Ginsenoside Rc
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MedKoo CAT#: 540168

CAS#: 11021-14-0

Description: Ginsenoside Rc is an AMPK inhibitor and potential TRPV1 antagonist found in species of Panax. It exhibits many biological activities, including decreasing oxidative stress, suppressing formalin-induced noiception, and increasing the life span in Caenorhabditis elegans.

Chemical Structure

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Ginsenoside Rc
CAS# 11021-14-0
Instruction

Theoretical Analysis

MedKoo Cat#: 540168
Name: Ginsenoside Rc
CAS#: 11021-14-0
Chemical Formula: C53H90O22
Exact Mass: 1,078.59
Molecular Weight: 1,079.280
Elemental Analysis: C, 58.98; H, 8.41; O, 32.61

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5mg USD 650
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Synonym: Ginsenoside RC; NSC 310104; NSC310104; NSC-310104; Panaxoside RC; HY-N0042; HYN0042; HY N0042; CS-3837; CS3837; CS 3837

IUPAC/Chemical Name: (2R,3S,4S,5R,6S)-2-((((2R,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)oxy)methyl)-6-(((2S)-2-((3S,8R,9R,10R,12R,13R,14R,17S)-3-(((2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-12-hydroxy-4,4,8,10,14-pentamethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)-6-methylhept-5-en-2-yl)oxy)tetrahydro-2H-pyran-3,4,5-triol

InChi Key: JDCPEKQWFDWQLI-JCGKBSFXSA-N

InChi Code: InChI=1S/C53H90O22/c1-23(2)10-9-14-53(8,75-47-43(67)39(63)37(61)29(72-47)22-68-45-41(65)36(60)28(21-56)69-45)24-11-16-52(7)33(24)25(57)18-31-50(5)15-13-32(49(3,4)30(50)12-17-51(31,52)6)73-48-44(40(64)35(59)27(20-55)71-48)74-46-42(66)38(62)34(58)26(19-54)70-46/h10,24-48,54-67H,9,11-22H2,1-8H3/t24-,25+,26+,27+,28-,29+,30?,31+,32-,33-,34+,35+,36-,37+,38-,39-,40-,41+,42+,43+,44+,45+,46-,47-,48-,50-,51+,52+,53-/m0/s1

SMILES Code: O[C@@H]([C@@H]([C@@H](CO)O1)O)[C@@H](O[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)O)O)[C@@H]1O[C@H]3CC[C@]4(C)[C@@]5([H])C[C@@H](O)[C@]6([H])[C@@H]([C@@](C)(O[C@H]7[C@@H]([C@H]([C@@H]([C@@H](CO[C@H]8[C@@H]([C@H]([C@H](CO)O8)O)O)O7)O)O)O)CC/C=C(C)\C)CC[C@](C)6[C@@](C)5CCC4C3(C)C

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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 1,079.28 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:
In vitro protocol:
In vivo protocol:

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1: Sun J, Wu W, Guo Y, Qin Q, Liu S. Pharmacokinetic study of ginsenoside Rc and simultaneous determination of its metabolites in rats using RRLC-Q-TOF-MS. J Pharm Biomed Anal. 2014 Jan;88:16-21. doi: 10.1016/j.jpba.2013.08.015. Epub 2013 Aug 21. PubMed PMID: 24013032.

2: Yang JW, Kim SS. Ginsenoside Rc promotes anti-adipogenic activity on 3T3-L1 adipocytes by down-regulating C/EBPα and PPARγ. Molecules. 2015 Jan 14;20(1):1293-303. doi: 10.3390/molecules20011293. PubMed PMID: 25594343.

3: Kim DH, Park CH, Park D, Choi YJ, Park MH, Chung KW, Kim SR, Lee JS, Chung HY. Ginsenoside Rc modulates Akt/FoxO1 pathways and suppresses oxidative stress. Arch Pharm Res. 2014 Jun;37(6):813-20. doi: 10.1007/s12272-013-0223-2. Epub 2013 Aug 6. PubMed PMID: 23918648.

4: Shin KC, Lee GW, Oh DK. Production of ginsenoside Rd from ginsenoside Rc by α-L-arabinofuranosidase from Caldicellulosiruptor saccharolyticus. J Microbiol Biotechnol. 2013 Apr;23(4):483-8. PubMed PMID: 23568202.

5: Xie J, Zhao D, Zhao L, Pei J, Xiao W, Ding G, Wang Z, Xu J. Characterization of a novel arabinose-tolerant α-L-arabinofuranosidase with high ginsenoside Rc to ginsenoside Rd bioconversion productivity. J Appl Microbiol. 2016 Mar;120(3):647-60. doi: 10.1111/jam.13040. Epub 2016 Feb 9. PubMed PMID: 26725313.

6: Liu QM, Jung HM, Cui CH, Sung BH, Kim JK, Kim SG, Lee ST, Kim SC, Im WT. Bioconversion of ginsenoside Rc into Rd by a novel α-L-arabinofuranosidase, Abf22-3 from Leuconostoc sp. 22-3: cloning, expression, and enzyme characterization. Antonie Van Leeuwenhoek. 2013 Apr;103(4):747-54. doi: 10.1007/s10482-012-9856-2. Epub 2012 Dec 7. PubMed PMID: 23224374.

7: Endale M, Im EJ, Lee JY, Kim SD, Yayeh T, Song YB, Kwak YS, Kim C, Kim SH, Roh SS, Cho JY, Rhee MH. Korean red ginseng saponin fraction rich in ginsenoside-Rb1, Rc and Rb2 attenuates the severity of mouse collagen-induced arthritis. Mediators Inflamm. 2014;2014:748964. doi: 10.1155/2014/748964. Epub 2014 Apr 16. PubMed PMID: 24833816; PubMed Central PMCID: PMC4009181.

8: Upadhyaya J, Yoon MS, Kim MJ, Ryu NS, Song YE, Kim YH, Kim MK. Purification and characterization of a novel ginsenoside Rc-hydrolyzing β-glucosidase from Armillaria mellea mycelia. AMB Express. 2016 Dec;6(1):112. doi: 10.1186/s13568-016-0277-x. Epub 2016 Nov 11. PubMed PMID: 27837549; PubMed Central PMCID: PMC5106418.

9: Chu Y, Zhang HC, Li SM, Wang JM, Wang XY, Li W, Zhang LL, Ma XH, Zhou SP, Zhu YH, Liu CX. Determination of ginsenoside Rc in rat plasma by LC-MS/MS and its application to a pharmacokinetic study. J Chromatogr B Analyt Technol Biomed Life Sci. 2013 Mar 1;919-920:75-8. doi: 10.1016/j.jchromb.2012.12.022. Epub 2013 Jan 16. PubMed PMID: 23411022.

10: Yu T, Rhee MH, Lee J, Kim SH, Yang Y, Kim HG, Kim Y, Kim C, Kwak YS, Kim JH, Cho JY. Ginsenoside Rc from Korean Red Ginseng (Panax ginseng C.A. Meyer) Attenuates Inflammatory Symptoms of Gastritis, Hepatitis and Arthritis. Am J Chin Med. 2016;44(3):595-615. doi: 10.1142/S0192415X16500336. Epub 2016 Apr 24. PubMed PMID: 27109153.

11: Liu J, Chen F, Yin J, Bu F, Zheng B, Yang M, Wang Y, Sun D, Meng Q. The effects of ginsenosides to amyloid fibril formation by RCMκ-casein. Int J Biol Macromol. 2015 Aug;79:49-55. doi: 10.1016/j.ijbiomac.2015.04.046. Epub 2015 Apr 29. PubMed PMID: 25934110.

12: Xu YZ, Ren Y, Wang JX, Sun M, Zhao XY, Liu Y. [Research on dynamic accumulation of nine ginsenosides and two pseudo-ginsenosides of Panax quinquefolium root of different growth years and harvest months in Canada]. Zhong Yao Cai. 2014 Oct;37(10):1743-8. Chinese. PubMed PMID: 25895377.

13: An DS, Cui CH, Sung BH, Yang HC, Kim SC, Lee ST, Im WT, Kim SG. Characterization of a novel ginsenoside-hydrolyzing α-L-arabinofuranosidase, AbfA, from Rhodanobacter ginsenosidimutans Gsoil 3054T. Appl Microbiol Biotechnol. 2012 May;94(3):673-82. doi: 10.1007/s00253-011-3614-7. Epub 2011 Dec 10. PubMed PMID: 22159603.

14: Lee JH, Lim H, Shehzad O, Kim YS, Kim HP. Ginsenosides from Korean red ginseng inhibit matrix metalloproteinase-13 expression in articular chondrocytes and prevent cartilage degradation. Eur J Pharmacol. 2014 Feb 5;724:145-51. doi: 10.1016/j.ejphar.2013.12.035. Epub 2013 Dec 31. PubMed PMID: 24384406.

15: Cui CH, Kim JK, Kim SC, Im WT. Characterization of a ginsenoside-transforming β-glucosidase from Paenibacillus mucilaginosus and its application for enhanced production of minor ginsenoside F₂. PLoS One. 2014 Jan 27;9(1):e85727. doi: 10.1371/journal.pone.0085727. eCollection 2014. PubMed PMID: 24475050; PubMed Central PMCID: PMC3903488.

16: Lee MS, Hwang JT, Kim SH, Yoon S, Kim MS, Yang HJ, Kwon DY. Ginsenoside Rc, an active component of Panax ginseng, stimulates glucose uptake in C2C12 myotubes through an AMPK-dependent mechanism. J Ethnopharmacol. 2010 Feb 17;127(3):771-6. doi: 10.1016/j.jep.2009.11.022. Epub 2009 Dec 2. PubMed PMID: 19961916.

17: Lee JH, Ahn JY, Shin TJ, Choi SH, Lee BH, Hwang SH, Kang J, Kim HJ, Park CW, Nah SY. Effects of Minor Ginsenosides, Ginsenoside Metabolites, and Ginsenoside Epimers on the Growth of Caenorhabditis elegans. J Ginseng Res. 2011 Sep;35(3):375-83. doi: 10.5142/jgr.2011.35.3.375. PubMed PMID: 23717083; PubMed Central PMCID: PMC3659541.

18: Shin KC, Oh HJ, Kim BJ, Oh DK. Complete conversion of major protopanaxadiol ginsenosides to compound K by the combined use of α-L-arabinofuranosidase and β-galactosidase from Caldicellulosiruptor saccharolyticus and β-glucosidase from Sulfolobus acidocaldarius. J Biotechnol. 2013 Aug 10;167(1):33-40. doi: 10.1016/j.jbiotec.2013.06.003. Epub 2013 Jun 14. PubMed PMID: 23774035.

19: Han Y, Sun B, Jiang B, Hu X, Spranger MI, Zhang Y, Zhao Y. Microbial transformation of ginsenosides Rb1, Rb3 and Rc by Fusarium sacchari. J Appl Microbiol. 2010 Sep;109(3):792-8. doi: 10.1111/j.1365-2672.2010.04707.x. PubMed PMID: 20337761.

20: Lee BH, Choi SH, Shin TJ, Hwang SH, Kang J, Kim HJ, Kim BJ, Nah SY. Effects of Ginsenoside Metabolites on GABAA Receptor-Mediated Ion Currents. J Ginseng Res. 2012 Jan;36(1):55-60. doi: 10.5142/jgr.2012.36.1.55. PubMed PMID: 23717104; PubMed Central PMCID: PMC3659565.