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Wikipedia

Nepetalactol

Nepetalactol is an iridoid. It is produced from 8-oxogeranial by the enzyme iridoid synthase.[1] Nepetalactol is a substrate for the enzyme iridoid oxidase (IO) which produces 7-deoxyloganetic acid. It has been identified in Actinidia polygama (the silver vine) as a major cat attractant, and a mosquito repellent. The fact that mosquitos bite cats with nepetalactol on their fur less often may explain why cats are attracted to silver vine in the first place.[2]

Nepetalactol
Names
IUPAC name
(4aS,7S,7aR)-4,7-Dimethyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-1-ol
Identifiers
  • 183071-73-0 4 stereocentres specified
3D model (JSmol)
  • Interactive image
3DMet
  • B03378
ChEBI
  • CHEBI:71494
ChemSpider
  • 28533620
KEGG
  • C09804
  • 11652906
  • InChI=1S/C10H16O2/c1-6-3-4-8-7(2)5-12-10(11)9(6)8/h5-6,8-11H,3-4H2,1-2H3/t6-,8+,9+,10?/m0/s1
    Key: OJGPEAXUHQRLNC-CEPLBNANSA-N
  • InChI=1/C10H16O2/c1-6-3-4-8-7(2)5-12-10(11)9(6)8/h5-6,8-11H,3-4H2,1-2H3/t6-,8+,9+,10u/m0/s1
    Key: OJGPEAXUHQRLNC-XUFCCMHBBP
  • C[C@H]1CC[C@H]2[C@@H]1C(OC=C2C)O
Properties
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).

References edit

  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. ^ Uenoyama, Reiko; Miyazaki, Tamako; Hurst, Jane L.; Beynon, Robert J.; Adachi, Masaatsu; Murooka, Takanobu; Onoda, Ibuki; Miyazawa, Yu; Katayama, Rieko; Yamashita, Tetsuro; Kaneko, Shuji; Nishikawa, Toshio; Miyazaki, Masao (2021). "The characteristic response of domestic cats to plant iridoids allows them to gain chemical defense against mosquitoes". Science Advances. 7 (4): eabd9135. doi:10.1126/sciadv.abd9135. PMC 7817105. PMID 33523929. S2CID 231681044.

nepetalactol, iridoid, produced, from, oxogeranial, enzyme, iridoid, synthase, substrate, enzyme, iridoid, oxidase, which, produces, deoxyloganetic, acid, been, identified, actinidia, polygama, silver, vine, major, attractant, mosquito, repellent, fact, that, . Nepetalactol is an iridoid It is produced from 8 oxogeranial by the enzyme iridoid synthase 1 Nepetalactol is a substrate for the enzyme iridoid oxidase IO which produces 7 deoxyloganetic acid It has been identified in Actinidia polygama the silver vine as a major cat attractant and a mosquito repellent The fact that mosquitos bite cats with nepetalactol on their fur less often may explain why cats are attracted to silver vine in the first place 2 Nepetalactol NamesIUPAC name 4aS 7S 7aR 4 7 Dimethyl 1 4a 5 6 7 7a hexahydrocyclopenta c pyran 1 olIdentifiersCAS Number 183071 73 0 4 stereocentres specified3D model JSmol Interactive image3DMet B03378ChEBI CHEBI 71494ChemSpider 28533620KEGG C09804PubChem CID 11652906InChI InChI 1S C10H16O2 c1 6 3 4 8 7 2 5 12 10 11 9 6 8 h5 6 8 11H 3 4H2 1 2H3 t6 8 9 10 m0 s1Key OJGPEAXUHQRLNC CEPLBNANSA NInChI 1 C10H16O2 c1 6 3 4 8 7 2 5 12 10 11 9 6 8 h5 6 8 11H 3 4H2 1 2H3 t6 8 9 10u m0 s1Key OJGPEAXUHQRLNC XUFCCMHBBPSMILES C C H 1CC C H 2 C H 1C OC C2C OPropertiesChemical formula C 10H 16O 2Molar mass 168 236 g mol 1Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox referencesReferences edit 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 Uenoyama Reiko Miyazaki Tamako Hurst Jane L Beynon Robert J Adachi Masaatsu Murooka Takanobu Onoda Ibuki Miyazawa Yu Katayama Rieko Yamashita Tetsuro Kaneko Shuji Nishikawa Toshio Miyazaki Masao 2021 The characteristic response of domestic cats to plant iridoids allows them to gain chemical defense against mosquitoes Science Advances 7 4 eabd9135 doi 10 1126 sciadv abd9135 PMC 7817105 PMID 33523929 S2CID 231681044 Retrieved from https en wikipedia org w index php title Nepetalactol amp oldid 1066216923, wikipedia, wiki, book, books, library,

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