Sitogluside | CAS#474-58-8 | Phytosterol-like Compound

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

MedKoo CAT#: 592525

CAS#: 474-58-8

Description: Sitogluside (also known as β-Sitosterol-D-glucoside, daucosterol, and eleutheroside) is a natural phytosterol-like compound. It is the glucoside of β-sitosterol.

Chemical Structure

Sitogluside

CAS# 474-58-8

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 592525
Name: Sitogluside
CAS#: 474-58-8
Chemical Formula: C35H60O6
Exact Mass: 576.44
Molecular Weight: 576.860
Elemental Analysis: C, 72.87; H, 10.48; O, 16.64

Price and Availability

Size	Price	Availability
5mg	USD 300	2 Weeks
10mg	USD 490	2 Weeks
25mg	USD 740	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. MedKoo 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: Sitogluside; NSC 165962; NSC-165962; NSC165962; Lyoniside, Daucosterol, Eleutheroside A, Alexandrin, Coriandrinol, Daucosterin, beta-Sitosterol glucoside, β-Sitosterol-D-glucoside

IUPAC/Chemical Name: (3-beta)-Stigmast-5-en-3-yl-beta-D-glucopyranoside

InChi Key: NPJICTMALKLTFW-VAWFKKCMSA-N

InChi Code: InChI=1S/C35H60O6/c1-7-22(20(2)3)9-8-21(4)26-12-13-27-25-11-10-23-18-24(14-16-34(23,5)28(25)15-17-35(26,27)6)40-33-32(39)31(38)30(37)29(19-36)41-33/h10,20-22,24-33,36-39H,7-9,11-19H2,1-6H3/t21-,22-,24-,25+,26-,27+,28+,29-,30-,31+,32-,33-,34+,35-/m1/s1

SMILES Code: O[C@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)[C@@H]1O[C@@H]2CC[C@]3(C)[C@@]4([H])CC[C@]5(C)[C@@H]([C@H](C)CC[C@H](C(C)C)CC)CC[C@@]5([H])[C@]4([H])CC=C3C2

Appearance: Solid powder

Purity: >70% (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: >3 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: 2934.99.03.00

More Info:

Product Data:

Product Data

Instruction:

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Biological target:	Sitogluside inhibits α-amylase and α-glucosidase and scavenges DPPH radicals (IC50s = 46.4, 17, and 155 µM, respectively). It inhibits the proliferation of HepG2 and SMMC-7721 hepatocellular carcinoma cells (IC50s = 143.4 and 138.73 µg/ml, respectively) and migration and invasion in the same cells when used at concentrations of 50 or 100 µg/ml.
In vitro activity:	Sitogluside is a promising therapeutic strategy for hepatocellular carcinoma (HCC) treatment by inhibiting cell migration and invasion in HCC cells via the Wnt/β-catenin signaling pathway. Sitogluside reduced the proliferation, migration, and invasion capacities of HCC cells in a concentration-dependent manner. In addition, sitogluside reduced the levels of β-catenin and p-β-catenin in HepG2 and SMMC-7721 cells. Reference: Molecules. 2017 Jun 2;22(6):862. https://pubmed.ncbi.nlm.nih.gov/28574485/
In vivo activity:	In this study, sitogluside showed in vivo antitumor effects that corroborate its previous in vitro effects. In a rat model of breast cancer, sitogluside at all doses reduced tumor volume, as well as protein, malondialdehyde (MDA), and CA 15-3 levels. Tumor sections in sitogluside-treated rats showed a lower proliferation of mammary ducts with mild to moderate inflammatory responses. Sitogluside also exhibited an antioxidant effect. Reference: Environ Toxicol. 2020 Oct;35(10):1125-1136. https://pubmed.ncbi.nlm.nih.gov/32449848/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	3.3	5.77

Preparing Stock Solutions

The following data is based on the product molecular weight 576.86 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:	1. Zeng J, Liu X, Li X, Zheng Y, Liu B, Xiao Y. Daucosterol Inhibits the Proliferation, Migration, and Invasion of Hepatocellular Carcinoma Cells via Wnt/β-Catenin Signaling. Molecules. 2017 Jun 2;22(6):862. doi: 10.3390/molecules22060862. PMID: 28574485; PMCID: PMC6152702. 2. Lee S, Kim JH, Kim M, Hong S, Park H, Kim EJ, Kim EY, Lee C, Sohn Y, Jung HS. Exploring the Anti-Osteoporotic Potential of Daucosterol: Impact on Osteoclast and Osteoblast Activities. Int J Mol Sci. 2023 Nov 17;24(22):16465. doi: 10.3390/ijms242216465. PMID: 38003654; PMCID: PMC10671633. In vivo study 1. Nguedia MY, Tueche AB, Yaya AJG, Yadji V, Ndinteh DT, Njamen D, Zingue S. Daucosterol from Crateva adansonii DC (Capparaceae) reduces 7,12-dimethylbenz(a)anthracene-induced mammary tumors in Wistar rats. Environ Toxicol. 2020 Oct;35(10):1125-1136. doi: 10.1002/tox.22948. Epub 2020 May 25. PMID: 32449848. 2. Zhang H, Song Y, Feng C. Improvement of cerebral ischemia/reperfusion injury by daucosterol palmitate-induced neuronal apoptosis inhibition via PI3K/Akt/mTOR signaling pathway. Metab Brain Dis. 2020 Aug;35(6):1035-1044. doi: 10.1007/s11011-020-00575-6. Epub 2020 May 4. PMID: 32363473.
In vitro protocol:	1. Zeng J, Liu X, Li X, Zheng Y, Liu B, Xiao Y. Daucosterol Inhibits the Proliferation, Migration, and Invasion of Hepatocellular Carcinoma Cells via Wnt/β-Catenin Signaling. Molecules. 2017 Jun 2;22(6):862. doi: 10.3390/molecules22060862. PMID: 28574485; PMCID: PMC6152702. 2. Lee S, Kim JH, Kim M, Hong S, Park H, Kim EJ, Kim EY, Lee C, Sohn Y, Jung HS. Exploring the Anti-Osteoporotic Potential of Daucosterol: Impact on Osteoclast and Osteoblast Activities. Int J Mol Sci. 2023 Nov 17;24(22):16465. doi: 10.3390/ijms242216465. PMID: 38003654; PMCID: PMC10671633.
In vivo protocol:	1. Nguedia MY, Tueche AB, Yaya AJG, Yadji V, Ndinteh DT, Njamen D, Zingue S. Daucosterol from Crateva adansonii DC (Capparaceae) reduces 7,12-dimethylbenz(a)anthracene-induced mammary tumors in Wistar rats. Environ Toxicol. 2020 Oct;35(10):1125-1136. doi: 10.1002/tox.22948. Epub 2020 May 25. PMID: 32449848. 2. Zhang H, Song Y, Feng C. Improvement of cerebral ischemia/reperfusion injury by daucosterol palmitate-induced neuronal apoptosis inhibition via PI3K/Akt/mTOR signaling pathway. Metab Brain Dis. 2020 Aug;35(6):1035-1044. doi: 10.1007/s11011-020-00575-6. Epub 2020 May 4. PMID: 32363473.

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1: Bin Sayeed MS, Ameen SS. Beta-Sitosterol: A Promising but Orphan Nutraceutical to Fight Against Cancer. Nutr Cancer. 2015;67(8):1214-20. doi: 10.1080/01635581.2015.1087042. Epub 2015 Oct 16. Review. PubMed PMID: 26473555.

2: Stefanaki C, Fasoulaki X, Kouris A, Caroni C, Papagianaki K, Mavrogianni P, Nicolaidou E, Gregoriou S, Antoniou C. A randomized trial of efficacy of beta-sitosterol and its glucoside as adjuvant to cryotherapy in the treatment of anogenital warts. J Dermatolog Treat. 2015 Apr;26(2):139-42. doi: 10.3109/09546634.2014.925535. Epub 2014 Jun 9. PubMed PMID: 24838062.

3: Sikder K, Das N, Kesh SB, Dey S. Quercetin and beta-sitosterol prevent high fat diet induced dyslipidemia and hepatotoxicity in Swiss albino mice. Indian J Exp Biol. 2014 Jan;52(1):60-6. PubMed PMID: 24617016.

4: Sook SH, Lee HJ, Kim JH, Sohn EJ, Jung JH, Kim B, Kim JH, Jeong SJ, Kim SH. Reactive oxygen species-mediated activation of AMP-activated protein kinase and c-Jun N-terminal kinase plays a critical role in beta-sitosterol-induced apoptosis in multiple myeloma U266 cells. Phytother Res. 2014 Mar;28(3):387-94. doi: 10.1002/ptr.4999. Epub 2013 May 3. PubMed PMID: 23640957.

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