Troxerutin

Troxerutin
Clinical data
Other names	Hydroxyethylrutoside (HER); Pherarutin; Trihydroxyethylrutin; 3',4',7-Tris[O-(2-hydroxyethyl)]rutin
AHFS/Drugs.com	International Drug Names
ATC code	C05CA04 (WHO) ;
Identifiers
	IUPAC name 2-[3,4-bis(2-hydroxyethoxy)phenyl]-5-hydroxy-7-(2-hydroxyethoxy)-4-oxo-4H-chromen-3-yl 6-O-(6-deoxy-β-D-mannopyranosyl)-β-D-glucopyranoside;
CAS Number	7085-55-4 ;
PubChem CID	9896814;
ChemSpider	4589027 ;
UNII	7Y4N11PXO8;
KEGG	D07180;
ChEMBL	ChEMBL3182320 ;
Chemical and physical data
Formula	C33H42O19
Molar mass	742.680 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)Oc3c(=O)c4c(cc(cc4oc3c5ccc(c(c5)OCCO)OCCO)OCCO)O)O)O)O)O)O)O;
	InChI InChI=1S/C33H42O19/c1-14-23(38)26(41)28(43)32(49-14)48-13-21-24(39)27(42)29(44)33(51-21)52-31-25(40)22-17(37)11-16(45-7-4-34)12-20(22)50-30(31)15-2-3-18(46-8-5-35)19(10-15)47-9-6-36/h2-3,10-12,14,21,23-24,26-29,32-39,41-44H,4-9,13H2,1H3/t14-,21+,23-,24+,26+,27-,28+,29+,32+,33-/m0/s1 ; Key:IYVFNTXFRYQLRP-VVSTWUKXSA-N ;
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Troxerutin is a flavonol, a type of flavonoid, derived from rutin.^[1] It is more accurately a hydroxyethylrutoside. It can be isolated from Sophora japonica, the Japanese pagoda tree.

It is used as a vasoprotective.^[2]

Troxerutin has been shown in mice to reverse CNS insulin resistance and reduce reactive oxygen species induced by a high-cholesterol diet.^[3]

References

^ Zhang ZF, Fan SH, Zheng YL, Lu J, Wu DM, Shan Q, Hu B (September 2014). "Troxerutin improves hepatic lipid homeostasis by restoring NAD(+)-depletion-mediated dysfunction of lipin 1 signaling in high-fat diet-treated mice". Biochemical Pharmacology. 91 (1): 74–86. doi:10.1016/j.bcp.2014.07.002. PMID 25026599.
^ Riccioni C, Sarcinella R, Izzo A, Palermo G, Liguori M (February 2004). "[Effectiveness of Troxerutin in association with Pycnogenol in the pharmacological treatment of venous insufficiency]". Minerva Cardioangiologica. 52 (1): 43–8. PMID 14765037.
^ Lu J, Wu DM, Zheng ZH, Zheng YL, Hu B, Zhang ZF (March 2011). "Troxerutin protects against high cholesterol-induced cognitive deficits in mice". Brain. 134 (Pt 3): 783–97. doi:10.1093/brain/awq376. PMID 21252113.

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Clinical data

Other names	Hydroxyethylrutoside (HER) Pherarutin Trihydroxyethylrutin 3',4',7-Tris[O-(2-hydroxyethyl)]rutin
AHFS/Drugs.com	International Drug Names
ATC code	C05CA04 (WHO)
Identifiers
IUPAC name 2-[3,4-bis(2-hydroxyethoxy)phenyl]-5-hydroxy-7-(2-hydroxyethoxy)-4-oxo-4H-chromen-3-yl 6-O-(6-deoxy-β-D-mannopyranosyl)-β-D-glucopyranoside
CAS Number	7085-55-4^N
PubChem CID	9896814
ChemSpider	4589027^N
UNII	7Y4N11PXO8
KEGG	D07180
ChEMBL	ChEMBL3182320^N
Chemical and physical data
Formula	C₃₃H₄₂O₁₉
Molar mass	742.680 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)Oc3c(=O)c4c(cc(cc4oc3c5ccc(c(c5)OCCO)OCCO)OCCO)O)O)O)O)O)O)O
InChI InChI=1S/C33H42O19/c1-14-23(38)26(41)28(43)32(49-14)48-13-21-24(39)27(42)29(44)33(51-21)52-31-25(40)22-17(37)11-16(45-7-4-34)12-20(22)50-30(31)15-2-3-18(46-8-5-35)19(10-15)47-9-6-36/h2-3,10-12,14,21,23-24,26-29,32-39,41-44H,4-9,13H2,1H3/t14-,21+,23-,24+,26+,27-,28+,29+,32+,33-/m0/s1^N Key:IYVFNTXFRYQLRP-VVSTWUKXSA-N^N
^NY (what is this?) (verify)