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Azadirachtin - analytical standard, high purity , CAS No.11141-17-6
Basic Description
Synonyms
NSC 368675 | Safer BioNEEM | Suneem | Azadirachtin-A | 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-meth
Specifications & Purity
analytical standard
Biochemical and Physiological Mechanisms
Triterpenoid found in need tree seeds, azadiractin suppresses feeding by many insect species and disrupts growth of most insect and other arthropod species, while having very low mammalian toxicity. Promising as a natural pesticide.
Storage Temp
Store at -20°C
Shipped In
Ice chest + Ice pads
This product requires cold chain shipping. Ground and other economy services are not available.
Grade
analytical standard
Product Description
Crude extract of the neem tree. Not intended for use as a quantitative standard.
Taxonomic Classification
Kingdom
Organic compounds
Superclass
Lipids and lipid-like molecules
Class
Prenol lipids
Subclass
Triterpenoids
Intermediate Tree Nodes
Not available
Direct Parent
Limonoids
Alternative Parents
Tetracarboxylic acids and derivatives Furopyrans Fatty acid esters Oxepanes Oxanes Pyrans Dihydrofurans Enoate esters Tetrahydrofurans Furans Tertiary alcohols Methyl esters Cyclic alcohols and derivatives Hemiacetals Secondary alcohols Acetals Dialkyl ethers Epoxides Oxacyclic compounds Hydrocarbon derivatives Carbonyl compounds Organic oxides
Molecular Framework
Aliphatic heteropolycyclic compounds
Substituents
Limonoid skeleton - Tetracarboxylic acid or derivatives - Furopyran - Fatty acid ester - Oxepane - Oxane - Fatty acyl - Pyran - Cyclic alcohol - Dihydrofuran - Furan - Alpha,beta-unsaturated carboxylic ester - Tertiary alcohol - Enoate ester - Tetrahydrofuran - Methyl ester - Hemiacetal - Carboxylic acid ester - Secondary alcohol - Dialkyl ether - Acetal - Carboxylic acid derivative - Ether - Oxirane - Organoheterocyclic compound - Oxacycle - Organooxygen compound - Alcohol - Carbonyl group - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Aliphatic heteropolycyclic compound
Description
This compound belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17.
External Descriptors
Apotirucallane triterpenoids
Data sources
1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.
Associated Targets(Human)
Associated Targets(non-human)
Mechanisms of Action
Mechanism of Action
Action Type
target ID
Target Name
Target Type
Target Organism
Binding Site Name
References
Names and Identifiers
IUPAC Name
dimethyl (1S,4S,5R,6S,7S,8R,11S,12R,14S,15R)-12-acetyloxy-4,7-dihydroxy-6-[(1S,2S,6S,8S,9R,11S)-2-hydroxy-11-methyl-5,7,10-trioxatetracyclo[6.3.1.02,6.09,11]dodec-3-en-9-yl]-6-methyl-14-[(E)-2-methylbut-2-enoyl]oxy-3,9-dioxatetracyclo[6.6.1.01,5.011,15]pentadecane-4,11-dicarboxylate
INCHI
InChI=1S/C35H44O16/c1-8-15(2)24(38)49-18-12-19(48-16(3)36)32(26(39)43-6)13-46-21-22(32)31(18)14-47-34(42,27(40)44-7)25(31)29(4,23(21)37)35-20-11-17(30(35,5)51-35)33(41)9-10-45-28(33)50-20/h8-10,17-23,25,28,37,41-42H,11-14H2,1-7H3/b15-8+/t17-,18+,19-,20+,21-,22-,23-,25+,28+,29-,30+,31+,32+,33+,34+,35+/m1/s1
InChIKey
FTNJWQUOZFUQQJ-NDAWSKJSSA-N
Smiles
CC=C(C)C(=O)OC1CC(C2(COC3C2C14COC(C4C(C3O)(C)C56C7CC(C5(O6)C)C8(C=COC8O7)O)(C(=O)OC)O)C(=O)OC)OC(=O)C
Isomeric SMILES
C/C=C(\C)/C(=O)O[C@H]1C[C@H]([C@]2(CO[C@@H]3[C@@H]2[C@]14CO[C@@]([C@H]4[C@]([C@@H]3O)(C)[C@@]56[C@@H]7C[C@H]([C@@]5(O6)C)[C@]8(C=CO[C@H]8O7)O)(C(=O)OC)O)C(=O)OC)OC(=O)C
WGK Germany
3
Molecular Weight
720.71
Reaxy-Rn
31992430
Reaxys-RN_link_address
https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=31992430&ln=
Certificates（CoA,COO,BSE/TSE and Analysis Chart)
Chemical and Physical Properties
Melt Point(°C)
165℃
Molecular Weight
720.700 g/mol
XLogP3
-0.600
Hydrogen Bond Donor Count
3
Hydrogen Bond Acceptor Count
16
Rotatable Bond Count
10
Exact Mass
720.263 Da
Monoisotopic Mass
720.263 Da
Topological Polar Surface Area
215.000 Ų
Heavy Atom Count
51
Formal Charge
0
Complexity
1660.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
16
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
1
Undefined Bond Stereocenter Count
0
The total count of all stereochemical bonds
1
Covalently-Bonded Unit Count
1
Citations of This Product
1.
Benshui Shu, Yanzheng Lin, Guozhao Qian, Xueming Cai, Luyang Liu, Jintian Lin.
(2022)
Integrated miRNA and transcriptome profiling to explore the molecular mechanism of Spodoptera frugiperda larval midgut in response to azadirachtin exposure. PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY,
187
(105192).
2.
Yu Haikuo, Yang Xianmei, Dai Jinghua, Li Yuning, Veeran Sethuraman, Lin Jintian, Shu Benshui.
(2023)
Effects of azadirachtin on detoxification-related gene expression in the fat bodies of the fall armyworm, Spodoptera frugiperda. ENVIRONMENTAL SCIENCE AND POLLUTION RESEARCH,
30
(15):
(42587-42595).
3.
Hai-bo Wu, Peng-xin Guo, Lin-hui Ma, Xi-meng Li, Ting-ting Liu.
(2021)
Nematicidal, antifungal and insecticidal activities of Artemisia halodendron extracts: New polyacetylenes involved. INDUSTRIAL CROPS AND PRODUCTS,
170
(113825).
4.
Benshui Shu, Haikuo Yu, Yuning Li, Hongxin Zhong, Xiangli Li, Liang Cao, Jintian Lin.
(2021)
Identification of azadirachtin responsive genes in Spodoptera frugiperda larvae based on RNA-seq. PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY,
172
(104745).
5.
Wen-kui Li, Song Wang, Yong-hong Wang, Yu-zhen Wu, Jia Li, Tian-hua Chai, Kang Wang, GuangYou Chen, Zhiqing Ma.
(2025)
Nanoporous 3D Polyurethane for Toosendanin Adsorption, Encapsulation, and High-Efficient Utilization. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY,
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5 Citations
C2531314