| Identification | Back Directory | [Name]
2-Methyl-5,7-dihydroxychromone | [CAS]
1013-69-0 | [Synonyms]
reugenin
Noreugenin
2-Methyl-5,7-dihydroxychromone
5,7-dihydroxy-2-methylchromen-4-one
5,7-Dihydroxy-2-methyl-4H-1-benzopyran-4-one
2-Methyl-5,7-dihydroxy-4H-1-benzopyran-4-one
4H-1-Benzopyran-4-one,5,7-dihydroxy-2-methyl- | [Molecular Formula]
C10H8O4 | [MDL Number]
MFCD03001435 | [MOL File]
1013-69-0.mol | [Molecular Weight]
192.17 |
| Chemical Properties | Back Directory | [Melting point ]
279 °C | [Boiling point ]
394.6±42.0 °C(Predicted) | [density ]
1.456±0.06 g/cm3(Predicted) | [storage temp. ]
Store at -20°C | [solubility ]
DMSO: 250 mg/mL (1300.93 mM); Water: < 0.1 mg/mL (insoluble) | [form ]
Solid | [pka]
6.58±0.40(Predicted) | [color ]
White to off-white | [InChI]
InChI=1S/C10H8O4/c1-5-2-7(12)10-8(13)3-6(11)4-9(10)14-5/h2-4,11,13H,1H3 | [InChIKey]
NCUJRUDLFCGVOE-UHFFFAOYSA-N | [SMILES]
C1(C)OC2=CC(O)=CC(O)=C2C(=O)C=1 |
| Hazard Information | Back Directory | [Uses]
Noreugenin, 5,7-dihydroxy-2-methyl-4H-chromen-4-one, is a new chromone from Aloe arborescens. (Amaryllidaceae)[1]. | [Definition]
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-). | [Synthesis]
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. | [storage]
Store at -20°C | [References]
[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 |
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