14-Deoxyandrographolide

Base Information

• Chemical Name: 14-Deoxyandrographolide
• CAS No.: 4176-97-0
• Molecular Formula: C₂₀H₃₀O₄
• Molecular Weight: 334.456
• UNII: WLN91FAQ6Z
• ChEMBL ID: CHEMBL415768
• DSSTox Substance ID: DTXSID80904638
• Metabolomics Workbench ID: 100284
• Nikkaji Number: J22.587H
• Wikidata: Q72462049
• Mol file: 4176-97-0.mol

Synonyms:14-deoxyandrographolide

Chemical Property of 14-Deoxyandrographolide

Chemical Property:

• Vapor Pressure: 1.63E-12mmHg at 25°C
• Melting Point: 176-178oC
• Boiling Point: 509.5°C at 760 mmHg
• PKA: 14.89±0.70(Predicted)
• Flash Point: 177.3°C
• PSA: 66.76000
• Density: 1.15
• LogP: 2.99180
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 334.21440943
• Heavy Atom Count: 24
• Complexity: 566

Purity/Quality:

≥98% ^*data from raw suppliers

14-Deoxyandrographolide 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC(C(C1CCC(=C)C2CCC3=CCOC3=O)(C)CO)O
• Isomeric SMILES: C[C@@]12CC[C@H]([C@@]([C@H]1CCC(=C)[C@H]2CCC3=CCOC3=O)(C)CO)O
• Uses: 14-Deoxyandrographolide is an Ayurvedic herb Kalmegh (Andrographis paniculata) that is used to fight against respiratory viral infections.

Technology Process of 14-Deoxyandrographolide

There total 9 articles about 14-Deoxyandrographolide 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: 87.0%

3,19-diacetyl-14-deoxyandrographolide (42895-61-4) → 14-deoxyandrographolide (4176-97-0)

Guidance literature:

With hydrogenchloride; In methanol; at 20 ℃; for 16h;

DOI:10.1016/j.ejmech.2018.08.046

Reference yield: 80.0%

(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) → 14-deoxyandrographolide (4176-97-0)

Guidance literature:

With sodium carbonate; In methanol; at 50 ℃; for 2h;

DOI:10.1016/j.ejmech.2013.09.002

Reference yield: 14.0%

andrographolide (142037-79-4,5508-58-7) → andrographolide + 3-dehydro-14-deoxyandrographolide (4176-99-2) + 12(S),13(S)-12-hydroxyandrographolide (1020673-18-0) + 12(R),13(R)-12-hydroxyandrographolide (1020673-19-1) + 3-oxo-14-deoxy-11,12-didehydroandrographolide + 3-dehydro-14-deoxyandrographolide-19-oic acid (1262950-30-0) + 3-oxo-14α-andrographolide (955428-65-6) + 3-dehydroisoandrographolide (1262950-29-7) + 14-deoxyandrographolide (4176-97-0) + 14-dehydroxy-11,12-didehydroandrographolide

Guidance literature:

With Rhizopus stolonifer ATCC 12939; In methanol; water; at 28 ℃; for 96h; Enzymatic reaction;

DOI:10.1016/j.molcatb.2009.11.002

upstream raw materials:

14-deoxyandrographolide 19-glucoside

(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

andrographolide

(1R,2R,4aS,5R,8aS)-5-((E)-2-((S)-4-acetoxy-2-oxodihydrofuran-3(2H)-ylidene)ethyl)-1-(acetoxymethyl)-1, 4a-dimethyl-6-methylenedecahydronaphthalen-2-yl acetate

Downstream raw materials:

14-deoxyandrographolide 19-glucoside

iso-14-deoxyandrographolide