42895-58-9

Basic information

• Product Name: 14-DEOXY-11,12-DIDEHYDROANDROGRAPHOLIDE
• Synonyms: 14-DEOXY-11,12-DIDEHYDROANDROGRAPHOLIDE;3-[(E)-2-[(1R,4aβ)-2-Methylene-5α-(hydroxymethyl)-5,8aα-dimethyl-6α-hydroxydecalin-1α-yl]ethenyl]-2,5-dihydrofuran-2-one;3-[(E)-2-[(1R,4aβ)-2-Methylene-5α-(hydroxymethyl)-6α-hydroxy-5,8aα-dimethyldecahydronaphthalene-1α-yl]ethenyl]-2,5-dihydrofuran-2-one;3-[(E)-2-[(1R,4aβ)-Decahydro-6α-hydroxy-5α-(hydroxymethyl)-5,8aα-dimethyl-2-methylenenaphthalen-1-yl]vinyl]furan-2(5H)-one;11,12-Didehydro-14-deoxyandrographolide;14-Deoxy-11,14-didehydroandrographolide;AP 10;Deoxy-11,12-Didehydroandrographolide, 14-
• CAS NO: 42895-58-9
• Molecular Formula: C₂₀H₂₈O₄
• Molecular Weight: 332.43
• EINECS: 226-852-5
• Mol File: 42895-58-9.mol
• Article Data: 12

Chemical Properties

• Melting Point: 204-205℃
• Boiling Point: 519.6oC at 760 mmHg
• Flash Point: 182.4oC
• Appearance: /
• Density: 1.17
• Vapor Pressure: 5.71E-13mmHg at 25°C
• Refractive Index: 1.566
• PKA: 14.80±0.70(Predicted)
• CAS DataBase Reference: 14-DEOXY-11,12-DIDEHYDROANDROGRAPHOLIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 14-DEOXY-11,12-DIDEHYDROANDROGRAPHOLIDE(42895-58-9)
• EPA Substance Registry System: 14-DEOXY-11,12-DIDEHYDROANDROGRAPHOLIDE(42895-58-9)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 42895-58-9(Hazardous Substances Data)

Usage

Description

14-Deoxy-11,12-didehydroandrographolide is an analog of the natural diterpenoid andrographolide, which can be isolated from the medicinal plant Andrographis 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 at 6.5 μg/ml.

Uses

Used in Pharmaceutical Applications:
14-Deoxy-11,12-didehydroandrographolide is used as an active pharmaceutical ingredient for its various therapeutic properties, including anti-inflammatory, antiallergenic, immuno-stimulatory, antiviral, antioxidant, hepatoprotective, and cardiovascular activities.
Used in Antihepatotoxic Applications:
In the pharmaceutical industry, 14-deoxy-11,12-didehydroandrographolide is used as an antihepatotoxic agent, showing significant action in P. berghei K173-induced hepatic damage in M. natalensis.
Used in Anti-inflammatory Applications:
14-Deoxy-11,12-didehydroandrographolide is used as an anti-inflammatory agent, inhibiting 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.
Used in Cardiovascular Protection:
In the field of cardiovascular medicine, 14-deoxy-11,12-didehydroandrographolide is used as a potential cardiovascular-protective agent due to its various beneficial properties.

InChI:InChI=1/C20H28O4/c1-13-4-7-16-19(2,10-8-17(22)20(16,3)12-21)15(13)6-5-14-9-11-24-18(14)23/h5-6,9,15-17,21-22H,1,4,7-8,10-12H2,2-3H3/b6-5+/t15-,16+,17-,19+,20+/m1/s1

Upstream product

• 372939-35-0 3,18-O-isopropylideneandrographolide 
• 372939-36-1 (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 
• 142037-79-4 [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 andrographolide 
• 67-56-1 methanol 

Downstream Products

• 1575716-72-1 C₄₃H₄₆O₇ 
• 1575716-76-5 C₄₄H₄₈O₇ 
• 947699-85-6 3-oxo-19-O-trityldehydehydroandrographolide 
• 955428-68-9 3-O-acetyl-19-O-trityldehydehydroandrographolide 
• 1575717-04-2 3-O-acetyl-19-O-(2-piperidinoacetyl)dehydroandrographolide 
• 1575717-10-0 3-O-acetyl-19-O-[2-(4-hydroxypiperidino)acetyl]dehydroandrographolide 
• 910582-16-0 19-O-trityldehydroandrographolide 

Relevant articles and documents

Synthesis of andrographolide cyclophosphate derivatives and their antitumor activities

A series of cyclophosphate andrographolide derivatives were synthesized from andrographolide, the cytotoxic constituent of the plant Andrographis paniculata. The derivative (PR, P′S)-S and (P S, P′S)-6 were synthesized and the proposed mechanism for their formation was discussed. The structures of all compounds were elucidated by IR, NMR, MS (ESI), and HR-MS. The stereochemistry of 6 was confirmed by X-ray analysis. All the derivatives were tested for antitumor activity in vitro, and some of them showed good results. Copyright Taylor & Francis Group, LLC.

Studies on the novel α-glucosidase inhibitory activity and structure-activity relationships for andrographolide analogues

A series of analogues of andrographolide were synthesized and evaluated as novel α-glucosidase inhibitors. Among them compound 23, 15-p-methoxylbenzylidene 14-deoxy-11,12-didehydroandrographolide, was a potent inhibitor against α-glucosidase whose IC

Synthesis of novel andrographolide beckmann rearrangement derivatives and evaluation of their HK2-related anti-inflammatory activities

Two series of andrographolide derivatives with introduction of amide moiety into ring A by Beckmann rearrangement were synthesized. In series 1, the ring A was converted to caprolactam, and an amide moiety was linked to C-19 of ring A in series 2. Among t

Preparation and α-glucosidase inhibition of andrographolide derivatives

Series of novel analogs, which were primarily modified on its lactone moiety, was synthesized based on Andrographolide (1), a natural product sesquiterpene inhibitor of α-glucosidase. Among new analogs, 14-deoxy-11,12-didehydro-15-(4-ethoxybenzylidene)andrographolide (3h) was determined to have the greatest potential of α-glucosidase inhibitor through the calculation of IC50 value of 160 ± 5.1 μM, a significant improvement compared to the clinical dose of Acarbose, which showed the IC50 value of 390 ± 8.1 μM. In addition, 14-deoxy-11,12-didehydro-3,19-(2′-hydroxybenzylidene)-15-(2-hydroxybenzylidene) andrographolide (7), a 15-benzylidene derivative of 14-deoxy-11,12-didehydroandrographolide containing a 1,3-dioxane moiety at C(3) and C(19), also displayed good inhibition with IC50 260 ± 13 μM. These results are promising avenues in the subsequent optimization of antidiabetic drugs.

Discovery of Potent Orally Active Protease-Activated Receptor 1 (PAR1) Antagonists Based on Andrographolide

Protease-activated receptor-1 (PAR1), a G-protein-coupled receptor, plays a critical role in thrombin-mediated platelet aggregation. It is regarded as a promising antithrombosis target that is unlikely to result in bleeding. Here, we describe the synthesi