Rosavin | CAS#84954-92-7 | antidepressant

MedKoo Cat#: 461416 | Name: Rosavin

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Description:

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

Rosavin is a bioactive antidepressant component isolated from Rhodiola rosea L.

Chemical Structure

Rosavin

CAS#84954-92-7

Theoretical Analysis

MedKoo Cat#: 461416

Name: Rosavin

CAS#: 84954-92-7

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 260.00
25mg	USD 620.00

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Related CAS #

No Data

Synonym

Rosavin;

IUPAC/Chemical Name

(2R,3R,4S,5S,6R)-2-(cinnamyloxy)-6-((((2S,3R,4S,5S)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-3,4,5-triol

InChi Key

RINHYCZCUGCZAJ-IPXOVKFZSA-N

InChi Code

InChI=1S/C20H28O10/c21-12-9-28-19(17(25)14(12)22)29-10-13-15(23)16(24)18(26)20(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](CO1)O)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:

Rosavin has been reported as having immunomodulatory effects, radiation protection, anti-cancer activities, protective effects on bleomycin-induced pulmonary fibrosis, and induced antidepressant-like effects in mouse models.

In vitro activity:

Rosavin repressed the viability and clone formation and promoted apoptosis and G0/G1 arrest of small-cell lung cancer (SCLC) cells. Rosavin suppressed migration and invasion of SCLC cells. After rosavin addition, protein levels of p-ERK/ERK and p-MEK/MEK decreased. Rosavin impaired malignant behaviors of SCLC cells in vitro. Reference: Acta Pharm. 2023 Jun 12;73(2):269-280. https://pubmed.ncbi.nlm.nih.gov/37307376/

In vivo activity:

In a PM2.5-induced lung injury rat model, rosavin prevented lung injury induced by PM2.5 stimulation and suppressed ferroptosis via upregulating PI3K/Akt/Nrf2 signaling pathway. Additionally, pretreatment with rosavin downregulated the levels of tissue iron, malondialdehyde, and 4-hydroxynonenal, and increased the levels of glutathione. Reference: Phytother Res. 2023 Jan;37(1):195-210. https://pubmed.ncbi.nlm.nih.gov/36097321/

	Solvent	mg/mL	mM
Solubility
	DMSO	85.0	198.40

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.

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. Liu R, Jiang C, Zhao Z, Lv Y, Wang G. Rosavin exerts an antitumor role and inactivates the MAPK/ERK pathway in small-cell lung carcinoma in vitro. Acta Pharm. 2023 Jun 12;73(2):269-280. doi: 10.2478/acph-2023-0015. PMID: 37307376. 2. Borgonetti V, Governa P, Biagi M, Dalia P, Corsi L. Rhodiola rosea L. modulates inflammatory processes in a CRH-activated BV2 cell model. Phytomedicine. 2020 Mar;68:153143. doi: 10.1016/j.phymed.2019.153143. Epub 2019 Dec 5. PMID: 32018209. 3. Zou H, Li L, Yang Z, Tang L, Wang C. Rosavin protects the blood-brain barrier against ischemia/reperfusion-induced cerebral injury by regulating MAPK-mediated MMPs pathway. Clin Exp Pharmacol Physiol. 2023 Aug;50(8):664-676. doi: 10.1111/1440-1681.13781. Epub 2023 May 31. PMID: 37254848. 4. Wang Y, Zhao S, Jia N, Shen Z, Huang D, Wang X, Wu Y, Pei C, Shi S, He Y, Wang Z. Pretreatment with rosavin attenuates PM2.5-induced lung injury in rats through antiferroptosis via PI3K/Akt/Nrf2 signaling pathway. Phytother Res. 2023 Jan;37(1):195-210. doi: 10.1002/ptr.7606. Epub 2022 Sep 12. PMID: 36097321.

In vitro protocol:

In vivo protocol:

1. Zou H, Li L, Yang Z, Tang L, Wang C. Rosavin protects the blood-brain barrier against ischemia/reperfusion-induced cerebral injury by regulating MAPK-mediated MMPs pathway. Clin Exp Pharmacol Physiol. 2023 Aug;50(8):664-676. doi: 10.1111/1440-1681.13781. Epub 2023 May 31. PMID: 37254848. 2. Wang Y, Zhao S, Jia N, Shen Z, Huang D, Wang X, Wu Y, Pei C, Shi S, He Y, Wang Z. Pretreatment with rosavin attenuates PM2.5-induced lung injury in rats through antiferroptosis via PI3K/Akt/Nrf2 signaling pathway. Phytother Res. 2023 Jan;37(1):195-210. doi: 10.1002/ptr.7606. Epub 2022 Sep 12. PMID: 36097321.

1: Chen D, Sun H, Shen J, Igor LP, Zheng X, Hu S, Xiang Z. A Simple and Rapid UPLC Method for the Determination of Rosavin in Rat Plasma and Its Application to a Pharmacokinetic Study. J Chromatogr Sci. 2016 Aug;54(7):1166-70. doi: 10.1093/chromsci/bmw044. Epub 2016 Apr 4. PubMed PMID: 27048645. 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: Nabavi SF, Braidy N, Orhan IE, Badiee A, Daglia M, Nabavi SM. Rhodiola rosea L. and Alzheimer's Disease: From Farm to Pharmacy. Phytother Res. 2016 Apr;30(4):532-9. doi: 10.1002/ptr.5569. Epub 2016 Jan 11. Review. PubMed PMID: 27059687. 4: Perfumi M, Mattioli L. Adaptogenic and central nervous system effects of single doses of 3% rosavin and 1% salidroside Rhodiola rosea L. extract in mice. Phytother Res. 2007 Jan;21(1):37-43. PubMed PMID: 17072830. 5: 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. 6: Pomari E, Stefanon B, Colitti M. Effects of Two Different Rhodiola rosea Extracts on Primary Human Visceral Adipocytes. Molecules. 2015 May 11;20(5):8409-28. doi: 10.3390/molecules20058409. PubMed PMID: 25970041. 7: 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. 8: 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. 9: 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. 10: Ioset KN, Nyberg NT, Van Diermen D, Malnoe P, Hostettmann K, Shikov AN, Jaroszewski JW. Metabolic profiling of Rhodiola rosea rhizomes by ¹H NMR spectroscopy. Phytochem Anal. 2011 Mar-Apr;22(2):158-65. doi: 10.1002/pca.1262. Epub 2010 Sep 16. PubMed PMID: 20848394. 11: Wang Z, Hu H, Chen F, Zou L, Yang M, Wang A, Foulsham JE, Lan K. Metabolic profiling assisted quality assessment of Rhodiola rosea extracts by high-performance liquid chromatography. Planta Med. 2012 May;78(7):740-6. doi: 10.1055/s-0031-1298373. Epub 2012 Mar 22. PubMed PMID: 22441833. 12: Jäger AK, Saaby L, Kudsk DS, Witt KC, Mølgaard P. Short communication: Influence of pasteurization on the active compounds in medicinal plants to be used in dairy products. J Dairy Sci. 2010 Jun;93(6):2351-3. doi: 10.3168/jds.2009-2910. PubMed PMID: 20494140. 13: Mudge E, Lopes-Lutz D, Brown PN, Schieber A. Purification of Phenylalkanoids and monoterpene glycosides from Rhodiola rosea L. roots by high-speed counter-current chromatography. Phytochem Anal. 2013 Feb;24(2):129-34. doi: 10.1002/pca.2391. Epub 2012 Jul 19. PubMed PMID: 22811209. 14: Booker A, Jalil B, Frommenwiler D, Reich E, Zhai L, Kulic Z, Heinrich M. The authenticity and quality of Rhodiola rosea products. Phytomedicine. 2016 Jun 15;23(7):754-62. doi: 10.1016/j.phymed.2015.10.006. Epub 2015 Oct 31. PubMed PMID: 26626192. 15: 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. 16: Elameen A, Dragland S, Klemsdal SS. Bioactive compounds produced by clones of Rhodiola rosea maintained in the Norwegian germplasm collection. Pharmazie. 2010 Aug;65(8):618-23. PubMed PMID: 20824964. 17: Cifani C, Micioni Di B MV, Vitale G, Ruggieri V, Ciccocioppo R, Massi M. Effect of salidroside, active principle of Rhodiola rosea extract, on binge eating. Physiol Behav. 2010 Dec 2;101(5):555-62. doi: 10.1016/j.physbeh.2010.09.006. Epub 2010 Sep 15. PubMed PMID: 20837037. 18: Peschel W, Prieto JM, Karkour C, Williamson EM. Effect of provenance, plant part and processing on extract profiles from cultivated European Rhodiola rosea L. for medicinal use. Phytochemistry. 2013 Feb;86:92-102. doi: 10.1016/j.phytochem.2012.10.005. Epub 2012 Nov 5. PubMed PMID: 23137726. 19: Verpeut JL, Walters AL, Bello NT. Citrus aurantium and Rhodiola rosea in combination reduce visceral white adipose tissue and increase hypothalamic norepinephrine in a rat model of diet-induced obesity. Nutr Res. 2013 Jun;33(6):503-12. doi: 10.1016/j.nutres.2013.04.001. Epub 2013 May 8. PubMed PMID: 23746567; PubMed Central PMCID: PMC3808124. 20: Kwon JY, Lee SH, Jhun J, Choi J, Jung K, Cho KH, Kim SJ, Yang CW, Park SH, Cho ML. The Combination of Probiotic Complex, Rosavin, and Zinc Improves Pain and Cartilage Destruction in an Osteoarthritis Rat Model. J Med Food. 2018 Apr;21(4):364-371. doi: 10.1089/jmf.2017.4034. Epub 2018 Jan 18. PubMed PMID: 29346012.