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H8664 Sigma

Steviol hydrate

≥98% (HPLC), powder

Synonym: (4α)-13-Hydroxykaur-16-en-18-oic acid hydrate

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Properties

Related Categories Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Cell Biology, Cell Signaling and Neuroscience, Detection and Quantitation,
assay   ≥98% (HPLC)
form   powder
color   white to tan
solubility   DMSO: >10 mg/mL
storage temp.   2-8°C

Description

Biochem/physiol Actions

Steviol is an inhibitor of hOAT1 and hOAT3 organic anion transporters. Human organic anion transporter hOAT1 belongs to a superfamily of organic anion transporters, which play critical roles in the body disposition of clinically important drugs including anti-HIV therapeutics, anti-tumor drugs, antibiotics, anti-hypertensives, and anti-inflammatories. Steviol is a useful tool for studying renal drug clearance.

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®,1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

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LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

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Safety & Documentation

Safety Information

WGK Germany 
3

Documents

Certificate of Analysis

Protocols & Articles

Peer-Reviewed Papers

References

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Interactions of stevioside and steviol with renal organic anion transporters in s2 cells and mouse renal cortical slices. Srimaroeng, C., et al. Pharmaceut. Res. 22, 858-866, (2005)

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Steviol glycosides: chemical diversity, metabolism, and function. Ceunen S and Geuns JM J. Nat. Prod. 76(6), 1201-28, (2013)

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Stability of steviol glycosides in several food matrices. Jooken E, Amery R, Struyf T, et al. J. Agric. Food Chem. 60(42), 10606-12, (2012)

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Identification and quantification of major steviol glycosides in Stevia rebaudiana purified extracts by 1H NMR spectroscopy. Pieri V, Belancic A, Morales S, et al. J. Agric. Food Chem. 59(9), 4378-84, (2011)

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UDP-dependent glycosyltransferases involved in the biosynthesis of steviol glycosides. Mohamed AA, Ceunen S, Geuns JM, et al. J. Plant Physiol. 168(10), 1136-41, (2011)

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Evaluation of steviol and its glycosides in Stevia rebaudiana leaves and commercial sweetener by ultra-high-performance liquid chromatography-mass spectrometry. Gardana C, Scaglianti M, and Simonetti P J. Chromatogr. A 1217(9), 1463-70, (2010)

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Direct analysis of steviol glycosides from Stevia leaves by ambient ionization mass spectrometry performed on whole leaves. Zhang JI, Li X, Ouyang Z, et al. Analyst 137(13), 3091-8, (2012)

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Steviol glycosides from Stevia: biosynthesis pathway review and their application in foods and medicine. Yadav SK and Guleria P Crit. Rev. Food Sci. Nutr 52(11), 988-98, (2012)

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Determination of six steviol glycosides of Stevia rebaudiana (Bertoni) from different geographical origin by LC-ESI-MS/MS. Montoro P, Molfetta I, Maldini M, et al. Food Chem. 141(2), 745-53, (2013)

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Influence of photoperiodism on the spatio-temporal accumulation of steviol glycosides in Stevia rebaudiana (Bertoni). Ceunen S and Geuns JM Plant Sci. 198, 72-82, (2013)

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Comparative toxicokinetics and metabolism of rebaudioside A, stevioside, and steviol in rats. Roberts A and Renwick AG Food Chem. Toxicol. 46 Suppl 7, S31-9, (2008)

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A critical review of the genetic toxicity of steviol and steviol glycosides. Brusick DJ Food Chem. Toxicol. 46 Suppl 7, S83-91, (2008)

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Synthesis of skeletally diverse and stereochemically complex library templates derived from isosteviol and steviol. Hutt OE, Doan TL, and Georg GI Org. Lett. 15(7), 1602-5, (2013)

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Tandem mass spectrometric fragmentation patterns of known and new steviol glycosides with structure proposals. Zimmermann BF Rapid Commun. Mass Spectrom. 25(11), 1575-82, (2011)

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Cancer preventive agents. Part 8: Chemopreventive effects of stevioside and related compounds. Takasaki M, Konoshima T, Kozuka M, et al. Bioorg. Med. Chem. 17(2), 600-5, (2009)

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Steviol glycoside safety: is the genotoxicity database sufficient? Urban JD, Carakostas MC, and Brusick DJ Food Chem. Toxicol. 51, 386-90, (2013)

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Synthesis and biological evaluation of novel exo-methylene cyclopentanone tetracyclic diterpenoids as antitumor agents. Jing Li et al Bioorg. Med. Chem. Lett. 21, 130-2, (2011)

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The use of a sweetener substitution method to predict dietary exposures for the intense sweetener rebaudioside A. Renwick AG Food Chem. Toxicol. 46 Suppl 7, S61-9, (2008)

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Validated high-performance thin-layer chromatography method for steviol glycosides in Stevia rebaudiana. Jaitak V, Gupta AP, Kaul VK, et al. J. Pharm. Biomed. Anal. 47(4-5), 790-4, (2008)

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Simultaneous determination of steviol and steviol glycosides by liquid chromatography-mass spectrometry. Shah R, De Jager LS, and Begley TH Food Addit. Contam. Part A. Chem. Anal. Control. Expo. Risk Assess. 29(12), 1861-71, (2012)

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Cytotoxic and apoptosis-inducing activities of steviol and isosteviol derivatives against human cancer cell lines. Ukiya M, Sawada S, Kikuchi T, et al. Chem. Biodivers. 10(2), 177-88, (2013)

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Synthesis and antituberculosis activity of novel unfolded and macrocyclic derivatives of ent-kaurane steviol. Khaybullin RN, Strobykina IY, Dobrynin AB, et al. Bioorg. Med. Chem. Lett. 22(22), 6909-13, (2012)

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Characterization of a novel steviol-producing β-glucosidase from Penicillium decumbens and optimal production of the steviol. Ko JA, Ryu YB, Kwon HJ, et al. Appl. Microbiol. Biotechnol. 97(18), 8151-61, (2013)

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A comprehensive analysis of fifteen genes of steviol glycosides biosynthesis pathway in Stevia rebaudiana (Bertoni). Kumar H, Kaul K, Bajpai-Gupta S, et al. Gene 492(1), 276-84, (2012)

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Preparative separation and purification of rebaudioside a from steviol glycosides using mixed-mode macroporous adsorption resins. Liu Y, Di D, Bai Q, et al. J. Agric. Food Chem. 59(17), 9629-36, (2011)

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Synthesis of ent-kaurane diterpene monoglycosides. Chaturvedula VS, Klucik J, Upreti M, et al. Molecules 16(10), 8402-9, (2011)

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High-performance thin-layer chromatography analysis of steviol glycosides in Stevia formulations and sugar-free food products, and benchmarking with (ultra) high-performance liquid chromatography. Morlock GE, Meyer S, Zimmermann BF, et al. J. Chromatogr. A 1350, 102-11, (2014)

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Steviol retards renal cyst growth through reduction of CFTR expression and inhibition of epithelial cell proliferation in a mouse model of polycystic kidney disease. Yuajit C, Muanprasat C, Gallagher AR, et al. Biochem. Pharmacol. 88(3), 412-21, (2014)

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Steviol effect, a glycoside of Stevia rebaudiana, on glucose clearances in rats. Melis MS, Rocha ST, and Augusto A Braz. J. Biol. 69(2), 371-4, (2009)

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Overexpression of SrUGT85C2 from Stevia reduced growth and yield of transgenic Arabidopsis by influencing plastidial MEP pathway. Guleria P, Masand S, and Yadav SK Gene 539(2), 250-7, (2014)

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Simultaneous analysis of steviol and steviol glycosides by liquid chromatography with ultraviolet detection on a mixed-mode column: application to Stevia plant material and Stevia-containing dietary supplements. Jaworska K, Krynitsky AJ, and Rader JI J. AOAC Int. 95(6), 1588-96, (2012)

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Synthetic study on the relationship between structure and sweet taste properties of steviol glycosides. Upreti M, Dubois G, and Prakash I Molecules 17(4), 4186-96, (2012)

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Gas-phase intramolecular elimination reaction studies of steviol glycosides in positive electrospray and tandem mass spectrometry. Upreti M, Clos JF, Somayajula KV, et al. Eur. J. Mass Spectrom. (Chichester, Eng.) 15(1), 11-21, (2009)

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[Steviol glycosides as sweetener in diabetes?]. Tuttas K and Kirch W Dtsch. Med. Wochenschr. 137(15), 806, (2012)

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Merck 14,10380

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