Troxerutin

Modify Date: 2024-01-02 10:32:13

Troxerutin Structure
Troxerutin structure
 Common Name Troxerutin
CAS Number 7085-55-4 Molecular Weight 742.675
Density 1.7±0.1 g/cm3 Boiling Point 1058.4±65.0 °C at 760 mmHg
Molecular Formula C33H42O19 Melting Point 168 - 176ºC
MSDS Chinese USA Flash Point 332.0±27.8 °C

 Use of Troxerutin


Troxerutin, also known as vitamin P4, is a tri-hydroxyethylated derivative of natural bioflavonoid rutins which can inhibit the production of reactive oxygen species (ROS) and depress ER stress-mediated NOD activation.

 Names

Name troxerutin
Synonym More Synonyms

 Troxerutin Biological Activity

Description Troxerutin, also known as vitamin P4, is a tri-hydroxyethylated derivative of natural bioflavonoid rutins which can inhibit the production of reactive oxygen species (ROS) and depress ER stress-mediated NOD activation.
Related Catalog
Target

ROS[1], NOD[2]

In Vitro The results reveal that the maximum protective effect against ROS induced cell damage in the HDP cells occurs following pretreatment with 10 μM Troxerutin. Treatment with H2O2 alone decreases cell viability to 77.33±2.44%; however, pretreatment with 10 μM Troxerutin maintains cell viability at 90.88±2.24% following H2O2 exposure (P<0.05). At concentrations of 5 and 10 μM, pretreatment with Troxerutin causes a decrease in the number of cells in the sub G1 phase, indicative of cell death. In the control and Troxerutin-only-treated cells, 3.58±0.15 and 0.89±0.11% are 2′7′-dichlorofluorescein (DCF)-positive (P<0.05), whereas treatment with H2O2 alone increases the level of ROS to 46.36±2.33%. The cells pretreated with Troxerutin are 19.92±1.95% DCF-positive following H2O2 treatment, indicating that Troxerutin reduces the H2O2-induced production of ROS in the HDP cells[1] .
In Vivo Troxerutin effectively lowers body weight and obesity-related metabolic parameters in high-fat diet (HFD)-treated mice. Oral administration of Troxerutin notably inhibits those liver injuries in HFD-treated mice, restores glucose intolerance and insulin signaling, and diminishes hepatic gluconeogenesis in HFD-treated mice. Troxerutin remarkably inhibits the nuclear translocation of NF-κB p65, as well as the expressions of its target genes, in the livers of HFD-treated mice. Troxerutin also depresses endoplasmic reticulum (ER) stress-mediated Nucleotide oligomerization domain (NOD) activation in HFD-treated mouse livers[2]. Lipid depositions in tunica intimae and tunica media are attenuated in Troxerutin-treated diabetic rats compare with untreated diabetic rats. Structural disarrangement and deformity of smooth muscle cells in aortic tissue of Troxerutin-treated diabetic rats are considerably lower than histology of untreated diabetic aorta. Administration of Troxerutin for four weeks to diabetic rats significantly reduces the level of malondialdehyde (MDA) compare to that of untreated diabetic rats (P<0.01)[3].
Cell Assay The cells are plated at a density of 4×103/well in a 96-well plate. At 70 to 80% confluence, the cells are treated with Troxerutin at concentrations ranging between 0 and 60 μM for 24 h at 37°C. Subsequently, 10 μL water soluble tetrazolium salt assay solution is added to each well and, following incubation for 30 min at 37°C, the optical density is measured at 490 nm using a reader. To examine Troxerutin mediated ROS protection, the cells are pretreated with Troxerutin at the following concentrations: 0, 5, 10 and 15 μM for 8 h. Subsequently, 750 μM H2O2 is added to each well. Following incubation for 24 h at 37°C, cell viability is evaluated using an Cell Viability Assay kit. The level of cell viability (%) is normalized to that of 0.1% dimethyl-sulfoxide (DMSO)-treated cells. Each experiment is repeated at least three times[1].
Animal Admin Thirty two adult male Wistar rats weighing 250 to 300 grams are used in this study. The animals are randomly divided into four groups (n=8/each) as: group I: control (C), group II: control with Troxerutin (C+TXR), group III: diabetic (D), and group IV: diabetic with Troxerutin (D+TXR). The control rats are received the same amount of citrate buffer alone. Development of diabetes is confirmed by measuring blood glucose levels, 72 hours later. Animals with blood glucose levels higher than 16.65 mM (300 mg/dL) are considered diabetic and those with blood glucose levels lower than this value are excluded from the experiment. Troxerutin (150 mg/kg/day) is administered orally, once daily for four weeks. After 10 weeks of induction of diabetes, diabetic animals as well as the time-matched controls are killed and aortic samples are collected[3].
References

[1]. Lim KM, et al. Analysis of changes in microRNA expression profiles in response to the troxerutin-mediated antioxidant effect in human dermal papilla cells. Mol Med Rep. 2015 Aug;12(2):2650-60.

[2]. Zhang Z, et al. Troxerutin Attenuates Enhancement of Hepatic Gluconeogenesis by Inhibiting NOD Activation-Mediated Inflammation in High-Fat Diet-Treated Mice. Int J Mol Sci. 2016 Dec 25;18(1). pii: E31.

[3]. Badalzadeh R, et al. Beneficial effect of troxerutin on diabetes-induced vascular damages in rat aorta: histopathological alterations and antioxidation mechanism. Int J Endocrinol Metab. 2015 Apr 30;13(2):e25969.

 Chemical & Physical Properties

Density 1.7±0.1 g/cm3
Boiling Point 1058.4±65.0 °C at 760 mmHg
Melting Point 168 - 176ºC
Molecular Formula C33H42O19
Molecular Weight 742.675
Flash Point 332.0±27.8 °C
Exact Mass 742.232056
PSA 297.12000
LogP -0.32
Vapour Pressure 0.0±0.3 mmHg at 25°C
Index of Refraction 1.690
Storage condition Refrigerator

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
LK8331500
CHEMICAL NAME :
Flavone, 3,5-dihydroxy-3',4',7-tris(2-hydroxyethoxy)-, 3-(6-O-(6-deoxy-alpha-L- mannopyranosyl)-beta-D-glucopyranoside)
CAS REGISTRY NUMBER :
7085-55-4
LAST UPDATED :
199612
DATA ITEMS CITED :
1
MOLECULAR FORMULA :
C33-H42-O19

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
27160 mg/kg
TOXIC EFFECTS :
Cardiac - arrhythmias (including changes in conduction) Cardiac - cardiomegaly Nutritional and Gross Metabolic - body temperature decrease
REFERENCE :
THERAP Therapie. (Doin, Editeurs, 8, Place de l'Odeon, F-75006 Paris, France) V.1- 1946- Volume(issue)/page/year: 20,879,1965

 Safety Information

Personal Protective Equipment Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Hazard Codes Xi
Safety Phrases S22-S24/25
RIDADR NONH for all modes of transport
WGK Germany 3
RTECS LK8331500
HS Code 2932999099

 Customs

HS Code 2932999099
Summary 2932999099. other heterocyclic compounds with oxygen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

 Articles29

More Articles
Analysis of changes in microRNA expression profiles in response to the troxerutin-mediated antioxidant effect in human dermal papilla cells.

Mol. Med. Report. 12 , 2650-60, (2015)

Dermal papilla (DP) cells function as important regulators of the hair growth cycle. The loss of these cells is a primary cause of diseases characterized by hair loss, including alopecia, and evidence...

Phlebotonics for haemorrhoids.

Cochrane Database Syst. Rev. 8 , CD004322, (2012)

Haemorrhoids are variceal dilatations of the anal and perianal venous plexus and often develop secondary to the persistently elevated venous pressure within the haemorrhoidal plexus (Kumar 2005). Phle...

Troxerutin, a plant flavonoid, protects cells against oxidative stress-induced cell death through radical scavenging mechanism.

Food Chem. 194 , 32-45, (2015)

Troxerutin (TRX) is a flavonoid present in tea, coffee, cereal grains, various fruits and vegetables have been reported to exhibit radioprotective, antithrombotic, nephro and hepato-protective effects...

 Synonyms

7,3',4'-Tris[O-(2-hydroxyethyl)]rutin
Posorutin
Venoruton P-4
Rufen P-4
Tri(hydroxyethyl)rutoside
Venoruton P4
Trioxyethylrutin
2-[3,4-Bis(2-hydroxyethoxy)phenyl]-3-[[6-O-(6-deoxy-a-L-mannopyranosyl)-b-D-glucopyranosyl]oxy]-5-hydroxy-7-(2-hydroxyethoxy)-4H-1-benzopyran-4-one
Venoruton
VASTRIBIL
MFCD00893813
Z-6000
4H-1-Benzopyran-4-one, 2-[3,4-bis(2-hydroxyethoxy)phenyl]-3-[[6-O-(6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl]oxy]-5-hydroxy-7-(2-hydroxyethoxy)-
Vitamin P4
7,3',4'-trihydroxyethyl rutin
Troxerutin
Troxerutine
Factor-P-zyma
T66 BO EVJ CR CO2Q DO2Q& GQ IO2Q DO- BT6OTJ CQ DQ EQ F1O-BT6OTJ CQ DQ EQ FQ &&Stereoisomer
2-[3,4-Bis(2-hydroxyethoxy)phenyl]-5-hydroxy-7-(2-hydroxyethoxy)-4-oxo-4H-chromen-3-yl 6-O-(6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranoside
RUVEN
EINECS 230-389-4
troxerutina
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