dl-Aloesol

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dl-Aloesol
Category Others
Catalog number BBF-04447
CAS 104871-04-7
Molecular Weight 234.25
Molecular Formula C13H14O4
Purity 98.5%

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Description

Dl-Aloesol is produced from the endophytic fungus HCCB06030.

Specification

Related CAS 94356-35-1 (S-isomer)
Synonyms 7-Hydroxy-2-(2'-hydroxypropyl)-5-methylchromone; DL-Aloesol; 4H-1-Benzopyran-4-one, 7-hydroxy-2-(2-hydroxypropyl)-5-methyl-
Storage Store at 2-8°C
IUPAC Name 7-hydroxy-2-(2-hydroxypropyl)-5-methylchromen-4-one
Canonical SMILES CC1=CC(=CC2=C1C(=O)C=C(O2)CC(C)O)O
InChI InChI=1S/C13H14O4/c1-7-3-9(15)5-12-13(7)11(16)6-10(17-12)4-8(2)14/h3,5-6,8,14-15H,4H2,1-2H3
InChI Key ZYCNQWOKCMJKEZ-UHFFFAOYSA-N

Properties

Appearance Crystal
Boiling Point 446.7±45.0°C at 760 mmHg
Melting Point 175-178°C
Density 1.3±0.1 g/cm3
Solubility Soluble in Methanol

Reference Reading

1. Metabolism of aloesin and related compounds by human intestinal bacteria: a bacterial cleavage of the C-glucosyl bond and the subsequent reduction of the acetonyl side chain
Q M Che, T Akao, M Hattori, K Kobashi, T Namba Chem Pharm Bull (Tokyo). 1991 Mar;39(3):704-8. doi: 10.1248/cpb.39.704.
By anaerobic incubation with a bacterial mixture from human feces, aloesin (aloeresin B; 1) was converted to 2-acetonyl-7-hydroxy-5-methylchromone (aloesone; 3) and dl-7-hydroxy-2-(2'-hydroxypropyl)-5-methylchromone (aloesol; 4a + 4b) through a cleavage of the C-glucosyl bond, followed by reduction of the acetonyl side chain. An analogous compound, aloeresin A (2), was converted to p-coumaric acid and aloesin (1), the latter being subsequently transformed to aloesone (3) and dl-aloesol (4a + 4b). On the other hand, 7-O-methylated derivatives (7, 5a and 5b) of aloesin and of 8-C-glucosylaloesol were not cleaved to the corresponding aglycones, suggesting the importance of a free hydroxy group adjacent to the C-glucosyl group in the molecule for the bacterial cleavage of aloesin derivatives. This is the first report on the cleavage of the C-glycosyl bond of chromone C-glucosides by intestinal bacteria.

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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