Dihydrocaffeic acid

Last updated
Dihydrocaffeic acid
Dihydrocaffeic acid.svg
Names
Preferred IUPAC name
3-(3,4-Dihydroxyphenyl)propanoic acid
Identifiers
3D model (JSmol)
2213449
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.012.804 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 214-083-8
482169
KEGG
PubChem CID
UNII
  • InChI=1S/C9H10O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1,3,5,10-11H,2,4H2,(H,12,13)
    Key: DZAUWHJDUNRCTF-UHFFFAOYSA-N
  • C1=CC(=C(C=C1CCC(=O)O)O)O
Properties
C9H10O4
Molar mass 182.175 g·mol−1
Melting point 136 °C (277 °F; 409 K)
42.8 g/L
Hazards
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Dihydrocaffeic acid (DHCA; systematic name 3-(3,4-dihydroxyphenyl)propionic acid [1] ) is a phytochemical found in grapes and other plants. DHCA is known to lower IL-6 production through down regulation of DNMT1 expression and inhibition of DNA methylation of the IL-6 gene in mice. DHCA in combination with malvidin-3′-O-glucoside (Mal-gluc) is effective in promoting resilience against stress by modulating brain synaptic plasticity and peripheral inflammation. DHCA/Mal-gluc also significantly lowered depression like phenotypes in mice that had increased peripheral inflammation caused by transplantation of hematopoietic progenitor cells from other more stress-susceptible mice. [2]

References

  1. ↑ PubChem. "3-(3,4-Dihydroxyphenyl)propionic acid". pubchem.ncbi.nlm.nih.gov. Retrieved 2019-12-13.
  2. ↑ Wang, Jun; Hodes, Georgia E.; Zhang, Hongxing; Zhang, Song; Zhao, Wei; Golden, Sam A.; Bi, Weina; Menard, Caroline; Kana, Veronika; Leboeuf, Marylene; Xie, Marc (2018-02-02). "Epigenetic modulation of inflammation and synaptic plasticity promotes resilience against stress in mice". Nature Communications. 9 (1): 477. doi:10.1038/s41467-017-02794-5. ISSN   2041-1723. PMC   5797143 . PMID   29396460. CC-BY icon.svg Material was copied from this source, which is available under a Creative Commons Attribution 4.0 International License.
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