L'Acido clorogenico è un componente naturale, un polifenolo molto diffuso, un estere cinnamato composto da acido trans-caffeico e acido chinico.

Si trova in :

• caffè
• frutta
• verdura

Il nome definisce la struttura della molecola:

• Chlorogenico deriva dal greco "chloros", che significa verde, e "genos", che significa dare origine a. Questo termine si riferisce alla capacità di questa sostanza di produrre un colore verde quando ossidata.
• Acido indica che si tratta di un acido, una sostanza che può donare ioni idrogeno e reagire con basi.

Materie prime utilizzate nella produzione:

L'acido clorogenico è un composto naturale presente in molte piante, in particolare nel caffè verde. È un estere dell'acido caffeico e dell'acido chinico.

Processo di sintesi chimica industriale passo per passo:

• Estrazione di acido clorogenico da fonti naturali, in genere chicchi di caffè verde non tostati.
• Macinazione dei chicchi e trattamento con solventi adatti per estrarre l'acido clorogenico.
• Purificazione dell'estratto per rimuovere impurità e residui di solvente.
• Concentrazione dell'estratto per aumentarne la purezza.
• Controllo di qualità per garantire il rispetto degli standard.
• Asciugatura dell'estratto per ottenere una forma in polvere.

Forma e Colore.

L'acido clorogenico si presenta come una polvere cristallina di colore giallo-verde o marrone chiaro.

Applicazioni Commerciali.

Utilizzato in integratori alimentari e prodotti per la salute, in particolare per le sue proprietà antiossidanti. È anche studiato per i suoi effetti potenziali sulla perdita di peso e sul metabolismo del glucosio.

Studi

Ha proprietà antiossidanti e antitumorali. (1)

E' stato studiato in concomitanza con l'assunzione del caffè. (2) (3).

Acido clorogenico studi

Formula molecolare: C₁₆H₁₈O₉

Peso molecolare: 354.311 g/mol

UNII: 318ADP12RI

CAS: 327-97-9  202650-88-2

EC Number: 206-325-6

PubChem Substance ID 329749317

MDL number MFCD00003862

Sinonimi: 

• 3-Caffeoylquinic acid
• 3-O-Caffeoylquinic acid
• 3-(3,4-Dihydroxycinnamoyl)quinic acid
• Chlorogenate
• Heriguard
• Hlorogenic acid
• Caffeoyl quinic acid
• 5-O-(3,4-Dihydroxycinnamoyl)-L-quinic acid
• 1,3,4,5-Tetrahydroxycyclohexanecarboxylic acid 3-(3,4-dihydroxycinnamate
• 5-Caffeoylquinic acid
• (1S,3R,4R,5R)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,4,5-trihydroxycyclohexane-1-carboxylic acid
• [1S-(1alpha,3beta,4alpha,5alpha)]-3-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylic acid
• [1S-(1alpha,3beta,4alpha,5alpha)]3-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylic acid
• Cyclohexanecarboxylic acid, 3-((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-1,4,5-trihydroxy-, (1S,3R,4R,5R)-
• cyclohexanecarboxylic acid, 3-[[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxy-, (1S,3R,4R,5R)-
• Cyclohexanecarboxylic acid, 3-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxy-, [1S-(1alpha,3beta,4alpha,5alpha)]-
• 3-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propenyl]oxy] 1,4,5-trihydroxycyclohexanecarboxylic acid
• 5-caffeoyl quinic acid
• (1S,3R,4R,5R)-3-(((E)-3-(3,4-dihydroxyphenyl)acryloyl)oxy)-1,4,5-trihydroxycyclohexane-1-carboxylic acid
• (1S,3R,4R,5R)-3-((E)-3-(3,4-dihydroxyphenyl)acryloyloxy)-1,4,5-trihydroxycyclohexanecarboxylic acid
• 3-Caffeoylquinate
• 1,3,4,5-tetrahydroxycyclohexanecarboxylic acid 3-(3,4-dihydroxycinnamate)
• 3-(3,4-Dihydroxycinnamoyl)quinate
• trans-5-O-caffeoyl-D-quinate
• Cyclohexanecarboxylic acid, 3-((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-1,4,5-trihydroxy-, (1S-(1-alpha,3-beta,4-alpha,5-alpha))-
• Cyclohexanecarboxylic acid, 3-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxy-, (1S,3R,4R,5R)-

Bibliografia________________________________________________________________________

(1) Kasai H, Fukada S, Yamaizumi Z, Sugie S, Mori H. Action of chlorogenic acid in vegetables and fruits as an inhibitor of 8-hydroxydeoxyguanosine formation in vitro and in a rat carcinogenesis model. Food Chem Toxicol. 2000 May;38(5):467-71. doi: 10.1016/s0278-6915(00)00014-4. PMID: 10762733.

Abstract. Various plant extracts, such as carrot, burdock (gobou), apricot and prune, showed inhibitory effects in an in vitro assay of lipid peroxide-induced 8-hydroxydeoxyguanosine (8-OH-dG) formation. The major inhibitor purified from various plants extracts was identified as chlorogenic acid (CA), on the basis of UV- and mass-spectra and comparison with a standard sample. To examine whether CA also inhibits 8-OH-dG formation in animal organs, an oxygen radical-forming carcinogen, 4-nitroquinoline-1-oxide, was administered to rats, with or without CA. The 8-OH-dG level in the DNA of the rat tongue, the target organ, was significantly reduced in the CA-treated group.

(2) Nardini M, Cirillo E, Natella F, Scaccini C. Absorption of phenolic acids in humans after coffee consumption. J Agric Food Chem. 2002 Sep 25;50(20):5735-41. doi: 10.1021/jf0257547. 

Abstract. Despite extensive literature describing the biological effects of polyphenols, little is known about their absorption from diet, one major unresolved point consisting of the absorption of the bound forms of polyphenols. In this view, in the present work we studied the absorption in humans of phenolic acids from coffee, a common beverage particularly rich in bound phenolic acids, such as caffeic acid, ferulic acid, and p-coumaric acid. Coffee brew was analyzed for free and total (free + bound) phenolic acids. Chlorogenic acid (5'-caffeoylquinic acid), a bound form of caffeic acid, was present in coffee at high levels, while free phenolic acids were undetectable. After alkaline hydrolysis, which released bound phenolic acids, ferulic acid, p-coumaric acid, and high levels of caffeic acid were detected. Plasma samples were collected before and 1 and 2 h after coffee administration and analyzed for free and total phenolic acid content. Two different procedures were applied to release bound phenolic acids in plasma: beta-glucuronidase treatment and alkaline hydrolysis. Coffee administration resulted in increased total plasma caffeic acid concentration, with an absorption peak at 1 h. Caffeic acid was the only phenolic acid found in plasma samples after coffee administration, while chlorogenic acid was undetectable. Most of caffeic acid was present in plasma in bound form, mainly in the glucuronate/sulfate forms. Due to the absence of free caffeic acid in coffee, plasma caffeic acid is likely to be derived from hydrolysis of chlorogenic acid in the gastrointestinal tract.

(3) Olthof MR, Hollman PC, Katan MB. Chlorogenic acid and caffeic acid are absorbed in humans. J Nutr. 2001 Jan;131(1):66-71. doi: 10.1093/jn/131.1.66. 

Abstract. Chlorogenic acid, an ester of caffeic acid and quinic acid, is a major phenolic compound in coffee; daily intake in coffee drinkers is 0.5-1 g. Chlorogenic acid and caffeic acid are antioxidants in vitro and might therefore contribute to the prevention of cardiovascular disease. However, data on the absorption of chlorogenic acid and caffeic acid in humans are lacking. We determined the absorption of chlorogenic acid and caffeic acid in a cross-over study with 4 female and 3 male healthy ileostomy subjects. In such subjects, degradation by the colonic microflora is minimal and absorption can be calculated as the amount ingested minus the amount excreted in ileostomy effluent. The ileostomy subjects ingested 2.8 mmol chlorogenic acid and 2.8 mmol caffeic acid on separate days in random order and subsequently collected ileostomy fluid and urine for 24 h. Absorption of chlorogenic acid was 33 +/- 17% (mean +/- SD) and of caffeic acid 95 +/- 4%. Traces of the ingested chlorogenic acid and 11% of the ingested caffeic acid were excreted in urine. Thus, one third of chlorogenic acid and almost all of the caffeic acid were absorbed in the small intestine of humans. This implies that part of chlorogenic acid from foods will enter into the blood circulation, but most will reach the colon.