1013-69-0

Noreugenin, 5,7-dihydroxy-2-methyl-4H-chromen-4-one, is a new chromone from Aloe arborescens. (Amaryllidaceae)[1].

ChEBI: Noreugenin is a member of the class of chromones in which the 1,4-benzopyrone skeleton is substituted with a methyl group at position 2 and with hydroxy groups at positions 5 and 7. A natural product, it is found in Pisonia aculeata. It has a role as a plant metabolite. It is a member of chromones and a member of resorcinols. It is a conjugate acid of a noreugenin(1-).

The general procedure for the synthesis of 5,7-dihydroxy-2-methyl-4H-benzopyran-4-one from the compound (CAS:1162-81-8) is as follows: 2-methyl-3-acetyl-5,7-diacetoxychromanone (15.9 g, 0.05 mol) was placed in a 1 L three-necked flask and 400 mL of sodium carbonate solution (10 mL) was added. The mixture was heated to reflux for 2 hours. After the reaction was completed, it was cooled to room temperature and filtered to remove insoluble material. The filtrate was adjusted to pH 7~8 with hydrochloric acid, at which time a large amount of solid precipitated. The solution was further cooled to below 10°C, filtered and the solids were collected. The filter cake was dried under vacuum at 40 °C for 4 h to give 8.98 g of off-white solid powder in 93.6% yield. The structure of the final product 2-methyl-5,7-dihydroxychromone was confirmed by 1H-NMR and mass spectrometry.

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[1] Wang Y, et al. Aspergchromones A and B, two new polyketides from the marine sponge-associated fungus Aspergillus sp. SCSIO XWS03F03. J Asian Nat Prod Res. 2017 Jul;19(7):684-690. DOI:10.1080/14786419.2014.951931