Aromadendrin

Aromadedrin

Names
IUPAC names Aromadendrin (2R,3R)-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
Other names Dihydrokaempferol Aromadendrol (+)-aromadendrin (+)-Dihydrokaempferol
Identifiers
CAS Number	480-20-6 N
3D model (JSmol)	Interactive image
ChEBI	CHEBI:15401 Y
ChEMBL	ChEMBL9323 Y
ChemSpider	109514 Y
ECHA InfoCard	100.213.374
PubChem CID	122850
CompTox Dashboard (EPA)	DTXSID8075411
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	288.25 g/mol
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

Aromadedrin (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 (+)-aromadedrin, NADPH, and H⁺.

Glycosides

(2R,3R)-trans-Aromadendrin-7-O-beta-D-glucopyranoside-6"-(4"-hydroxy-2"-methylene butanoate) is an acetylated 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

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