Dihydrocaffeic acid

Dihydrocaffeic acid
Names
	Preferred IUPAC name 3-(3,4-Dihydroxyphenyl)propanoic acid
Identifiers
CAS Number	1078-61-1 ;
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 ;
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
Molar mass	182.175 g·mol−1
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

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

^ PubChem. "3-(3,4-Dihydroxyphenyl)propionic acid". pubchem.ncbi.nlm.nih.gov. Retrieved 2019-12-13.
^ 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. Material was copied from this source, which is available under a Creative Commons Attribution 4.0 International License.

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[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. Material was copied from this source, which is available under a Creative Commons Attribution 4.0 International License.

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