(Z)-Guggulsterone
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 561042

CAS#: 39025-23-5

Description: (Z)-Guggulsterone is a phytosteroid found in the resin of the guggul plant, Commiphora mukul. It acts as an antagonist of the farnesoid X receptor in humans.


Chemical Structure

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(Z)-Guggulsterone
CAS# 39025-23-5

Theoretical Analysis

MedKoo Cat#: 561042
Name: (Z)-Guggulsterone
CAS#: 39025-23-5
Chemical Formula: C21H28O2
Exact Mass: 312.2089
Molecular Weight: 312.453
Elemental Analysis: C, 80.73; H, 9.03; O, 10.24

Price and Availability

Size Price Availability Quantity
10.0mg USD 340.0 2 Weeks
25.0mg USD 550.0 2 Weeks
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Synonym: (Z)-Guggulsterone; Z-Guggulsterone

IUPAC/Chemical Name: (8R,9S,10R,13S,14S,17Z)-17-Ethylidene-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15-decahydrocyclopenta[a]phenanthrene-3,16-dione

InChi Key: WDXRGPWQVHZTQJ-OSJVMJFVSA-N

InChi Code: InChI=1S/C21H28O2/c1-4-16-19(23)12-18-15-6-5-13-11-14(22)7-9-20(13,2)17(15)8-10-21(16,18)3/h4,11,15,17-18H,5-10,12H2,1-3H3/b16-4+/t15-,17+,18+,20+,21-/m1/s1

SMILES Code: O=C(C=C1CC[C@@]2([H])[C@]3([H])CC/4=O)CC[C@]1(C)[C@@]2([H])CC[C@]3(C)C4=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

Preparing Stock Solutions

The following data is based on the product molecular weight 312.453 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

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1: Huang C, Wang J, Lu X, Hu W, Wu F, Jiang B, Ling Y, Yang R, Zhang W. Z-guggulsterone negatively controls microglia-mediated neuroinflammation via blocking IκB-α-NF-κB signals. Neurosci Lett. 2016 Apr 21;619:34-42. doi: 10.1016/j.neulet.2016.02.021. Epub 2016 Feb 12. PubMed PMID: 26879835.

2: Agrawal P, Vegda R, Laddha K. Simultaneous Estimation of Withaferin A and Z-Guggulsterone in Marketed Formulation by RP-HPLC. J Chromatogr Sci. 2015 Jul;53(6):940-4. doi: 10.1093/chromsci/bmu153. Epub 2015 Jan 8. PubMed PMID: 25572656.

3: Chen Z, Huang C, Ding W. Z-Guggulsterone Improves the Scopolamine-Induced Memory Impairments Through Enhancement of the BDNF Signal in C57BL/6J Mice. Neurochem Res. 2016 Dec;41(12):3322-3332. Epub 2016 Sep 28. PubMed PMID: 27677871.

4: Xu HB, Yu J, Xu LZ, Fu J. Regulation of P-glycoprotein efflux activity by Z-guggulsterone of Commiphora mukul at the blood-brain barrier. J Neurol Sci. 2016 Apr 15;363:147-52. doi: 10.1016/j.jns.2016.02.046. Epub 2016 Feb 20. PubMed PMID: 27000241.

5: Akhade MS, Agrawal PA, Laddha KS. Development and Validation of RP-HPLC Method for Simultaneous Estimation of Picroside I, Plumbagin, and Z-guggulsterone in Tablet Formulation. Indian J Pharm Sci. 2013 Jul;75(4):476-82. doi: 10.4103/0250-474X.119835. PubMed PMID: 24302803; PubMed Central PMCID: PMC3831730.

6: Chhonker YS, Chandasana H, Mukkavilli R, Prasad YD, Laxman TS, Vangala S, Bhatta RS. Assessment of in vitro metabolic stability, plasma protein binding, and pharmacokinetics of E- and Z-guggulsterone in rat. Drug Test Anal. 2016 Sep;8(9):966-75. doi: 10.1002/dta.1885. Epub 2015 Nov 26. PubMed PMID: 26608935.

7: Yang D, Yang J, Shi D, Xiao D, Chen YT, Black C, Deng R, Yan B. Hypolipidemic agent Z-guggulsterone: metabolism interplays with induction of carboxylesterase and bile salt export pump. J Lipid Res. 2012 Mar;53(3):529-39. doi: 10.1194/jlr.M014688. Epub 2012 Jan 14. PubMed PMID: 22246918; PubMed Central PMCID: PMC3276476.

8: Liu FG, Hu WF, Wang JL, Wang P, Gong Y, Tong LJ, Jiang B, Zhang W, Qin YB, Chen Z, Yang RR, Huang C. Z-Guggulsterone Produces Antidepressant-Like Effects in Mice through Activation of the BDNF Signaling Pathway. Int J Neuropsychopharmacol. 2017 Jun 1;20(6):485-497. doi: 10.1093/ijnp/pyx009. PubMed PMID: 28339691; PubMed Central PMCID: PMC5458345.

9: Jiang G, Xiao X, Zeng Y, Nagabhushanam K, Majeed M, Xiao D. Targeting beta-catenin signaling to induce apoptosis in human breast cancer cells by z-guggulsterone and Gugulipid extract of Ayurvedic medicine plant Commiphora mukul. BMC Complement Altern Med. 2013 Aug 3;13:203. doi: 10.1186/1472-6882-13-203. PubMed PMID: 23914993; PubMed Central PMCID: PMC3735424.

10: Yang L, Broderick D, Jiang Y, Hsu V, Maier CS. Conformational dynamics of human FXR-LBD ligand interactions studied by hydrogen/deuterium exchange mass spectrometry: insights into the antagonism of the hypolipidemic agent Z-guggulsterone. Biochim Biophys Acta. 2014 Sep;1844(9):1684-93. doi: 10.1016/j.bbapap.2014.06.007. Epub 2014 Jun 18. PubMed PMID: 24953769; PubMed Central PMCID: PMC4137978.

11: Kulhari A, Sheorayan A, Chaudhury A, Sarkar S, Kalia RK. Quantitative determination of guggulsterone in existing natural populations of Commiphora wightii (Arn.) Bhandari for identification of germplasm having higher guggulsterone content. Physiol Mol Biol Plants. 2015 Jan;21(1):71-81. doi: 10.1007/s12298-014-0271-1. Epub 2014 Nov 22. PubMed PMID: 25648764; PubMed Central PMCID: PMC4312330.

12: Zhong F, Yang J, Tong ZT, Chen LL, Fan LL, Wang F, Zha XL, Li J. Guggulsterone inhibits human cholangiocarcinoma Sk-ChA-1 and Mz-ChA-1 cell growth by inducing caspase-dependent apoptosis and downregulation of survivin and Bcl-2 expression. Oncol Lett. 2015 Sep;10(3):1416-1422. Epub 2015 Jun 19. PubMed PMID: 26622683; PubMed Central PMCID: PMC4533301.

13: Agrawal H, Kaul N, Paradkar AR, Mahadik KR. HPTLC method for guggulsterone. I. Quantitative determination of E- and Z-guggulsterone in herbal extract and pharmaceutical dosage form. J Pharm Biomed Anal. 2004 Sep 21;36(1):33-41. PubMed PMID: 15351045.

14: Bhatta RS, Kumar D, Chhonker YS, Jain GK. Simultaneous estimation of E- and Z-isomers of guggulsterone in rabbit plasma using liquid chromatography tandem mass spectrometry and its application to pharmacokinetic study. Biomed Chromatogr. 2011 Sep;25(9):1054-60. doi: 10.1002/bmc.1574. Epub 2011 Jan 26. PubMed PMID: 21268049.

15: Wang J, Huang Y, Hou X, Wu W, Nie L, Tian Y, Lu Y, Yin Y. Morphologic Damage of Rat Alveolar Epithelial Type II Cells Induced by Bile Acids Could Be Ameliorated by Farnesoid X Receptor Inhibitor Z-Guggulsterone In Vitro. Biomed Res Int. 2016;2016:9283204. doi: 10.1155/2016/9283204. Epub 2016 Jun 1. PubMed PMID: 27340672; PubMed Central PMCID: PMC4908247.

16: Xiao D, Singh SV. z-Guggulsterone, a constituent of Ayurvedic medicinal plant Commiphora mukul, inhibits angiogenesis in vitro and in vivo. Mol Cancer Ther. 2008 Jan;7(1):171-80. doi: 10.1158/1535-7163.MCT-07-0491. PubMed PMID: 18202020.

17: Mesrob B, Nesbitt C, Misra R, Pandey RC. High-performance liquid chromatographic method for fingerprinting and quantitative determination of E- and Z-guggulsterones in Commiphora mukul resin and its products. J Chromatogr B Biomed Sci Appl. 1998 Dec 11;720(1-2):189-96. PubMed PMID: 9892081.

18: Nagarajan M, Waszkuc TW, Sun J. Simultaneous determination of E- and Z-guggulsterones in dietary supplements containing Commiphora mukul extract (guggulipid) by liquid chromatography. J AOAC Int. 2001 Jan-Feb;84(1):24-8. PubMed PMID: 11234828.

19: Verma N, Singh SK, Gupta RC. Simultaneous determination of the stereoisomers of guggulsterone in serum by high-performance liquid chromatography. J Chromatogr B Biomed Sci Appl. 1998 Apr 24;708(1-2):243-8. PubMed PMID: 9653969.

20: Mithila MV, Khanum F. The appetite regulatory effect of guggulsterones in rats: a repertoire of plasma hormones and neurotransmitters. J Diet Suppl. 2014 Sep;11(3):262-71. doi: 10.3109/19390211.2014.937045. Epub 2014 Jul 15. PubMed PMID: 25025986.