ISOSTEVIOL Chemical Properties

Melting point:

228.0 to 232.0 °C

Boiling point:

455.6±38.0 °C(Predicted)

Density 

1.15±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO:81.5(Max Conc. mg/mL);255.92(Max Conc. mM)

form 

Solid

pka

4.69±0.60(Predicted)

color 

White to Almost white

InChI

InChI=1/C20H30O3/c1-17-9-5-14-18(2)7-4-8-19(3,16(22)23)13(18)6-10-20(14,12-17)11-15(17)21/h13-14H,4-12H2,1-3H3,(H,22,23)/t13-,14?,17-,18+,19+,20-/s3

InChIKey

KFVUFODCZDRVSS-MVXPDRGUNA-N

SMILES

C12CC[C@@]3(C(=O)C[C@@]1(CC[C@]1([H])[C@](C)(C(=O)O)CCC[C@@]21C)C3)C |&1:3,7,10,12,20,r|

Safety Information

WGK Germany 

3

HS Code 

2918.30.9000

ISOSTEVIOL Usage And Synthesis

Chemical Properties

White crystals, soluble in organic solvents such as methanol, ethanol, and DMSO, derived from Stevia rebaudiana Bertoni, also known as stevia and sweet grass.

Uses

Isosteviol is a tetracyclic diterpenoid with a beyerane core has drawn attention because it can exhibit antihypertensive activity, reduce blood glucose, suppress cancer cells.

Definition

ChEBI: Isosteviol is a diterpenoid.

Synthesis

A new structure based on (2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl((4R,4aS,6aR,9S,11aR,11bS)-9-(((2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-(((2S,3R,4S,5S,6R )-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy-4,11b-dimethyl-8-methylenetetradecahydro-6a,9-methylcyclohepta[a]naphthalene-4-carboxylic acid ester was synthesized by 10% sulfuric acid hydrolysis reaction. The reaction conditions were conventional hydrolysis conditions without additional catalyst or special temperature control. The product was purified in 93% yield with the melting point of 228.4-230.8 °C. The structure of the product was confirmed by IR, 1H NMR, 13C NMR and HRMS.The IR spectrum showed that the characteristic absorption peaks were located at 3448, 2955, 2924, 2848, 1736, 1692, 1453, 1404, 1373, 1320, 1268, 1214, 1180, 1150, 1108, 973, 950, 796, 589 cm-1 . 796, 589 cm-1.1H NMR (400 MHz, CDCl3) δ: 2.64 (dd, J = 18.64, 3.76 Hz, 1H), 2.17 (d, J = 13.40 Hz, 1H), 1.90-1.37 (m, 13H), 1.25 (s, 3H), 1.22-1.14 (m, 3H), 1.06- 1.03 (m, 1H), 0.98 (s, 3H), 0.95-0.88 (m, 1H), 0.78 (s, 3H).13C NMR (100 MHz, CDCl3) δ: 224.22, 184.33, 56.79, 57.62, 56.09, 54.83, 49.73, 49.59, 44.38. 42.02, 40.42, 38.99, 38.34, 32.80, 29.69, 22.32, 20.57, 19.55, 14.04. HRMS (ESI) m/z: [M + Na]+ Calculated value C20H30O3Na 341.2093, measured value 341.2085.

References

[1] Chemistry and Biodiversity, 2013, vol. 10, # 2, p. 177 - 188
[2] Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 19, p. 2485 - 2490
[3] European Journal of Medicinal Chemistry, 2016, vol. 115, p. 26 - 40
[4] Journal of Chemical Crystallography, 2009, vol. 39, # 2, p. 108 - 111
[5] Journal of Chemical Crystallography, 2011, vol. 41, # 4, p. 519 - 522

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