Kaempferol

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Kaempferol
Skeletal formula of kaempferol
Ball-and-stick model of the kaempferol molecule
Names
IUPAC name
3,4′,5,7-Tetrahydroxyflavone
Systematic IUPAC name
3,5,7-Trihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
Other names
Kaempherol; Robigenin; Pelargidenolon; Rhamnolutein; Rhamnolutin; Populnetin; Trifolitin; Kempferol; Swartziol
Identifiers
3D model (
JSmol
)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
 100.007.535 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C15H10O6/c16-8-3-1-7(2-4-8)15-14(20)13(19)12-10(18)5-9(17)6-11(12)21-15/h1-6,16-18,20H
    Key: IYRMWMYZSQPJKC-UHFFFAOYSA-N
  • O=c1c(O)c(-c2ccc(O)cc2)oc2cc(O)cc(O)c12
Properties
C15H10O6
Molar mass 286.23 g/mol
Density 1.688 g/mL
Melting point 276–278 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Kaempferol (3,4′,5,7-tetrahydroxyflavone) is a natural

ethers, and DMSO. Kaempferol is named for 17th-century German naturalist Engelbert Kaempfer.[2]

Natural occurrence

Kaempferol is a secondary metabolite found in many plants, plant-derived foods, and traditional medicines.[3] Its flavor is considered bitter.

In plants and food

Kaempferol is common in

Ilex.[3] It also is present in endive.[9]

Foods Kaempferol

(mg/100 g)

capers
, raw 		259[10]
saffron 205[10]
capers
, canned 		131[10]
arugula, raw 59[10]
kale, raw 47[10]
mustard greens, raw 38[10]
ginger 34[10]
common bean, raw 26[10]
chinese cabbage, raw 23[10]
dill, fresh 13[10]
garden cress, raw 13[10]
chive, raw 10[10]
dock, raw 10[10]
endive, raw 10[10]
collard, raw 9[10]
broccoli, raw 8[10]
fennel leaves 7[10]
goji berry, dried 6[10]
drumstick leaves, raw 6[10]
chard, raw 4[10]

Biosynthesis

The biosynthesis of kaempferol occurs in four major steps:[3]

  • 4-coumaroyl-CoA
  • 4-Coumaroyl-CoA combines with three molecules of malonyl-CoA to form naringenin chalcone (tetrahydroxychalcone) through the action of the enzyme chalcone synthase
  • Naringenin chalcone is converted to
    dihydrokaempferol
  • Dihydrokaempferol has a double bond introduced into it to form kaempferol

The amino acid phenylalanine is formed from the Shikimate pathway, which is the pathway that plants use in order to make aromatic amino acids. This pathway is located in the plant plastid, and is the entry to the biosynthesis of phenylpropanoids.[11]

The

phenylpropanoid pathway is the pathway that converts phenylalanine into tetrahydroxychalcone. Flavonols, including kaempferol, are products of this pathway.[12]

Notes

  1. PMID 31996451
    .
  2. ^ Kaempferol at Merriam-Webster.com; retrieved October 20, 2017
  3. ^
    PMID 21428901
    .
  4. ^
    PMID 23674808
    .
  5. ^
    PMID 24578792
    .
  6. PMID 25281912
    .
  7. PMID 25383680
    .
  8. PMID 17089328
    .
  9. S2CID 25720976
    .
  10. ^ a b c d e f g h i j k l m n o p q r s t "USDA Database for the Flavonoid Content of Selected Foods, Release 3" (PDF). U.S. Department of Agriculture. 2011.
  11. PMID 20035037
    .
  12. PMID 24084717
    .

External links
Retrieved from "https://en.wikipedia.org/w/index.php?title=Kaempferol&oldid=1208687085"