14-Deoxy-11,12-didehydroandrographolide

Base Information

• Chemical Name: 14-Deoxy-11,12-didehydroandrographolide
• CAS No.: 42895-58-9
• Molecular Formula: C20H28O4
• Molecular Weight: 332.44
• UNII: 5S0X4YZJ0E
• DSSTox Substance ID: DTXSID301347789
• Nikkaji Number: J89.498B
• Wikidata: Q27138150
• Metabolomics Workbench ID: 132831
• ChEMBL ID: CHEMBL361568
• Mol file: 42895-58-9.mol

Synonyms:14-deoxy-11,12-didehydroandrographolide

Chemical Property of 14-Deoxy-11,12-didehydroandrographolide

Chemical Property:

• Vapor Pressure: 5.71E-13mmHg at 25°C
• Melting Point: 204-205oC
• Boiling Point: 519.6oC at 760 mmHg
• PKA: 14.80±0.70(Predicted)
• Flash Point: 182.4oC
• PSA: 66.76000
• Density: 1.17g/cm3
• LogP: 2.76780
• XLogP3: 3.2
• 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:

98%,99%, ^*data from raw suppliers

14-Deoxy-11,12-didehydroandrographolide analytical standard ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC(C(C1CCC(=C)C2C=CC3=CCOC3=O)(C)CO)O
• Isomeric SMILES: C[C@@]12CC[C@H]([C@@]([C@H]1CCC(=C)[C@H]2/C=C/C3=CCOC3=O)(C)CO)O
• Description: 14-deoxy-11,12-didehydro Andrographolide is an analog of the natural diterpenoid andrographolide that can be isolated from A. paniculata. It retains the anti-inflammatory, antiallergenic, immuno-stimulatory, antiviral, antioxidant, hepatoprotective, and cardiovascular activities of andrographolide without producing cytotoxicity in KB cells (ED50 >20 μg/ml) that can occur with andrographolide 6.5 μg/ml.
• Uses: 14-Deoxy-11,12-didehydroandrographolide is the derivative of Andrographolide(A637475) is a labdane diterpenoid (2). Andrographolide is the main bioactive component isolated from the medicinal plant Andrographis paniculata (2). Andrographolide showed significant antihepatotoxic action in P. berghei K173-induced hepatic damage in M. natalensis(1). Andrographolide inhibits tumor necrosis factor-α (TNF-α)-induced intercellular adhesion mol.-1 (ICAM-1) expression and adhesion of HL-60 cells onto human umbilical vein endothelial cells (HUVEC), which are associated with inflammatory diseases (2). These findings suggest that Andrographolide may have potential as a cardiovascular-protective agent.

Technology Process of 14-Deoxy-11,12-didehydroandrographolide

There total 6 articles about 14-Deoxy-11,12-didehydroandrographolide 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: 93.0%

[1R-[1α(E),4aβ,5α,6α,8aα]]-3-[2-[decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl]ethylidene]dihydro-4-hydroxy-2(3H)-furanone (142037-79-4,5508-58-7) → 14-deoxy-11,12-didehydroandrographolide (42895-58-9)

Guidance literature:

With pyridine; aluminum oxide; at 115 ℃; for 12h;

DOI:10.1016/j.ejmech.2019.04.022

Reference yield: 91.0%

andrographolide (142037-79-4,5508-58-7) → 14-deoxy-11,12-didehydroandrographolide (42895-58-9)

Guidance literature:

With pyridine; aluminum oxide; for 10h; Heating;

DOI:10.1080/00397910500377594

Reference yield: 85.0%

(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) → 14-deoxy-11,12-didehydroandrographolide (42895-58-9)

Guidance literature:

With dmap; In dichloromethane; at 50 ℃; for 24h;

DOI:10.1016/j.ejmech.2018.08.046

upstream raw materials:

methanol

andrographolide

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

Downstream raw materials:

14-deoxy-11,12-didehydro-15-(2-hydroxybenzylidene)andrographolide

Refernces

• 1、 Yan, Lin,Xu, Haiwei,Liu, Fengwu,Zhao, Jin,Liu, Hongmin. "Synthesis and biological evaluation of andrographolide C-glycoside derivatives as &α-glycosidase inhibitors". . p. 914 - 918. Retrieved 2012.
• 2、 Wang, Zhen,Chen, Yi,Wu, Feipeng. "Oligo-polyethene glycol (PEG)-modified 14-deoxy-11,12-didehydroandrographolide derivatives: Synthesis, solubility and anti-bacterial activity". . p. 2265 - 2270. Retrieved 2016.
• 3、 Lomlim, Luelak,Jirayupong, Noppong,Plubrukarn, Anuchit. "Heat-accelerated degradation of solid-state andrographolide". . p. 24 - 26. Retrieved 2003.
• 4、 Song, Zhiqiang,Huang, Sujie,He, Yuchen,Li, Jiabin,Lin, Kejiang,Xue, Xiaowen. "Synthesis and anti-fibrosis activity study of 14-deoxyandrographolide-19-oic acid and 14-deoxydidehydroandrographolide-19-oic acid derivatives". . p. 805 - 816. Retrieved 2018/08/24.