Chemistry:Aromadendrin

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	480-20-6 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:15401 Y
ChEMBL	ChEMBL9323 Y
ChemSpider	109514 Y
KEGG	C00974 Y
PubChem CID	122850
UNII	7YA4640575 Y
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/s1 Y Key: PADQINQHPQKXNL-LSDHHAIUSA-N Y 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/s1 Key: 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−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Tracking categories (test):

• SizeSet

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.