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

MedKoo CAT#: 592677

CAS#: 138-52-3

Description: Salicin inhibits angiogenesis by blocking the ROS-ERK pathways.

Chemical Structure

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Salicin
CAS# 138-52-3
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 592677
Name: Salicin
CAS#: 138-52-3
Chemical Formula: C13H18O7
Exact Mass: 286.11
Molecular Weight: 286.280
Elemental Analysis: C, 54.54; H, 6.34; O, 39.12

Price and Availability

Size Price Availability Quantity
5g USD 350 2 weeks
10g USD 500 2 Weeks
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Synonym: Salicin; NSC 5751; NSC-5751; NSC5751

IUPAC/Chemical Name: alpha-Hydroxy-o-tolyl beta-D-glucopyranoside

InChi Key: NGFMICBWJRZIBI-UJPOAAIJSA-N

InChi Code: InChI=1S/C13H18O7/c14-5-7-3-1-2-4-8(7)19-13-12(18)11(17)10(16)9(6-15)20-13/h1-4,9-18H,5-6H2/t9-,10-,11+,12-,13-/m1/s1

SMILES Code: O[C@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)[C@@H]1OC2=CC=CC=C2CO

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 and water

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:
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Biological target: Salicin is a non-selective COX inhibitor with IC50 values > 100 µM for COX-1 and COX-2.
In vitro activity: Salicin is a protective agent in retinal endothelial cells with potential therapeutic use for retinal disease. Salicin exhibits potent anti-inflammatory properties by reducing oxidative stress, preserving mitochondrial health, and inhibiting the production of inflammatory molecules. It also helps maintain the function of important endothelial components and reduces cytotoxicity. Reference: Artif Cells Nanomed Biotechnol. 2019 Dec;47(1):1995-2002. https://pubmed.ncbi.nlm.nih.gov/31106593/
In vivo activity: In a pneumonia model of mice infected with S. aureus, salicin reduced the content of lung bacteria, reduce the virulence of S. aureus, and prolonged mouse survival. Salicin was identified as a novel anti-infective candidate compound with the potential to target coagulase and inhibit its activity by binding to it. Reference: ChemMedChem. 2023 Sep 27:e202300302. https://pubmed.ncbi.nlm.nih.gov/37755368/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 150.0 523.96
Water 12.5 43.66

Preparing Stock Solutions

The following data is based on the product molecular weight 286.28 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.

Recalculate based on batch purity %
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. Song Y, Tian X, Wang X, Feng H. Vascular protection of salicin on IL-1β-induced endothelial inflammatory response and damages in retinal endothelial cells. Artif Cells Nanomed Biotechnol. 2019 Dec;47(1):1995-2002. doi: 10.1080/21691401.2019.1608220. PMID: 31106593. 2. Wölfle U, Haarhaus B, Kersten A, Fiebich B, Hug MJ, Schempp CM. Salicin from Willow Bark can Modulate Neurite Outgrowth in Human Neuroblastoma SH-SY5Y Cells. Phytother Res. 2015 Oct;29(10):1494-500. doi: 10.1002/ptr.5400. Epub 2015 Jun 19. PMID: 26096905. 3. Jiang Y, Hou J, Liu C, Zhao C, Xu Y, Song W, Shu Z, Wang B. Inhibitory Effect of Salicin on Staphylococcus aureus Coagulase. ChemMedChem. 2023 Sep 27:e202300302. doi: 10.1002/cmdc.202300302. Epub ahead of print. PMID: 37755368. 4. Li Y, Wu Q, Deng Y, Lv H, Qiu J, Chi G, Feng H. D(-)-Salicin inhibits the LPS-induced inflammation in RAW264.7 cells and mouse models. Int Immunopharmacol. 2015 Jun;26(2):286-94. doi: 10.1016/j.intimp.2015.04.016. Epub 2015 Apr 20. PMID: 25907238.
In vitro protocol: 1. Song Y, Tian X, Wang X, Feng H. Vascular protection of salicin on IL-1β-induced endothelial inflammatory response and damages in retinal endothelial cells. Artif Cells Nanomed Biotechnol. 2019 Dec;47(1):1995-2002. doi: 10.1080/21691401.2019.1608220. PMID: 31106593. 2. Wölfle U, Haarhaus B, Kersten A, Fiebich B, Hug MJ, Schempp CM. Salicin from Willow Bark can Modulate Neurite Outgrowth in Human Neuroblastoma SH-SY5Y Cells. Phytother Res. 2015 Oct;29(10):1494-500. doi: 10.1002/ptr.5400. Epub 2015 Jun 19. PMID: 26096905.
In vivo protocol: 1. Jiang Y, Hou J, Liu C, Zhao C, Xu Y, Song W, Shu Z, Wang B. Inhibitory Effect of Salicin on Staphylococcus aureus Coagulase. ChemMedChem. 2023 Sep 27:e202300302. doi: 10.1002/cmdc.202300302. Epub ahead of print. PMID: 37755368. 2. Li Y, Wu Q, Deng Y, Lv H, Qiu J, Chi G, Feng H. D(-)-Salicin inhibits the LPS-induced inflammation in RAW264.7 cells and mouse models. Int Immunopharmacol. 2015 Jun;26(2):286-94. doi: 10.1016/j.intimp.2015.04.016. Epub 2015 Apr 20. PMID: 25907238.

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1: Li Y, Wu Q, Deng Y, Lv H, Qiu J, Chi G, Feng H. D(-)-Salicin inhibits the LPS-induced inflammation in RAW264.7 cells and mouse models. Int Immunopharmacol. 2015 Jun;26(2):286-94. doi: 10.1016/j.intimp.2015.04.016. Epub 2015 Apr 20. PubMed PMID: 25907238.

2: Kong CS, Kim KH, Choi JS, Kim JE, Park C, Jeong JW. Salicin, an extract from white willow bark, inhibits angiogenesis by blocking the ROS-ERK pathways. Phytother Res. 2014 Aug;28(8):1246-51. doi: 10.1002/ptr.5126. Epub 2014 Feb 17. PubMed PMID: 24535656.

3: Wölfle U, Haarhaus B, Kersten A, Fiebich B, Hug MJ, Schempp CM. Salicin from Willow Bark can Modulate Neurite Outgrowth in Human Neuroblastoma SH-SY5Y Cells. Phytother Res. 2015 Oct;29(10):1494-500. doi: 10.1002/ptr.5400. Epub 2015 Jun 19. PubMed PMID: 26096905.

4: Verma N, Verma R, Kumari R, Ranjha R, Paul J. Effect of salicin on gut inflammation and on selected groups of gut microbiota in dextran sodium sulfate induced mouse model of colitis. Inflamm Res. 2014 Feb;63(2):161-9. doi: 10.1007/s00011-013-0685-1. Epub 2013 Nov 17. PubMed PMID: 24240229.

5: Rudeekulthamrong P, Kaulpiboon J. Application of amylomaltase for the synthesis of salicin-α-glucosides as efficient anticoagulant and anti-inflammatory agents. Carbohydr Res. 2016 Sep 2;432:55-61. doi: 10.1016/j.carres.2016.06.011. Epub 2016 Jun 29. PubMed PMID: 27394039.

6: Kim CS, Subedi L, Park KJ, Kim SY, Choi SU, Kim KH, Lee KR. Salicin derivatives from Salix glandulosa and their biological activities. Fitoterapia. 2015 Oct;106:147-52. doi: 10.1016/j.fitote.2015.08.013. Epub 2015 Sep 4. PubMed PMID: 26344424.

7: Wei W, Rena K, Yang XW. New salicin derivatives from the leaves of Populus euphratica. J Asian Nat Prod Res. 2015 May;17(5):491-6. doi: 10.1080/10286020.2015.1028920. Epub 2015 Apr 23. PubMed PMID: 25903097.

8: Campbell MC, Ranciaro A, Zinshteyn D, Rawlings-Goss R, Hirbo J, Thompson S, Woldemeskel D, Froment A, Rucker JB, Omar SA, Bodo JM, Nyambo T, Belay G, Drayna D, Breslin PA, Tishkoff SA. Origin and differential selection of allelic variation at TAS2R16 associated with salicin bitter taste sensitivity in Africa. Mol Biol Evol. 2014 Feb;31(2):288-302. doi: 10.1093/molbev/mst211. Epub 2013 Oct 30. PubMed PMID: 24177185; PubMed Central PMCID: PMC3907056.

9: Karmakar M. Inducing effect of salicin for extracellular endoglucanase synthesis in Rhizopus oryzae PR7 MTCC 9642. Prikl Biokhim Mikrobiol. 2013 Jul-Aug;49(4):391-5. PubMed PMID: 24455865.

10: Stepanova EV, Belyanin ML, Filimonov VD. Synthesis of acyl derivatives of salicin, salirepin, and arbutin. Carbohydr Res. 2014 Mar 31;388:105-11. doi: 10.1016/j.carres.2014.02.014. Epub 2014 Feb 20. PubMed PMID: 24632218.

11: Chen F, Mo K, Liu Z, Yang F, Hou K, Li S, Zu Y, Yang L. Ionic liquid-based vacuum microwave-assisted extraction followed by macroporous resin enrichment for the separation of the three glycosides salicin, hyperin and rutin from Populus bark. Molecules. 2014 Jul 7;19(7):9689-711. doi: 10.3390/molecules19079689. PubMed PMID: 25004075.

12: Mahdi JG. Biosynthesis and metabolism of β-d-salicin: A novel molecule that exerts biological function in humans and plants. Biotechnol Rep (Amst). 2014 Aug 28;4:73-79. doi: 10.1016/j.btre.2014.08.005. eCollection 2014 Dec. PubMed PMID: 28626665; PubMed Central PMCID: PMC5466123.

13: Iizuka T, Tamura T, Sezutsu H, Mase K, Okada E, Asaoka K. Genetic analysis of the electrophysiological response to salicin, a bitter substance, in a polyphagous strain of the silkworm Bombyx mori. PLoS One. 2012;7(5):e37549. doi: 10.1371/journal.pone.0037549. Epub 2012 May 23. PubMed PMID: 22649537; PubMed Central PMCID: PMC3359296.

14: Doyle D. Thomas MacLagan's 1876 demonstration of the dramatic effects of salicin in rheumatic fever. J R Soc Med. 2014 Jul;107(7):287-289. Epub 2014 Jul 10. PubMed PMID: 25013096; PubMed Central PMCID: PMC4093759.

15: Gopaul R, Knaggs HE, Lephart JF, Holley KC, Gibson EM. An evaluation of the effect of a topical product containing salicin on the visible signs of human skin aging. J Cosmet Dermatol. 2010 Sep;9(3):196-201. doi: 10.1111/j.1473-2165.2010.00512.x. PubMed PMID: 20883292.

16: Mielańczyk A, Odrobińska J, Grządka S, Mielańczyk Ł, Neugebauer D. Miktoarm star copolymers from D-(-)-salicin core aggregated into dandelion-like structures as anticancer drug delivery systems: synthesis, self-assembly and drug release. Int J Pharm. 2016 Dec 30;515(1-2):515-526. doi: 10.1016/j.ijpharm.2016.10.034. Epub 2016 Oct 19. PubMed PMID: 27771487.

17: Tomassini L, Serafini M, Foddai S, Ventrone A, Nicoletti M. New acylated salicin bis-glucosides from Viburnum veitchii. Nat Prod Res. 2013;27(13):1208-12. doi: 10.1080/14786419.2012.722092. Epub 2012 Sep 6. PubMed PMID: 22950836.

18: Desai SK, Nandimath K, Mahadevan S. Diverse pathways for salicin utilization in Shigella sonnei and Escherichia coli carrying an impaired bgl operon. Arch Microbiol. 2010 Oct;192(10):821-33. doi: 10.1007/s00203-010-0610-8. Epub 2010 Aug 10. PubMed PMID: 20697693.

19: Schmitt GC, Arbo MD, Lorensi AL, Maciel ES, Krahn CL, Mariotti KC, Dallegrave E, Leal MB, Limberger RP. Toxicological effects of a mixture used in weight loss products: p-synephrine associated with ephedrine, salicin, and caffeine. Int J Toxicol. 2012 Mar;31(2):184-91. doi: 10.1177/1091581811435708. Epub 2012 Mar 9. PubMed PMID: 22408069.

20: Gopaul R, Knaggs HE, Lephart J. Salicin regulates the expression of functional 'youth gene clusters' to reflect a more youthful gene expression profile. Int J Cosmet Sci. 2011 Oct;33(5):416-20. doi: 10.1111/j.1468-2494.2011.00645.x. Epub 2011 Mar 30. PubMed PMID: 21449910.