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H8664

Sigma-Aldrich

Steviol hydrate

≥98% (HPLC), powder

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C20H30O3 · xH2O
CAS Number:
471-80-7
Molecular Weight:
318.45 (anhydrous basis)
MDL number:
MFCD20441965
UNSPSC Code:
12161501
PubChem Substance ID:
329815252
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

white to tan

solubility

DMSO: >10 mg/mL

storage temp.

2-8°C

SMILES string

O.C[C@@]12CCC[C@](C)([C@H]1CC[C@]34CC(=C)[C@](O)(CC[C@@H]23)C4)C(O)=O

InChI

1S/C20H30O3.H2O/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);1H2/t14-,15-,17+,18+,19+,20-;/m0./s1

InChI key

SGPAFVVDOPSBEU-CRRYNOPCSA-N

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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Sigma-Aldrich

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Stevioside primary reference standard

05420590

Stevioside

Venkata Sai Prakash Chaturvedula et al.
Molecules (Basel, Switzerland), 16(10), 8402-8409 (2011-10-05)
Synthesis of two ent-kaurane diterpene glycosides, steviol 19-O-β-D-glucopyranosiduronic acid (steviol glucuronide, 5), and 13-hydroxy ent-kaur-16-en-19-oic acid-β-D-glucopyranosyl ester (7) has been achieved from a common starting material, steviol, using phase transfer catalyst. Also, synthesis of an additional 17-nor-ent-kaurane glycoside, namely 13-methyl-16-oxo-17-nor-ent-kauran-19-oic
Ravil N Khaybullin et al.
Bioorganic & medicinal chemistry letters, 22(22), 6909-6913 (2012-10-11)
New derivatives of steviol 1, the aglycone of the glycosides of Stevia rebaudiana, including a novel class of semisynthetic diterpenoids, namely macrocyclic ent-kauranes were synthesized. These compounds possess antituberculosis activity inhibiting the in vitro growth of Mycobacterium Tuberculosis (H37R(V) strain)
Stijn Ceunen et al.
Plant science : an international journal of experimental plant biology, 198, 72-82 (2012-12-04)
The effect of photoperiodism on steviol glycoside (SVgly) accumulation was investigated in Stevia rebaudiana. Topped plants were cultivated to develop new branches under a 16h or 8h photoperiod. During different ontogenetic phases, leaves, stems, lateral shoots, roots and reproductive organs
Midori Takasaki et al.
Bioorganic & medicinal chemistry, 17(2), 600-605 (2009-01-10)
In a search for potential cancer chemopreventive agents from natural resources, stevioside (1), a sweetener, and six related compounds, including two aglycones steviol (6) and isosteviol (7), were screened in an in vitro assay for inhibitory effects on Epstein-Barr virus
[Steviol glycosides as sweetener in diabetes?].
K Tuttas et al.
Deutsche medizinische Wochenschrift (1946), 137(15), 806-806 (2012-04-12)
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