Actinidine

Source: Wikipedia, the free encyclopedia.
Not to be confused with
Actinidin, Actinide, or Actinium
.
Actinidine
Structural formula of actinidine
Space-filling
Names
Preferred IUPAC name
(7S)-4,7-Dimethyl-6,7-dihydro-5H-cyclopenta[c]pyridine
Identifiers
3D model (
JSmol
)
81308
ChEBI
ChemSpider
KEGG
UNII
  • InChI=1S/C10H13N/c1-7-3-4-9-8(2)5-11-6-10(7)9/h5-7H,3-4H2,1-2H3/t7-/m0/s1 checkY
    Key: ZHQQRIUYLMXDPP-ZETCQYMHSA-N checkY
  • InChI=1/C10H13N/c1-7-3-4-9-8(2)5-11-6-10(7)9/h5-7H,3-4H2,1-2H3/t7-/m0/s1
    Key: ZHQQRIUYLMXDPP-ZETCQYMHBZ
  • C[C@@H](CC1)C2=C1C(C)=CN=C2
  • n1cc(c2c(c1)[C@H](CC2)C)C
Properties
C10H13N
Molar mass 147.221 g·mol−1
Melting point < 25 °C (77 °F; 298 K)
Boiling point 100 to 103 °C (212 to 217 °F; 373 to 376 K) at 9 mmHg[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Actinidine is an iridoid produced in nature by a wide variety of plants and animals. It was the first cyclopentanoid monoterpene alkaloid to be discovered.[2] It is one of several compounds that may be extracted from the valerian (Valeriana officinalis) root[3] and silver vine (Actinidia polygama), as well as several types of insects in the larval and imaginal stages.[4] Actinidine is a cat attractant, with effects like those of nepetalactone, the active compound found in catnip.[5]

Certain species of stick insects, including Megacrania batesii and Megacrania tsudai, possess a chemical defense mechanism which involves the secretion of an actinidine-containing substance from the prothoracic glands, when threatened by a predator.[6]

Biosynthesis

A potential biosynthesis of actinidine from L-citronellal is shown below.[7]

References

  1. doi:10.1246/bcsj.32.315
    .
  2. doi:10.1021/cr50030a003
    .
  3. PMID 547813
    .
  4. PMID 11267897
    .
  5. PMID 32426505
    .
  6. S2CID 216322536
    .
  7. ^ Funayama S, Cordell GA, eds. (2015). "14: Alkaloids Derived from Terpenoids". Alkaloids. Academic Press. pp. 233–255.
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