Dihydrocaffeic acid

Last updated
Dihydrocaffeic acid
Dihydrocaffeic acid.svg
Names
Preferred IUPAC name
3-(3,4-Dihydroxyphenyl)propanoic acid
Identifiers
3D model (JSmol)
3DMet
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]

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CH
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<span class="mw-page-title-main">Giulio Maria Pasinetti</span>

Giulio Maria Pasinetti is the Program Director of the Center on Molecular Integrative Neuroresilience and is the Saunders Family Chair in Neurology at the Icahn School of Medicine at Mount Sinai (ISMMS) in New York City. Pasinetti is a Professor of Neurology, Psychiatry, Neuroscience, and Geriatrics and Palliative Medicine at ISMMS.

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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.