60020
Caffeic acid
purum, ≥95.0% (HPLC)
Synonym(s):
3,4-Dihydroxybenzeneacrylic acid, 3,4-Dihydroxycinnamic acid, 3-(3,4-Dihydroxyphenyl)-2-propenoic acid
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About This Item
Linear Formula:
(HO)2C6H3CH=CHCO2H
CAS Number:
Molecular Weight:
180.16
EC Number:
206-361-2
UNSPSC Code:
12352100
PubChem Substance ID:
Beilstein/REAXYS Number:
1954563
MDL number:
Assay:
≥95.0% (HPLC)
Form:
powder
grade
purum
assay
≥95.0% (HPLC)
form
powder
mp
211-213 °C (dec.) (lit.)
SMILES string
OC(=O)\C=C\c1ccc(O)c(O)c1
InChI
1S/C9H8O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1-5,10-11H,(H,12,13)/b4-2+
InChI key
QAIPRVGONGVQAS-DUXPYHPUSA-N
Gene Information
human ... ELA2(1991)
rat ... Alox5(25290)
Biochem/physiol Actions
A natural dietary phenolic compound found in plants that is an anti-oxidant. Inhibits the synthesis of leukotrienes that are involved in immunoregulation, inflammation and allergy. Inhibits Cu2+-induced LDL oxidation.
Anti-oxidant phenolic compound found in plants; Inhibits the synthesis of leukotrienes.
Other Notes
Inhibits 5-lipoxygenase activity in mastocyma cells
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Y Koshihara et al.
Biochimica et biophysica acta, 792(1), 92-97 (1984-01-17)
.eukotrienes are significantly involved in immunoregulation and in a variety of diseases, including asthma, inflammation and various allergic conditions. They are initially biosynthesized by 5-lipoxygenase from arachidonic acid, which can also be metabolized to prostaglandin endoperoxide by cyclooxygenase. The specific
Emmanoel Vilaça Costa et al.
Journal of natural products, 73(6), 1180-1183 (2010-05-19)
Phytochemical investigation of the bark of Guatteria hispida afforded three new alkaloids, 9-methoxy-O-methylmoschatoline (1), 9-methoxyisomoschatoline (2), and isocerasonine (3), along with 10 known alkaloids, 8-oxopseudopalmatine (4), O-methylmoschatoline (5), lysicamine (6), liriodenine (7), 10-methoxyliriodenine (8), nornuciferine (9), anonaine (10), xylopine (11)
Susanne Vogel et al.
Journal of natural products, 71(7), 1237-1241 (2008-07-10)
The minor hop ( Humulus lupulus) chalcones 3'-geranylchalconaringenin (3), 5'-prenylxanthohumol (4), flavokawin (5), xanthohumol H (8), xanthohumol C (9), and 1'',2''-dihydroxanthohumol C (10) were synthesized. The non-natural chalcones 3'-geranyl-6'-O-methylchalconaringenin (2), 3'-methylflavokawin (6), and 2'-O-methyl-3'-prenylchalconaringenin (7) were also synthesized. Cytotoxicity was