Aurone

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Not to be confused with Auron (disambiguation).
Aurone
Aurone Z configuration
Names
IUPAC name
2-Benzylidene-1-benzofuran-3-one
Identifiers
582-04-7 YesY
75318-34-2 (E)
37542-14-6 (Z)
ChemSpider 533325 YesY
Jmol 3D model Interactive image
PubChem 613552
  • InChI=1S/C15H10O2/c16-15-12-8-4-5-9-13(12)17-14(15)10-11-6-2-1-3-7-11/h1-10H YesY
    Key: OMUOMODZGKSORV-UHFFFAOYSA-N YesY
  • InChI=1/C15H10O2/c16-15-12-8-4-5-9-13(12)17-14(15)10-11-6-2-1-3-7-11/h1-10H
    Key: OMUOMODZGKSORV-UHFFFAOYAF
  • C1=CC=C(C=C1)C=C2C(=O)C3=CC=CC=C3O2
Properties
C15H10O2
Molar mass 222.24 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY verify (what is YesYN ?)
Infobox references

Aurone is a heterocyclic chemical compound which is a type of flavonoid.[1] There are two isomers of the molecule, with (E)- and (Z)-configurations. The molecule contains a benzofuran element associated with a benzylidene linked in position 2. In aurone, a chalcone-like group is closed into a 5-membered ring instead of the 6-membered ring more typical of flavonoids.

Skeletal structure of an (Z)-aurone with numbering scheme used for nomenclature of derivatives

Aurone forms the core for a family of derivatives which are known collectively as aurones. Aurones are plant flavonoids that provide yellow color to the flowers of some popular ornamental plants, such as snapdragon and cosmos.[2] Aurones including 4'-chloro-2-hydroxyaurone (C15H11O3Cl) and 4'-chloroaurone (C15H9O2Cl) can also be found in the brown alga Spatoglossum variabile.[3]

Most aurones are in a (Z)-configuration, which is the more stable configuration according to Austin Model 1 computation,[3] but there are also some in the (E)-configurations such as (E)-3'-O-β-d-glucopyranosyl-4,5,6,4'-tetrahydroxy-7,2'-dimethoxyaurone, found in Gomphrena agrestis.[4]

Analogy with flavonoids suggests that aurones could have interesting biological properties.[5]

Related compound examples

Metabolism

References

  1. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  2. ↑ 2.0 2.1 Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ 3.0 3.1 Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  6. ↑ Hispidol on metabolomics.jp
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