| Identification | Back Directory | [Name]
ISOSTEVIOL | [CAS]
27975-19-5 | [Synonyms]
Ccris 6121
Nsc 231875
ISOSTEVIOL
Isosteviol, BR
(-)-Isosteviol
ISOSTEVIOL STANDARD
ISOSTEVIOL USP/EP/BP
Iso-Stevio 27975-19-5
Isosteviol (NSC 231875)
Isosteviol ((-)-Isosteviol
(8β,13S)-13-Methyl-16-oxo-17-norkauran-18-oic acid
(4α,8β,13β)-13--Methyl-16-oxo-17-norkauran-18-oic acid
13-beta-kauran-18-oicacid,13-methyl-16-oxo-17-nor-8-bet
Isosteviol, 98%, from Stevia rebaudiana (Bertoni) Hemsl
17-Norkauran-18-oic acid, 13-methyl-16-oxo-, (4α,8β,13β)-
17-Nor-8-beta,13-beta-kauran-18-oic acid, 13-methyl-16-oxo-
13-methyl-16-oxo-,(4-alpha,8-beta,13-beta)-17-norkauran-18-oicaci
(4-alpha,8-beta,13-beta)-13-methyl-16-oxo-17-norkauran-18-oicacid
17-NORKAURAN-18-OIC ACID, 13-METHYL-16-OXO-, (4-ALPHA,8-BETA,13-BETA)-
(4aα,11aα)-4,9,11bβ-Trimethyl-8-oxo-6aα,9α-methanotetradecahydro-1H-cyclohepta[a]naphthalene-4β-carboxylic acid
(4R,4aS,6aR,9S,11aR,11bS)-4,9,11b-trimethyl-8-oxotetradecahydro-6a,9-methanocyclohepta[a]naphthalene-4-carboxylic acid | [Molecular Formula]
C20H30O3 | [MDL Number]
MFCD00210315 | [MOL File]
27975-19-5.mol | [Molecular Weight]
318.45 |
| Chemical Properties | Back Directory | [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 ]
neat | [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| |
| Hazard Information | Back Directory | [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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