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Kaempferol
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
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
100.007.535
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
C15 H10 O6
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).
Chemical compound
Kaempferol (3,4′,5,7-tetrahydroxyflavone) is a natural
flavonol , a type of
flavonoid , found in a variety of plants and plant-derived foods including
kale ,
beans ,
tea ,
spinach , and
broccoli .
[1] Kaempferol is a yellow crystalline solid with a melting point of 276–278 °C (529–532 °F). It is slightly soluble in water and highly soluble in hot
ethanol ,
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
Pteridophyta ,
Pinophyta , and
Angiospermae . Within Pteridophyta and Pinophyta, kaempferol has been found in diverse families. Kaempferol has also been identified in
Dicotyledons and
Monocotyledons of Angiosperms.
[3] The total average intake of flavonols and flavones in a normal diet is estimated as 23 mg/day, to which kaempferol contributes approximately 17%.
[4] Common foods that contain kaempferol include:
apples ,
[5]
grapes ,
[5]
tomatoes ,
[5]
green tea ,
[5]
potatoes ,
[4]
onions ,
[3]
broccoli ,
[3]
Brussels sprouts ,
[3]
squash ,
[3]
cucumbers ,
[3]
lettuce ,
[3]
green beans ,
[3]
peaches ,
[3]
blackberries ,
[3]
raspberries ,
[3] and
spinach .
[3] Plants that are known to contain kaempferol include
Aloe vera ,
[3]
Coccinia grandis ,
[3]
Cuscuta chinensis ,
[6]
Euphorbia pekinensis ,
[3]
Glycine max ,
[3]
Hypericum perforatum ,
[3]
Pinus sylvestris ,
[7]
Moringa oleifera ,
[8]
Rosmarinus officinalis ,
[3]
Sambucus nigra ,
[3]
Toona sinensis ,
[3] and
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]
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
^ Holland TM, Agarwal P, Wang Y, Leurgans SE, Bennett DA, Booth SL,
Morris MC (2020-01-29).
"Dietary flavonols and risk of Alzheimer dementia" . Neurology . 94 (16): e1749–e1756.
doi :
10.1212/WNL.0000000000008981 .
ISSN
0028-3878 .
PMC
7282875 .
PMID
31996451 .
^
Kaempferol at
Merriam-Webster .com; retrieved October 20, 2017
^
a
b
c
d
e
f
g
h
i
j
k
l
m
n
o
p
q
r
s
t
u
v
w Calderón Montaño JM, Burgos Morón E, Pérez Guerrero C, López Lázaro M (April 2011). "A review on the dietary flavonoid kaempferol". Mini Reviews in Medicinal Chemistry . 11 (4): 298–344.
doi :
10.2174/138955711795305335 .
PMID
21428901 .
^
a
b Liu RH (May 2013).
"Health-promoting components of fruits and vegetables in the diet" . Advances in Nutrition . 4 (3): 384S–392S.
doi :
10.3945/an.112.003517 .
PMC
3650511 .
PMID
23674808 .
^
a
b
c
d Kim SH, Choi KC (December 2013).
"Anti-cancer Effect and Underlying Mechanism(s) of Kaempferol, a Phytoestrogen, on the Regulation of Apoptosis in Diverse Cancer Cell Models" . Toxicological Research . 29 (4): 229–234.
doi :
10.5487/TR.2013.29.4.229 .
PMC
3936174 .
PMID
24578792 .
^ Donnapee S, Li J, Yang X, Ge AH, Donkor PO, Gao XM, Chang YX (November 2014). "Cuscuta chinensis Lam.: A systematic review on ethnopharmacology, phytochemistry and pharmacology of an important traditional herbal medicine". Journal of Ethnopharmacology . 157 (C): 292–308.
doi :
10.1016/j.jep.2014.09.032 .
PMID
25281912 .
^ de la Luz Cádiz-Gurrea M, Fernández-Arroyo S, Segura-Carretero A (November 2014).
"Pine bark and green tea concentrated extracts: antioxidant activity and comprehensive characterization of bioactive compounds by HPLC-ESI-QTOF-MS" . International Journal of Molecular Sciences . 15 (11): 20382–20402.
doi :
10.3390/ijms151120382 .
PMC
4264173 .
PMID
25383680 .
^ Anwar F, Latif S, Ashraf M, Gilani AH (January 2007).
"Moringa oleifera: a food plant with multiple medicinal uses" . Phytotherapy Research . 21 (1): 17–25.
doi :
10.1002/ptr.2023 .
PMID
17089328 .
^ DuPont MS, Day AJ, Bennett RN, Mellon FA, Kroon PA (June 2004). "Absorption of kaempferol from endive, a source of kaempferol-3-glucuronide, in humans". European Journal of Clinical Nutrition . 58 (6): 947–954.
doi :
10.1038/sj.ejcn.1601916 .
PMID
15164116 .
S2CID
25720976 .
^
a
b
c
d
e
f
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h
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t
"USDA Database for the Flavonoid Content of Selected Foods, Release 3" (PDF) . U.S. Department of Agriculture. 2011.
^ Vogt T (January 2010).
"Phenylpropanoid biosynthesis" . Molecular Plant . 3 (1): 2–20.
doi :
10.1093/mp/ssp106 .
PMID
20035037 .
^ Flamini R, Mattivi F, De Rosso M, Arapitsas P, Bavaresco L (September 2013).
"Advanced knowledge of three important classes of grape phenolics: anthocyanins, stilbenes and flavonols" . International Journal of Molecular Sciences . 14 (10): 19651–19669.
doi :
10.3390/ijms141019651 .
PMC
3821578 .
PMID
24084717 .
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