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Scopolin

Alias: Scopolin ScopolosideMurrayin NSC404560 NSC-404560NSC 404560
Cat No.:V8561 Purity: ≥98%
Scopolin is a novel and potent glucoside.
Scopolin
Scopolin Chemical Structure CAS No.: 531-44-2
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
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Product Description

Scopolin is a novel and potent glucoside. Which is a a coumarin isolated from Arabidopsis thaliana (Arabidopsis) roots and attenuated hepatic steatosis through activation of SIRT1-mediated signaling cascades.

Biological Activity I Assay Protocols (From Reference)
ln Vitro
In HepG2 cells, scopin (100 μM, 24 hours) prevents base buildup brought on by oleic acid by raising SIRT1 activity [2]. The pre-osteoclast RAW 264.7 cells' ability to secrete osteoclasts generated by RANKL is inhibited by Scopolin (10 μM, 5 days) [5].
ln Vivo
In HFD-fed infants, scopicon (0.02% (w/w) in the diet for 8 weeks) decreases myocardial steatosis and reduces weight gain [2]. Extracellular choline in stored brain increases to about 300% when scopolin (2 μmol, icv) is added [3]. By inhibiting both angiogenesis and adjuvant, scopolamine (50, 100 mg/kg, intraperitoneal injection) prevents adjuvant-induced arthritis [4].
Animal Protocol
Animal/Disease Models: HFD-fed C57BL/6 N mice [2]
Doses: 0.02% (w/w) HFD in diet (equivalent to 20 mg/kg body weight)
Route of Administration: Supplementation in diet, 8 weeks
Experimental Results: Reversal HFD-induced hepatic TG, cholesterol, and fatty acid accumulation increased by 35%, 49%, and 35%, respectively. Reversed the HFD-induced decrease in plasma adiponectin levels by 76% and diminished elevated plasma MCP-1, TNFα, and IL-6 levels. The HFD-induced downregulation of SIRT1 activity was restored.

Animal/Disease Models: Adjuvant-induced arthritis (AIA) rats [4]
Doses: 50, 100 mg/kg
Route of Administration: intraperitoneal (ip) injection
Experimental Results: Inhibition of swelling and joint index scores in vaccinated and unvaccinated paws. Reduce new blood vessels and reduce the expression of IL-6, VEGF and FGF-2 in rat synovial tissue.
References

[1]. Identification of QTLs affecting scopolin and scopoletin biosynthesis in Arabidopsisthaliana. BMC Plant Biol. 2014 Oct 18;14:280.

[2]. Scopolin ameliorates high-fat diet induced hepatic steatosis in mice: potential involvement of SIRT1-mediated signaling cascades in the liver. Sci Rep. 2017 May 22;7(1):2251.

[3]. Acetylcholinesterase inhibitory activity of scopolin and scopoletin discovered by virtual screening of natural products. J Med Chem. 2004 Dec 2;47(25):6248-54.

[4]. Scopolin isolated from Erycibe obtusifolia Benth stems suppresses adjuvant-induced rat arthritis by inhibiting inflammation and angiogenesis. Int Immunopharmacol. 2009 Jul;9(7-8):859-69.

[5]. Scopoletin and scopolin isolated from Artemisia iwayomogi suppress differentiation of osteoclastic macrophage RAW 264.7 cells by scavenging reactive oxygen species. J Nat Prod. 2013 Apr 26;76(4):615-20.

Additional Infomation
Scopolin is a member of the class of coumarins that is scopoletin attached to a beta-D-glucopyranosyl residue at position 7 via a glycosidic linkage. It has a role as a plant metabolite. It is a monosaccharide derivative, a member of coumarins and a beta-D-glucoside. It is functionally related to a scopoletin.
Scopolin has been reported in Erycibe obtusifolia, Mandragora autumnalis, and other organisms with data available.
See also: Chamaemelum nobile flower (part of).
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C16H18O9
Molecular Weight
354.31
Exact Mass
354.095
CAS #
531-44-2
PubChem CID
439514
Appearance
White to off-white solid powder
Density
1.6±0.1 g/cm3
Boiling Point
650.2±55.0 °C at 760 mmHg
Melting Point
217ºC
Flash Point
241.5±25.0 °C
Vapour Pressure
0.0±2.0 mmHg at 25°C
Index of Refraction
1.639
LogP
-1.87
Hydrogen Bond Donor Count
4
Hydrogen Bond Acceptor Count
9
Rotatable Bond Count
4
Heavy Atom Count
25
Complexity
510
Defined Atom Stereocenter Count
5
SMILES
O1[C@]([H])([C@@]([H])([C@]([H])([C@@]([H])([C@@]1([H])C([H])([H])O[H])O[H])O[H])O[H])OC1C([H])=C2C(C([H])=C([H])C(=O)O2)=C([H])C=1OC([H])([H])[H]
InChi Key
SGTCGCCQZOUMJJ-YMILTQATSA-N
InChi Code
InChI=1S/C16H18O9/c1-22-9-4-7-2-3-12(18)23-8(7)5-10(9)24-16-15(21)14(20)13(19)11(6-17)25-16/h2-5,11,13-17,19-21H,6H2,1H3/t11-,13-,14+,15-,16-/m1/s1
Chemical Name
6-methoxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-2-one
Synonyms
Scopolin ScopolosideMurrayin NSC404560 NSC-404560NSC 404560
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: This product requires protection from light (avoid light exposure) during transportation and storage.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~100 mg/mL (~282.24 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (7.06 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (7.06 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (7.06 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.8224 mL 14.1119 mL 28.2239 mL
5 mM 0.5645 mL 2.8224 mL 5.6448 mL
10 mM 0.2822 mL 1.4112 mL 2.8224 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

Biological Data
  • Chromatograms of scopoletin standard and methanol extracts from Arabidopsis thaliana roots. The column effluent was monitored with fluorescence detector with excitation at 340 nm and emission at 460 nm. The peak for glucoside of scopoletin – scopolin (scl); the peak for scopoletin (sct). (A) Chromatogram of scopoletin standard. (B) Chromatogram of methanol extract from Arabidopsis roots before enzymatic hydrolysis. (C) Chromatogram of methanol root extract subjected to hydrolysis using β-glucosidase. The peak for scopoletin is a dominant peak of total chromatogram.[1].Siwinska J, et al. Identification of QTLs affecting scopolin and scopoletin biosynthesis in Arabidopsisthaliana. BMC Plant Biol. 2014 Oct 18;14:280.
  • Relative levels of scopolin and scopoletin in the roots of seven Arabidopsis thaliana accessions. (A) Scopolin level in methanol root extracts without hydrolysis (H-). (B) Scopoletin content in the methanol extracts that were subjected to enzymatic hydrolysis (H+) prior to quantification. The statistically significant differences between group means for scopolin and scopoletin accumulation were determined by one-way ANOVA (p < 0.001 and p < 0.0001, respectively). Values that are not significantly different based on the post hoc test (least significant differences [LSD]) are indicated by the same letters. The data analysis consisted of scopolin and scopoletin relative levels measured as area% of total chromatogram signals. Error bars represent the SD from three measurements.[1].Siwinska J, et al. Identification of QTLs affecting scopolin and scopoletin biosynthesis in Arabidopsisthaliana. BMC Plant Biol. 2014 Oct 18;14:280.
  • Frequency distribution of scopolin and scopoletin relative levels in the AI-RILs and parental lines roots. Plants used for genetic mapping were grown in in vitro liquid cultures under a photoperiod of 16 h light (35 μmol m−2 s−1) at 20°C and 8 h dark at 18°C. Coumarins content in the roots of the AI-RILs population and parental lines (accessions Col-0 and Est-1) were determined by HPLC. (A) Scopolin contents were determined in methanol extracts without hydrolysis. (B) Methanol extracts subjected to enzymatic hydrolysis were used for scopoletin quantification. The data analysis consisted of scopolin and scopoletin relative levels measured as area% of total chromatogram signals. The average values of Col-0 and Est-1 are indicated with arrows.[1].Siwinska J, et al. Identification of QTLs affecting scopolin and scopoletin biosynthesis in Arabidopsisthaliana. BMC Plant Biol. 2014 Oct 18;14:280.
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