Azadirachtin

Names

[ Name ]:
Azadirachtin

[Synonym ]:
Azaditrachtin
dimethyl (2aR,3S,4S,4aR,5S,7aS,8S,10R,10aS,10bR)-10-acetoxy-3,5-dihydroxy-4-[(1aR,2S,3aS,6aS,7S,7aS)-6a-hydroxy-7a-methyl-3a,6a,7,7a-tetrahydro-2,7-methanofuro[2,3-b]oxireno[e]oxepin-1a(2H)-yl]-4-methyl-8-{[(2E)-2-methylbut-2-enoyl]oxy}octahydro-1H-naphtho[1,8a-c:4,5-b’c’]difuran-5,10a(8H)-dicarboxylate
dimethyl (2aR,3S,4S,4aR,5S,7aS,8S,10R,10aS,10bR)-10-(acetyloxy)octahydro-3,5-dihydroxy-4-methyl-8-[[(2E)-2-methyl-1-oxo-2-buten-1-yl]oxy]-4-[(1aR,2S,3aS,6aS,7S,7aS)-3a,6a,7,7a-tetrahydro-6a-hydroxy-7a-methyl-2,7-methanofuro[2,3-b]oxireno[e]oxepin-1a(2H)-yl]-1H,7H-naphtho[1,8-bc:4,4a-c’]difuran-5,10a(8H)-dicarboxylate
dimethyl (2aR,3S,4S,4aR,5S,7aS,8S,10R,10aS,10bR)-10-(acetyloxy)-3,5-dihydroxy-4-[(1aR,2S,3aS,6aS,7S,7aS)-6a-hydroxy-7a-methyl-3a,6a,7,7a-tetrahydro-2,7-methanofuro[2,3-b]oxireno[e]oxepin-1a(2H)-yl]-4-methyl-8-{[(2E)-2-methylbut-2-enoyl]oxy}octahydro-1H-naphtho[1,8a-c:4,5-b'c']difuran-5,10a(8H)-dicarboxylate
MFCD00083241
1H,7H-Naphtho[1,8a-c:4,5-b'c']difuran-5,10a(8H)-dicarboxylic acid, 10-(acetyloxy)octahydro-3,5-dihydroxy-4-methyl-8-[[(2E)-2-methyl-1-oxo-2-buten-1-yl]oxy]-4-[(1aR,2S,3aS,6aS,7S,7aS)-3a,6a,7,7a-tetrahydro-6a-hydroxy-7a-methyl-2,7-methanofuro[2,3-b]oxireno[e]oxepin-1a(2H)-yl]-, dimethyl ester, (2aR,3S,4S,4aR,5S,7aS,8S,10R,10aS,10bR)-
Azadirachtin
(2aR,3S,4S,4aR,5S,7aS,8S,10R,10aS,10bR)-10-Acétoxy-3,5-dihydroxy-4-[(1S,2S,6S,8S,9R,11S)-2-hydroxy-11-méthyl-5,7,10-trioxatétracyclo[6.3.1.0.0]dodéc-3-én-9-yl]-4-méthyl-8-{[(2E)-2-méthyl-2-butènan-1-oyl]oxy}octahydro-1H-furo[3',4':4,4a]naphto[1,8-bc]furane-5,10a(8H)-dicarboxylate de diméthyle
AZADIRACHTIN A
Dimethyl (2aR,3S,4S,4aR,5S,7aS,8S,10R,10aS,10bR)-10-acetoxy-3,5-dihydroxy-4-[(1S,2S,6S,8S,9R,11S)-2-hydroxy-11-methyl-5,7,10-trioxatetracyclo[6.3.1.0.0]dodec-3-en-9-yl]-4-methyl-8-{[(2E)-2-methylbut-2-enoyl]oxy}octahydro-1H-furo[3',4':4,4a]naphtho[1,8-bc]furan-5,10a(8H)-dicarboxylate
Dimethyl (2aR,3S,4S,4aR,5S,7aS,8S,10R,10aS,10bR)-10-acetoxy-3,5-dihydroxy-4-[(1S,2S,6S,8S,9R,11S)-2-hydroxy-11-methyl-5,7,10-trioxatetracyclo[6.3.1.0.0]dodec-3-en-9-yl]-4-methyl-8-{[(2E)-2- methyl-2-butenoyl]oxy}octahydro-1H-furo[3',4':4,4a]naphtho[1,8-bc]furan-5,10a(8H)-dicarboxylate
Dimethyl-(2aR,3S,4S,4aR,5S,7aS,8S,10R,10aS,10bR)-10-acetoxy-3,5-dihydroxy-4-[(1S,2S,6S,8S,9R,11S)-2-hydroxy-11-methyl-5,7,10-trioxatetracyclo[6.3.1.0.0]dodec-3-en-9-yl]-4-methyl-8-{[(2E)-2-methylbut-2-enoyl]oxy}octahydro-1H-furo[3',4':4,4a]naphtho[1,8-bc]furan-5,10a(8H)-dicarboxylat

Biological Activity

[Description]:

Azadirachtin, one of the most promising botanical insecticides, is widely used for pest control. Azadirachtin induces apoptosis in insect cell lines, including Sf9, SL-1 and BTI-Tn-5B1-4[1].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Others

[References]

[1]. Shu B, Jia J, Zhang J, Sethuraman V, Yi X, Zhong G. DnaJ homolog subfamily A member1 (DnaJ1) is a newly discovered anti-apoptotic protein regulated by azadirachtin in Sf9 cells. BMC Genomics. 2018;19(1):413. Published 2018 May 29.

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Boiling Point ]:
792.4±60.0 °C at 760 mmHg

[ Melting Point ]:
159ºC

[ Molecular Formula ]:
C₃₅H₄₄O₁₆

[ Molecular Weight ]:
720.714

[ Flash Point ]:
244.8±26.4 °C

[ Exact Mass ]:
720.262939

[ PSA ]:
212.04000

[ LogP ]:
1.75

[ Vapour Pressure ]:
0.0±6.3 mmHg at 25°C

[ Index of Refraction ]:
1.623

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Risk Phrases ]:
22

[ Safety Phrases ]:
22-45

[ RIDADR ]:
UN 3077

[ WGK Germany ]:
3

[ Packaging Group ]:
III

[ HS Code ]:
13021920

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

The joint action of destruxins and botanical insecticides (rotenone, azadirachtin and paeonolum) against the cotton aphid, Aphis gossypii Glover.

Molecules 17(6) , 7533-42, (2012)

The joint action of destruxins and three botanical insecticides, rotenone (Rot), azadirachtin (Aza) and paeonolum (Pae) against the cotton aphid, Aphis gossypii, was bioassayed. In laboratory experime...

A COMPREHENSIVE STUDY ON APOPTOSIS INDUCTION BY AZADIRACHTIN IN Spodoptera frugiperda CULTURED CELL LINE Sf9.

Arch. Insect Biochem. Physiol. 89 , 153-68, (2015)

The induction of apoptosis by azadirachtin, a well-known botanical tetranortriterpenoid isolated from the neem tree (Azadirachta indica A. Juss) and other members of the Meliaceae, was investigated in...

Comprehensive analyses of genomes, transcriptomes and metabolites of neem tree.

PeerJ 3 , e1066, (2015)

Neem (Azadirachta indica A. Juss) is one of the most versatile tropical evergreen tree species known in India since the Vedic period (1500 BC-600 BC). Neem tree is a rich source of limonoids, having a...