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Hydrangenol

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Hydrangenol
Chemical structure of hydrangenol
Names
Preferred IUPAC name 8-Hydroxy-3-(4-hydroxyphenyl)-1H-2-benzopyran-1-one
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C15H12O4/c16-11-6-4-9(5-7-11)13-8-10-2-1-3-12(17)14(10)15(18)19-13/h1-7,13,16-17H,8H2Key: DGKDFNDHPXVXHW-UHFFFAOYSA-N
  • InChI=1/C15H12O4/c16-11-6-4-9(5-7-11)13-8-10-2-1-3-12(17)14(10)15(18)19-13/h1-7,13,16-17H,8H2Key: DGKDFNDHPXVXHW-UHFFFAOYAS
SMILES
  • C1C(OC(=O)C2=C1C=CC=C2O)C3=CC=C(C=C3)O
Properties
Chemical formula C15H12O4
Molar mass 256.25 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Hydrangenol is a dihydroisocoumarin. It can be found in Hydrangea macrophylla, as well as its 8-O-glucoside. (−)-Hydrangenol 4′-O-glucoside and (+)-hydrangenol 4′-O-glucoside can be found in Hydrangeae Dulcis Folium, the processed leaves of H. macrophylla var. thunbergii.

References

  1. Matsuda, Hisashi; Simoda, Hiroshi; Yamahara, Johji; Yoshikawa, Masayuki (1999). "Effects of phyllodulcin, hydrangenol, and their 8-O-glucosides, and thunberginols A and F from Hydrangea macrophylla Seringe var. thunbergii Makino on passive cutaneous anaphylaxis reaction in rats". Biological & Pharmaceutical Bulletin. 22 (8): 870–872. doi:10.1248/bpb.22.870. PMID 10480329. INIST 1959604.
  2. Yoshikawa, M; Uchida, E; Chatani, N; Kobayashi, H; Naitoh, Y; Okuno, Y; Matsuda, H; Yamahara, J; Murakami, N (1992). "Thunberginols C, D, and E, new antiallergic and antimicrobial dihydroisocoumarins, and thunberginol G 3′-O-glucoside and (−)-hydrangenol 4′-O-glucoside, new dihydroisocoumarin glycosides, from Hydrangeae Dulcis Folium". Chemical & Pharmaceutical Bulletin. 40 (12): 3352–3354. doi:10.1248/cpb.40.3352. PMID 1363465.
  3. Yoshikawa, M; Matsuda, H; Shimoda, H; Shimada, H; Harada, E; Naitoh, Y; Miki, A; Yamahara, J; Murakami, N (1996). "Development of bioactive functions in Hydrangeae Dulcis Folium. V. On the antiallergic and antimicrobial principles of Hydrangeae Dulcis Folium. (2). Thunberginols C, D, and E, thunberginol G 3′-O-glucoside, (−)-hydrangenol 4′-O-glucoside, and (+)-hydrangenol 4′-O-glucoside". Chemical & Pharmaceutical Bulletin. 44 (8): 1440–1447. doi:10.1248/cpb.44.1440. PMID 8795265. INIST 3226693.
Types of isocoumarins
Aglycones
Dihydroisocoumarins


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