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

Hodoodo CAT#: H540188

CAS#: 95975-55-6

Description: Guggulsterone is a FXR antagonist found in myrrh. It displays a wide variety of biological activities, including disrupting cytoskeletal organization, inhibiting doxorubicin-induced toxicity in cardiomyoc

Chemical Structure

Guggulsterone

CAS# 95975-55-6

Instruction

Theoretical Analysis

Hodoodo Cat#: H540188
Name: Guggulsterone
CAS#: 95975-55-6
Chemical Formula: C21H28O2
Exact Mass: 312.21
Molecular Weight: 312.453
Elemental Analysis: C, 80.73; H, 9.03; O, 10.24

Price and Availability

Size	Price	Availability
5mg	USD 285	2 Weeks
10mg	USD 500	2 Weeks
25mg	USD 950	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. Hodoodo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Guggulsterone; Guglip; Pregna-4,17(20)-diene-3,16-dione

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

Instruction:

View handling instruction

Biological target:
In vitro activity:
In vivo activity:

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.

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: Shi JJ, Jia XL, Li M, Yang N, Li YP, Zhang X, Gao N, Dang SS. Guggulsterone induces apoptosis of human hepatocellular carcinoma cells through intrinsic mitochondrial pathway. World J Gastroenterol. 2015 Dec 21;21(47):13277-87. doi: 10.3748/wjg.v21.i47.13277. PubMed PMID: 26715810; PubMed Central PMCID: PMC4679759.

2: 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.

3: Shishodia S, Azu N, Rosenzweig JA, Jackson DA. Guggulsterone for Chemoprevention of Cancer. Curr Pharm Des. 2016;22(3):294-306. Review. PubMed PMID: 26561056.

4: 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.

5: Xu HB, Xu LZ, Mao XP, Fu J. Guggulsterone of Commiphora mukul resin reverses drug resistance in imatinib-resistant leukemic cells by inhibiting cyclooxygenase-2 and P-glycoprotein. Phytomedicine. 2014 Jun 15;21(7):1004-9. doi: 10.1016/j.phymed.2014.02.014. Epub 2014 Mar 26. PubMed PMID: 24680616.

6: Yamada T, Sugimoto K. Guggulsterone and Its Role in Chronic Diseases. Adv Exp Med Biol. 2016;929:329-361. PubMed PMID: 27771932.

7: 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.

8: 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.

9: Xu HB, Shen ZL, Fu J, Xu LZ. Reversal of doxorubicin resistance by guggulsterone of Commiphora mukul in vivo. Phytomedicine. 2014 Sep 25;21(11):1221-9. doi: 10.1016/j.phymed.2014.06.003. Epub 2014 Jul 25. PubMed PMID: 25172783.

10: Noh EM, Chung EY, Youn HJ, Jung SH, Hur H, Lee YR, Kim JS. Cis-guggulsterone inhibits the IKK/NF-κB pathway, whereas trans-guggulsterone inhibits MAPK/AP-1 in MCF 7 breast cancer cells: guggulsterone regulates MMP 9 expression in an isomer-specific manner. Int J Mol Med. 2013 Feb;31(2):393-9. doi: 10.3892/ijmm.2012.1214. Epub 2012 Dec 14. PubMed PMID: 23242121.

11: Chen XZ, Xu HB, Xu LZ, Mao XP, Li L. Guggulsterone regulates the function and expression of P-glycoprotein in rat brain microvessel endothelial cells. Eur J Pharmacol. 2013 Oct 15;718(1-3):24-9. doi: 10.1016/j.ejphar.2013.09.010. Epub 2013 Sep 13. PubMed PMID: 24041929.

12: Pal P, Kanaujiya JK, Lochab S, Tripathi SB, Sanyal S, Behre G, Trivedi AK. Proteomic analysis of rosiglitazone and guggulsterone treated 3T3-L1 preadipocytes. Mol Cell Biochem. 2013 Apr;376(1-2):81-93. doi: 10.1007/s11010-012-1551-0. Epub 2012 Dec 30. PubMed PMID: 23275126.

13: Zhong F, Tong ZT, Fan LL, Zha LX, Wang F, Yao MQ, Gu KS, Cao YX. Guggulsterone-induced apoptosis in cholangiocarcinoma cells through ROS/JNK signaling pathway. Am J Cancer Res. 2016 Jan 15;6(2):226-37. eCollection 2016. PubMed PMID: 27186398; PubMed Central PMCID: PMC4859655.

14: Kim BH, Yoon JH, Yang JI, Myung SJ, Lee JH, Jung EU, Yu SJ, Kim YJ, Lee HS, Kim CY. Guggulsterone attenuates activation and survival of hepatic stellate cell by inhibiting nuclear factor kappa B activation and inducing apoptosis. J Gastroenterol Hepatol. 2013 Dec;28(12):1859-68. doi: 10.1111/jgh.12314. PubMed PMID: 23808824.

15: 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.

16: 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.

17: Kong JN, He Q, Wang G, Dasgupta S, Dinkins MB, Zhu G, Kim A, Spassieva S, Bieberich E. Guggulsterone and bexarotene induce secretion of exosome-associated breast cancer resistance protein and reduce doxorubicin resistance in MDA-MB-231 cells. Int J Cancer. 2015 Oct 1;137(7):1610-20. doi: 10.1002/ijc.29542. Epub 2015 Apr 27. PubMed PMID: 25833198; PubMed Central PMCID: PMC4503537.

18: 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.

19: Dixit D, Ghildiyal R, Anto NP, Ghosh S, Sharma V, Sen E. Guggulsterone sensitizes glioblastoma cells to Sonic hedgehog inhibitor SANT-1 induced apoptosis in a Ras/NFκB dependent manner. Cancer Lett. 2013 Aug 19;336(2):347-58. doi: 10.1016/j.canlet.2013.03.025. Epub 2013 Mar 31. PubMed PMID: 23548480.

20: Kim DG, Bae GS, Choi SB, Jo IJ, Shin JY, Lee SK, Kim MJ, Kim MJ, Jeong HW, Choi CM, Seo SH, Choo GC, Seo SW, Song HJ, Park SJ. Guggulsterone attenuates cerulein-induced acute pancreatitis via inhibition of ERK and JNK activation. Int Immunopharmacol. 2015 May;26(1):194-202. doi: 10.1016/j.intimp.2015.03.030. Epub 2015 Apr 2. PubMed PMID: 25843255.

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