Neochlorogenic acid

Neochlorogenic acid

Names
IUPAC name (1R,3R,4S,5R)-3-{[(2E)-3-(3,4-Dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexanecarboxylic acid
Other names 5-O-Caffeoylquinic acid
Identifiers
CAS Number	906-33-2
ChEBI	CHEBI:16384
ChEMBL	ChEMBL249450
ChemSpider	4444237
Jmol interactive 3D	Image
PubChem	5280633
UNII	O4601UER1Z
InChI InChI=1S/C16H18O9/c17-9-3-1-8(5-10(9)18)2-4-13(20)25-12-7-16(24,15(22)23)6-11(19)14(12)21/h1-5,11-12,14,17-19,21,24H,6-7H2,(H,22,23)/b4-2+/t11-,12-,14+,16-/m1/s1 Key: CWVRJTMFETXNAD-NXLLHMKUSA-N InChI=1/C16H18O9/c17-9-3-1-8(5-10(9)18)2-4-13(20)25-12-7-16(24,15(22)23)6-11(19)14(12)21/h1-5,11-12,14,17-19,21,24H,6-7H2,(H,22,23)/b4-2+/t11-,12-,14+,16-/m1/s1 Key: CWVRJTMFETXNAD-NXLLHMKUBY
SMILES O=C(O)[C@@]2(O)C[C@@H](O)[C@H](O)[C@H](OC(=O)\C=C\c1ccc(O)c(O)c1)C2
Properties
Chemical formula	C16H18O9
Molar mass	354.31 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Neochlorogenic acid is a natural polyphenolic compound found in some types of dried fruits and a variety of other plant sources such as peaches.^[1] It is an isomer of chlorogenic acid.

Neochlorogenic acid may have potential as a chemopreventive dietary compound.^[2] Neochlorogenic acid could be involved in the laxative effect observed in prunes.^[3]

References

1. Postharvest sensory and phenolic characterization of ‘Elegant Lady’ and ‘Carson’ peaches. Rodrigo Infante, Loreto Contador, Pía Rubio, Danilo Aros and Álvaro Peña-Neira, Chilean Journal Of Agricultural Research, 71(3), July-September 2011, pages 445-451 (article)
2. Noratto, G; Porter, W; Byrne, D; Cisneros-Zevallos, L (2009). "Identifying peach and plum polyphenols with chemopreventive potential against estrogen-independent breast cancer cells". Journal of Agricultural and Food Chemistry 57 (12): 5219–26. doi:10.1021/jf900259m. PMID 19530711.
3. Stacewicz-Sapuntzakis, M; Bowen, PE; Hussain, EA; Damayanti-Wood, BI; Farnsworth, NR (2001). "Chemical composition and potential health effects of prunes: a functional food?". Critical reviews in food science and nutrition 41 (4): 251–86. doi:10.1080/20014091091814. PMID 11401245.