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Aromadendrin

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(Redirected from Dihydrokaempferol)
Aromadendrin
Names
IUPAC name (2R,3R)-3,4′,5,7-Tetrahydroxyflavan-4-one
Systematic IUPAC name (2R,3R)-3,5,7-Trihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one
Other names Aromadendrin
Dihydrokaempferol
Aromadendrol
(+)-Aromadendrin
(+)-Dihydrokaempferol
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.213.374 Edit this at Wikidata
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C15H12O6/c16-8-3-1-7(2-4-8)15-14(20)13(19)12-10(18)5-9(17)6-11(12)21-15/h1-6,14-18,20H/t14-,15+/m0/s1Key: PADQINQHPQKXNL-LSDHHAIUSA-N
  • InChI=1/C15H12O6/c16-8-3-1-7(2-4-8)15-14(20)13(19)12-10(18)5-9(17)6-11(12)21-15/h1-6,14-18,20H/t14-,15+/m0/s1Key: PADQINQHPQKXNL-LSDHHAIUBO
SMILES
  • C1=CC(=CC=C1C2C(C(=O)C3=C(C=C(C=C3O2)O)O)O)O
Properties
Chemical formula C15H12O6
Molar mass 288.255 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

Aromadendrin (aromodendrin or dihydrokaempferol) is a flavanonol, a type of flavonoid. It can be found in the wood of Pinus sibirica.

Metabolism

The enzyme dihydrokaempferol 4-reductase uses cis-3,4-leucopelargonidin and NADP to produce (+)-aromadendrin, NADPH, and H.

Glycosides

(2R,3R)-trans-Aromadendrin-7-O-beta-D-glucopyranoside-6′′-(4′′′-hydroxy-2′′′-methylene butanoate) is an acylated glucoside of aromadendrin isolated from the stem bark of Afzelia bella (Fabaceae).

Phellamurin is the 8-prenyl 7-glucoside derivative of aromadendrin.

Chemistry

(+)-Leucopelargonidin, (2R,3S,4R)-3,4,5,7,4'-pentahydroxyflavan, can be synthesized from (+)-aromadendrin by sodium borohydride reduction.

References

  1. V. I. Lutskii, A. S. Gromova and N. A. Tyukavkina (1971). "Aromadendrin, apigenin, and kaempferol from the wood of Pinus sibirica". Chemistry of Natural Compounds. 7 (2): 197–198. doi:10.1007/BF00568701.
  2. Binutu, OA; Cordell, GA (2001). "Constituents of Afzelia bella stem bark". Phytochemistry. 56 (8): 827–30. doi:10.1016/S0031-9422(01)00006-1. PMID 11324912.
  3. Heller, Werner; Britsch, Lothar; Forkmann, Gert; Grisebach, Hans (1985). "Leucoanthocyanidins as intermediates in anthocyanidin biosynthesis in flowers of Matthiola incana R. Br". Planta. 163 (2): 191–196. doi:10.1007/BF00393505. PMID 24249337.

External links

Flavanonols and their glycosides
3-Hydroxyflavanones:
O-methylated flavanonols
dihydroflavonol 3-O-glycosides
Glycosides
Acetylated glycosides
Categories: