Rubusoside
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MedKoo CAT#: 558151

CAS#: 64849-39-4

Description: Rubusoside is a natural sweetener.


Price and Availability

Size
Price

10mg
USD 450
Size
Price

Size
Price

Rubusoside, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 558151
Name: Rubusoside
CAS#: 64849-39-4
Chemical Formula: C32H50O13
Exact Mass: 642.33
Molecular Weight: 642.74
Elemental Analysis: C, 59.80; H, 7.84; O, 32.36


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]


Technical Data

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).

Harmonized System Code:
293490


References

1: Prakash I, Bunders C, Devkota KP, Charan RD, Hartz RM, Sears TL, Snyder TM, Ramirez C. Degradation products of rubusoside under acidic conditions. Nat Prod Commun. 2015 Apr;10(4):559-62. PubMed PMID: 25973475.

2: Wang Z, Wang J, Jiang M, Wei Y, Pang H, Wei H, Huang R, Du L. Selective production of rubusoside from stevioside by using the sophorose activity of β-glucosidase from Streptomyces sp. GXT6. Appl Microbiol Biotechnol. 2015 Nov;99(22):9663-74. doi: 10.1007/s00253-015-6802-z. Epub 2015 Jul 22. PubMed PMID: 26198882.

3: Nguyen TT, Jung SJ, Kang HK, Kim YM, Moon YH, Kim M, Kim D. Production of rubusoside from stevioside by using a thermostable lactase from Thermus thermophilus and solubility enhancement of liquiritin and teniposide. Enzyme Microb Technol. 2014 Oct;64-65:38-43. doi: 10.1016/j.enzmictec.2014.07.001. Epub 2014 Jul 11. PubMed PMID: 25152415.

4: Chu J, Zhang T, He K. Cariogenicity features of Streptococcus mutans in presence of rubusoside. BMC Oral Health. 2016 May 11;16(1):54. doi: 10.1186/s12903-016-0212-1. PubMed PMID: 27169524; PubMed Central PMCID: PMC4864916.

5: Zhang F, Koh GY, Hollingsworth J, Russo PS, Stout RW, Liu Z. Reformulation of etoposide with solubility-enhancing rubusoside. Int J Pharm. 2012 Sep 15;434(1-2):453-9. doi: 10.1016/j.ijpharm.2012.06.013. Epub 2012 Jun 12. PubMed PMID: 22698860.

6: Zhang J, Chou G, Liu Z, Liu M. Employing rubusoside to improve the solubility and permeability of antitumor compound betulonic acid. Nanomedicine (Lond). 2016 Oct 19. [Epub ahead of print] PubMed PMID: 27759492.

7: Ko JA, Kim YM, Ryu YB, Jeong HJ, Park TS, Park SJ, Wee YJ, Kim JS, Kim D, Lee WS. Mass production of rubusoside using a novel stevioside-specific β-glucosidase from Aspergillus aculeatus. J Agric Food Chem. 2012 Jun 20;60(24):6210-6. doi: 10.1021/jf300531e. Epub 2012 Jun 1. PubMed PMID: 22530920.

8: George Thompson AM, Iancu CV, Nguyen TT, Kim D, Choe JY. Inhibition of human GLUT1 and GLUT5 by plant carbohydrate products; insights into transport specificity. Sci Rep. 2015 Aug 26;5:12804. doi: 10.1038/srep12804. PubMed PMID: 26306809; PubMed Central PMCID: PMC4549712.

9: Jiang Z, Chen Y, Liu H. [Identification and biotransformation properties of a bacterium that converts stevioside into rubusoside]. Wei Sheng Wu Xue Bao. 2011 Jan;51(1):43-9. Chinese. PubMed PMID: 21465788.

10: Sugimoto N, Sato K, Liu HM, Kikuchi H, Yamazaki T, Maitani T. Analysis of rubusoside and related compounds in tenryocha extract sweetener. Shokuhin Eiseigaku Zasshi. 2002 Aug;43(4):250-3. PubMed PMID: 12436720.

11: Liu Z, Zhang F, Koh GY, Dong X, Hollingsworth J, Zhang J, Russo PS, Yang P, Stout RW. Cytotoxic and antiangiogenic paclitaxel solubilized and permeation-enhanced by natural product nanoparticles. Anticancer Drugs. 2015 Feb;26(2):167-79. doi: 10.1097/CAD.0000000000000173. PubMed PMID: 25243454; PubMed Central PMCID: PMC4272611.

12: Ohtani K, Aikawa Y, Ishikawa H, Kasai R, Kitahata S, Mizutani K, Doi S, Nakaura M, Tanaka O. Further study on the 1,4-alpha-transglucosylation of rubusoside, a sweet steviol-bisglucoside from Rubus suavissimus. Agric Biol Chem. 1991 Feb;55(2):449-53. PubMed PMID: 1368695.

13: Ko JA, Ryu YB, Park JY, Kim CY, Kim JS, Nam SH, Lee WS, Kim YM. Glucosyl Rubusosides by Dextransucrases Improve the Quality of Taste and Sweetness. J Microbiol Biotechnol. 2016 Mar;26(3):493-7. doi: 10.4014/jmb.1512.12085. PubMed PMID: 26809800.

14: Compadre CM, Hussain RA, Nanayakkara NP, Pezzuto JM, Kinghorn AD. Mass spectral analysis of some derivatives and in vitro metabolites of steviol, the aglycone of the natural sweeteners, stevioside, rebaudioside A, and rubusoside. Biomed Environ Mass Spectrom. 1988 Feb 15;15(4):211-22. Erratum in: Biomed Environ Mass Spectrom 1988 Jun 1;15(11):635. PubMed PMID: 3370361.

15: Well C, Frank O, Hofmann T. Quantitation of sweet steviol glycosides by means of a HILIC-MS/MS-SIDA approach. J Agric Food Chem. 2013 Nov 27;61(47):11312-20. doi: 10.1021/jf404018g. Epub 2013 Nov 19. PubMed PMID: 24206531.

16: Chaturvedula VS, Upreti M, Prakash I. Diterpene glycosides from Stevia rebaudiana. Molecules. 2011 Apr 28;16(5):3552-62. doi: 10.3390/molecules16053552. PubMed PMID: 21527882.

17: Ohtani K, Aikawa Y, Fujisawa Y, Kasai R, Tanaka O, Yamasaki K. Solubilization of steviolbioside and steviolmonoside with gamma-cyclodextrin and its application to selective syntheses of better sweet glycosides from stevioside and rubusoside. Chem Pharm Bull (Tokyo). 1991 Dec;39(12):3172-4. PubMed PMID: 1814608.

18: Zhang F, Koh GY, Jeansonne DP, Hollingsworth J, Russo PS, Vicente G, Stout RW, Liu Z. A novel solubility-enhanced curcumin formulation showing stability and maintenance of anticancer activity. J Pharm Sci. 2011 Jul;100(7):2778-89. doi: 10.1002/jps.22512. Epub 2011 Feb 10. PubMed PMID: 21312196.

19: Liu D, Chen Z. The effect of curcumin on breast cancer cells. J Breast Cancer. 2013 Jun;16(2):133-7. doi: 10.4048/jbc.2013.16.2.133. Epub 2013 Jun 28. PubMed PMID: 23843843; PubMed Central PMCID: PMC3706856.

20: Jeansonne DP, Koh GY, Zhang F, Kirk-Ballard H, Wolff L, Liu D, Eilertsen K, Liu Z. Paclitaxel-induced apoptosis is blocked by camptothecin in human breast and pancreatic cancer cells. Oncol Rep. 2011 May;25(5):1473-80. doi: 10.3892/or.2011.1187. Epub 2011 Feb 17. PubMed PMID: 21331447.