Nepetalactol

Nepetalactol
Names
	IUPAC name (4aS,7S,7aR)-4,7-Dimethyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-1-ol
Identifiers
CAS Number	183071-73-0 4 stereocentres specified;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:71494;
ChemSpider	28533620;
KEGG	C09804;
PubChem CID	11652906;
	InChI 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;
	SMILES C[C@H]1CC[C@H]2[C@@H]1C(OC=C2C)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

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]

References

^ 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.

[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.

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