A diastereoisomer of catechin
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(−)-Catechin

Item No. 18644

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2S,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
CAS Number
18829-70-4
Synonyms
  • (2S,3R)-Catechin
  • ent-Catechin
  • L-Catechin
  • NSC 81746
Molecular Formula
C15H14O6
Formula Weight
290.3
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 25 mg/mlDMSO: 15 mg/mlEthanol: 5 mg/mlPBS (pH 7.2): 1 mg/ml
λmax
279 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-HIFRSBDPSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Product Description

    (−)-Catechin is a diastereoisomer of catechin having a trans 2S,3R configuration at the chiral center. Catechins, in general, are polyphenolic flavonoids that can be isolated from a variety of natural sources including tea leaves, grape seeds, and the wood and bark of trees such as acacia and mahogany. Catechins are potent antioxidants that inhibit the free radical-induced oxidation of isolated LDL by AAPH (Item No. 82235).1,2 Catechins and other related procyanidin compounds have antitumor activity when tested in a two-stage mouse epidermal carcinoma model employing topical application.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Frémont, L., Belguendouz, L., and Delpal, S. Antioxidant activity of resveratrol and alcohol-free wine polyphenols related to LDL oxidation and polyunsaturated fatty acids. Life Sci. 64(26), 2511-2521 (1999).

    2. 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).