Dehydroandrographolide

Base Information

• Chemical Name: Dehydroandrographolide
• CAS No.: 1032910-41-0
• Molecular Formula: C₂₀H₂₈O₄
• Molecular Weight: 332.44
• UNII: TKB45D7LVX
• Nikkaji Number: J2.836.057F
• Metabolomics Workbench ID: 129288
• ChEMBL ID: CHEMBL2436162
• Mol file: 1032910-41-0.mol

Synonyms:dehydroandrographolide

Chemical Property of Dehydroandrographolide

Chemical Property:

• XLogP3: 3.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 332.19875937
• Heavy Atom Count: 24
• Complexity: 605

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC12CCC(C(C1CCC(=C)C2CC=C3C=COC3=O)(C)CO)O
• Isomeric SMILES: C[C@@]12CC[C@H]([C@@]([C@H]1CCC(=C)[C@H]2C/C=C/3\C=COC3=O)(C)CO)O

Technology Process of Dehydroandrographolide

There total 5 articles about Dehydroandrographolide 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: 89.2%

(S,E)-5-oxo-4-(2-((4aR,6aS,7R,10aS, 10bR)-3,3,6a,10b-tetramethyl-8-methylenedecahydro-1H-naphtho[2,1-d][1,3]dioxin-7-yl)ethylidene)tetrahydrofuran-3-yl acetate (372939-36-1) → dehydroandrographolide (1032910-41-0)

Guidance literature:

With dmap; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1016/j.ejmech.2018.08.046

Reference yield:

(E)-3-(2-((4aR,6aS,7R,10bR)-3,3,6a,10b-tetramethyl-8-methylenedecahydro-1H-naphtho[2,1-d][1,3]dioxin-7-yl)ethylidene)furan-2(3H)-one (727723-05-9) → dehydroandrographolide (1032910-41-0)

Guidance literature:

With Amberlyst 15; In methanol; at 20 ℃; for 12h;

DOI:10.1021/np5007179

Reference yield:

andrographolide (142037-79-4,5508-58-7) → dehydroandrographolide (1032910-41-0) + (4S)-4-hydroxyl-3-(2-((1R,4aS,5R,6R,8aS)-6-hydroxyl-5-(hydroxymethyl)-5,8a-dimethyl-2-methylenedecahydronaphthalen-1-yl)ethyl)dihydrofuran-2(3H)-one (496848-48-7)

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; at 20 ℃; for 2.08333h; Overall yield = 75 %;

DOI:10.1016/j.ejmech.2013.09.002

upstream raw materials:

andrographolide

(E)-3-(2-((4aR,6aS,7R,10bR)-3,3,6a,10b-tetramethyl-8-methylenedecahydro-1H-naphtho[2,1-d][1,3]dioxin-7-yl)ethylidene)furan-2(3H)-one

3,18-O-isopropylideneandrographolide

(S,E)-5-oxo-4-(2-((4aR,6aS,7R,10aS, 10bR)-3,3,6a,10b-tetramethyl-8-methylenedecahydro-1H-naphtho[2,1-d][1,3]dioxin-7-yl)ethylidene)tetrahydrofuran-3-yl acetate