Salicortin | CAS#29836-41-7 | phenolic glucoside

MedKoo Cat#: 461718 | Name: Salicortin

Description:

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

Salicortin is a phenolic glucoside isolated from Populus euramericana bark extract that has been shown to have anti-amnesic and anti-adipogenic effects.

Chemical Structure

Salicortin

CAS#29836-41-7

Theoretical Analysis

MedKoo Cat#: 461718

Name: Salicortin

CAS#: 29836-41-7

Chemical Formula: C20H24O10

Exact Mass: 424.1369

Molecular Weight: 424.40

Elemental Analysis: C, 56.60; H, 5.70; O, 37.70

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

No Data

Synonym

Salicortin;

IUPAC/Chemical Name

2-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)benzyl 1-hydroxy-6-oxocyclohex-2-ene-1-carboxylate

InChi Key

CZDNLUMNELLDDD-QZFWYPLZSA-N

InChi Code

InChI=1S/C20H24O10/c21-9-13-15(23)16(24)17(25)18(30-13)29-12-6-2-1-5-11(12)10-28-19(26)20(27)8-4-3-7-14(20)22/h1-2,4-6,8,13,15-18,21,23-25,27H,3,7,9-10H2/t13-,15-,16+,17-,18-,20?/m1/s1

SMILES Code

O[C@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)[C@@H]1OC2=CC=CC=C2COC(C3(O)C=CCCC3=O)=O

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

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 424.40 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

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PubMed PMID: 23781256; PubMed Central PMCID: PMC3678421. 4: Lee M, Lee SH, Kang J, Yang H, Jeong EJ, Kim HP, Kim YC, Sung SH. Salicortin-derivatives from Salix pseudo-lasiogyne twigs inhibit adipogenesis in 3T3-L1 cells via modulation of C/EBPα and SREBP1c dependent pathway. Molecules. 2013 Aug 30;18(9):10484-96. doi: 10.3390/molecules180910484. PubMed PMID: 23999723. 5: Feistel F, Paetz C, Lorenz S, Schneider B. The absolute configuration of salicortin, HCH-salicortin and tremulacin from Populus trichocarpa × deltoides Beaupré. Molecules. 2015 Mar 30;20(4):5566-73. doi: 10.3390/molecules20045566. PubMed PMID: 25830788. 6: Knuth S, Schübel H, Hellemann M, Jürgenliemk G. Catechol, a bioactive degradation product of salicortin, reduces TNF-α induced ICAM-1 expression in human endothelial cells. Planta Med. 2011 Jul;77(10):1024-6. doi: 10.1055/s-0030-1270722. Epub 2011 Feb 8. PubMed PMID: 21305449. 7: Babst BA, Harding SA, Tsai CJ. Biosynthesis of phenolic glycosides from phenylpropanoid and benzenoid precursors in populus. J Chem Ecol. 2010 Mar;36(3):286-97. doi: 10.1007/s10886-010-9757-7. Epub 2010 Feb 23. PubMed PMID: 20177744. 8: Martineau LC, Muhammad A, Saleem A, Hervé J, Harris CS, Arnason JT, Haddad PS. Anti-adipogenic activities of Alnus incana and Populus balsamifera bark extracts, part II: bioassay-guided identification of actives salicortin and oregonin. Planta Med. 2010 Oct;76(14):1519-24. doi: 10.1055/s-0029-1240991. Epub 2010 Mar 18. PubMed PMID: 20301058. 9: Zhu J, Withers SG, Reichardt PB, Treadwell E, Clausen TP. Salicortin: a repeat-attack new-mechanism-based Agrobacterium faecalis beta-glucosidase inhibitor. Biochem J. 1998 Jun 1;332 ( Pt 2):367-71. PubMed PMID: 9601065; PubMed Central PMCID: PMC1219491. 10: Rubert-Nason KF, Hedman CJ, Holeski LM, Lindroth RL. Determination of salicinoids by micro-high-performance liquid chromatography and photodiode array detection. Phytochem Anal. 2014 May-Jun;25(3):185-91. PubMed PMID: 24847528. 11: Lee HJ, Kim JS, Kim YK, Ryu JH. Phenolic glycosides as inhibitors of inducible nitric oxide synthase from Populus davidiana in LPS-activated RAW 264.7 murine macrophages. Pharmazie. 2012 Oct;67(10):870-3. PubMed PMID: 23136723. 12: Richardson AM, Chen CH, Snider BB. Synthesis of methyl 1-hydroxy-6-oxo-2-cyclohexenecarboxylate, a component of salicortin and tremulacin, and the monomer of idesolide. J Org Chem. 2007 Oct 12;72(21):8099-102. Epub 2007 Sep 15. PubMed PMID: 17867704. 13: Chedgy RJ, Köllner TG, Constabel CP. Functional characterization of two acyltransferases from Populus trichocarpa capable of synthesizing benzyl benzoate and salicyl benzoate, potential intermediates in salicinoid phenolic glycoside biosynthesis. Phytochemistry. 2015 May;113:149-59. doi: 10.1016/j.phytochem.2014.10.018. Epub 2015 Jan 2. PubMed PMID: 25561400. 14: Abreu IN, Ahnlund M, Moritz T, Albrectsen BR. UHPLC-ESI/TOFMS determination of salicylate-like phenolic gycosides in Populus tremula leaves. J Chem Ecol. 2011 Aug;37(8):857-70. doi: 10.1007/s10886-011-9991-7. Epub 2011 Jul 6. PubMed PMID: 21748301; PubMed Central PMCID: PMC3148433. 15: Wu Y, Dobermann D, Beale MH, Ward JL. Acutifoliside, a novel benzoic acid glycoside from Salix acutifolia. Nat Prod Res. 2016 Aug;30(15):1731-9. doi: 10.1080/14786419.2015.1137571. Epub 2016 Jan 28. PubMed PMID: 26820172. 16: Mason CJ, Rubert-Nason KF, Lindroth RL, Raffa KF. Aspen defense chemicals influence midgut bacterial community composition of gypsy moth. J Chem Ecol. 2015 Jan;41(1):75-84. doi: 10.1007/s10886-014-0530-1. Epub 2014 Dec 5. PubMed PMID: 25475786. 17: Boeckler GA, Paetz C, Feibicke P, Gershenzon J, Unsicker SB. Metabolism of poplar salicinoids by the generalist herbivore Lymantria dispar (Lepidoptera). Insect Biochem Mol Biol. 2016 Nov;78:39-49. doi: 10.1016/j.ibmb.2016.08.001. Epub 2016 Aug 5. PubMed PMID: 27503687. 18: Knuth S, Abdelsalam RM, Khayyal MT, Schweda F, Heilmann J, Kees MG, Mair G, Kees F, Jürgenliemk G. Catechol conjugates are in vivo metabolites of Salicis cortex. Planta Med. 2013 Nov;79(16):1489-94. doi: 10.1055/s-0033-1350898. Epub 2013 Oct 21. PubMed PMID: 24146062. 19: Harding SA, Xue LJ, Du L, Nyamdari B, Lindroth RL, Sykes R, Davis MF, Tsai CJ. Condensed tannin biosynthesis and polymerization synergistically condition carbon use, defense, sink strength and growth in Populus. Tree Physiol. 2014 Nov;34(11):1240-51. doi: 10.1093/treephys/tpt097. Epub 2013 Dec 10. PubMed PMID: 24336515. 20: Orians CM. Preserving leaves for tannin and phenolic glycoside analyses: A comparison of methods using three willow taxa. J Chem Ecol. 1995 Sep;21(9):1235-43. doi: 10.1007/BF02027558. PubMed PMID: 24234623.