Aromadedrin

Aromadedrin
IUPAC name 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
PubChem	122850
ChemSpider	109514 Y
ChEBI	CHEBI:15401 Y
ChEMBL	CHEMBL9323 Y
Jmol-3D images	Image 1
SMILES C1=CC(=CC=C1C2C(C(=O)C3=C(C=C(C=C3O2)O)O)O)O
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
Properties
Molecular formula	C15H12O6
Molar mass	288.25 g/mol
Exact mass	288.063388
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Aromadedrin (dihydrokaempferol) is a flavanonol, a type of flavonoid. It can be found in the wood of Pinus sibirica.^[1]

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^[2] (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.^[3]

References

1. ^ Aromadendrin, apigenin, and kaempferol from the wood of Pinus sibirica, V. I. Lutskii, A. S. Gromova and N. A. Tyukavkina, 1971
2. ^ Constituents of Afzelia bella stem bark. Binutu OA, Cordell GA.
3. ^ Leucoanthocyanidins as intermediates in anthocyanidin biosynthesis in flowers of Matthiola incana R. Br. Werner Heller, Lothar Britsch, Gert Forkmann and Hans Grisebach, 1984

This article about a natural phenol is a stub. You can help Wikipedia by expanding it.v · Categories: Flavanonols Resorcinols Natural phenol stubs Wikimedia Foundation. 2010. Игры ⚽ Поможем решить контрольную работу (+)-CPCA Taxifolin Look at other dictionaries: Flavanonol — Flavanonol, numbering The flavanonols (with two o s aka 3 hydroxyflavanone or 2,3 dihydroflavonol) are a class of flavonoids that use the 3 hydroxy 2,3 dihydro 2 phenylchromen 4 one (IUPAC name) backbone. Some examples include: Taxifolin (or… …   Wikipedia Ampelopsin — IUPAC name (2R,3R) 3,5,7 trihydroxy 2 (3,4,5 trihydroxyphenyl) 2,3 dihydrochromen 4 one …   Wikipedia Taxifolin — IUPAC name (2R,3R) 2 (3,4 dihydroxyphenyl) 3,5,7 trihydroxy 2, 3 dihydrochromen 4 one …   Wikipedia Fustin — IUPAC name 2 (3,4 dihydroxyphenyl) 3,7 dihydroxy 2,3 dihydrochromen 4 one …   Wikipedia Leucopelargonidin — IUPAC name (2R,3S,4S) 2 (4 hydroxyphenyl) 3,4 dihydro 2H chromene 3,4,5,7 tetrol …   Wikipedia Dictionary of natural phenols and polyphenols molecular formulas — Natural polyphenols molecular formulas are generally formed from C, H and O. The entries are sorted by mass. Formula Example Exact mass (u) C8H10O 4 Ethylphenol, others 122.073164 C6H6O3 Hydroxyquinol, others 126.031694 C7H6O3 2 Hydroxybenzoic… …   Wikipedia Dihydrogossypetin — IUPAC name (2R,3R) 2 (3,4 dihydroxyphenyl) 3,5,7,8 tetrahydroxy 2,3 dihydrochromen 4 one …   Wikipedia Dihydrokaempferide — IUPAC name 3,5,7 trihydroxy 2 (4 methoxyphenyl) 2,3 dihydrochromen 4 one …   Wikipedia Dihydromorin — IUPAC name (2R,3R) 2 (2,4 dihydroxyphenyl) 3,5,7 trihydroxy 2,3 dihydrochromen 4 one …   Wikipedia Astilbin — IUPAC name (2R,3R) 2 (3,4 dihydroxyphenyl) 5,7 dihydroxy 3 [(2S,3R,4R,5R,6S) 3,4,5 trihydroxy 6 …   Wikipedia 18+ © Academic, 2000-2024 Contact us: Technical Support, Advertising Dictionaries export, created on PHP, Joomla, Drupal, WordPress, MODx. Mark and share Search through all dictionaries Translate… Search Internet Share the article and excerpts Direct link … Do a right-click on the link above and select “Copy Link”