Iridodial

Iridodial
Names
Preferred IUPAC name
(1S,2S,5R)-2-Methyl-5-[(2S)-1-oxopropan-2-yl]cyclopentane-1-carbaldehyde
Identifiers
CAS Number
  • 550-45-8
3D model (JSmol)
  • Interactive image
PubChem CID
  • 53297343
UNII
  • KZ2T7V54AZ checkY
CompTox Dashboard (EPA)
  • DTXSID10970361 Edit this at Wikidata
InChI
  • InChI=1S/C10H16O2/c1-7-3-4-9(8(2)5-11)10(7)6-12/h5-10H,3-4H2,1-2H3/t7-,8+,9+,10-/m0/s1
    Key: HMCYXRFNNOPPPR-JLIMGVALSA-N
  • C[C@H]1CC[C@@H]([C@H]1C=O)[C@H](C)C=O
Properties
Chemical formula
 C10H16O2
Molar mass 168.236 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Chemical compound

Iridodial is an iridoid. It is produced from 8-oxogeranial by the enzyme iridoid synthase (IS).[1] Iridodial is one of the substrates for the enzyme iridoid oxidase (IO) which produces 7-deoxyloganetic acid.

Although it may not be known at this time whether the compound proper iridodial is actually present in natural plant species or not, the use of analogous ion iridodial cation is mentioned in several papers on iridoid biosyntheses in plant species. [2][3]

References

  1. ^ Geu-Flores, Fernando; Sherden, Nathaniel H.; Courdavault, Vincent; Burlat, Vincent; Glenn, Weslee S.; Wu, Cen; Nims, Ezekiel; Cui, Yuehua; O’Connor, Sarah E. (2012). "An alternative route to cyclic terpenes by reductive cyclization in iridoid biosynthesis". Nature. 492 (7427): 138–42. Bibcode:2012Natur.492..138G. doi:10.1038/nature11692. PMID 23172143. S2CID 4431685.
  2. ^ Uesato (1984). "Biosynthetic pathway of iridoid glucosides in Gardenia jasminoides f. grandiflora cell suspension cultures after iridodial cation formation". Tetrahedron Letters. 25 (5): 573–576. doi:10.1016/S0040-4039(00)99941-6.
  3. ^ Sampaio-Santos (2001). "Biosynthesis significance of iridoids in chemosystematics". Journal of the Brazilian Chemical Society (12): 144–153.