Limonoic acid 16,17-lactone

Base Information

• Chemical Name: Limonoic acid 16,17-lactone
• CAS No.: 22149-50-4
• Molecular Formula: C26H32 O9
• Molecular Weight: 488.52688
• Mol file: 22149-50-4.mol

Synonyms:Furo[3',4':5,6]naphth[2,1-c]oxireno[d]pyran-9-aceticacid, 1a-(3-furyl)-1,3,3aa,4b,5,6,6aa,7,9a,9a,9ba,10,11,11a-tetradecahydro-9ab-(hydroxymethyl)-4bb,7,7,11aa-tetramethyl-3,5-dioxo-(8CI); Limonoic acid, 16,17-lactone; Furo[3',4':5,6]naphth[2,1-c]oxireno[d]pyran-9-aceticacid,1-(3-furanyl)tetradecahydro-9a-(hydroxymethyl)-4b,7,7,11a-tetramethyl-3,5-dioxo-,[1S-(1a,3aa,4aS*,4bb,6aa,9b,9ab,9ba,11aa)]-; Limonin monolactone D; Limonoic acid D-ringlactone

Chemical Property of Limonoic acid 16,17-lactone

Chemical Property:

• PSA: 135.80000
• LogP: 2.65750

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Limonoic acid 16,17-lactone

There total 2 articles about Limonoic acid 16,17-lactone 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:

Limonin (1180-71-8,42867-83-4) → ((1S,4S,5S,8R,9R,10R,13R,14R,15S)-4-Furan-3-yl-14-hydroxymethyl-5,9,17,17-tetramethyl-2,11-dioxo-tetradecahydro-3,16,19-trioxa-cyclopropa[1,10]cyclopenta[a]phenanthren-15-yl)-acetic acid (22149-50-4)

Guidance literature:

With potassium hydroxide; for 4h; Reflux;

DOI:10.1002/anie.202104228

Reference yield:

→ ((1S,4S,5S,8R,9R,10R,13R,14R,15S)-4-Furan-3-yl-14-hydroxymethyl-5,9,17,17-tetramethyl-2,11-dioxo-tetradecahydro-3,16,19-trioxa-cyclopropa[1,10]cyclopenta[a]phenanthren-15-yl)-acetic acid (22149-50-4)

Guidance literature:

aus Limonin, NaOH;

DOI:10.1016/S0031-9422(00)85820-3

Reference yield:

((1S,4S,5S,8R,9R,10R,13R,14R,15S)-4-Furan-3-yl-14-hydroxymethyl-5,9,17,17-tetramethyl-2,11-dioxo-tetradecahydro-3,16,19-trioxa-cyclopropa[1,10]cyclopenta[a]phenanthren-15-yl)-acetic acid (22149-50-4) → C33H37NO8

Guidance literature:

Multi-step reaction with 2 steps

1: iodine; potassium iodide / water / 0.08 h

2: triethylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 0.5 h / 30 °C

With iodine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; potassium iodide; In water; N,N-dimethyl-formamide;

DOI:10.1002/anie.202104228

upstream raw materials:

Limonin

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