Flavonoids and Polyphenols

<p>Applications Imperatorin (cas# 482-44-0) is a compound useful in organic synthesis.<br></p>

<p>Applications A metabolite of trans Resveratrol (150000).<br>References Schroder, H., et al.: Clin. Nutr., 20, 429 (2001), Yu, C., et al.: Pharm. Res., 19, 1907 (2002), Rimando, A., et al.: J. Agric. Food Chem., 52, 4713 (2004), Walle, T., et al.: Drug Metab. Dispos., 32, 1377 (2004), Ito, H., et al.: Br. J. Nutr., 94, 500 (2005),<br></p>

<p>Applications Hexahydrocurcumin-d6 is an isotope labelled degradation product of Curcumin (C838500), a dietary anti-inflammatory and chemopreventive agent consisting of two methoxyphenol rings connected by a conjugated heptadienedione chain.<br>References Gordon, D.N., et al.: J. Biol. Chem., 290, 4817 (2015);<br></p>

<p>Applications Sulfuric Acid conjugated Genistein metabolite.<br>References Kinjo, J., et al.: Biol. Pharm. Bull., 27, 185 (2004), Tsuchihashi, R., et al.: Nat. Med., 58, 71 (2004), Bursztyka, J., et al.: Food Chem. Toxicol., 46, 939 (2008),<br></p>

<p>Applications Allyl Bromide is used as a reagent in the synthesis of Resveratrol derivatives. Resveratrol (R150000) is a minor constituent of wine, correlated with serum lipid reduction and inhibition of platelet aggregation. Resveratrol is a specific inhibitor of COX-1, and it also inhibits the hydroperoxidase activity of COX-1. It has been shown to inhibit events associated with tumor initiation, promotion and progression.<br> E0<br>References Powell, R.G., et al.: Phytochemistry, 35, 335 (1994), Jeandet, P., et al.: J. Phytopathol., 143, 135 (1995), Mattivi, F., et al.: J. Agric. Food Chem., 43, 1820 (1995); Mulakayala, C. et al.: J. Mol. Graph. Model., 41, 43 (2013);<br></p>

<p>Applications Triclosan is used as bactericide and preservative for cosmetic and detergent compositions (1). Broadly used as an antiseptic and disinfectant (2).This compound is a contaminant of emerging concern (CECs). Drinking water contaminant candidate list 3 (CCL 3) compound as per United States Environmental Protection Agency (EPA). Environmental contaminants; Food contaminants.<br> Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package<br>References 1. Lindström, A. et al.: Environ. Sci. Technol. 2002 Jun 1;36(11):2322-9. 2. Ruszkiewicz, J. et al.: J. Toxicol. Environ. Health B. Crit. Rev. 2017;20(2):104-117.<br></p>

<p>M02441 - Rolipram</p>

<p>Applications Exhibits specific inhibitory activity against tyrosine kinases,including autophosphorylation of epidermal growth factor receptor kinase (IC50 - 2.6uM). Also inhibits other protein kinases through competitive inhibition of ATP. Inhibits tumor cell proliferation and induces tumor cell differentiation. Produces cell-cycle arrest and apoptosis in Jurat T-leukemia cells. However, it prevents anti-CD3 monoclonal antibody-induced thymic apoptosis. Genistein also inhibits topoisomerase II activity in vitro. Genistein has also been shown to inhibit the action of GABA on recombinant GABAA receptors2. uv(max)ethanol: 262.5 nm (e= 138). moderately sol. in hot alcohol<br>References Akiyama, T., et al.: J. Biol. Chem., 262, 5592 (1987), O'Dell, T.J., et al.: Nature, 353, 588 (1991), Aharonovits, O., et al.: Biochim Biophys. Acta, 1112, 181 (1992), Platanias, L.C., et al.: J. Biol. Chem., 267, 24053 (1992), Yoshida, H., et al.: Biochim. Biophys. Acta, 1137, 321 (1992), Uckun, F.M., et al.: Science, 267, 886 (1995)Merck Index 12th ed. 43952. Huang, R.Q.; Fang, M.J.; Dillon, G.H., Mol. Brain Res. 67: 177-183 (1999)<br></p>

<p>Impurity Diosmin EP Impurity E<br>Stability Hygroscopic<br>Applications Linarine (Diosmin EP Impurity E) is a naturally occurring flavone glycoside that was identified to possess potential sedative and anticonvulsant properties.<br>References Nugroho, A., et al.: Arch. Pharma. Res., 36, 51 (2013); Jung, H.A., et al.: Arch. Pharma. Res., 35, 1021 (2012); Shen, H.J., et al.: J. Med. Plants. Res., 5, 6555 (2011);<br></p>

<p>Applications Isoferulic Acid 3-O-β-D-Glucuronide is the glucuronide conjugate of Isoferulic Acid (H946180). Isoferulic Acid 3-O-β-D-Glucuronide is one of the circulating metabolites in human plasma after coffee consumption.<br>References Fumeaux, R. et al.: Org. Biomol. Chem., 8, 5199 (2010); Redeuil, K. et al.: J. Chrom. A, 1218, 4678 (2011);<br></p>

<p>Applications An antioxidant flavenoid.<br>References Dixon, D., et al.: J. Biol. Chem., 285, 36322 (2010), Sheu, M., et al.: Chem. Pharm. Bull., 58, 1187 (2010),<br></p>

<p>Applications Triclosan O-β-D-Glucuronide is a metabolite of the bacteriostat, Triclosan (T774250).<br>References Moss, T. et al.: Food Chem. Toxicol., 38, 361 (2000); Wu, J. et al.: Sepu, 27, 724 (2009);<br></p>

<p>Applications An isoflavone with anticancer proliferation, differentiation and chemopreventitive properties. Inhibits metabolic activation of benzo[a]pyrene.<br>References Chae, Y.H., et al.: Chem. Biol. Interactions, 82, 181 (1992), Jing, Y. and Waxman, S.: Anticancer Res., 15(4), 1147 (1995)<br></p>

<p>Applications An anthocyanin responsible for red pigment in fruits and berries. It is an antioxidant, protecting the cell against damage from SOD.<br>References Riihinen, K., et al.: Food Chem., 110, 156 (2008), Khanizadeh, S., et al.: J. Food Comp. Anal., 21, 396 (2008), Viskelis, P., et al.: J. Food Sci., 74, C157 (2009), Comeskey, D., et al.: J. Agric. Food Chem., 57, 2035 (2009),<br></p>

<p>Impurity Diosmin EP Impurity A<br>Applications Isoacetovanillone (Diosmin EP Impurity A) is a volatile compound isolated from oak wood. Also a byproduct in the production of Acetovanillone.<br>References Smith, C., et al.: Toxicol. Sci., 69, 265 (2002), Sun, L., et al.: Anticancer Res., 24, 179 (2004), Fernandez de Simon, B., et al.: J. Agric. Food Chem., 57, 3217 (2009),<br></p>

<p>Applications Labelled Chloroxylenol. Chloroxylenol is an antiseptic and germicide. Chloroxylenol is used for mildew prevention. Chloroxylenol is also an antibacterial.<br>References Heberer, T., et al.: Toxicol. Lett., 131, 5 (2002); Nikolaou, A., et al.: Anal. Bioanal. Chem., 387, 1225 (2007); Focazio, M., et al.: Sci. Total Environ., 402, 201 (2008); Miege, C., et al.: Environ. Pollut., 157, 1721 (2009);<br></p>

<p>Applications A natural phenolic compound. Potent anti-tumor agent having anti-inflammatory and antioxidant properties. Induces apoptosis in cancer cells and inhibits phorbol ester-induced protein kinase C (PKC) activity. Reported to inhibit production of inflammatory cytokines by peripheral blood monocytes and alveolar macrophages. Potent inhibitor of EGFR tyrosine kinase and IκB kinase. Inhibits inducible nitric oxide synthase (iNOS), cycloxygenase and lipoxygenase. Easily penetrates into the cytoplasm of cells, accumulating in membranous structures such as plasma membrane, endoplasmic reticulum and nuclear envelope.Curcumin is currently being examined as a possible therapeutic for the treatment of Alzheimers disease. Neuroprotective. Dyes and metabolites.<br>References Srinivasan, et al.: J. Pharm. Pharmacol., 5, 448 (1953), Tu, B., et al.: J .Cell Biol., 164, 341 (2004), Xu, G., et al.: Biochemistry, 44, 9817 (2005), Johnson, J., et al.: Cancer Lett., 255, 170 (2007), Chem. and Eng. News 90(31), 44 (2012)<br></p>

<p>Applications Gallic Acid exhibits a number of cellular effects including apoptosis and inhibits the growth of calf pulmonary arterial endothelial cell (CPAEC);Also, it is a polyphenol widely found in numerous fruits and vegetables that has been reported to exert anticancer effects, including apoptosis, against cancer cell lines.<br>References Park, W. H.: Mol. Med. Rep., 16, 7805-7812 (2017); Yang, C., et al.: RSC Adv., 8, 12449-12458 (2018)<br></p>

<p>Applications A major component of green coffee the extracts of which promote weight loss in overweight and obese people. Chlorogenic Acid is an important intermediate in lignin biosynthesis. Chlorogenic Acid is an antioxidant and an inhibitor of the tumor promoting activity of phorbol ester. It has protective effect against streptozotocin-nicotinamide generated oxidative stress induced diabetes and may also protect against cardiovascular disease.<br>References Chem. and Eng. News p. 20 April 15, 2013; Karthikesan, K. et al.: J. Func. Foods, 2, 134 (2010); Lincoln, W.M. et al.: Clin. Exp. Phamacol. Physiol., 27, 152 (2000); Gamborg, O.L. et al.: Can. J. Biochem., 45, 1451 (1967);<br></p>

<p>Stability Hygroscopic<br>Applications 4-O-Caffeoylquinic Acid is used as an antibiotic, and antioxidant agent.<br>References Xu, H. et al.: Food Sci. Biotech., 23, 2013 (2014);<br></p>

<p>Applications Bisdemethoxycurcumin is one of the three major forms of curcuminoids found in the rhizomes of turmeric. Bisdemethoxycurcumin displays antioxidant, anti-inflammatory as well as chemotherapeutic activity. Bisdemethoxycurcumin acts as an inhibitor of human pancreatic α-amylase, a target for type-2 diabetes .<br>References Ponnusamy, S. et al.: Food Chem., 135, 2638 (2012); Hung, C.-M. et al.: J. Agric. Food. Chem., 60, 8427 (2012); Jayaprakasha, G.K. et al.: Food Chem., 98, 720 (2006);<br></p>

<p>Applications Cannflavin B is a prenylated flavone which can be isolated from the cannabinoid free ethanolic extract of Cannabis sativa L.<br>References Barrett, M. L., Experientia, 42, 452-3, (1986)<br></p>

<p>Applications trans-p-Coumaric Acid is the E-isomer of p-Coumaric Acid (C755365), a hydroxy derivative of Cinnamic Acid with antioxidant properties. p-Coumaric acid is a is a major component of lignocellulose. Studies suggest that p-Coumaric Acid may reduce the risk of cancer by reducing the formation of carcinogenic nitrosamines.<br>References Kikugawa, K. et al.: J. Agric. Food Chem., 1, 780 (1983); Ferguson, L.R. et al.: Mol. Nutrit. Food Res., 585 (2005); Chung, F.L. et al.: IARC Sci. Pub., 57, 797 (1984);<br></p>

<p>Applications Minor constituent of wine, correlated with serum lipid reduction and inhibition of platelet aggregation. Resveratrol is a specific inhibitor of COX-1, and it also inhibits the hydroperoxidase activity of COX-1. It has been shown to inhibit events associated with tumor initiation, promotion and progression.<br>References Powell, R.G., et al.: Phytochemistry, 35, 335 (1994), Jeandet, P., et al.: J. Phytopathol., 143, 135 (1995), Mattivi, F., et al.: J. Agric. Food Chem., 43, 1820 (1995),<br></p>

<p>Stability Light Sensitive<br>Applications Bisdemethoxycurcumin is one of the three major forms of curcuminoids found in the rhizomes of turmeric. Bisdemethoxycurcumin displays antioxidant, anti-inflammatory as well as chemotherapeutic activity. Bisdemethoxycurcumin acts as an inhibitor of human pancreatic α-amylase, a target for type-2 diabetes .<br>References Ponnusamy, S. et al.: Food Chem., 135, 2638 (2012); Hung, C.-M. et al.: J. Agric. Food. Chem., 60, 8427 (2012); Jayaprakasha, G.K. et al.: Food Chem., 98, 720 (2006);<br></p>

<p>Stability Hygroscopic<br>Applications Digallic Acid is an intermolecular ester of Gallic acid (G188900), a phenolic acid with antioxidant activity. Gallic acid was found to protect human cells against oxidative damage and showed cytotoxicity against cancer cells. Gallic Acid and its esters also show antiviral and antifungal activities.<br>References Yen, G. et al.: Food Chem., 79, 307 (2002); Chen, C. et al.: Mol. Nutrit. Food Res., 51, 962 (2007); Kratz, J. et al.: Mem. Inst. Oswaldo Cruz, 103, 437 (2008); Osborne, L. et al.: Infect. Immun., 33, 769 (1981)<br></p>

<p>Applications Isotope labelled Triclosan is used as bactericide and preservative for cosmetic and detergent compositions (1). Broadly used as an antiseptic and disinfectant (2). This compound is a contaminant of emerging concern (CECs). Drinking water contaminant candidate list 3 (CCL 3) compound as per United States Environmental Protection Agency (EPA). Environmental contaminants; Food contaminants.<br> Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package<br>References 1. Lindström, A. et al.: Environ. Sci. Technol. 2002 Jun 1;36(11):2322-9. 2. Ruszkiewicz, J. et al.: J. Toxicol. Environ. Health B. Crit. Rev. 2017;20(2):104-117.<br></p>

<p>Applications 2-tert-Butyl-4-hydroxyanisole shows insecticidal activity.<br>References Newberne, P., et al.: Food Technol., 54, 66 (2000), Passone, M., et al.: Food Control, 19, 364 (2008),<br></p>

<p>Applications Isoamyl 4-Methoxycinnamate is used in the highly protective sunscreen composition against the UVA/UVB.<br>References Cuderman, P., et al: Anal. Bioanal. Chem., 387, 1343 (2007), Zhao, X., et al.: Environ. Sci. Technol., 42, 1201 (2008), Dubrovski, P., et al.: Text Res. J., 79, 351 (2009),<br></p>

<p>Applications (E)-Neochlorogenic Acid is an antioxidant compound used in the treatment of oxidative stress and related afflictions.<br>References Wang, J. et al.: Molecules, 19, 21226 (2014); Jimenez-Zamora, A. et al.: LWT-Food Sci. Tech., 61, 12 (2015);<br></p>

<p>Stability Hygroscopic<br>Applications Feruloylputrescine is an effector of plant root systems, influencing development of nutrient gathering root systems. Inhibition of the formation of this compound causes the development of a dominant or ‘tap’ root.<br>References Ben-Hayyim G. et al.: FEBS Lett., 4, 145 (1994);<br></p>

<p>Applications 2,5-Dichlorophenol is an intermediates in the manufacture of more complex chemical compounds such as fungicides.<br> Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package<br>References Wang, F., et al.: Bull. Enviro. Contamin. Toxicol., 89, 316 (2012); Zhong, W., et al.: J. Hazard. Mat., 217, 286 (2012);<br></p>

<p>Applications Coumarin is a pharmaceutic aid (flavor) that is found in tonka beans, levender oil, woodruff, sweet clover.<br> Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package<br>References Hazleton, L., et al.: J. Pharmacol. Exp. Ther., 118, 348 (1956); Lake, B., et al.: Food Chem. Toxicol., 37, 423 (1999); Frerot, E., et al.: Flavour Fragrance J., 17, 218 (2002); Yang, Z., et al.: Food Chem., 114, 289 (2009);<br></p>

<p>Applications Antioxidant.<br>References Arnous, A., et al.: J. Agr. Food Chem., 49, 5736 (2001), Guendez, R., et al.: Food Chem., 89, 1 (2005), Proestos, C., et al.: Food Control,16, 319 (2005)<br></p>

<p>Stability Light Sensitive, Temperature Sensitive<br>Applications A metabolite of cis Resveratrol.<br>References Schroder, H., et al.: Clin. Nutr., 20, 429 (2001), Yu, C., et al.: Pharm. Res., 19, 1907 (2002), Rimando, A., et al.: J. Agric. Food Chem., 52, 4713 (2004), Walle, T., et al.: Drug Metab. Dispos., 32, 1377 (2004), Ito, H., et al.: Br. J. Nutr., 94, 500 (2005),<br></p>

<p>Applications (+/-)-Catechin xHydrate is an antioxidant flavonoid.<br>References Liao, J. et al.: J. Agri. Food. Chem., 65, 3013 (2017);<br></p>

<p>Applications A protected caffeine metabolite with high antioxidant activity. It is a very sensitive biomarker for the consumption of relatively small amount of coffee.<br>References Buchanan, C., et al.: J. Sci. Food Agric., 71, 459 (1996), Andreasen, M., et al.: J. Agric. Food Chem., 49, 5679 (2001), Poquet, L., et al.: Drug Metab. Dispos., 36, 190 (2008),<br></p>

<p>M04142 - Naphthol AS-BI beta-D-glucuronide</p>

<p>Applications trans-Caffeic Acid is a useful synthetic intermediate. It was used as a reactant to synthesize N-caffeoylphenalkylamide derivatives as bacterial efflux pump inhibitors. It is also used to prepare caffeic acid phenethyl ester analogs with antitumor structures.<br>References Michalet, S., et al.: Bioorg. Med. Chem. Lett., 17, 1755 (2007); Nagaoka, T., et al.: Bioorg. Med. Chem., 10, 3351 (2002)<br></p>