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H8664

Sigma-Aldrich

Steviol

≥98% (HPLC), powder

Sinónimos:

(4α)-13-hydroxykaur-16-en-18-oic acid

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About This Item

Fórmula empírica (notación de Hill):
C20H30O3 · xH2O
Número de CAS:
471-80-7
Peso molecular:
318.45 (anhydrous basis)
MDL number:
MFCD20441965
UNSPSC Code:
12161501
PubChem Substance ID:
329815252
NACRES:
NA.77

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.
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

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Certificados de análisis (COA)

Lot/Batch Number
106M4732V
083M4720V
122M4721V
071M4726V
040M4602

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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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