Aromadendrin: Difference between revisions

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Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEBI', 'CASNo').
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{{chembox
{{chembox
| Verifiedfields = changed
| verifiedrevid = 456242954
| verifiedrevid = 457152925
⚫
| Name = Aromadedrin
| Name = Aromadendrin
| ImageFile = Aromadedrin.svg
⚫
| ImageFile = Aromadedrin.svg
| ImageSize = 250px
| ImageSize = 200px
⚫
| IUPACName = Aromadendrin<br>(2''R'',3''R'')-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
| ImageFile2 = Aromadendrin 3D BS.png
⚫
| OtherNames = Dihydrokaempferol<br>Aromadendrol<br>(+)-aromadendrin<br>(+)-Dihydrokaempferol
| ImageSize2 = 200px
⚫
| Section1= {{Chembox Identifiers
| IUPACName = (2''R'',3''R'')-3,4′,5,7-Tetrahydroxyflavan-4-one
| CASNo = <!-- blanked - oldvalue: 480-20-6 -->
⚫
| SystematicName = (2''R'',3''R'')-3,5,7-Trihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4''H''-1-benzopyran-4-one
⚫
| ChEBI = 15401
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| OtherNames = Aromadendrin<br>Dihydrokaempferol<br>Aromadendrol<br>(+)-Aromadendrin<br>(+)-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
| PubChem = 122850
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 9323
| ChEMBL = 9323
| SMILES = C1=CC(=CC=C1C2C(C(=O)C3=C(C=C(C=C3O2)O)O)O)O
| SMILES = C1=CC(=CC=C1C2C(C(=O)C3=C(C=C(C=C3O2)O)O)O)O
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 109514
| 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
| 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
| InChIKey = PADQINQHPQKXNL-LSDHHAIUBO
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| 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
| 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_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = PADQINQHPQKXNL-LSDHHAIUSA-N
| StdInChIKey = PADQINQHPQKXNL-LSDHHAIUSA-N
}}
}}
|Section2= {{Chembox Properties
|Section2={{Chembox Properties
| C=15 | H=12 | O=6
| Formula = C<sub>15</sub>H<sub>12</sub>O<sub>6</sub>
⚫
| Appearance =
| MolarMass = 288.25 g/mol
| Density=
| ExactMass = 288.063388
⚫
| MeltingPt=
⚫
| Appearance =
| Density=
| BoilingPt=
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| Solubility =
⚫
| MeltingPt=
| BoilingPt=
⚫
| Solubility =
}}
}}
|Section3= {{Chembox Hazards
|Section3={{Chembox Hazards
| MainHazards=
| MainHazards=
| FlashPt=
| FlashPt=
| AutoignitionPt =
| Autoignition=
}}
}}
}}
}}


'''Aromadedrin''' ('''dihydrokaempferol''') is a [[flavanonol]], a type of [[flavonoid]]. It can be found in the wood of ''[[Pinus sibirica]]''.<ref>[http://www.springerlink.com/content/p71547638613614r/ Aromadendrin, apigenin, and kaempferol from the wood of Pinus sibirica, V. I. Lutskii, A. S. Gromova and N. A. Tyukavkina, 1971]</ref>
'''Aromadendrin''' ('''aromodendrin''' or '''dihydrokaempferol''') is a [[flavanonol]], a type of [[flavonoid]]. It can be found in the wood of ''[[Pinus sibirica]]''.<ref>{{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}}</ref>


==Metabolism==
==Metabolism==
The enzyme [[dihydrokaempferol 4-reductase]] uses [[leucopelargonidin|''cis''-3,4-leucopelargonidin]] and [[Nicotinamide adenine dinucleotide phosphate|NADP<sup>+</sup>]] to produce (+)-aromadedrin, NADPH, and H<sup>+</sup>.
The enzyme [[dihydrokaempferol 4-reductase]] uses [[leucopelargonidin|''cis''-3,4-leucopelargonidin]] and [[Nicotinamide adenine dinucleotide phosphate|NADP<sup>+</sup>]] to produce (+)-aromadendrin, NADPH, and H<sup>+</sup>.


===Glycosides===
===Glycosides===
(2''R'',3''R'')-''trans''-Aromadendrin-7-''O''-''beta''-<small>D</small>-glucopyranoside-6"-(4"-hydroxy-2"-methylene butanoate) is an acetylated glucoside of aromadendrin isolated from the stem bark of ''[[Afzelia bella]]''<ref>[http://www.ncbi.nlm.nih.gov/pubmed/11324912 Constituents of Afzelia bella stem bark. Binutu OA, Cordell GA.]</ref> (Fabaceae).
(2''R'',3''R'')-''trans''-Aromadendrin-7-''O''-''beta''-<small>D</small>-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]]''<ref>{{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}}</ref> (Fabaceae).


[[Phellamurin]] is the 8-[[prenyl]] 7-[[glucoside]] derivative of aromadendrin.
[[Phellamurin]] is the 8-[[prenyl]] 7-[[glucoside]] derivative of aromadendrin.


==Chemistry==
==Chemistry==
(+)-[[Leucopelargonidin]], (2''R'',3''S'',4''R'')-3,4,5,7,4-pentahydroxyflavan, can be synthesized from (+)-aromadendrin by [[sodium borohydride]] reduction.<ref>[http://www.springerlink.com/content/v2142k53542347l5/ Leucoanthocyanidins as intermediates in anthocyanidin biosynthesis in flowers of Matthiola incana R. Br. Werner Heller, Lothar Britsch, Gert Forkmann and Hans Grisebach, 1984]</ref>
(+)-[[Leucopelargonidin]], (2''R'',3''S'',4''R'')-3,4,5,7,4'-pentahydroxyflavan, can be synthesized from (+)-aromadendrin by [[sodium borohydride]] reduction.<ref>{{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}}</ref>


==References==
==References==
{{reflist}}
{{reflist}}

==External links==
*{{Commons category-inline|Aromadedrin}}


{{Flavanonol}}
{{Flavanonol}}
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[[Category:Flavanonols]]
[[Category:Flavanonols]]
[[Category:Resorcinols]]
[[Category:Resorcinols]]


{{Natural-phenol-stub}}
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