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; 3-O-Caffeoylquinic acid
Identifiers
CAS Number	906-33-2 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:16384 ;
ChEMBL	ChEMBL249450 ;
ChemSpider	4444237 ;
ECHA InfoCard	100.011.816
PubChem CID	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	354.311 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 or 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 also found in Sunflower seed meal, Globe artichoke heads, Chicory [Red], Half-highbush blueberry, Highbush blueberry, Lovage, Burdock root, and Highbush blueberry.[2] It is an isomer of chlorogenic acid; both of these are members of the caffeoylquinic acid class of molecules.

Neochlorogenic acid may have potential as a chemopreventive dietary compound.[3] Neochlorogenic acid could be involved in the laxative effect observed in prunes.[4]

Urtica dioica is a good source.[5]

References

Infante, Rodrigo; Contador, Loreto; Rubio, Pía; Aros, Danilo; Peña-Neira, Álvaro (July–September 2011). "Postharvest sensory and phenolic characterization of 'Elegant Lady' and 'Carson' peaches". Chilean Journal of Agricultural Research. 71 (3): 445–451. doi:10.4067/S0718-58392011000300016.
"Phenol Explorer". 2015-06-01.
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.
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. S2CID 31159565.
Francišković, Marina; Gonzalez-Pérez, Raquel; Orčić, Dejan; Sánchez de Medina, Fermín; Martínez-Augustin, Olga; Svirčev, Emilija; Simin, Nataša; Mimica-Dukić, Neda (2017). "Chemical Composition and Immuno-Modulatory Effects of Urtica dioica L. (Stinging Nettle) Extracts". Phytotherapy Research. 31 (8): 1183–1191. doi:10.1002/ptr.5836. ISSN 0951-418X. PMID 28544187. S2CID 33903986.

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[1] Infante, Rodrigo; Contador, Loreto; Rubio, Pía; Aros, Danilo; Peña-Neira, Álvaro (July–September 2011). "Postharvest sensory and phenolic characterization of 'Elegant Lady' and 'Carson' peaches". Chilean Journal of Agricultural Research. 71 (3): 445–451. doi:10.4067/S0718-58392011000300016.

[2] "Phenol Explorer". 2015-06-01.

[3] 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.

[4] 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. S2CID 31159565.

[FranciškovićGonzalez-Pérez2017-5] Francišković, Marina; Gonzalez-Pérez, Raquel; Orčić, Dejan; Sánchez de Medina, Fermín; Martínez-Augustin, Olga; Svirčev, Emilija; Simin, Nataša; Mimica-Dukić, Neda (2017). "Chemical Composition and Immuno-Modulatory Effects of Urtica dioica L. (Stinging Nettle) Extracts". Phytotherapy Research. 31 (8): 1183–1191. doi:10.1002/ptr.5836. ISSN 0951-418X. PMID 28544187. S2CID 33903986.