Aromadendrin

{{chembox

| Verifiedfields = changed

| verifiedrevid = 457152925

| Name = Aromadendrin

| ImageFile = Aromadedrin.svg

| ImageSize = 200px

| ImageFile2 = Aromadendrin 3D BS.png

| ImageSize2 = 200px

| IUPACName = (2R,3R)-3,4′,5,7-Tetrahydroxyflavan-4-one

| SystematicName = (2R,3R)-3,5,7-Trihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one

| OtherNames = Aromadendrin
Dihydrokaempferol
Aromadendrol
(+)-Aromadendrin
(+)-Dihydrokaempferol

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 480-20-6

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 7YA4640575

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = C00974

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 15401

| PubChem = 122850

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 9323

| SMILES = C1=CC(=CC=C1C2C(C(=O)C3=C(C=C(C=C3O2)O)O)O)O

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 109514

| 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

| InChIKey = PADQINQHPQKXNL-LSDHHAIUBO

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = PADQINQHPQKXNL-LSDHHAIUSA-N

}}

|Section2={{Chembox Properties

| C=15 | H=12 | O=6

| Appearance =

| Density=

| MeltingPt=

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| Solubility =

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|Section3={{Chembox Hazards

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Aromadendrin (aromodendrin or dihydrokaempferol) is a flavanonol, a type of flavonoid. It can be found in the wood of Pinus sibirica.{{cite journal | title = Aromadendrin, apigenin, and kaempferol from the wood of Pinus sibirica | author = V. I. Lutskii, A. S. Gromova and N. A. Tyukavkina | year = 1971 | doi = 10.1007/BF00568701 | journal = Chemistry of Natural Compounds | volume = 7 | issue = 2 | pages = 197–198}}

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{{prime}}{{prime}}-(4{{prime}}{{prime}}{{prime}}-hydroxy-2{{prime}}{{prime}}{{prime}}-methylene butanoate) is an acylated glucoside of aromadendrin isolated from the stem bark of Afzelia bella{{cite journal | pmid = 11324912 | year = 2001 | last1 = Binutu | first1 = OA | last2 = Cordell | first2 = GA | title = Constituents of Afzelia bella stem bark | volume = 56 | issue = 8 | pages = 827–30 | journal = Phytochemistry | doi = 10.1016/S0031-9422(01)00006-1}} (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.{{cite journal | doi = 10.1007/BF00393505 | title = Leucoanthocyanidins as intermediates in anthocyanidin biosynthesis in flowers of Matthiola incana R. Br | year = 1985 | last1 = Heller | first1 = Werner | last2 = Britsch | first2 = Lothar | last3 = Forkmann | first3 = Gert | last4 = Grisebach | first4 = Hans | journal = Planta | volume = 163 | issue = 2 | pages = 191–196 | pmid=24249337}}

References

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