ChemicalBook--->CAS DataBase List--->17388-39-5

17388-39-5

17388-39-5 Structure

17388-39-5 Structure
IdentificationMore
[Name]

Swertiamarine
[CAS]

17388-39-5
[Synonyms]

SWERTIAMAIN
SWERTIAMARIN
(4ar-(4a-alpha,5-beta,6-alpha))-ranosyloxy)-4a-hydroxy
1h,3h-pyrano(3,4-c)pyran-1-one,4,4a,5,6-tetrahydro-5-ethenyl-6-(beta-d-glucopy
1H,3H-Pyrano[3,4-c]pyran-1-one,4,4.alpha.,5,6-tetrahydro-5-ethenyl-6-(.beta.-D-glucopyranosyloxy)-4.alpha.-hydroxy-,[4ar-(4.alpha.-.alpha.,5-.beta.,D-.alpha.)]-
3H-Pyrano[3,4-c]pyran-1-one,4,4.alpha.,5,6-tetrahydro-5-ethenyl-6-(.beta.-D-glucopyranosyloxy)-4.1H
4-c)pyran-1-one,4,4a,5,6-tetrahydro-5-ethenyl-6-(beta-d-glucopyranosyloxy)-4a-hydroxy-3h-pyrano(1
Swertiamarin(6CI,7CI,8CI)
Swertiamarine
Swertiamaroside
SWERTIAMARIN, 98+% BY HPLC
Swertiamarin std.
SWERTIAMARIN(P)
(5R,6S)-5-Ethenyl-4a-hydroxy-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4,5,6-tetrahydropyrano[5,4-c]pyran-1-one
glucopyranosyloxy)-4,4a,5,6-tetrahydro-4a-hydroxy-,(4aR,5R, 6S)-
Swertiamarin,Swertiamarine,Swertiamaroside
(4aR)-4aα-Hydroxy-5β-vinyl-6α-(β-D-glucopyranosyloxy)-4,4a,5,6-tetrahydro-1H,3H-pyrano[3,4-c]pyran-1-one
4aα-Hydroxy-6α-(β-D-glucopyranosyloxy)-5β-vinyl-4,4a,5,6-tetrahydro-1H,3H-pyrano[3,4-c]pyran-1-one
6α-(β-D-Glucopyranosyloxy)-4,4a,5,6-tetrahydro-4aα-hydroxy-5β-vinyl-1H,3H-pyrano[3,4-c]pyran-1-one
[Molecular Formula]

C16H22O10
[MDL Number]

MFCD07783984
[Molecular Weight]

374.34
[MOL File]

17388-39-5.mol
Chemical PropertiesBack Directory
[Melting point ]

113-114°
[alpha ]

D20 -127° (c = 1 in 96% ethanol)
[Boiling point ]

649.3±55.0 °C(Predicted)
[density ]

1.57±0.1 g/cm3(Predicted)
[storage temp. ]

Sealed in dry,Store in freezer, under -20°C
[solubility ]

DMSO : 250 mg/mL (667.84 mM; Need ultrasonic)
[form ]

neat
[pka]

11.56±0.60(Predicted)
[color ]

White to Yellow to Orange
[λmax]

238nm(MeOH)(lit.)
[Merck ]

14,9010
[BRN ]

55278
[Stability:]

Hygroscopic
[Major Application]

metabolomics
vitamins, nutraceuticals, and natural products
[InChIKey]

HEYZWPRKKUGDCR-QBXMEVCASA-N
[SMILES]

OC[C@H]1O[C@@H](O[C@@H]2OC=C3C(=O)OCC[C@@]3(O)[C@H]2C=C)[C@H](O)[C@@H](O)[C@@H]1O
[CAS DataBase Reference]

17388-39-5(CAS DataBase Reference)
Safety DataBack Directory
[Safety Statements ]

24/25
[WGK Germany ]

3
[RTECS ]

UQ1366700
[HS Code ]

29389090
[Storage Class]

11 - Combustible Solids
[Toxicity]

mouse,LD50,intraperitoneal,> 8gm/kg (8000mg/kg),BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY),Zhongcaoyao. Chinese Traditional and Herbal Medicine. Vol. 13, Pg. 464, 1982.
Hazard InformationBack Directory
[Chemical Properties]

White crystals, easily soluble in water, methanol, and ethanol, almost insoluble in chloroform, ether, and petroleum ether, derived from Gentiana macrophylla (Tibet), Swertia japonica, Green Leaf Gallbladder, and Houttuynia cordata.
[Uses]

Swertimarine is an extract from Enicostemma littorale which is an herb used in the treatment of type 1 and 2 diabetes. Used to sensitize the cells to hypolipidemic conditions and insulin.
[Definition]

ChEBI: Swertiamarin is a glycoside.
[Biological Activity]

Swertiamarin has shown potential as antiatherogenic agent by inhibiting HMG-CoA reductase activity in high cholesterol fed rats. The high cholesterol fed rats treated with Swertiamarin showed prevention of increased serum total cholesteroltriglyceridesLDLs and VLDLs.
[in vivo]

Swertiamarin (50, 75 mg/kg; once daily; 7 days; p.o.) has a lipid-lowering effect in hypercholesterolemic rats[1]. Swertiamarin (100, 200 mg/kg; once daily; 8 weeks; i.g.) has antioxidant and hepatoprotective effects on carbon tetrachloride induced rat hepatotoxicity through the Nrf2/HO-1 pathway[2]. Swertiamarin (2, 5, 10 mg/kg; once daily; 2 weeks; p.o.) prevents bone erosion in arthritis rats by regulating RANKL/RANK/OPG signaling transduction[3]. Swertiamarin (2, 5, 10 mg/kg; once daily; 2 weeks; p.o.) attenuates inflammatory mediators by regulating NF - κ B/I, κ B, and JAK2/STAT3 transcription factors in adjuvant induced arthritis rats[4].

Animal Model:Male Sprague Dawley (SD) rats with hypercholesterolemia induced by supplementing a diet rich in cholesterol[1].
Dosage:50, 75 mg/kg
Administration:Oral gavage (p.o.); once daily; 7 days
Result:Reduced serum total cholesterol, triglyceride concentration and atherosclerosis index.
Animal Model:Male Sprague Dawley (SD) rat model of liver injury induced by CCl4[2].
Dosage:100, 200 mg/kg
Administration:i.g. ; once daily; 8 weeks
Result:Reduced the levels of serum marker enzymes ALT, AST, and ALP representing liver damage, and restored antioxidant enzyme activity and GSH content in rat liver.
Animal Model:Induced arthritis rat model by intradermal injection of 0.1ml Freund's complete adjuvant (FCA) in 1ml paraffin oil into the right hind paw of rats[3][4].
Dosage:2, 5, 10 mg/kg
Administration:Oral gavage (p.o.); once daily; 2 weeks
Result:Reduced calcium and TRAP, ACP, and ALP levels in serum and urine of arthritis rats, and increased phosphorus and collagen levels[3]. Inhibited paw thickness, lysosomal enzyme levels, and increased body weight in rats[4].
Spectrum DetailBack Directory
[Spectrum Detail]

Swertiamarine(17388-39-5)1HNMR
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