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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
3D model (JSmol)	Interactive image
ChEBI	CHEBI:15401
ChEMBL	ChEMBL9323
ChemSpider	109514
ECHA InfoCard	100.213.374
KEGG	C00974
PubChem CID	122850
UNII	7YA4640575
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/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

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

• Media related to Aromadedrin at Wikimedia Commons

• Flavanonols
• Resorcinols