; acetic acid; at 20 ℃; for 1.5h;

Reference yield: 77.6%

lappaconitine (32854-75-4) → N-desacetyllappaconitine

Guidance literature:

With hydrogenchloride; In water; at 80 ℃; for 1h;

upstream raw materials:

4β-(2-acetylaminobenzoyloxy)-1α,14α,16β-trimethoxyaconitane-8,9-diol

ethyl bromide

Downstream raw materials:

8,9-diacetyllappaconitine

(1a,14a,16β)-20-ethyl-1,14,16-trimethoxyaconitane-8,9-(methylenedioxy)-4-ol 4-(2-acetamidobenzoate)

4β-(2-acetylaminobenzoyloxy)-1α,14α,16β-trimethoxyaconitane-8,9-diol

N-deacetyllappaconitine

Refernces