Aurone

Not to be confused with Auron (disambiguation).

An 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.

Aurone

Aurone Z configuration
Names
Preferred IUPAC name 2-Benzylidene-1-benzofuran-3(2H)-one
Other names 2-Benzylidenebenzofuran-3(2H)-one 2-Benzylidene-1-benzofuran-3-one
Identifiers
CAS Number	582-04-7 Y 75318-34-2 (E) N 37542-14-6 (Z) N
3D model (JSmol)	Interactive image
ChemSpider	533325 Y
PubChem CID	613552
CompTox Dashboard (EPA)	DTXSID70424870
InChI 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 Y Key: OMUOMODZGKSORV-UHFFFAOYSA-N Y 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
SMILES C1=CC=C(C=C1)C=C2C(=O)C3=CC=CC=C3O2
Properties
Chemical formula	C15H10O2
Molar mass	222.243 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Aurone derivatives

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]

Biosynthesis

Aurones are biosynthesized starting from coumaryl-CoA.^[5] Aureusidin synthase catalyzes the creation of aurones from chalcones through hydroxylation and oxidative cyclization.^[2]

Applications

Some aurone derivatives possess antifungal properties^[6] and analogy with flavonoids suggests that aurones could have other biological properties.^[7]

Related compound examples

• Aureusidin
• Hispidol (6,4'-dihydroxyaurone)^[8]
• Leptosidin
• Sulfuretin (6,3',4'-trihydroxyaurone)
• 4,5,6-Trihydroxyaurone