Rubusoside | CAS#64849-39-4 | natural sweetener

MedKoo Cat#: 558151 | Name: Rubusoside

Description:

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

Rubusoside is a natural sweetener with applications in treating neuroinflammation as a potential treatment for Parkinson's disease.

Chemical Structure

Rubusoside

CAS#64849-39-4

Theoretical Analysis

MedKoo Cat#: 558151

Name: Rubusoside

CAS#: 64849-39-4

Chemical Formula: C32H50O13

Exact Mass: 642.3300

Molecular Weight: 642.74

Elemental Analysis: C, 59.80; H, 7.84; O, 32.36

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 700.00

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Related CAS #

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Synonym

UNII-TCV5K3M3GX;

IUPAC/Chemical Name

Kaur-16-en-18-oic acid, 13-(beta-D-glucopyranosyloxy)-, beta-D-glucopyranosyl ester, (4alpha)-

InChi Key

YWPVROCHNBYFTP-OSHKXICASA-N

InChi Code

InChI=1S/C32H50O13/c1-15-11-31-9-5-18-29(2,7-4-8-30(18,3)28(41)44-26-24(39)22(37)20(35)16(12-33)42-26)19(31)6-10-32(15,14-31)45-27-25(40)23(38)21(36)17(13-34)43-27/h16-27,33-40H,1,4-14H2,2-3H3/t16-,17-,18+,19+,20-,21-,22+,23+,24-,25-,26+,27+,29-,30-,31-,32+/m1/s1

SMILES Code

C=C([C@@](CC1)(O[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)O)O)C3)C[C@@]43CC[C@]5([H])[C@@](C(O[C@H]6[C@@H]([C@H]([C@@H]([C@@H](CO)O6)O)O)O)=O)(C)CCC[C@@]5(C)[C@@]41[H]

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

>2 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 642.74 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: Zhang J, Shu J, Stout RW, Russo PS, Liu Z. Solubilization of Paclitaxel with Natural Compound Rubusoside toward Improving Oral Bioavailability in a Rodent Model. Pharmaceutics. 2024 Aug 22;16(8):1104. doi: 10.3390/pharmaceutics16081104. PMID: 39204449; PMCID: PMC11359394. 2: Jiang J, Fan H, Zhou J, Qin J, Qin Z, Chen M, Shen Y, Liu X. In vitro inhibitory effect of five natural sweeteners on α-glucosidase and α-amylase. Food Funct. 2024 Feb 19;15(4):2234-2248. doi: 10.1039/d3fo05234f. PMID: 38318730. 3: Meng T, Zhang Y, Huang J, Pandey V, Fu S, Ma S. Rubusoside mitigates neuroinflammation and cellular apoptosis in Parkinson's disease, and alters gut microbiota and metabolite composition. Phytomedicine. 2024 Feb;124:155309. doi: 10.1016/j.phymed.2023.155309. Epub 2023 Dec 20. PMID: 38237261. 4: Liu Y, Wu Z, Chen Y, Guan Y, Guo H, Yang M, Yue P. Rubusoside As a Multifunctional Stabilizer for Novel Nanocrystal-Based Solid Dispersions with a High Drug Loading: A Case Study. J Pharm Sci. 2024 Mar;113(3):699-710. doi: 10.1016/j.xphs.2023.08.024. Epub 2023 Sep 1. PMID: 37659720. 5: Xu Y, Han L, Cheng Y, Zhang Y, Wu Y, Liu Y, Li J, Du G, Lv X, Liu L. ATP- Binding Cassette Exporter PDR11-Mediated Terpenoid Secretion in Engineered Yeast. ACS Synth Biol. 2023 Apr 21;12(4):1146-1153. doi: 10.1021/acssynbio.2c00635. Epub 2023 Apr 4. PMID: 37014059. 6: Su YT, Zhang J. Solubility Enhancement and Antioxidation Maintenance of CBD Encapsulated in the P407-RUB Nano-micelle System. Curr Drug Deliv. 2024;21(2):271-282. doi: 10.2174/1567201820666230330090025. PMID: 36999183. 7: Wellmann J, Wilms J, Hartmann B, Zirpel B, Brückner SI, Hillebrand S, Ley J, Winterhalter P. Novel α-glycosyl compounds from glycosylation of rubusoside. Food Chem. 2023 Apr 16;406:135033. doi: 10.1016/j.foodchem.2022.135033. Epub 2022 Nov 25. PMID: 36450197. 8: Pan H, Xiao L, Tang K, Xia H, Li Y, Jia H, Wei P, Yan M. Screening UDP- Glycosyltransferases for Effectively Transforming Stevia Glycosides: Enzymatic Synthesis of Glucosylated Derivatives of Rubusoside. J Agric Food Chem. 2022 Dec 7;70(48):15178-15188. doi: 10.1021/acs.jafc.2c06185. Epub 2022 Nov 24. PMID: 36424346. 9: O'Hara FM, Liu Z, Davis JA, Swale DR. Catalyzing systemic movement of inward rectifier potassium channel inhibitors for antifeedant activity against the cotton aphid, Aphis gossypii (Glover). Pest Manag Sci. 2023 Jan;79(1):194-205. doi: 10.1002/ps.7188. Epub 2022 Oct 3. PMID: 36116013. 10: Xu Y, Wang X, Zhang C, Zhou X, Xu X, Han L, Lv X, Liu Y, Liu S, Li J, Du G, Chen J, Ledesma-Amaro R, Liu L. De novo biosynthesis of rubusoside and rebaudiosides in engineered yeasts. Nat Commun. 2022 Jun 1;13(1):3040. doi: 10.1038/s41467-022-30826-2. PMID: 35650215; PMCID: PMC9160076. 11: Tian X, Zhong F, Xia Y. Dynamic characteristics of sweetness and bitterness and their correlation with chemical structures for six steviol glycosides. Food Res Int. 2022 Jan;151:110848. doi: 10.1016/j.foodres.2021.110848. Epub 2021 Dec 2. PMID: 34980386. 12: Ko JA, Kim SY, Ahn HS, Go JG, Ryu YB, Lee WS, Wee YJ, Park JS, Kim D, Kim YM. Characterization of a lactic acid bacterium-derived β-glucosidase for the production of rubusoside from stevioside. Enzyme Microb Technol. 2022 Jan;153:109939. doi: 10.1016/j.enzmictec.2021.109939. Epub 2021 Nov 11. PMID: 34798448. 13: Yan Z, Cao X, Yang X, Yang S, Xu L, Jiang X, Xiao M. A Novel β-Glucosidase From Chryseobacterium scophthalmum 1433 for Efficient Rubusoside Production From Stevioside. Front Microbiol. 2021 Oct 12;12:744914. doi: 10.3389/fmicb.2021.744914. PMID: 34712213; PMCID: PMC8546341. 14: Mao Y, Chen Z, Ren Y, Sun Y, Wang Y. Whole-Cell Biocatalyst for Rubusoside Production in Saccharomyces cerevisiae. J Agric Food Chem. 2021 Nov 10;69(44):13155-13163. doi: 10.1021/acs.jafc.1c04873. Epub 2021 Oct 26. PMID: 34699718. 15: Huang K, Huang J, Lin J, Li H, Xin J, Ma Z, Sang J, Hong Z, Zeng G, Hu X, Li O. Directional bioconversion and optimization of stevioside into rubusoside by Lelliottia sp. LST-1. J Appl Microbiol. 2022 Mar;132(3):1887-1899. doi: 10.1111/jam.15316. Epub 2021 Oct 10. PMID: 34606155. 16: Liu Z, Ren K, Feng Y, Uong T, Krepich S, You H. Rapid and Economic Determination of 13 Steviol Glycosides in Market-Available Food, Dietary Supplements, and Ingredients: Single-Laboratory Validation of an HPLC Method. J Agric Food Chem. 2020 Sep 16;68(37):10142-10148. doi: 10.1021/acs.jafc.0c03453. Epub 2020 Aug 31. PMID: 32790304. 17: Zhao L, Wang Y, Li Z, Wang X, Chen Y, Wu X. Enzymatic Monoglucosylation of Rubusoside and the Structure-Sweetness/Taste Relationship of Monoglucosyl Derivatives. J Agric Food Chem. 2020 Aug 12;68(32):8702-8709. doi: 10.1021/acs.jafc.0c03236. Epub 2020 Jul 30. PMID: 32686405. 18: Typek R, Dawidowicz AL, Stankevič M. Stability of stevioside in food processing conditions: unexpected recombination of stevioside hydrolysis products in ESI source. Food Chem. 2020 Nov 30;331:127262. doi: 10.1016/j.foodchem.2020.127262. Epub 2020 Jun 6. PMID: 32563799. 19: Guan C, Che F, Zhou H, Li Y, Li Y, Chu J. Effect of Rubusoside, a Natural Sucrose Substitute, on Streptococcus mutans Biofilm Cariogenic Potential and Virulence Gene Expression In Vitro. Appl Environ Microbiol. 2020 Aug 3;86(16):e01012-20. doi: 10.1128/AEM.01012-20. PMID: 32503907; PMCID: PMC7414950. 20: Myint KZ, Chen JM, Zhou ZY, Xia YM, Lin J, Zhang J. Structural dependence of antidiabetic effect of steviol glycosides and their metabolites on streptozotocin-induced diabetic mice. J Sci Food Agric. 2020 Aug;100(10):3841-3849. doi: 10.1002/jsfa.10421. Epub 2020 May 8. PMID: 32297310.