Chlorogenic Acid

Cayman Chemical Item Number 70930

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

Chlorogenic Acid (CAS 327-97-9)

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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
  • 3-O-Caffeoylquinic acid
  • Heriguard
  • NSC 407296
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%
λmax 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
InCHI Code
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​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
InCHI Key
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CWVRJTMFETXNAD-PCNKEKKESA-N

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Chlorogenic Acid is available in the following screening library:

Size Price Quantity Subtotal
100 mg $6.00 $0.00
500 mg $27.00 $0.00
1 g $48.00 $0.00
5 g $175.00 $0.00
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Cart Total $0.00

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Pricing updated 2014-04-24. Prices are subject to change without notice.

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