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CAS No.: | 23180-57-6 |
---|---|
Name: | Paeoniflorin |
Article Data: | 2 |
Molecular Structure: | |
Formula: | C23H28O11 |
Molecular Weight: | 480.469 |
Synonyms: | 5b-((Benzoyloxy)methyl)tetrahydro-5-hydroxy-2-methyl-2,5-methano-lH-3,4-dioxacyclobuta(cd)pentalen-1a(2H)-yl-beta-D-glucopyranoside;a-D-Glucopyranoside,(1aR,2S,3aR,5R,5aR,5bS)- 5b-[(benzoyloxy)methyl]tetrahydro-5-hydroxy- 2-methyl-2,5-methano-1H-3,4-dioxacyclobuta[ cd]pentalen-1a(2H)-yl;beta-d-Glucopyranoside, 5b-((benzoyloxy)methyl)tetrahydro-5-hydroxy-2-methyl-2,5-methano-1H-3,4-dioxacyclobuta(cd)pentalen-1a(2H)-yl, (1aR-(1aalpha,2beta,3aalpha,5alpha,5aalpha,5balpha))-;.beta.-D-Glucopyranoside, (1aR,2S,3aR,5R,5aR,5bS)-5b-[(benzoyloxy)methyl]tetrahydro-5-hydroxy-2-methyl-2,5-methano-1H-3,4-dioxacyclobuta[cd]pentalen-1a(2H)-yl;Paeonia moutan;beta-D-Glucopyranoside, (1aS,2R,3aR,5R,5aR,5bS)-5b-((benzoyloxy)methyl)tetrahydro-5-hydroxy-2-methyl-2,5-methano-1H-3,4-dioxacyclobuta(cd)pentalen-1a(2H)-yl;White Peony P.E.-Paeoniflorin;White Peony Root P.E.;Boswellin Extract;Paeoniflorm; |
EINECS: | 245-476-2 |
Density: | 1.63 g/cm3 |
Melting Point: | approximate 124℃ (dec.) |
Boiling Point: | 683.3 °C at 760 mmHg |
Flash Point: | 235.9 °C |
Appearance: | White fine powder |
Hazard Symbols: | Xn,N,T,F |
Risk Codes: | R22; R50; R39/23/24/25; R23/24/25 |
Safety: | 24/25 |
PSA: | 164.37000 |
LogP: | -1.35750 |
paeoniflorin
Conditions | Yield |
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With hydrogen; palladium dihydroxide In methanol; water; ethyl acetate | 100% |
2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl trichloroacetimidate
paeoniflorin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 67 percent / BF3*Et2O / toluene / -78 °C 2: 100 percent / H2 / Pd(OH)2 / methanol; ethyl acetate; H2O View Scheme |
paeoniflorin
Conditions | Yield |
---|---|
Multi-step reaction with 13 steps 1: Et3N / CH2Cl2 2: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -60 deg C, 2.) CH2Cl2 3: KCN, 18-crown-6*MeCN / acetonitrile 4: 0.1 M aq. HCl / tetrahydrofuran 5: PhI(OAc)2, I2 / benzene / Irradiation 6: HCl / dioxane / 40 °C 7: (COCl)2, DMF / benzene 8: pyridine, DMAP / toluene 9: 1.) O2, 2.) (MeO)3P / 1.) toluene, 80 deg C, 2.) toluene 10: 71 percent / Et3N, DMAP / CH2Cl2 11: 1.) O3, MeOH, 2.) p-NO2-C6H4COCl, Et3N, DMAP / 1.) CH2Cl2, -78 deg C, 2.) CH2Cl2 12: 67 percent / BF3*Et2O / toluene / -78 °C 13: 100 percent / H2 / Pd(OH)2 / methanol; ethyl acetate; H2O View Scheme |
paeoniflorin
Conditions | Yield |
---|---|
Multi-step reaction with 15 steps 1: 47 percent / dicyclohexylcarbodiimide, DMAP / CH2Cl2 2: LiAlH4 / tetrahydrofuran 3: Et3N / CH2Cl2 4: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -60 deg C, 2.) CH2Cl2 5: KCN, 18-crown-6*MeCN / acetonitrile 6: 0.1 M aq. HCl / tetrahydrofuran 7: PhI(OAc)2, I2 / benzene / Irradiation 8: HCl / dioxane / 40 °C 9: (COCl)2, DMF / benzene 10: pyridine, DMAP / toluene 11: 1.) O2, 2.) (MeO)3P / 1.) toluene, 80 deg C, 2.) toluene 12: 71 percent / Et3N, DMAP / CH2Cl2 13: 1.) O3, MeOH, 2.) p-NO2-C6H4COCl, Et3N, DMAP / 1.) CH2Cl2, -78 deg C, 2.) CH2Cl2 14: 67 percent / BF3*Et2O / toluene / -78 °C 15: 100 percent / H2 / Pd(OH)2 / methanol; ethyl acetate; H2O View Scheme |
paeoniflorin
Conditions | Yield |
---|---|
Multi-step reaction with 16 steps 1: NaBH4 / methanol / -20 °C 2: 47 percent / dicyclohexylcarbodiimide, DMAP / CH2Cl2 3: LiAlH4 / tetrahydrofuran 4: Et3N / CH2Cl2 5: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -60 deg C, 2.) CH2Cl2 6: KCN, 18-crown-6*MeCN / acetonitrile 7: 0.1 M aq. HCl / tetrahydrofuran 8: PhI(OAc)2, I2 / benzene / Irradiation 9: HCl / dioxane / 40 °C 10: (COCl)2, DMF / benzene 11: pyridine, DMAP / toluene 12: 1.) O2, 2.) (MeO)3P / 1.) toluene, 80 deg C, 2.) toluene 13: 71 percent / Et3N, DMAP / CH2Cl2 14: 1.) O3, MeOH, 2.) p-NO2-C6H4COCl, Et3N, DMAP / 1.) CH2Cl2, -78 deg C, 2.) CH2Cl2 15: 67 percent / BF3*Et2O / toluene / -78 °C 16: 100 percent / H2 / Pd(OH)2 / methanol; ethyl acetate; H2O View Scheme |
paeoniflorin
Conditions | Yield |
---|---|
Multi-step reaction with 12 steps 1: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -60 deg C, 2.) CH2Cl2 2: KCN, 18-crown-6*MeCN / acetonitrile 3: 0.1 M aq. HCl / tetrahydrofuran 4: PhI(OAc)2, I2 / benzene / Irradiation 5: HCl / dioxane / 40 °C 6: (COCl)2, DMF / benzene 7: pyridine, DMAP / toluene 8: 1.) O2, 2.) (MeO)3P / 1.) toluene, 80 deg C, 2.) toluene 9: 71 percent / Et3N, DMAP / CH2Cl2 10: 1.) O3, MeOH, 2.) p-NO2-C6H4COCl, Et3N, DMAP / 1.) CH2Cl2, -78 deg C, 2.) CH2Cl2 11: 67 percent / BF3*Et2O / toluene / -78 °C 12: 100 percent / H2 / Pd(OH)2 / methanol; ethyl acetate; H2O View Scheme |
paeoniflorin
Conditions | Yield |
---|---|
Multi-step reaction with 11 steps 1: KCN, 18-crown-6*MeCN / acetonitrile 2: 0.1 M aq. HCl / tetrahydrofuran 3: PhI(OAc)2, I2 / benzene / Irradiation 4: HCl / dioxane / 40 °C 5: (COCl)2, DMF / benzene 6: pyridine, DMAP / toluene 7: 1.) O2, 2.) (MeO)3P / 1.) toluene, 80 deg C, 2.) toluene 8: 71 percent / Et3N, DMAP / CH2Cl2 9: 1.) O3, MeOH, 2.) p-NO2-C6H4COCl, Et3N, DMAP / 1.) CH2Cl2, -78 deg C, 2.) CH2Cl2 10: 67 percent / BF3*Et2O / toluene / -78 °C 11: 100 percent / H2 / Pd(OH)2 / methanol; ethyl acetate; H2O View Scheme |
C20H22O5
paeoniflorin
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 71 percent / Et3N, DMAP / CH2Cl2 2: 1.) O3, MeOH, 2.) p-NO2-C6H4COCl, Et3N, DMAP / 1.) CH2Cl2, -78 deg C, 2.) CH2Cl2 3: 67 percent / BF3*Et2O / toluene / -78 °C 4: 100 percent / H2 / Pd(OH)2 / methanol; ethyl acetate; H2O View Scheme |
Benzoic acid (1S,3aS,5R,6R,7aR)-5-cyano-5-hydroxy-7a-isopropenyl-3a-methyl-hexahydro-3-oxa-1,6-cyclo-inden-1-ylmethyl ester
paeoniflorin
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1: PhI(OAc)2, I2 / benzene / Irradiation 2: HCl / dioxane / 40 °C 3: (COCl)2, DMF / benzene 4: pyridine, DMAP / toluene 5: 1.) O2, 2.) (MeO)3P / 1.) toluene, 80 deg C, 2.) toluene 6: 71 percent / Et3N, DMAP / CH2Cl2 7: 1.) O3, MeOH, 2.) p-NO2-C6H4COCl, Et3N, DMAP / 1.) CH2Cl2, -78 deg C, 2.) CH2Cl2 8: 67 percent / BF3*Et2O / toluene / -78 °C 9: 100 percent / H2 / Pd(OH)2 / methanol; ethyl acetate; H2O View Scheme |
C21H21NO4
paeoniflorin
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1: HCl / dioxane / 40 °C 2: (COCl)2, DMF / benzene 3: pyridine, DMAP / toluene 4: 1.) O2, 2.) (MeO)3P / 1.) toluene, 80 deg C, 2.) toluene 5: 71 percent / Et3N, DMAP / CH2Cl2 6: 1.) O3, MeOH, 2.) p-NO2-C6H4COCl, Et3N, DMAP / 1.) CH2Cl2, -78 deg C, 2.) CH2Cl2 7: 67 percent / BF3*Et2O / toluene / -78 °C 8: 100 percent / H2 / Pd(OH)2 / methanol; ethyl acetate; H2O View Scheme |
Molecular Structure of Paeoniflorin (CAS NO.23180-57-6):
Empirical Formula: C23H28O11
Molecular Weight: 480.4618
H bond acceptors: 11
H bond donors: 5
Freely Rotating Bonds: 12
Polar Surface Area: 164.37 Å2
Index of Refraction: 1.682
Molar Refractivity: 111.58 cm3
Molar Volume: 294.2 cm3
Surface Tension: 87.3 dyne/cm
Density: 1.63 g/cm3
Flash Point: 238.4 °C
Enthalpy of Vaporization: 106.23 kJ/mol
Boiling Point: 690.2 °C at 760 mmHg
Vapour Pressure: 5.33E-20 mmHg at 25°C
EINECS: 245-476-2
Product Categories: Heterocycles; Natural Plant Extract; The group of Paeoniflorin;Veterinaries; Steroids; API's
InChI
InChI=1/C23H28O11/c1-20-9-22(29)13-7-23(20,32-18-16(27)15(26)14(25)12(8-24)31-18)21(13,19(33-20)34-22)10-30-17(28)11-5-3-2-4-6-11/h2-6,12-16,18-19,24-27,29H,7-10H2,1H3/t12-,13-,14-,15+,16-,18+,19-,20-,21+,22+,23+/m1/s1
Smiles
O1[C@@H](O[C@@]23[C@@]4([C@@H]([C@@]5(C[C@@]2(C)O[C@@H]4O5)O)C3)COC(=O)c2ccccc2)[C@@H]([C@H]([C@@H]([C@H]1CO)O)O)O
1. | ipr-mus LD50:9530 mg/kg | YKKZAJ Yakugaku Zasshi. Journal of Pharmacy. 89 (1969),879. | ||
2. | ivn-mus LD50:3530 mg/kg | YKKZAJ Yakugaku Zasshi. Journal of Pharmacy. 89 (1969),879. |
Moderately toxic by intravenous route. Mildly toxic by intraperitoneal route. When heated to decomposition it emits acrid smoke and irritating fumes.
Paeoniflorin , with CAS number of 23180-57-6, can be called 5beta-[(Benzoyloxy)methyl]tetrahydro-5-hydroxy-2-methyl-2,5-methano-1H-3,4-dioxacyclobuta[cd]pentalen-1alpha(2H)-yl-beta-D-glucopyranoside .