WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H329686
CAS#: 482-35-9 (EMIQ)
Description: Enzymatically modified isoquercitrin, also known as EMIQ, is a flavonoid. EMIQ is a mixture of quercetin monoglucoside and its alpha-oligoglucosides that has been shown to have significantly greater bioavailability than other available forms. In animals, EMIQ was shown to produce a 40 fold increase in Cmax (peak plasma concentration) and an 18-fold increase in the area under the curve compared to quercetin. In humans, EMIQ supplementation increased plasma concentrations to a significantly greater degree than other forms,3 including aglycone and isoquercitrin, with randomized placebo-controlled trials documenting improvement in allergic symptoms. EMIQ has also shown significantly enhanced biological activity especially in animal models of allergy and neoplasia.
Hodoodo Cat#: H329686
Name: Enzymatically modified isoquercitrin
CAS#: 482-35-9 (EMIQ)
Chemical Formula:
Exact Mass: 0.00
Molecular Weight: 0.000
Elemental Analysis:
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Related CAS #: 482-35-9 (EMIQ) 482-35-9 (Isoquercetin) 17-39-5 (quercetin)
Synonym: Isoquercitrin; Isoquercitrin; iso-quercetin; Isoquercitroside; Isoquercitin; Trifoliin; Isotrifolin; Trifoliin A; Isohyperoside; Isotrifoliin; Quercetin-3-glucoside; Quercetin-3-O-glucoside.
IUPAC/Chemical Name: Alpha-oligoglucosyl quercetin 3-O-glucoside.
InChi Key: OVSQVDMCBVZWGM-QSOFNFLRSA-N
InChi Code: InChI=1S/C21H20O12/c22-6-13-15(27)17(29)18(30)21(32-13)33-20-16(28)14-11(26)4-8(23)5-12(14)31-19(20)7-1-2-9(24)10(25)3-7/h1-5,13,15,17-18,21-27,29-30H,6H2/t13-,15-,17+,18-,21+/m1/s1
SMILES Code: OC1=CC=C(C=C1O)C(OC2=C(C3=O)C(O)=CC(O)=C2)=C3O[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO[C@H]5[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O5)O4
Appearance: Yellow to orange solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
More Info: Enzymatically modified (α-glucosylated) isoquercitrin" (EMIQ). EMIQ has shown significant effects in improving ocular symptoms of hay fever in doubleblind clinical studies. In one study, 20 subjects with hay fever due to Japanese cedar pollinosis took two capsules daily of 100 mg EMIQ or a placebo for 8 weeks during the pollen season.7 During the entire study period, total ocular score and ocular itching score for the EMIQ group were significantly lower than the placebo group. In another study of hay fever due to Japanese cedar pollinosis, 24 subjects took 100 mg EMIQ or a placebo for 8 weeks, starting 4 weeks prior to the onset of pollen release.8 During the entire study period, ocular symptom and medication scores for the EMIQ group was significantly lower than the placebo group. When limited to the pollen release period, ocular symptom and ocular congestion scores for the EMIQ group were significantly lower than the placebo group. Other scores for the EMIQ group, such as ocular itching scores, lacrimation scores, and ocular congestion scores, all tended to be lower.
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| In vivo activity: |
The following data is based on the product molecular weight 0.00 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
| Formulation protocol: | |
| In vitro protocol: | |
| In vivo protocol: |
1: Makino T, Kanemaru M, Okuyama S, Shimizu R, Tanaka H, Mizukami H. Anti-allergic effects of enzymatically modified isoquercitrin (α-oligoglucosyl quercetin 3-O-glucoside), quercetin 3-O-glucoside, α-oligoglucosyl rutin, and quercetin, when administered orally to mice. J Nat Med. 2013 Oct;67(4):881-6. doi: 10.1007/s11418-013-0760-5. Epub 2013 Mar 14. PubMed PMID: 23494818.
2: Fujii Y, Kimura M, Ishii Y, Yamamoto R, Morita R, Hayashi SM, Suzuki K, Shibutani M. Effect of enzymatically modified isoquercitrin on preneoplastic liver cell lesions induced by thioacetamide promotion in a two-stage hepatocarcinogenesis model using rats. Toxicology. 2013 Mar 8;305:30-40. doi: 10.1016/j.tox.2013.01.002. Epub 2013 Jan 11. PubMed PMID: 23318833.
3: Hara S, Morita R, Ogawa T, Segawa R, Takimoto N, Suzuki K, Hamadate N, Hayashi SM, Odachi A, Ogiwara I, Shibusawa S, Yoshida T, Shibutani M. Tumor suppression effects of bilberry extracts and enzymatically modified isoquercitrin in early preneoplastic liver cell lesions induced by piperonyl butoxide promotion in a two-stage rat hepatocarcinogenesis model. Exp Toxicol Pathol. 2014 Aug;66(5-6):225-34. doi: 10.1016/j.etp.2014.02.002. Epub 2014 Mar 26. PubMed PMID: 24680176.
4: Morita R, Shimamoto K, Ishii Y, Kuwata K, Ogawa B, Imaoka M, Hayashi SM, Suzuki K, Shibutani M, Mitsumori K. Suppressive effect of enzymatically modified isoquercitrin on phenobarbital-induced liver tumor promotion in rats. Arch Toxicol. 2011 Nov;85(11):1475-84. doi: 10.1007/s00204-011-0696-z. Epub 2011 Mar 29. PubMed PMID: 21445586.
5: Valentová K, Vrba J, Bancířová M, Ulrichová J, Křen V. Isoquercitrin: pharmacology, toxicology, and metabolism. Food Chem Toxicol. 2014 Jun;68:267-82. doi: 10.1016/j.fct.2014.03.018. Epub 2014 Mar 27. Review. PubMed PMID: 24680690.
6: Shimada Y, Dewa Y, Ichimura R, Suzuki T, Mizukami S, Hayashi SM, Shibutani M, Mitsumori K. Antioxidant enzymatically modified isoquercitrin suppresses the development of liver preneoplastic lesions in rats induced by beta-naphthoflavone. Toxicology. 2010 Feb 9;268(3):213-8. doi: 10.1016/j.tox.2009.12.019. Epub 2010 Jan 5. PubMed PMID: 20045035.
7: Kangawa Y, Yoshida T, Maruyama K, Okamoto M, Kihara T, Nakamura M, Ochiai M, Hippo Y, Hayashi SM, Shibutani M. Cilostazol and enzymatically modified isoquercitrin attenuate experimental colitis and colon cancer in mice by inhibiting cell proliferation and inflammation. Food Chem Toxicol. 2017 Feb;100:103-114. doi: 10.1016/j.fct.2016.12.018. Epub 2016 Dec 15. PubMed PMID: 27989839.
8: Nishimura J, Saegusa Y, Dewa Y, Jin M, Kawai M, Kemmochi S, Harada T, Hayashi SM, Shibutani M, Mitsumori K. Antioxidant enzymatically modified isoquercitrin or melatonin supplementation reduces oxidative stress-mediated hepatocellular tumor promotion of oxfendazole in rats. Arch Toxicol. 2010 Feb;84(2):143-53. doi: 10.1007/s00204-009-0497-9. Epub 2009 Dec 22. PubMed PMID: 20033131.
9: Wang J, Gong A, Yang CF, Bao Q, Shi XY, Han BB, Wu XY, Wu FA. An effective biphase system accelerates hesperidinase-catalyzed conversion of rutin to isoquercitrin. Sci Rep. 2015 Mar 3;5:8682. doi: 10.1038/srep08682. PubMed PMID: 25731802; PubMed Central PMCID: PMC4346833.
10: Hirano T, Kawai M, Arimitsu J, Ogawa M, Kuwahara Y, Hagihara K, Shima Y, Narazaki M, Ogata A, Koyanagi M, Kai T, Shimizu R, Moriwaki M, Suzuki Y, Ogino S, Kawase I, Tanaka T. Preventative effect of a flavonoid, enzymatically modified isoquercitrin on ocular symptoms of Japanese cedar pollinosis. Allergol Int. 2009 Sep;58(3):373-82. doi: 10.2332/allergolint.08-OA-0070. Epub 2009 May 25. PubMed PMID: 19454839.
11: Yokohira M, Yamakawa K, Saoo K, Matsuda Y, Hosokawa K, Hashimoto N, Kuno T, Imaida K. Antioxidant effects of flavonoids used as food additives (purple corn color, enzymatically modified isoquercitrin, and isoquercitrin) on liver carcinogenesis in a rat medium-term bioassay. J Food Sci. 2008 Sep;73(7):C561-8. doi: 10.1111/j.1750-3841.2008.00862.x. Epub 2008 Jul 24. PubMed PMID: 18803703.
12: Kawai M, Hirano T, Arimitsu J, Higa S, Kuwahara Y, Hagihara K, Shima Y, Narazaki M, Ogata A, Koyanagi M, Kai T, Shimizu R, Moriwaki M, Suzuki Y, Ogino S, Kawase I, Tanaka T. Effect of enzymatically modified isoquercitrin, a flavonoid, on symptoms of Japanese cedar pollinosis: a randomized double-blind placebo-controlled trial. Int Arch Allergy Immunol. 2009;149(4):359-68. doi: 10.1159/000205582. Epub 2009 Mar 17. PubMed PMID: 19295240.
13: Emura K, Yokomizo A, Toyoshi T, Moriwaki M. Effect of enzymatically modified isoquercitrin in spontaneously hypertensive rats. J Nutr Sci Vitaminol (Tokyo). 2007 Feb;53(1):68-74. PubMed PMID: 17484383.
14: Makino T, Shimizu R, Kanemaru M, Suzuki Y, Moriwaki M, Mizukami H. Enzymatically modified isoquercitrin, alpha-oligoglucosyl quercetin 3-O-glucoside, is absorbed more easily than other quercetin glycosides or aglycone after oral administration in rats. Biol Pharm Bull. 2009 Dec;32(12):2034-40. PubMed PMID: 19952424.
15: Motoyama K, Koyama H, Moriwaki M, Emura K, Okuyama S, Sato E, Inoue M, Shioi A, Nishizawa Y. Atheroprotective and plaque-stabilizing effects of enzymatically modified isoquercitrin in atherogenic apoE-deficient mice. Nutrition. 2009 Apr;25(4):421-7. doi: 10.1016/j.nut.2008.08.013. Epub 2008 Nov 20. PubMed PMID: 19026522.
16: Salim EI, Kaneko M, Wanibuchi H, Morimura K, Fukushima S. Lack of carcinogenicity of enzymatically modified isoquercitrin in F344/DuCrj rats. Food Chem Toxicol. 2004 Dec;42(12):1949-69. PubMed PMID: 15500932.
17: Yoshida T, Murayama H, Kawashima M, Nagahara R, Kangawa Y, Mizukami S, Kimura M, Abe H, Hayashi SM, Shibutani M. Apocynin and enzymatically modified isoquercitrin suppress the expression of a NADPH oxidase subunit p22phox in steatosis-related preneoplastic liver foci of rats. Exp Toxicol Pathol. 2017 Jan;69(1):9-16. doi: 10.1016/j.etp.2016.10.003. Epub 2016 Oct 24. PubMed PMID: 27789131.
18: Kangawa Y, Yoshida T, Abe H, Seto Y, Miyashita T, Nakamura M, Kihara T, Hayashi SM, Shibutani M. Anti-inflammatory effects of the selective phosphodiesterase 3 inhibitor, cilostazol, and antioxidants, enzymatically-modified isoquercitrin and α-lipoic acid, reduce dextran sulphate sodium-induced colorectal mucosal injury in mice. Exp Toxicol Pathol. 2017 Apr 4;69(4):179-186. doi: 10.1016/j.etp.2016.12.004. Epub 2017 Jan 12. PubMed PMID: 28089463.
19: Liu S, Liu F, Xue Y, Gao Y. Evaluation on oxidative stability of walnut beverage emulsions. Food Chem. 2016 Jul 15;203:409-16. doi: 10.1016/j.foodchem.2016.02.037. Epub 2016 Feb 4. PubMed PMID: 26948632.
20: Taniai E, Yafune A, Nakajima M, Hayashi SM, Nakane F, Itahashi M, Shibutani M. Ochratoxin A induces karyomegaly and cell cycle aberrations in renal tubular cells without relation to induction of oxidative stress responses in rats. Toxicol Lett. 2014 Jan 3;224(1):64-72. doi: 10.1016/j.toxlet.2013.10.001. Epub 2013 Oct 11. PubMed PMID: 24120684.
