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7-Deoxyloganetic acid

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7-Deoxyloganetic acid
Names
Preferred IUPAC name
(1R,4aS,7S,7aR)-1-Hydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
  • InChI=1S/C10H14O4/c1-5-2-3-6-7(9(11)12)4-14-10(13)8(5)6/h4-6,8,10,13H,2-3H2,1H3,(H,11,12)/t5-,6+,8+,10+/m0/s1
    Key: DKGYTSKPMLWLEI-FIZOKRMRSA-N
  • InChI=1/C10H14O4/c1-5-2-3-6-7(9(11)12)4-14-10(13)8(5)6/h4-6,8,10,13H,2-3H2,1H3,(H,11,12)/t5-,6+,8+,10+/m0/s1
    Key: DKGYTSKPMLWLEI-FIZOKRMRBX
  • C[C@H]1CC[C@H]2[C@@H]1[C@@H](OC=C2C(=O)O)O
Properties
C10H14O4
Molar mass 198.218 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

7-Deoxyloganetic acid is an iridoid monoterpene. It is produced from nepetalactol or iridodial by the enzyme iridoid oxidase (IO).[1] 7-Deoxyloganetic acid is a substrate for 7-deoxyloganetic acid glucosyltransferase (7-DLGT) which synthesizes 7-deoxyloganic acid.[2]

References

  1. ^ Miettinen, Dong, Navrot, Schneider, Burlat, et al. (2014) The seco-iridoid pathway from Catharanthus roseus. Nat Commun. 5
  2. ^ Salim, Wiens, Masada-Atsumi, Yu and De Luca (2014) 7-Deoxyloganetic acid synthase catalyzes a key 3 step oxidation to form 7-deoxyloganetic acid in Catharanthus roseus iridoid biosynthesis. Phytochemistry. 101(0). 23-31


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