WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 461718
CAS#: 29836-41-7
Description: Salicortin is a phenolic glucoside isolated from Populus euramericana bark extract that has been shown to have anti-amnesic and anti-adipogenic effects.
MedKoo Cat#: 461718
Name: Salicortin
CAS#: 29836-41-7
Chemical Formula: C20H24O10
Exact Mass: 424.1369
Molecular Weight: 424.4
Elemental Analysis: C, 56.60; H, 5.70; O, 37.70
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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
The following data is based on the product molecular weight 424.4 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 |
1: Kwon DJ, Bae YS, Ju SM, Youn GS, Choi SY, Park J. Salicortin suppresses
lipopolysaccharide-stimulated inflammatory responses via blockade of NF-κB and
JNK activation in RAW 264.7 macrophages. BMB Rep. 2014 Jun;47(6):318-23. PubMed
PMID: 24286322; PubMed Central PMCID: PMC4163874.
2: Nie S, Xu J, Zhang C, Xu C, Liu M, Yu D. Salicortin inhibits osteoclast
differentiation and bone resorption by down-regulating JNK and NF-κB/NFATc1
signaling pathways. Biochem Biophys Res Commun. 2016 Jan 29;470(1):61-7. doi:
10.1016/j.bbrc.2015.12.115. Epub 2015 Dec 29. PubMed PMID: 26740180.
3: Harbilas D, Vallerand D, Brault A, Saleem A, Arnason JT, Musallam L, Haddad
PS. Populus balsamifera Extract and Its Active Component Salicortin Reduce
Obesity and Attenuate Insulin Resistance in a Diet-Induced Obese Mouse Model.
Evid Based Complement Alternat Med. 2013;2013:172537. doi: 10.1155/2013/172537.
Epub 2013 May 27. 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.
