Azadirachtin

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Structural formula
Structural formula of azadirachtin
General
Surname Azadirachtin
other names

Azadirachtin A

Molecular formula C 35 H 44 O 16
External identifiers / databases
CAS number 11141-17-6
EC number 601-089-4
ECHA InfoCard 100.115.924
PubChem 5281303
ChemSpider 4444685
Wikidata Q793471
properties
Molar mass 720.71 g mol −1
Physical state

firmly

Melting point

155-158 ° C

safety instructions
GHS labeling of hazardous substances
07 - Warning 08 - Dangerous to health 09 - Dangerous for the environment

Caution

H and P phrases H: 317-361d-400
P: 261-273-280-321-405-501
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Azadirachtin is a chemical compound that belongs to the limonoids . It is a secondary metabolite and insecticidal active ingredient of the seed of the neem tree . Azadirachtin is an oxidized tetranortri terpenoid with enol ether , acetal , hemiacetal and epoxy functions.

Seeds of the neem tree; Occurrence of azadirachtin

Azadirachtin is the main component of neem oil , which is obtained from the pressed seeds of the neem tree ( Azadirachta indica ). The substance inhibits the larval development of numerous insects ( ecdyson- like effect), but is said to be relatively harmless to mammals .

The effect of neem tree extract has been known for a long time. The active ingredient azadirachtin, which is probably mainly responsible for the effect, was first isolated from the seeds of the tree in 1968. In 1985 the structure of the molecule was developed by Wolfgang Kraus et al. finally clarified and published at the University of Hohenheim . It has 16 stereocenters , a complicated pattern of oxygen-containing functional groups as well as a strong intramolecular hydrogen bonds influenced conformation and reactivity . It is also very unstable when exposed to UV light , with a loss of half-life of 13 to 94 hours.

After 22 years of research, the synthetic production of azadirachtin was first achieved in 2007 by a British team led by Steven Ley at Cambridge University .

literature

Individual evidence

  1. ↑ a b Entry on Azadirachtin. In: Römpp Online . Georg Thieme Verlag, accessed on June 13, 2014.
  2. ↑ a b Safety data sheet according to 1907/2006 / EC, Article 31. (PDF) In: LGC Standards GmbH. February 3, 2020, accessed on July 17, 2020 .
  3. ↑ Wolfgang Kraus et al .: Final structure of Azadirachtin . In: Tetrahedron Letters . 1985. doi : 10.1016 / S0040-4039 (00) 99020-8 .
  4. ↑ KMS Sundaram, J. Curry: Effect of some UV light absorbers on the photostabilization of azadirachtin, a neem-based biopesticide. In: Chemosphere . 32, 1996, pp. 649-659, doi : 10.1016 / 0045-6535 (95) 00370-3 .
  5. ↑ Wei-hong TAN, Zhan-qian SONG: Research on Effect of Four Natural Ultraviolet Light Absorbers on Photostabilization of Azadirachtin-A. In: Agricultural Sciences in China. 5, 2006, pp. 855-858, doi : 10.1016 / S1671-2927 (06) 60135-1 .
  6. ↑ Steven V. Ley: Synthesis and chemistry of the insect antifeedant azadirachtin In: Pure and Applied Chemistry . Volume 66, No. 10/11, pp. 2099-2102, IUPAC 1994.
  7. ^ Organic-chemie.ch: Synthesis of azadirachtin .
  8. ↑ Gemma E. Veitch, Edith Beckmann, Brenda J. Burke, Alistair Boyer, Carles Ayats, Steven V. Ley: A Relay Route for the Synthesis of Azadirachtin. In: Angewandte Chemie . 119, 2007, pp. 7777-7779, doi : 10.1002 / anie.200703028 .