Scopolin | CAS#531-44-2 | Anti-inflammatory glucoside

MedKoo Cat#: 461940 | Name: Scopolin

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Scopolin is a coumarin glucoside form of scopoletin that has been found in O. africana and has anti-inflammatory activity. It decreases the production of prostaglandin E2 (PGE2) and leukotriene C4 (LTC4) induced by A23187 in isolated mouse peritoneal macrophages when used at a concentration of 100 µM. Scopolin (50 and 100 mg/kg) reduces synovial inflammation and fibrosis, as well as bone and cartilage erosion, in the inflamed joints in a rat model of rheumatoid arthritis induced by complete Freund’s adjuvant and M. butyricum.

Chemical Structure

Scopolin

CAS#531-44-2

Theoretical Analysis

MedKoo Cat#: 461940

Name: Scopolin

CAS#: 531-44-2

Chemical Formula: C16H18O9

Exact Mass: 354.0951

Molecular Weight: 354.31

Elemental Analysis: C, 54.24; H, 5.12; O, 40.64

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 550.00	2 Weeks
10mg	USD 950.00	2 Weeks

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Related CAS #

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Synonym

Scopolin; Murrayin; Scopoloside; NSC 404560; NSC404560; NSC-404560;

IUPAC/Chemical Name

6-methoxy-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-2H-chromen-2-one

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

SMILES Code

O=C1C=CC2=CC(OC)=C(O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](CO)O3)O)O)O)C=C2O1

Appearance

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

>3 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

2934.99.03.00

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Scopolin attenuated hepatic steatosis through activation of SIRT1-mediated signaling cascades.

In vitro activity:

Both scopolin and scopoletin attenuated the production of general ROS and superoxide anions during the differentiation of preosteoclastic RAW 264.7 cells into osteoclasts. The study suggests that the suppressive effects of scopoline and scopoletin on the differentiation of preosteoclastic cells may be attributed, in part, to their intracellular antioxidant capacity. Reference: J Nat Prod. 2013 Apr 26;76(4):615-20. https://pubmed.ncbi.nlm.nih.gov/23510022/

In vivo activity:

Scopolin has potential for the treatment and prevention of osteoporosis. Scopolin treatment prevented bone mineral density loss in ovariectomized-induced osteoporotic mice. Reference: Nutrients. 2020 Nov 20;12(11):3565.

	Solvent	mg/mL	mM
Solubility
	DMSO	100.0	282.24

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 354.31 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:

1. Siwinska J, Kadzinski L, Banasiuk R, Gwizdek-Wisniewska A, Olry A, Banecki B, Lojkowska E, Ihnatowicz A. Identification of QTLs affecting scopolin and scopoletin biosynthesis in Arabidopsis thaliana. BMC Plant Biol. 2014 Oct 18;14:280. doi: 10.1186/s12870-014-0280-9. PMID: 25326030; PMCID: PMC4252993. 2. Lee SH, Ding Y, Yan XT, Kim YH, Jang HD. 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. doi: 10.1021/np300824h. Epub 2013 Mar 19. PMID: 23510022. 3. Park E, Kim J, Jin HS, Choi CW, Choi TH, Choi S, Huh D, Jeong SY. Scopolin Attenuates Osteoporotic Bone Loss in Ovariectomized Mice. Nutrients. 2020 Nov 20;12(11):3565. doi: 10.3390/nu12113565. PMID: 33233714; PMCID: PMC7699886. 4. Park E, Lee CG, Kim J, Lim E, Yeo S, Jeong SY. Scopolin Prevents Adipocyte Differentiation in 3T3-L1 Preadipocytes and Weight Gain in an Ovariectomy-Induced Obese Mouse Model. Int J Mol Sci. 2020 Nov 18;21(22):8699. doi: 10.3390/ijms21228699. PMID: 33218042; PMCID: PMC7698923.

In vitro protocol:

In vivo protocol:

1. Park E, Kim J, Jin HS, Choi CW, Choi TH, Choi S, Huh D, Jeong SY. Scopolin Attenuates Osteoporotic Bone Loss in Ovariectomized Mice. Nutrients. 2020 Nov 20;12(11):3565. doi: 10.3390/nu12113565. PMID: 33233714; PMCID: PMC7699886. 2. Park E, Lee CG, Kim J, Lim E, Yeo S, Jeong SY. Scopolin Prevents Adipocyte Differentiation in 3T3-L1 Preadipocytes and Weight Gain in an Ovariectomy-Induced Obese Mouse Model. Int J Mol Sci. 2020 Nov 18;21(22):8699. doi: 10.3390/ijms21228699. PMID: 33218042; PMCID: PMC7698923.

1: Siwinska J, Kadzinski L, Banasiuk R, Gwizdek-Wisniewska A, Olry A, Banecki B, Lojkowska E, Ihnatowicz A. Identification of QTLs affecting scopolin and scopoletin biosynthesis in Arabidopsis thaliana. BMC Plant Biol. 2014 Oct 18;14:280. doi: 10.1186/s12870-014-0280-9. PubMed PMID: 25326030; PubMed Central PMCID: PMC4252993. 2: Xu XK, Chen ZY, Liao LP, Zhang ZJ, Wang ZT. [Determination of scopolin, chlorogenic acid, scopoletin, isochlorogenic acid A, isochlorogenic acid B and isochlorogenic acid C in plants of Erycibe]. Zhongguo Zhong Yao Za Zhi. 2015 Mar;40(6):1119-22. Chinese. PubMed PMID: 26226756. 3: Tan R, Wang YJ, Zhang YX, Zhou LS, Tan E, Ping A, Zhang Y. [Determination of skimmin, scopolin and umbelliferone in Tibetan medicine Saussurea hieracioides by HPLC]. Zhongguo Zhong Yao Za Zhi. 2014 Mar;39(6):1054-7. Chinese. PubMed PMID: 24956850. 4: Lee SH, Ding Y, Yan XT, Kim YH, Jang HD. 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. doi: 10.1021/np300824h. Epub 2013 Mar 19. PubMed PMID: 23510022. 5: Pan R, Dai Y, Gao X, Xia Y. 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. doi: 10.1016/j.intimp.2009.02.019. Epub 2009 Mar 25. PubMed PMID: 19327410. 6: Ahn YO, Shimizu B, Sakata K, Gantulga D, Zhou C, Bevan DR, Esen A. Scopolin-hydrolyzing beta-glucosidases in roots of Arabidopsis. Plant Cell Physiol. 2010 Jan;51(1):132-43. doi: 10.1093/pcp/pcp174. Epub 2009 Dec 3. Erratum in: Plant Cell Physiol. 2010 Feb;51(2):339. Zhou, Zhanghe [corrected to Zhou, Changhe]. PubMed PMID: 19965874. 7: Gilleta F, Roisin C, Fliniaux MA, Jacquin-Dubreuil A, Barbotin JN, Nava-Saucedo JE. Immobilization of Nicotiana tabacum plant cell suspensions within calcium alginate gel beads for the production of enhanced amounts of scopolin. Enzyme Microb Technol. 2000 Feb 1;26(2-4):229-234. PubMed PMID: 10689082. 8: Xia YF, Dai Y, Wang Q, Cai F. A high-performance liquid chromatographic method for determination of scopolin in rat plasma: application to pharmacokinetic studies. Biomed Chromatogr. 2008 Oct;22(10):1137-42. doi: 10.1002/bmc.1036. PubMed PMID: 18506740. 9: Bayoumi SA, Rowan MG, Blagbrough IS, Beeching JR. Biosynthesis of scopoletin and scopolin in cassava roots during post-harvest physiological deterioration: the E-Z-isomerisation stage. Phytochemistry. 2008 Dec;69(17):2928-36. doi: 10.1016/j.phytochem.2008.09.023. Epub 2008 Nov 10. PubMed PMID: 19004461. 10: DEWEY LJ, STEPKA W. Scopolin: its isolation, characterization and relation to nicotine metabolism in harvested tobacco. Arch Biochem Biophys. 1963 Jan;100:91-6. PubMed PMID: 14027434. 11: Rollinger JM, Hornick A, Langer T, Stuppner H, Prast H. Acetylcholinesterase inhibitory activity of scopolin and scopoletin discovered by virtual screening of natural products. J Med Chem. 2004 Dec 2;47(25):6248-54. PubMed PMID: 15566295. 12: Shimizu B, Miyagawa H, Ueno T, Sakata K, Watanabe K, Ogawa K. Morning glory systemically accumulates scopoletin and scopolin after interaction with Fusarium oxysporum. Z Naturforsch C. 2005 Jan-Feb;60(1-2):83-90. PubMed PMID: 15787250. 13: Taguchi G, Fujikawa S, Yazawa T, Kodaira R, Hayashida N, Shimosaka M, Okazaki M. Scopoletin uptake from culture medium and accumulation in the vacuoles after conversion to scopolin in 2,4-D-treated tobacco cells. Plant Sci. 2000 Feb 21;151(2):153-161. PubMed PMID: 10808071. 14: Skoog F, Montaldi E. AUXIN-KINETIN INTERACTION REGULATING THE SCOPOLETIN AND SCOPOLIN LEVELS IN TOBACCO TISSUE CULTURES. Proc Natl Acad Sci U S A. 1961 Jan;47(1):36-49. PubMed PMID: 16590807; PubMed Central PMCID: PMC285229. 15: Yoo A, Narayan VP, Hong EY, Whang WK, Park T. 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. doi: 10.1038/s41598-017-02416-6. PubMed PMID: 28533555; PubMed Central PMCID: PMC5440403. 16: DIETERMAN LJ, LIN CY, ROHRBAUGH LM, WENDER SH. ACCUMULATION OF AYAPIN AND SCOPOLIN IN SUNFLOWER PLANTS TREATED WITH 2,4-DICHLOROPHENOXYACETIC ACID. Arch Biochem Biophys. 1964 Jul 20;106:275-9. PubMed PMID: 14217169. 17: DIETERMAN LJ, LIN CY, ROHRBAUGH L, THIESFELD V, WENDER SH. IDENTIFICATION AND QUANTITATIVE DETERMINATION OF SCOPOLIN AND SCOPOLETIN IN TOBACCO PLANTS TREATED WITH 2,4-DICHLOROPHENOXYACETIC ACID. Anal Biochem. 1964 Oct;9:139-45. PubMed PMID: 14227219. 18: Riov J, Goren R, Monselise SP, Kahan RS. Effect of gamma radiation on the synthesis of scopoletin and scopolin in grapefruit peel in relation to radiation damage. Radiat Res. 1971 Feb;45(2):326-34. PubMed PMID: 5543516. 19: Hino F, Okazaki M, Miura Y. Effect of 2,4-dichlorophenoxyacetic Acid on glucosylation of scopoletin to scopolin in tobacco tissue culture. Plant Physiol. 1982 Apr;69(4):810-3. PubMed PMID: 16662301; PubMed Central PMCID: PMC426310. 20: Steck W. Biosynthesis of scopolin in tobacco. Can J Biochem. 1967 Jun;45(6):889-96. PubMed PMID: 6034703.