Dihydrocaffeic acid

Dihydrocaffeic acid

Names
Preferred IUPAC name 3-(3,4-Dihydroxyphenyl)propanoic acid
Identifiers
CAS Number	1078-61-1 Y
3D model (JSmol)	Interactive image
3DMet	B03934
Beilstein Reference	2213449
ChEBI	CHEBI:48400
ChEMBL	ChEMBL136927
ChemSpider	308986
ECHA InfoCard	100.012.804
EC Number	214-083-8
Gmelin Reference	482169
KEGG	C10447
PubChem CID	348154
UNII	MSW0228VUB Y
CompTox Dashboard (EPA)	DTXSID40221919
InChI 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
SMILES C1=CC(=C(C=C1CCC(=O)O)O)O
Properties
Chemical formula	C9H10O4
Melting point	136 °C (277 °F; 409 K)
Solubility in water	42.8 g/L
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	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). Infobox references

3(3,4-dihydroxy-phenyl) propionic acid commonly referred to as dihydrocaffeic acid or DHCA 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.