Aromadendrin

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title: "Aromadendrin" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["flavanonols", "resorcinols"] topic_path: "general/flavanonols" source: "https://en.wikipedia.org/wiki/Aromadendrin" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| 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 = | CASNo = 480-20-6 | UNII_Ref = | UNII = 7YA4640575 | KEGG_Ref = | KEGG = C00974 | ChEBI_Ref = | ChEBI = 15401 | PubChem = 122850 | ChEMBL_Ref = | ChEMBL = 9323 | SMILES = C1=CC(=CC=C1C2C(C(=O)C3=C(C=C(C=C3O2)O)O)O)O | ChemSpiderID_Ref = | 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 = | 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 = | StdInChIKey = PADQINQHPQKXNL-LSDHHAIUSA-N |Section2={{Chembox Properties | C=15 | H=12 | O=6 | Appearance = | Density= | MeltingPt= | BoilingPt= | Solubility = |Section3={{Chembox Hazards | MainHazards= | FlashPt= | AutoignitionPt =

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

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.
  2. (2001). "Constituents of Afzelia bella stem bark". Phytochemistry.
  3. (1985). "Leucoanthocyanidins as intermediates in anthocyanidin biosynthesis in flowers of Matthiola incana R. Br". Planta.

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flavanonolsresorcinols