(-)-Epicatechin (CAS 490-46-0) | Cayman Chemical
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(−)-Epicatechin

Item № 11807
CAS № 490-46-0
Purity ≥90%
product image
                (CAS 490-46-0)
SIZE PRICE QUANTITY SUBTOTAL
CART TOTAL
     1 mg $25.00 0.00
     5 mg $88.00 0.00
     10 mg $138.00 0.00
     25 mg $281.00 0.00

Pricing updated 2019-01-16. Prices are subject to change without notice.

Description
Synonyms
  • epi-Catechin
  • NSC 81161

Catechin is a polyphenolic flavonoid that has been isolated from a variety of natural sources including tea leaves, grape seeds, and the wood and bark of trees such as acacia and mahogany.1,2 Catechin is a more potent antioxidant than ascorbate or α-tocopherol in certain in vitro lipid peroxidation assays.3 (−)-Epicatechin is a 2R,3R stereoisomer of catechin. Like catechin, (−)-epicatechin is a powerful antioxidant.4 It inhibits cyclooxygenase 1 (IC50 = 3.2 μM).5 Also, at 100 µM, (−)-epicatechin induces apoptosis in human adenocarcinoma PC-9 cells and stimulates the inhibition of tumor necrosis factor-α release from BALB-c/3T3 cells treated with epigallocatechin gallate.6

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Technical Information
Formal Name
2R-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3R,5,7-triol
CAS Number
490-46-0
Synonyms
  • epi-Catechin
  • NSC 81161
Molecular Formula
C15H14O6
Formula Weight
290.3
Purity
≥90%
Formulation
A crystalline solid
λmax
278 nm
SMILES
OC1=CC2=C(C[C@@H](O)[C@@H](C3=CC=C(O)C(O)=C3)O2)C(O)=C1
InChI Code
InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1
InChI Key
PFTAWBLQPZVEMU-UKRRQHHQSA-N

Warning - this product is not for human or veterinary use.

Shipping & Storage
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
Stability
≥ 2 years
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Additional Information

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References & Product Citations
Product Description References

1. Bonilla, F., Mayen, M., Merida, J., et al. Extraction of phenolic compounds from red grape marc for use as food lipid antioxidants Food Chemistry 66, 209-215 (1999).

2. Ravindranath, M.H., Ramasamy, V., Moon, S., et al. Differential growth suppression of human melanoma cells by tea (Camellia sinensis) epicatechins (ECG, EGC and EGCG) Evidence-Based Complementary and alternative Medicine 6(4), 523-530 (2009).

3. Zhao, J., Wang, J., Chen, Y., et al. Anti-tumor-promoting activity of a polyphenolic fraction isolated from grape seeds in the mouse skin two-stage initiation-promotion protocol and identification of procyanidin B5-3'-gallate as the most effective antioxidant constituent Carcinogenesis 20, 1737-1745 (1999).

4. Xu, J.Z., Yeung, S.Y.V., Chang, Q., et al. Comparison of antioxidant activity and bioavailability of tea epicatechins with their epimers British Journal of Nutrition 91(6), 873-881 (2004).

5. Waffo-Téguo, P., Hawthorne, M.E., Cuendet, M., et al. Potential cancer-chemopreventive activities of wine stilbenoids and flavans extracted from grape (Vitis vinifera) cell cultures Nutrition and Cancer 40(2), 173-179 (2001).

6. Suganuma, M., Okabe, S., Kai, Y., et al. Synergisitc effects of (--)-epigallocatechin gallate with (--)-epicatechin, sulindac, or tamoxifen on cancer-preventive activity in the human lung cancer cell line PC-9 Cancer Research 59(1), 44-47 (1999).

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