Aurone

Aurone

Names
IUPAC name 2-Benzylidene-1-benzofuran-3-one
Identifiers
CAS Number	582-04-7 75318-34-2 (E) 37542-14-6 (Z)
ChemSpider	533325
Jmol interactive 3D	Image
PubChem	613552
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 Key: OMUOMODZGKSORV-UHFFFAOYSA-N 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	222.24 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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

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

Metabolism

• Aureusidin synthase^[2]

References

1. Nakayama, T (2002). "Enzymology of aurone biosynthesis". Journal of Bioscience and Bioengineering 94 (6): 487–91. doi:10.1016/S1389-1723(02)80184-0. PMID 16233339.
2. Nakayama, T; Sato, T; Fukui, Y; Yonekura-Sakakibara, K; Hayashi, H; Tanaka, Y; Kusumi, T; Nishino, T (2001). "Specificity analysis and mechanism of aurone synthesis catalyzed by aureusidin synthase, a polyphenol oxidase homolog responsible for flower coloration". FEBS Letters 499 (1–2): 107–11. doi:10.1016/S0014-5793(01)02529-7. PMID 11418122.
3. Atta-Ur-Rahman; Choudhary, MI; Hayat, S; Khan, AM; Ahmed, A (2001). "Two new aurones from marine brown alga Spatoglossum variabile". Chemical & pharmaceutical bulletin 49 (1): 105–7. doi:10.1248/cpb.49.105. PMID 11201212.
4. Ferreira, EO; Salvador, MJ; Pral, EM; Alfieri, SC; Ito, IY; Dias, DA (2004). "A new heptasubstituted (E)-aurone glucoside and other aromatic compounds of Gomphrena agrestis with biological activity" (PDF). Zeitschrift für Naturforschung C 59 (7–8): 499–505. PMID 15813368.
5. Villemin, Didier; Martin, Benoit; Bar, Nathalie (1998). "Application of Microwave in Organic Synthesis. Dry Synthesis of 2-Arylmethylene-3(2)-naphthofuranones". Molecules 3 (3): 88. doi:10.3390/30300088.
6. Hispidol on metabolomics.jp