4176-97-0

Basic information

• Product Name: 3-[2-[(1R,4aβ)-2-Methylene-5α-(hydroxymethyl)-5,8aα-dimethyl-6α-hydroxydecalin-1α-yl]ethyl]-2,5-dihydrofuran-2-one
• Synonyms: 3-[2-[(1R,4aβ)-2-Methylene-5α-(hydroxymethyl)-5,8aα-dimethyl-6α-hydroxydecalin-1α-yl]ethyl]-2,5-dihydrofuran-2-one;3-[2-[(1R,4aβ)-Decahydro-6α-hydroxy-5α-hydroxymethyl-5,8aα-dimethyl-2-methylenenaphthalen-1α-yl]ethyl]furan-2(5H)-one;3-[2-[(1R,4aS,5R,6R,8aS)-Decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl]ethyl]-2(5H)-furanone;AD 04130-4
• CAS NO: 4176-97-0
• Molecular Formula: C₂₀H₃₀O₄
• Molecular Weight: 334.453
• EINECS: 2017-001-1
• Mol File: 4176-97-0.mol
• Article Data: 6

Chemical Properties

• Melting Point: 176-178℃
• Boiling Point: 509.5°C at 760 mmHg
• Flash Point: 177.3°C
• Appearance: /
• Density: 1.15
• Vapor Pressure: 1.63E-12mmHg at 25°C
• Refractive Index: 1.551
• PKA: 14.89±0.70(Predicted)
• CAS DataBase Reference: 3-[2-[(1R,4aβ)-2-Methylene-5α-(hydroxymethyl)-5,8aα-dimethyl-6α-hydroxydecalin-1α-yl]ethyl]-2,5-dihydrofuran-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-[2-[(1R,4aβ)-2-Methylene-5α-(hydroxymethyl)-5,8aα-dimethyl-6α-hydroxydecalin-1α-yl]ethyl]-2,5-dihydrofuran-2-one(4176-97-0)
• EPA Substance Registry System: 3-[2-[(1R,4aβ)-2-Methylene-5α-(hydroxymethyl)-5,8aα-dimethyl-6α-hydroxydecalin-1α-yl]ethyl]-2,5-dihydrofuran-2-one(4176-97-0)

Safety Data

• Hazardous Substances Data: 4176-97-0(Hazardous Substances Data)

Usage

Uses

14-Deoxyandrographolide is an Ayurvedic herb Kalmegh (Andrographis paniculata) that is used to fight against respiratory viral infections.

InChI:InChI=1/C20H30O4/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/h9,15-17,21-22H,1,4-8,10-12H2,2-3H3/t15-,16+,17-,19+,20+/m1/s1

Upstream product

• 142037-79-4 andrographolide 
• 496848-48-7 (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 
• 82209-72-1 14-deoxyandrographolide 19-glucoside 
• 42895-61-4 3,19-diacetyl-14-deoxyandrographolide 
• 79233-05-9 (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 Products

• 82209-72-1 14-deoxyandrographolide 19-glucoside 
• 79233-15-1 iso-14-deoxyandrographolide 

Relevant articles and documents

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Synthesis of andrographolide analogues and their neuroprotection and neurite outgrowth-promoting activities

Alzheimer's disease (AD) is the most prevalent neurodegenerative disease and remains incurable. Currently, neuronal injury and synapse loss have been considered to be main features in the pathophysiology of AD. Thus, modulation of neuronal survival and neurite outgrowth may represent an efficient strategy for the treatment of AD. Based on the isolates from the traditional medicine Andrographis paniculata, a series of andrographolide analogues were prepared and evaluated for the neuroprotection and neurotrophic activity. Two compounds (3 and 12) could effectively inhibit LPS-induced NO production and iNOS expression as well as proinflammatory cytokines TNF-α and IL-6. Moreover, pretreatment with 3 and 12 could protect neurons against microglia-mediated neurotoxicity. Further, H2O2 ? and 6-OHDA induced neurotoxicity in PC12 cells were also attenuated by the novel 12. Our next study indicated that compounds 1, 4 and 10 promoted NGF-induced neurite outgrowth in PC12 cells, with 10 the most potent. To clarify the underlying mechanisms of active compounds (3, 10 and 12), system pharmacology was employed. The results revealed that muscarinic acetylcholine receptors (mAChRs) may be the main targets of 12 against AD, while thyroid hormone signaling pathway was involved in the mechanisms of 10. These study point to the therapeutic potential of andrographolide analogues against AD.

Synthesis of new andrographolide derivatives and evaluation of their antidyslipidemic, LDL-oxidation and antioxidant activity

Andrographis paniculata, native to Taiwan, Mainland China and India, is a medicinal herb, which possesses various biological activities including anti-atherosclerosis. Andrographolide (1) has been identified as one of the active constituents against atherosclerosis. In continuation of our drug discovery program we synthesized few novel derivatives of 1 to improve their antidyslipidemic, LDL-oxidation and antioxidant activity. The tosylated derivative 7 has been turned out to be more potent than the parent compound and comparable activity with marketed antidyslipidemic drugs.

Chemical transformation of andrographolide

Tosylation of andrographolide 1, with p-TsCl pyridine furnishes compounds 3 and 4. The reaction of 1 with in situ generated nickel boride yields compounds 6 and 8. Monotosylation of 6 followed by reaction with NaI refluxing in acetone furnishes the iodide 13. But all attempts to generate an oxetane moiety in 13 corresponding to compund 2 failed.