Chlorogenic Acid

Chlorogenic Acid

Cayman Chemical Item Number 70930

NSC 407296; Heriguard; 3-O-Caffeoylquinic acid (CAS 327-97-9)

Chlorogenic Acid (CAS 327-97-9)

Description

Chlorogenic acid is a phenolic natural product isolated from the leaves and fruits of dicotyledonous plants, including the coffee bean. Structurally, chlorogenic acid is the ester of caffeic acid with the 3-hydroxyl group of quinic acid. Chlorogenic acid is an important factor in plant metabolism. It is also an antioxidant and an inhibitor of the tumor promoting activity of phorbol esters.^1,2 Chlorogenic acid, at concentrations as high as 100 µM, does not inhibit the 5-lipoxygenase activity of ionophore-stimulated human polymorphonuclear leukocytes.³

1 Huang, M.T., Smart, R.C., Wong, C., et al. Inhibitory effect of curcumin, chlorogenic acid, caffeic acid, and ferulic acid on tumor promotion in mouse skin by 12-O-tetradecanoylphorbol-13-acetate. Cancer Res 48 5941-5946 (1988).

2 Conney, A.H., Lysz, T., Ferraro, T., et al. Inhibitory effect of curcumin and some related dietary compounds on tumor promotion and arachidonic acid metabolism in mouse skin. Adv Enzyme Regul 31 385-396 (1991).

3 Kimura, Y., Okuda, H., Okuda, T., et al. Studies on the activities of tannins and related compounds, X. Effects of caffeetannins and related compounds on arachidonate metabolism in human polymorphonuclear leukocytes. J Nat Prod 50 392-399 (1987).

Synonyms

NSC 407296
Heriguard
3-O-Caffeoylquinic acid

Formal Name

3R-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1S,4R,5R-trihydroxy-cyclohexanecarboxylic acid

CAS Number

327-97-9

Molecular Formula

C₁₆H₁₈O₉

Formula Weight

354.3

Formulation

A crystalline solid

Purity

≥95%

λ_max

219, 246, 331 nm

Stability

2 years

Storage

4°C

Shipping

Room temperature in continental US; may vary elsewhere

SMILES

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OC1=CC=C(/C=C/C(O[C@H]2[C@H](O)[C@H](O)C[C@@](O)(C(O)=O)C2)=O)C=C1O

Background Reading

Conney, A.H., Lysz, T., Ferraro, T., et al. Inhibitory effect of curcumin and some related dietary compounds on tumor promotion and arachidonic acid metabolism in mouse skin. Adv Enzyme Regul 31 385-396 (1991).

Huang, M.T., Smart, R.C., Wong, C., et al. Inhibitory effect of curcumin, chlorogenic acid, caffeic acid, and ferulic acid on tumor promotion in mouse skin by 12-O-tetradecanoylphorbol-13-acetate. Cancer Res 48 5941-5946 (1988).

Kimura, Y., Okuda, H., Okuda, T., et al. Studies on the activities of tannins and related compounds, X. Effects of caffeetannins and related compounds on arachidonate metabolism in human polymorphonuclear leukocytes. J Nat Prod 50 392-399 (1987).

Grace, S.C., Salgo, M.G., and Pryor, W.A. Scavenging of peroxynitrite by a phenolic/peroxidase system prevents oxidative damage to DNA. FEBS Lett 246 24-28 (1998).

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Size

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