Neochlorogenic acid

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Neochlorogenic acid

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^N
PubChem	5280633
ChemSpider	4444237^Y
ChEBI	CHEBI:16384^Y
ChEMBL	CHEMBL249450^Y
Jmol-3D images	{{#if: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\|Image 1
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
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^Y Key: CWVRJTMFETXNAD-NXLLHMKUSA-N^Y 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
Properties
Molecular formula	C₁₆H₁₈O₉
Molar mass	354.31 g mol⁻¹
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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] Neochloroenic acid could be involved in the laxative effect observed in prunes.^[3]

References

↑ 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)
↑ 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.

Types of hydroxycinnamic acids

Aglycones

Precursor	Cinnamic acid

Monohydroxycinnamic acids (Coumaric acids)	p-Coumaric acid o-Coumaric acid m-Coumaric acid

Dihydroxycinnamic acids	Caffeic acid (3,4-dihydroxycinnamic acid) Umbellic acid (2,4-dihydroxycinnamic acid) 2,3-Dihydroxycinnamic acid 2,5-Dihydroxycinnamic acid 3,5-Dihydroxycinnamic acid

Trihydroxycinnamic acids	3,4,6-Trihydroxycinnamic acid

O-methylated forms	Ferulic acid 5-Hydroxyferulic acid Sinapinic acid

others	Plicatin A Plicatin B

Esters

glycoside-likes

Esters of
caffeic acid
with cyclitols

esters of quinic acid	Chlorogenic acid (3-caffeoylquinic acid) Cryptochlorogenic acid (4-O-caffeoylquinic acid) Neochlorogenic acid (5-O-Caffeoylquinic acid) Cynarine (1,5-dicaffeoylquinic acid) 3,4-dicaffeoylquinic acid 3,5-dicaffeoylquinic acid

esters of shikimic acid	Dactylifric acid (3-O-caffeoylshikimic acid)

Glycosides

Ferulic acid glucoside
p-Coumaric acid glucoside
1-Sinapoyl-D-glucose

Tartaric acid esters

Caftaric acid
Cichoric acid (Dicaffeoyltartaric acid)
Coutaric acid
Fertaric acid
Grape reaction product (caftaric acid conjugated with glutathione)

Other esters
with caffeic acid

Ethyl caffeate
Methyl caffeate
CAPE (Caffeic acid phenethyl ester)
Rosmarinic acid (ester with 3,4-dihydroxyphenyl lactic acid)

Oligomeric forms

Dimers	Diferulic acids (DiFA) : 5,5'-Diferulic acid, 8-O-4'-Diferulic acid, 8,5'-Diferulic acid, 8,5'-DiFA (DC), 8,5'-DiFA (BF), 8,8'-Diferulic acid

Trimers	Triferulic acids : 5-5',8'-O-4"-Triferulic acid

Tetramers	Tetraferulic acids

Conjugates with coenzyme A

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