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MedKoo Cat#: 329679 | Name: Steviol
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Description:

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

Steviol is the aglycon derivative of steviol glycosides, which are natural sweeteners isolated from S. rebaudiana. Steviol inhibits human organic anion transporters (hOATs) in uptake assays using murine cells from the S2 segment of proximal tubules. Steviol glycosides enhance pancreatic beta-cell function and taste sensation by potentiation of TRPM5 channel activity.

Chemical Structure

Steviol
Steviol
CAS#471-80-7

Theoretical Analysis

MedKoo Cat#: 329679

Name: Steviol

CAS#: 471-80-7

Chemical Formula: C20H30O3

Exact Mass: 318.2195

Molecular Weight: 318.46

Elemental Analysis: C, 75.43; H, 9.50; O, 15.07

Price and Availability

Size Price Availability Quantity
10mg USD 450.00 2 weeks
25mg USD 800.00 2 weeks
50mg USD 1,250.00 2 weeks
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Related CAS #
No Data
Synonym
Steviol; 13-O-Glucosylsteviol; Hydroxydehydrostevic Acid; 13-hydroxy Kaurenoic Acid; NSC 226902.
IUPAC/Chemical Name
(4R,4aS,6aR,9S,11aR,11bS)-9-hydroxy-4,11b-dimethyl-8-methylenetetradecahydro-6a,9-methanocyclohepta[a]naphthalene-4-carboxylic acid
InChi Key
QFVOYBUQQBFCRH-VQSWZGCSSA-N
InChi Code
InChI=1S/C20H30O3/c1-13-11-19-9-5-14-17(2,7-4-8-18(14,3)16(21)22)15(19)6-10-20(13,23)12-19/h14-15,23H,1,4-12H2,2-3H3,(H,21,22)/t14-,15-,17+,18+,19+,20-/m0/s1
SMILES Code
C=C1[C@@]2(O)C[C@]3(C1)CC[C@]4([H])[C@](C)(C(O)=O)CCC[C@@]4(C)[C@]3([H])CC2
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
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Steviol is selective for hOAT1 and hOAT3 over hOAT2 and hOAT4 (IC50s = 11.4, 36.5, 1,000, and 285 μM, respectively).
In vitro activity:
The inhibition of OAT-mediated transport by steviol could alter renal drug clearance. Steviol markedly inhibited substrate uptake in all S2hOAT cells. Steviol had low IC50 for hOAT1 (11.4 microM) and hOAT3 (36.5 microM) similar to that of probenecid, whereas IC50 for hOAT2 (1000 microM) and hOAT4 (285 microM) was much higher. Reference: Pharm Res. 2005 Jun;22(6):858-66. https://pubmed.ncbi.nlm.nih.gov/15948029/
In vivo activity:
The toxicokinetics and metabolism of rebaudioside A, stevioside, and steviol were studied in rats to compare their effects. Results showed that these compounds were rapidly absorbed and eliminated, with similar patterns in plasma concentration over time. Metabolite profiles were similar, with steviol being the main component in plasma. The majority of radioactivity was excreted in feces, with minimal urinary excretion. Reference: Food Chem Toxicol. 2008 Jul;46 Suppl 7:S31-9. https://pubmed.ncbi.nlm.nih.gov/18562068/
Solvent mg/mL mM
Solubility
DMF 30.0 94.20
DMSO 25.0 78.50
Ethanol 30.0 94.20
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 318.46 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
Formulation protocol:
1. Yuajit C, Muanprasat C, Homvisasevongsa S, Chatsudthipong V. Steviol stabilizes polycystin 1 expression and promotes lysosomal degradation of CFTR and β-catenin proteins in renal epithelial cells. Biomed Pharmacother. 2017 Oct;94:820-826. doi: 10.1016/j.biopha.2017.07.165. Epub 2017 Aug 10. PMID: 28802235. 2. Srimaroeng C, Jutabha P, Pritchard JB, Endou H, Chatsudthipong V. Interactions of stevioside and steviol with renal organic anion transporters in S2 cells and mouse renal cortical slices. Pharm Res. 2005 Jun;22(6):858-66. doi: 10.1007/s11095-005-4580-5. Epub 2005 Jun 8. PMID: 15948029. 3. Roberts A, Renwick AG. Comparative toxicokinetics and metabolism of rebaudioside A, stevioside, and steviol in rats. Food Chem Toxicol. 2008 Jul;46 Suppl 7:S31-9. doi: 10.1016/j.fct.2008.05.006. Epub 2008 May 16. PMID: 18562068.
In vitro protocol:
1. Yuajit C, Muanprasat C, Homvisasevongsa S, Chatsudthipong V. Steviol stabilizes polycystin 1 expression and promotes lysosomal degradation of CFTR and β-catenin proteins in renal epithelial cells. Biomed Pharmacother. 2017 Oct;94:820-826. doi: 10.1016/j.biopha.2017.07.165. Epub 2017 Aug 10. PMID: 28802235. 2. Srimaroeng C, Jutabha P, Pritchard JB, Endou H, Chatsudthipong V. Interactions of stevioside and steviol with renal organic anion transporters in S2 cells and mouse renal cortical slices. Pharm Res. 2005 Jun;22(6):858-66. doi: 10.1007/s11095-005-4580-5. Epub 2005 Jun 8. PMID: 15948029.
In vivo protocol:
1. Roberts A, Renwick AG. Comparative toxicokinetics and metabolism of rebaudioside A, stevioside, and steviol in rats. Food Chem Toxicol. 2008 Jul;46 Suppl 7:S31-9. doi: 10.1016/j.fct.2008.05.006. Epub 2008 May 16. PMID: 18562068.
1: Ruddat M, Heftmann E, Lang A. Biosynthesis of steviol. Arch Biochem Biophys. 1965 Jun;110(3):496-9. doi: 10.1016/0003-9861(65)90441-8. PMID: 5840681. 2: Ruddat M, Heftmann E, Lang A. Conversion of steviol to a gibberellin-like compound by Fusarium moniliforme. Arch Biochem Biophys. 1965 Jul;111(1):187-90. doi: 10.1016/0003-9861(65)90338-3. PMID: 5851871. 3: Ruddat M. Inhibition of the biosynthesis of steviol by a growth retardant. Nature. 1966 Aug 27;211(5052):971-2. doi: 10.1038/211971a0. PMID: 4165504. 4: Schraudolf H. Wirkung von terpenderivaten (helminthosporol, helminthosporsäure, dihydrohelminthosporsäure und steviol) auf die antheridienbildung in Anemia phyllitidis [Effect of terpenoid derivatives (helminthosporol, helminthosporic acid, dihydrohelminthosporic acid, and steviol) on antheridinum induction in Anemia phyllitidis]. Planta. 1967 Jun;74(2):188-93. German. doi: 10.1007/BF00388328. PMID: 24549890. 5: Bearder JR, Frydman VM, Gaskin P, MacMillan J, Wels CM, Phinney BO. Fungal products. Part XVI. Conversion of isosteviol and steviol acetate into gibberellin analogues by mutant b1-41a of Gibberella fujikuroi and the preparation of (3H)gibberellin A20. J Chem Soc Perkin 1. 1976;(2):173-8. doi: 10.1039/p19760000173. PMID: 942958. 6: Wingard RE Jr, Brown JP, Enderlin FE, Dale JA, Hale RL, Seitz CT. Intestinal degradation and absorption of the glycosidic sweeteners stevioside and rebaudioside A. Experientia. 1980 May 15;36(5):519-20. doi: 10.1007/BF01965774. PMID: 7379936. 7: DuBois GE, Dietrich PS, Lee JF, McGarraugh GV, Stephenson RA. Diterpenoid sweeteners. Synthesis and sensory evaluation of stevioside analogues nondegradable to steviol. J Med Chem. 1981 Nov;24(11):1269-71. doi: 10.1021/jm00143a001. PMID: 7310801. 8: Okamoto H, Yoshida D, Mizusaki S. Inhibition of 12-O-tetradecanoylphorbol-13-acetate-induced induction in Epstein-Barr virus early antigen in Raji cells. Cancer Lett. 1983 May;19(1):47-53. doi: 10.1016/0304-3835(83)90134-9. PMID: 6850568. 9: Okamoto H, Yoshida D, Saito Y, Mizusaki S. Inhibition of 12-O-tetradecanoylphorbol-13-acetate-induced ornithine decarboxylase activity in mouse epidermis by sweetening agents and related compounds. Cancer Lett. 1983 Nov;21(1):29-35. doi: 10.1016/0304-3835(83)90079-4. PMID: 6315213. 10: Kinghorn AD, Soejarto DD, Nanayakkara NP, Compadre CM, Makapugay HC, Hovanec-Brown JM, Medon PJ, Kamath SK. A phytochemical screening procedure for sweet ent-kaurene glycosides in the genus Stevia. J Nat Prod. 1984 May- Jun;47(3):439-44. doi: 10.1021/np50033a007. PMID: 6481357. 11: Yamamoto NS, Kelmer Bracht AM, Ishii EL, Kemmelmeier FS, Alvarez M, Bracht A. Effect of steviol and its structural analogues on glucose production and oxygen uptake in rat renal tubules. Experientia. 1985 Jan 15;41(1):55-7. doi: 10.1007/BF02005871. PMID: 3838156. 12: Kelmer Bracht A, Alvarez M, Bracht A. Effects of Stevia rebaudiana natural products on rat liver mitochondria. Biochem Pharmacol. 1985 Mar 15;34(6):873-82. doi: 10.1016/0006-2952(85)90769-5. PMID: 2858211. 13: Pezzuto JM, Compadre CM, Swanson SM, Nanayakkara D, Kinghorn AD. Metabolically activated steviol, the aglycone of stevioside, is mutagenic. Proc Natl Acad Sci U S A. 1985 Apr;82(8):2478-82. doi: 10.1073/pnas.82.8.2478. PMID: 3887402; PMCID: PMC397582. 14: Pezzuto JM, Nanayakkara NP, Compadre CM, Swanson SM, Kinghorn AD, Guenthner TM, Sparnins VL, Lam LK. Characterization of bacterial mutagenicity mediated by 13-hydroxy-ent-kaurenoic acid (steviol) and several structurally-related derivatives and evaluation of potential to induce glutathione S-transferase in mice. Mutat Res. 1986 Mar;169(3):93-103. doi: 10.1016/0165-1218(86)90088-1. PMID: 3512998. 15: Campell BR, Bonner BA. Evidence for Phytochrome Regulation of Gibberellin A(20) 3beta-Hydroxylation in Shoots of Dwarf (lele) Pisum sativum L. Plant Physiol. 1986 Dec;82(4):909-15. doi: 10.1104/pp.82.4.909. PMID: 16665165; PMCID: PMC1056232. 16: Ishii EL, Bracht A. Glucose release by the liver under conditions of reduced activity of glucose 6-phosphatase. Braz J Med Biol Res. 1987;20(6):837-43. PMID: 3455265. 17: Nanayakkara NP, Klocke JA, Compadre CM, Hussain RA, Pezzuto JM, Kinghorn AD. Characterization and feeding deterrent effects on the aphid, Schizaphis graminum, of some derivatives of the sweet compounds, stevioside and rebaudioside A. J Nat Prod. 1987 May-Jun;50(3):434-41. doi: 10.1021/np50051a015. PMID: 3668559. 18: Compadre CM, Hussain RA, Nanayakkara NP, Pezzuto JM, Kinghorn AD. Mass spectral analysis of some derivatives and in vitro metabolites of steviol, the aglycone of the natural sweeteners, stevioside, rebaudioside A, and rubusoside. Biomed Environ Mass Spectrom. 1988 Feb 15;15(4):211-22. doi: 10.1002/bms.1200150405. Erratum in: Biomed Environ Mass Spectrom 1988 Jun 1;15(11):635. PMID: 3370361. 19: Matsui M, Matsui K, Nohmi T, Mizusawa H, Ishidate M. [Mutagenicity of steviol: an analytical approach using the Southern blotting system]. Eisei Shikenjo Hokoku. 1989;(107):83-7. Japanese. PMID: 2700079. 20: Shibata H, Sonoke S, Ochiai H, Nishihashi H, Yamada M. Glucosylation of Steviol and Steviol-Glucosides in Extracts from Stevia rebaudiana Bertoni. Plant Physiol. 1991 Jan;95(1):152-6. doi: 10.1104/pp.95.1.152. PMID: 16667943; PMCID: PMC1077498.

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CP 46665

CP 46665