42895-58-9

42895-58-9 structure

Name: 14-Deoxy-11,12-didehydroandrographolide
Chemical Name: 14-Deoxy-11,12-didehydroandrographolide
CAS Number: 42895-58-9
Molecular Formula: C₂₀H₂₈O₄
Molecular Weight: 332.434
Catalog: API Synthetic anti-infective drugs Natural source anti-infectives
Create Date: 2018-11-27 23:13:27
Modify Date: 2024-01-02 22:34:56
14-Deoxy-11,12-didehydroandrographolide is an analogue of Andrographolide that can be isolated from A. paniculata. 14-Deoxy-11,12-didehydroandrographolide inhibits NF-κB activation.

Name	14-Deoxy-11,12-didehydroandrographolide
Synonyms	2(5H)-Furanone, 3-[(E)-2-[(1R,4aS,5R,6R,8aR)-decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl]ethenyl]- 4-[2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethyl]-2H-furan-5-one 3-{(E)-2-[(1R,4aS,5R,6R,8aR)-6-Hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylenedecahydronaphthalen-1-yl]vinyl}furan-2(5H)-one 3-{(E)-2-[(1R,4aS,5R,6R,8aR)-6-Hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylenedecahydro-1-naphthalenyl]vinyl}-2(5H)-furanone

Description	14-Deoxy-11,12-didehydroandrographolide is an analogue of Andrographolide that can be isolated from A. paniculata. 14-Deoxy-11,12-didehydroandrographolide inhibits NF-κB activation.
Related Catalog	Research Areas >> Inflammation/Immunology Natural Products >> Terpenoids and Glycosides
Target	NF-κB
In Vitro	14-deoxy-11,12-didehydroandrographolide, a naturally occurring noncytotoxic analogue of Andrographolide, effectively reduces Ovalbumin (OVA)-induced inflammatory cell recruitment into bronchoalveolar lavage (BAL) fluid, IL-4, IL-5, IL-13, and eotaxin production, serum IgE synthesis, pulmonary eosinophilia, mucus hypersecretion, mast cell degranulation, and airway hyper-responsiveness (AHR) in a mouse asthma model, probably via inhibition of NF-κB activity[1].
In Vivo	14-deoxy-11,12-didehydroandrographolide (1 mg/kg) dramatically reduces resistance (Rl) and restores Cdyn in OVA-challenged mice in response to methacholine[1].
Cell Assay	A549 cells (3×103/well), BEAS-2B cells (5×103/well), and RBL-2H3 cells (3×103/well) are seeded in flat-bottomed 96-well plates overnight and then incubated with increasing concentrations (3-120 μM) of 14-deoxy-11,12-didehydroandrographolide or Andrographolide for 24 and 48 h at 37°C. Cell viability is analyzed using the CellTiter 96 AQueous cell proliferation assay. This MTS assay is based on the ability of viable cells to convert a soluble tetrazolium salt to a colored formazan product. Absorbance is recorded at 490 nm[1].
Animal Admin	Mice[1] Female BALB/c mice, 6 to 8 weeks old, are sensitized and challenged with OVA. Briefly, mice are sensitized by ip injections of 20 μg of OVA and 4 mg of Al(OH)3 suspended in 0.1 mL of saline on days 0 and 14. On days 22, 23, and 24, mice are challenged with 1% OVA aerosol for 30 min. 14-deoxy-11,12-didehydroandrographolide (0.1, 0.5, and 1 mg/kg) or vehicle (1% DMSO) in 0.1 mL of saline is given by ip injections 2 h before and 10 h after each OVA aerosol challenge. Saline aerosol is used as a negative control.
References	[1]. Guan SP, et al. Protective role of 14-deoxy-11,12-didehydroandrographolide, a noncytotoxic analogue ofandrographolide, in allergic airway inflammation. J Nat Prod. 2011 Jun 24;74(6):1484-90.

Density	1.2±0.1 g/cm3
Boiling Point	519.6±50.0 °C at 760 mmHg
Melting Point	204-205ºC
Molecular Formula	C₂₀H₂₈O₄
Molecular Weight	332.434
Flash Point	182.4±23.6 °C
Exact Mass	332.198761
PSA	66.76000
LogP	1.89
Vapour Pressure	0.0±3.1 mmHg at 25°C
Index of Refraction	1.567
Storage condition	-20°C

RIDADR	NONH for all modes of transport

142037-79-4

~91%

42895-58-9

Literature: Xu, Hai-Wei; Zhang, Jianye; Liu, Hong-Min; Wang, Jun-Feng Synthetic Communications, 2006 , vol. 36, # 4 p. 407 - 414

67-56-1

142037-79-4

42895-58-9

92587-11-6

Literature: Matsuda; Kuroyanagi; Sugiyama; Umehara; Ueno; Nishi Chemical and Pharmaceutical Bulletin, 1994 , vol. 42, # 6 p. 1216 - 1225

Precursor 1
67-56-1
DownStream 0

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