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(-)-Catechin

SKU: C0453

Category: Phytochemicals

Synonyms: (2S,3R)-Catechin , ent-Catechin , L-Catechin , NSC 81746 , (-)-Catechol , (-)-trans-3,3',4',5,7-Pentahydroxyflavane , (2S,3R)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol; 18829-70-4
CAS-Number: C₁₅H₁₄O₆
Molecular Formula: 290.27
Molecular Weight

For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.

Product Data
Handling
Safety Information
Details

Specifications

Purity: ≥97% (HPLC)
Appearance: White to off-white powder
Identity: 1H-NMR

Properties

Solvents: DMSO (15 mg/ml), ethanol (5 mg/ml) or water (1 mg/ml).
Melting Point: 175-177 °C
Boiling Point: 630.4 °C (predicted)
Optical Activity: -16 ° (acetone/water)
Density: 1.593 g/cm3 (predicted)

Shipping: AMBIENT
Short Term Storage: +4°C
Long Term Storage: -20°C
Handling Advice: Protect from light and moisture.
Use / Stability: Stable for at least 2 years after receipt when stored at -20°C.

Transportation: Not dangerous goods

Description: Catechins have wide biological functionality, including antioxidant, anti-inflammatory, antiviral and anticancer activities. Catechins also play a key role in regulating carbohydrate and lipid metabolism. (-)-Catechin is comparatively less bioavailable than the stereoisomer (+)-catechin for intestinal absorption. It shows antioxidant (free radical scavenging) and antidiabetic activities. (-)-Catechin has been shown to be a stereoselective PPARγ agonist. It activates PPARγ in a dose-dependent fashion, promotes adipocyte differentiation and increases sensitivity to insulin. It markedly suppresses the expression of Kruppel-like factor 7 (KLF7) protein, which has recently been reported to inhibit the expression of adiponectin and other adipogenesis related genes, including leptin, PPARγ, C/EBPα, and aP2 in adipocytes. It also has shown to have anti-reverse transcriptase activity and maltase inhibitory activity. (-)-Catechin can also been used as a reference compound in high-performance liquid chromatography for quantification of polyphenols from plant extracts (HPLC).
Smiles: OC1=C2C(O[C@@H](C3=CC=C(O)C(O)=C3)[C@H](O)C2)=CC(O)=C1
InChi Key: PFTAWBLQPZVEMU-HIFRSBDPSA-N
References: (1) O. Inanami, et al., Free Rad. Res. 29, 359 (1998) , (2) S.-Y. Jeon, et al., Bioorg. Med. Chem. Lett. 13, 3905 (2003) , (3) J.L. Donovan, et al., Free Rad. Res. 40, 1029 (2006) , (4) S.Y. Cho, et al., Endocrinol. Metabol. 292, e1166 (2007) , (5) T. Matsui, et al., J. Agric. Food Chem. 55, 1 (2007) , (6) M.J. Jung, et al., Food Chem. 108, 482 (2008) , (7) D.W. Shin, et al., Biochem. Pharmacol. 77, 125 (2009) , (8) C. Ritter, et al., Anal. Bioanalyt. Chem. 397, 723 (2010)
InChi: 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

Catechins have wide biological functionality, including antioxidant, anti-inflammatory, antiviral and anticancer activities. Catechins also play a key role in regulating carbohydrate and lipid metabolism. (-)-Catechin is comparatively less bioavailable than the stereoisomer (+)-catechin for intestinal absorption. It shows antioxidant (free radical scavenging) and antidiabetic activities. (-)-Catechin has been shown to be a stereoselective PPARγ agonist. It activates PPARγ in a dose-dependent fashion, promotes adipocyte differentiation and increases sensitivity to insulin. It markedly suppresses the expression of Kruppel-like factor 7 (KLF7) protein, which has recently been reported to inhibit the expression of adiponectin and other adipogenesis related genes, including leptin, PPARγ, C/EBPα, and aP2 in adipocytes. It also has shown to have anti-reverse transcriptase activity and maltase inhibitory activity. (-)-Catechin can also been used as a reference compound in high-performance liquid chromatography for quantification of polyphenols from plant extracts (HPLC).

Artikelnummer: C0453 Kategorie: Phytochemicals

Zusätzliche Informationen

Zusätzliche Informationen

Synonyms	(2S,3R)-Catechin, ent-Catechin, L-Catechin, NSC 81746, (-)-Catechol, (-)-trans-3,3',4',5,7-Pentahydroxyflavane, (2S,3R)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol
Purity	≥97% (HPLC)
Appearance	White to off-white powder
CAS-Number	18829-70-4
Molecular Formula	C15H14O6
Molecular Weight	290.27
Identity	1H-NMR
Solvents	DMSO (15 mg/ml), ethanol (5 mg/ml) or water (1 mg/ml).
Melting Point	175-177 °C
Boiling Point	630.4 °C (predicted)
Optical Activity	-16 ° (acetone/water)
Density	1.593 g/cm3 (predicted)
Smiles	OC1=C2C(O[C@@H](C3=CC=C(O)C(O)=C3)[C@H](O)C2)=CC(O)=C1
InChi Key	PFTAWBLQPZVEMU-HIFRSBDPSA-N
Shipping	AMBIENT
Short Term Storage	+4°C
Long Term Storage	-20°C
Handling Advice	Protect from light and moisture.
Use / Stability	Stable for at least 2 years after receipt when stored at -20°C.
Transportation	Not dangerous goods
References	(1) O. Inanami, et al., Free Rad. Res. 29, 359 (1998), (2) S.-Y. Jeon, et al., Bioorg. Med. Chem. Lett. 13, 3905 (2003), (3) J.L. Donovan, et al., Free Rad. Res. 40, 1029 (2006), (4) S.Y. Cho, et al., Endocrinol. Metabol. 292, e1166 (2007), (5) T. Matsui, et al., J. Agric. Food Chem. 55, 1 (2007), (6) M.J. Jung, et al., Food Chem. 108, 482 (2008), (7) D.W. Shin, et al., Biochem. Pharmacol. 77, 125 (2009), (8) C. Ritter, et al., Anal. Bioanalyt. Chem. 397, 723 (2010)
InChi	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
Quantity	5 mg, 25 mg, Bulk