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MedKoo Cat#: 561042 | Name: Z-Guggulsterone
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Description:

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

(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

Z-Guggulsterone
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: 312.45

Elemental Analysis: C, 80.73; H, 9.03; O, 10.24

Price and Availability

Size Price Availability Quantity
5mg USD 350.00 2 Weeks
10mg USD 600.00 2 Weeks
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Related CAS #
No Data
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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 312.45 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
1: Huang P, Zhao H, Dai H, Li J, Pan X, Pan W, Xia C, Liu F. FXR deficiency induced ferroptosis via modulation of the CBP-dependent p53 acetylation to suppress breast cancer growth and metastasis. Cell Death Dis. 2024 Nov 14;15(11):826. doi: 10.1038/s41419-024-07222-3. PMID: 39543094; PMCID: PMC11564727. 2: Liang X, Liu K, Jia X, Cheng C, Zhang M, Kong L, Li Q, Liu Z, Li M, Li J, Wang Y, Xu A. Suppressing FXR promotes antiviral effects of bile acids via enhancing the interferon transcription. Acta Pharm Sin B. 2024 Aug;14(8):3513-3527. doi: 10.1016/j.apsb.2024.05.005. Epub 2024 May 13. PMID: 39220861; PMCID: PMC11365379. 3: Li JP, Ye BL, Li Q, Zhang LL, Zhuang L, Yuan YW. FXR contributes to obstructive jaundice-induced vascular hyporeactivity in mesenteric arteries by reconstituting BKCa channels. Clin Res Hepatol Gastroenterol. 2024 Oct;48(8):102448. doi: 10.1016/j.clinre.2024.102448. Epub 2024 Aug 17. PMID: 39159828. 4: Jin X, Shang B, Wang J, Sun J, Li J, Liang B, Wang X, Su L, You W, Jiang S. Farnesoid X receptor promotes non-small cell lung cancer metastasis by activating Jak2/STAT3 signaling via transactivation of IL-6ST and IL-6 genes. Cell Death Dis. 2024 Feb 15;15(2):148. doi: 10.1038/s41419-024-06495-y. PMID: 38360812; PMCID: PMC10869786. 5: Sun H, Su X, Liu Y, Li G, Du Q. Roseburia intestinalis relieves intrahepatic cholestasis of pregnancy through bile acid/FXR-FGF15 in rats. iScience. 2023 Nov 3;26(12):108392. doi: 10.1016/j.isci.2023.108392. PMID: 38025767; PMCID: PMC10679810. 6: Sabarathinam S, Satheesh S, Satish Kumar RC. Physicochemical investigation and molecular docking analysis of Maha yogaraj Guggulu tablet and virtual screening of its major bioactive compound. Nat Prod Res. 2023 Sep 22:1-7. doi: 10.1080/14786419.2023.2261071. Epub ahead of print. PMID: 37737139. 7: Xiao L, Xu G, Chen S, He Y, Peng F, Yuan C. Kaempferol ameliorated alcoholic liver disease through inhibiting hepatic bile acid synthesis by targeting intestinal FXR-FGF15 signaling. Phytomedicine. 2023 Nov;120:155055. doi: 10.1016/j.phymed.2023.155055. Epub 2023 Sep 5. PMID: 37678053. 8: Chando A, Basudkar V, Gharat S, Momin M, Khan T. Development and preclinical assessment of nanoemulgel loaded with phytoconstituents for the management of rheumatoid arthritis. Drug Deliv Transl Res. 2024 Feb;14(2):524-541. doi: 10.1007/s13346-023-01416-6. Epub 2023 Aug 22. Erratum in: Drug Deliv Transl Res. 2024 Feb;14(2):571. doi: 10.1007/s13346-023-01436-2. PMID: 37606759. 9: Schäfer J, Klösgen VJ, Omer EA, Kadioglu O, Mbaveng AT, Kuete V, Hildebrandt A, Efferth T. In Silico and In Vitro Identification of P-Glycoprotein Inhibitors from a Library of 375 Phytochemicals. Int J Mol Sci. 2023 Jun 16;24(12):10240. doi: 10.3390/ijms241210240. PMID: 37373385; PMCID: PMC10299530. 10: Gupta N, Mohan CD, Shanmugam MK, Jung YY, Chinnathambi A, Alharbi SA, Ashrafizadeh M, Mahale M, Bender A, Kumar AP, Putti TC, Rangappa KS, Zhang X, Ahn KS, Sethi G. CXCR4 expression is elevated in TNBC patient derived samples and Z-guggulsterone abrogates tumor progression by targeting CXCL12/CXCR4 signaling axis in preclinical breast cancer model. Environ Res. 2023 Sep 1;232:116335. doi: 10.1016/j.envres.2023.116335. Epub 2023 Jun 7. PMID: 37290620. 11: Liu T, Bai M, Liu M, Li T, Liao Y, Zhao C, Yao M, Wang J, Wen A, Ding Y. Novel synergistic mechanism of 11-keto-β-boswellic acid and Z-Guggulsterone on ischemic stroke revealed by single-cell transcriptomics. Pharmacol Res. 2023 Jul;193:106803. doi: 10.1016/j.phrs.2023.106803. Epub 2023 May 23. PMID: 37230158. 12: Kaur M, Malik J, Naura AS. Protective effect of oleo-gum resin of Commiphora wightii against elastase-induced chronic obstructive pulmonary disease-linked lung inflammation and emphysema: Isolation and identification of key bioactive phytoconstituent. J Ethnopharmacol. 2023 Oct 5;314:116623. doi: 10.1016/j.jep.2023.116623. Epub 2023 May 18. PMID: 37196815. 13: Wu Y, Zhou T, Qian D, Liu X, Xu Y, Hong W, Meng X, Tang H. Z-Guggulsterone Induces Cell Cycle Arrest and Apoptosis by Targeting the p53/CCNB1/PLK1 Pathway in Triple-Negative Breast Cancer. ACS Omega. 2023 Jan 3;8(2):2780-2792. doi: 10.1021/acsomega.2c07480. PMID: 36687039; PMCID: PMC9851028. 14: Brevini T, Maes M, Webb GJ, John BV, Fuchs CD, Buescher G, Wang L, Griffiths C, Brown ML, Scott WE 3rd, Pereyra-Gerber P, Gelson WTH, Brown S, Dillon S, Muraro D, Sharp J, Neary M, Box H, Tatham L, Stewart J, Curley P, Pertinez H, Forrest S, Mlcochova P, Varankar SS, Darvish-Damavandi M, Mulcahy VL, Kuc RE, Williams TL, Heslop JA, Rossetti D, Tysoe OC, Galanakis V, Vila-Gonzalez M, Crozier TWM, Bargehr J, Sinha S, Upponi SS, Fear C, Swift L, Saeb-Parsy K, Davies SE, Wester A, Hagström H, Melum E, Clements D, Humphreys P, Herriott J, Kijak E, Cox H, Bramwell C, Valentijn A, Illingworth CJR; UK-PBC Consortium; Dahman B, Bastaich DR, Ferreira RD, Marjot T, Barnes E, Moon AM, Barritt AS 4th, Gupta RK, Baker S, Davenport AP, Corbett G, Gorgoulis VG, Buczacki SJA, Lee JH, Matheson NJ, Trauner M, Fisher AJ, Gibbs P, Butler AJ, Watson CJE, Mells GF, Dougan G, Owen A, Lohse AW, Vallier L, Sampaziotis F. FXR inhibition may protect from SARS-CoV-2 infection by reducing ACE2. Nature. 2023 Mar;615(7950):134-142. doi: 10.1038/s41586-022-05594-0. Epub 2022 Dec 5. PMID: 36470304; PMCID: PMC9977684. 15: Gupta M, Ghufran SM, Kausar T, Ali R, Biswas S, Nayeem SM, Ishrat R, Ali S, Ahmad A, Rather IA, Sarwat M. Z-Guggulsterone Is a Potential Lead Molecule of Dawa-ul-Kurkum against Hepatocellular Carcinoma. Molecules. 2022 Aug 11;27(16):5104. doi: 10.3390/molecules27165104. PMID: 36014345; PMCID: PMC9413334. 16: Ulrich J, Stiltz S, St-Gelais A, El Gaafary M, Simmet T, Syrovets T, Schmiech M. Phytochemical Composition of Commiphora Oleogum Resins and Their Cytotoxicity against Skin Cancer Cells. Molecules. 2022 Jun 17;27(12):3903. doi: 10.3390/molecules27123903. PMID: 35745024; PMCID: PMC9229828. 17: Liu J, Lin Y, Yang Y, Guo Y, Shang Y, Zhou B, Liu T, Fan J, Wei C. Z-Guggulsterone attenuates cognitive defects and decreases neuroinflammation in APPswe/PS1dE9 mice through inhibiting the TLR4 signaling pathway. Biochem Pharmacol. 2022 Aug;202:115149. doi: 10.1016/j.bcp.2022.115149. Epub 2022 Jun 14. PMID: 35714682. 18: Dang SJ, Wei WB, Li RL, Song CX, Xu J. Z-Guggulsterone Relieves Neuropathic Pain by Inhibiting the Expression of Astrocytes and Proinflammatory Cytokines in the Spinal Dorsal Horn. J Pain Res. 2022 May 5;15:1315-1324. doi: 10.2147/JPR.S360126. PMID: 35546904; PMCID: PMC9084390. 19: Liu M, Wang W, Wang J, Fang C, Liu T. Z-Guggulsterone alleviates renal fibrosis by mitigating G2/M cycle arrest through Klotho/p53 signaling. Chem Biol Interact. 2022 Feb 25;354:109846. doi: 10.1016/j.cbi.2022.109846. Epub 2022 Feb 4. PMID: 35123992. 20: Ma N, Fan L, Dong Y, Xu X, Yu C, Chen J, Ren J. New PCSK9 inhibitor miR-552-3p reduces LDL-C via enhancing LDLR in high fat diet-fed mice. Pharmacol Res. 2021 May;167:105562. doi: 10.1016/j.phrs.2021.105562. Epub 2021 Mar 16. PMID: 33737240.

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