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MedKoo Cat#: 461417 | Name: Rosarin
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Description:

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

Rosarin is a cinnamyl alcohol glycoside isolated from Rhodiola rosea.

Chemical Structure

Rosarin
Rosarin
CAS#84954-93-8

Theoretical Analysis

MedKoo Cat#: 461417

Name: Rosarin

CAS#: 84954-93-8

Chemical Formula: C20H28O10

Exact Mass: 428.1682

Molecular Weight: 428.43

Elemental Analysis: C, 56.07; H, 6.59; O, 37.34

Price and Availability

Size Price Availability Quantity
5mg USD 500.00
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Related CAS #
No Data
Synonym
Rosarin;
IUPAC/Chemical Name
(2R,3R,4S,5S,6R)-2-(cinnamyloxy)-6-((((2R,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)oxy)methyl)tetrahydro-2H-pyran-3,4,5-triol
InChi Key
IEBFEMIXXHIISM-YZOUKVLTSA-N
InChi Code
InChI=1S/C20H28O10/c21-9-12-14(22)17(25)20(29-12)28-10-13-15(23)16(24)18(26)19(30-13)27-8-4-7-11-5-2-1-3-6-11/h1-7,12-26H,8-10H2/b7-4+/t12-,13+,14-,15+,16-,17+,18+,19+,20+/m0/s1
SMILES Code
O[C@H]([C@H]([C@@H]([C@@H](CO[C@H]1[C@@H]([C@H]([C@H](CO)O1)O)O)O2)O)O)[C@@H]2OC/C=C/C3=CC=CC=C3
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:
Rosarin prevents LPS-induced increases in induced nitric oxide synthase (iNOS), TNF-α, IL-1β, and IL-6 levels in BV-2 microglia. Rosarin reduces LPS-induced nitric oxide production in BV-2 microglia. It increases the growth of Jurkat T cells induced by concanavalin A or anti-CD3 and anti-CD28 antibodies (IC50s = 60 and 68 µM, respectively).
In vitro activity:
Against salidroside, rosarin, rosavin and rosin, the initial screening for cell viability in Jurkat T cells and for apoptosis of mouse T cells showed the strongest activity for rosavin and rosarin. Rosarin promoted TRAIL up-regulation. Rosarin increased the frequencies of CD3+TRAIL+ T cells and the fold inhibition of ERK phosphorylation. Reference: Food Chem Toxicol. 2017 Oct;108(Pt B):419-428. https://pubmed.ncbi.nlm.nih.gov/28189478/
In vivo activity:
The LPS-induced expression of iNOS and cytokines in BV2 cells was suppressed by the constituents of Rhodiola rosea, one being rosarin, in a concentration-dependent manner. L-glutamate-induced neurotoxicity was not suppressed by rosarin Reference: Evid Based Complement Alternat Med. 2013;2013:514049. https://pubmed.ncbi.nlm.nih.gov/23690847/
Solvent mg/mL mM
Solubility
DMSO 100.0 233.41
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 428.43 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. Marchev AS, Dimitrova P, Koycheva IK, Georgiev MI. Altered expression of TRAIL on mouse T cells via ERK phosphorylation by Rhodiola rosea L. and its marker compounds. Food Chem Toxicol. 2017 Oct;108(Pt B):419-428. doi: 10.1016/j.fct.2017.02.009. Epub 2017 Feb 8. PMID: 28189478. 2. Lee Y, Jung JC, Jang S, Kim J, Ali Z, Khan IA, Oh S. Anti-Inflammatory and Neuroprotective Effects of Constituents Isolated from Rhodiola rosea. Evid Based Complement Alternat Med. 2013;2013:514049. doi: 10.1155/2013/514049. Epub 2013 Apr 16. PMID: 23690847; PMCID: PMC3652169.
In vitro protocol:
1. Marchev AS, Dimitrova P, Koycheva IK, Georgiev MI. Altered expression of TRAIL on mouse T cells via ERK phosphorylation by Rhodiola rosea L. and its marker compounds. Food Chem Toxicol. 2017 Oct;108(Pt B):419-428. doi: 10.1016/j.fct.2017.02.009. Epub 2017 Feb 8. PMID: 28189478.
In vivo protocol:
1. Lee Y, Jung JC, Jang S, Kim J, Ali Z, Khan IA, Oh S. Anti-Inflammatory and Neuroprotective Effects of Constituents Isolated from Rhodiola rosea. Evid Based Complement Alternat Med. 2013;2013:514049. doi: 10.1155/2013/514049. Epub 2013 Apr 16. PMID: 23690847; PMCID: PMC3652169.
1: Fukuzumi S, Ohkubo K, Ishida M, Preihs C, Chen B, Borden WT, Kim D, Sessler JL. Formation of Ground State Triplet Diradicals from Annulated Rosarin Derivatives by Triprotonation. J Am Chem Soc. 2015 Aug 12;137(31):9780-3. doi: 10.1021/jacs.5b05309. Epub 2015 Jul 29. PubMed PMID: 26203891. 2: Grech-Baran M, Sykłowska-Baranek K, Krajewska-Patan A, Wyrwał A, Pietrosiuk A. Biotransformation of cinnamyl alcohol to rosavins by non-transformed wild type and hairy root cultures of Rhodiola kirilowii. Biotechnol Lett. 2014 Mar;36(3):649-56. doi: 10.1007/s10529-013-1401-5. Epub 2013 Nov 5. PubMed PMID: 24190481; PubMed Central PMCID: PMC3964300. 3: Setsune J, Toda M, Yoshida T, Imamura K, Watanabe K. The synthesis and dynamic structures of multinuclear complexes of large porphyrinoids expanded by phenylene and thienylene spacers. Chemistry. 2015 Sep 1;21(36):12715-27. doi: 10.1002/chem.201501570. Epub 2015 Jul 21. PubMed PMID: 26216524. 4: Mirmazloum I, Ladányi M, György Z. Changes in the Content of the Glycosides, Aglycons and their Possible Precursors of Rhodiola rosea during the Vegetation Period. Nat Prod Commun. 2015 Aug;10(8):1413-6. PubMed PMID: 26434130. 5: Thu OK, Nilsen OG, Hellum B. In vitro inhibition of cytochrome P-450 activities and quantification of constituents in a selection of commercial Rhodiola rosea products. Pharm Biol. 2016 Dec;54(12):3249-3256. Epub 2016 Aug 29. PubMed PMID: 27572116. 6: Lee Y, Jung JC, Jang S, Kim J, Ali Z, Khan IA, Oh S. Anti-Inflammatory and Neuroprotective Effects of Constituents Isolated from Rhodiola rosea. Evid Based Complement Alternat Med. 2013;2013:514049. doi: 10.1155/2013/514049. Epub 2013 Apr 16. PubMed PMID: 23690847; PubMed Central PMCID: PMC3652169. 7: Panossian A, Nikoyan N, Ohanyan N, Hovhannisyan A, Abrahamyan H, Gabrielyan E, Wikman G. Comparative study of Rhodiola preparations on behavioral despair of rats. Phytomedicine. 2008 Jan;15(1-2):84-91. Epub 2007 Dec 3. PubMed PMID: 18054474. 8: Ma YC, Wang XQ, Hou FF, Ma J, Luo M, Lu S, Jin P, Terevsky N, Chen A, Xu I, Patel AV, Gorecki D. Rapid resolution liquid chromatography (RRLC) analysis for quality control of Rhodiola rosea roots and commercial standardized products. Nat Prod Commun. 2011 May;6(5):645-50. PubMed PMID: 21615025. 9: Ishida M, Kim SJ, Preihs C, Ohkubo K, Lim JM, Lee BS, Park JS, Lynch VM, Roznyatovskiy VV, Sarma T, Panda PK, Lee CH, Fukuzumi S, Kim D, Sessler JL. Protonation-coupled redox reactions in planar antiaromatic meso-pentafluorophenyl-substituted o-phenylene-bridged annulated rosarins. Nat Chem. 2013 Jan;5(1):15-20. doi: 10.1038/nchem.1501. Epub 2012 Dec 9. PubMed PMID: 23247172. 10: Ma YC, Wang XQ, Hou F, Ma J, Luo M, Lu S, Jin P, Chen A, Xu I, Patel AV, Gorecki D. Simultaneous quantification of polyherbal formulations containing Rhodiola rosea L. and Eleutherococcus senticosus Maxim. using rapid resolution liquid chromatography (RRLC). J Pharm Biomed Anal. 2011 Jul 15;55(5):908-15. doi: 10.1016/j.jpba.2011.03.013. Epub 2011 Mar 12. PubMed PMID: 21466940. 11: Ke XS, Kim T, Brewster JT 2nd, Lynch VM, Kim D, Sessler JL. Expanded Rosarin: A Versatile Fullerene (C(60)) Receptor. J Am Chem Soc. 2017 Apr 5;139(13):4627-4630. doi: 10.1021/jacs.7b00735. Epub 2017 Mar 24. PubMed PMID: 28318261. 12: Booker A, Zhai L, Gkouva C, Li S, Heinrich M. From Traditional Resource to Global Commodities:-A Comparison of Rhodiola Species Using NMR Spectroscopy-Metabolomics and HPTLC. Front Pharmacol. 2016 Aug 29;7:254. doi: 10.3389/fphar.2016.00254. eCollection 2016. PubMed PMID: 27621703; PubMed Central PMCID: PMC5002433. 13: Tomassini L, Gao J, Foddai S, Serafini M, Ventrone A, Nicoletti M. Iridoid glucosides from Viburnum chinshanense. Nat Prod Res. 2006 Jul 10;20(8):697-700. PubMed PMID: 16753900. 14: Marchev AS, Dimitrova P, Koycheva IK, Georgiev MI. Altered expression of TRAIL on mouse T cells via ERK phosphorylation by Rhodiola rosea L. and its marker compounds. Food Chem Toxicol. 2017 Oct;108(Pt B):419-428. doi: 10.1016/j.fct.2017.02.009. Epub 2017 Feb 8. PubMed PMID: 28189478. 15: Huang SC, Lee FT, Kuo TY, Yang JH, Chien CT. Attenuation of long-term Rhodiola rosea supplementation on exhaustive swimming-evoked oxidative stress in the rat. Chin J Physiol. 2009 Oct 31;52(5):316-24. PubMed PMID: 20034236. 16: Comte G, Chulia AJ, Vercauteren J, Allais DP. Phenylpropane glycosides from Juniperus phoenicea. Planta Med. 1996 Feb;62(1):88-9. PubMed PMID: 17252422. 17: Kucinskaite A, Pobłocka-Olech L, Krauze-Baranowska M, Sznitowska M, Savickas A, Briedis V. Evaluation of biologically active compounds in roots and rhizomes of Rhodiola rosea L. cultivated in Lithuania. Medicina (Kaunas). 2007;43(6):487-94. PubMed PMID: 17637521. 18: Rosarin FS, Arulmozhi V, Nagarajan S, Mirunalini S. Antiproliferative effect of silver nanoparticles synthesized using amla on Hep2 cell line. Asian Pac J Trop Med. 2013 Jan;6(1):1-10. doi: 10.1016/S1995-7645(12)60193-X. PubMed PMID: 23317879. 19: Ganzera M, Yayla Y, Khan IA. Analysis of the marker compounds of Rhodiola rosea L. (golden root) by reversed phase high performance liquid chromatography. Chem Pharm Bull (Tokyo). 2001 Apr;49(4):465-7. PubMed PMID: 11310675. 20: Akgul Y, Ferreira D, Abourashed EA, Khan IA. Lotaustralin from Rhodiola rosea roots. Fitoterapia. 2004 Sep;75(6):612-4. PubMed PMID: 15351122.

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