23180-57-6Relevant articles and documents
The structure of lactiflorin, an artefact during isolation?
Lang,Li,Wang,Yu,Liang
, p. 3123 - 3128 (1990)
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Version: 1.0
Creation Date: Aug 11, 2017
Revision Date: Aug 11, 2017
Product name | Paeoniflorin |
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Product number | - |
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Other names | Paeony root |
Identified uses | For industry use only. |
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Uses advised against | no data available |
Emergency phone number | - |
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Service hours | Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours). |
More Details:23180-57-6 SDS
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 |
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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 |
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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 |
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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 |
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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 |
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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 |
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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 |
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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 |
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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 |
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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 |
C21H22O6
paeoniflorin
Conditions | Yield |
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Multi-step reaction with 7 steps 1: (COCl)2, DMF / benzene 2: pyridine, DMAP / toluene 3: 1.) O2, 2.) (MeO)3P / 1.) toluene, 80 deg C, 2.) toluene 4: 71 percent / Et3N, DMAP / CH2Cl2 5: 1.) O3, MeOH, 2.) p-NO2-C6H4COCl, Et3N, DMAP / 1.) CH2Cl2, -78 deg C, 2.) CH2Cl2 6: 67 percent / BF3*Et2O / toluene / -78 °C 7: 100 percent / H2 / Pd(OH)2 / methanol; ethyl acetate; H2O View Scheme |
paeoniflorin
Conditions | Yield |
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Multi-step reaction with 6 steps 1: pyridine, DMAP / toluene 2: 1.) O2, 2.) (MeO)3P / 1.) toluene, 80 deg C, 2.) toluene 3: 71 percent / Et3N, DMAP / CH2Cl2 4: 1.) O3, MeOH, 2.) p-NO2-C6H4COCl, Et3N, DMAP / 1.) CH2Cl2, -78 deg C, 2.) CH2Cl2 5: 67 percent / BF3*Et2O / toluene / -78 °C 6: 100 percent / H2 / Pd(OH)2 / methanol; ethyl acetate; H2O View Scheme |
paeoniflorin
Conditions | Yield |
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Multi-step reaction with 10 steps 1: 0.1 M aq. HCl / tetrahydrofuran 2: PhI(OAc)2, I2 / benzene / Irradiation 3: HCl / dioxane / 40 °C 4: (COCl)2, DMF / benzene 5: pyridine, DMAP / toluene 6: 1.) O2, 2.) (MeO)3P / 1.) toluene, 80 deg C, 2.) toluene 7: 71 percent / Et3N, DMAP / CH2Cl2 8: 1.) O3, MeOH, 2.) p-NO2-C6H4COCl, Et3N, DMAP / 1.) CH2Cl2, -78 deg C, 2.) CH2Cl2 9: 67 percent / BF3*Et2O / toluene / -78 °C 10: 100 percent / H2 / Pd(OH)2 / methanol; ethyl acetate; H2O View Scheme |
(1S,3aS,5R,6R,7aR)-7a-Isopropenyl-5-((R)-2-methoxy-2-phenyl-acetoxy)-3a-methyl-hexahydro-3-oxa-1,6-cyclo-indene-1-carboxylic acid methyl ester
paeoniflorin
Conditions | Yield |
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Multi-step reaction with 14 steps 1: LiAlH4 / tetrahydrofuran 2: Et3N / CH2Cl2 3: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -60 deg C, 2.) CH2Cl2 4: KCN, 18-crown-6*MeCN / acetonitrile 5: 0.1 M aq. HCl / tetrahydrofuran 6: PhI(OAc)2, I2 / benzene / Irradiation 7: HCl / dioxane / 40 °C 8: (COCl)2, DMF / benzene 9: pyridine, DMAP / toluene 10: 1.) O2, 2.) (MeO)3P / 1.) toluene, 80 deg C, 2.) toluene 11: 71 percent / Et3N, DMAP / CH2Cl2 12: 1.) O3, MeOH, 2.) p-NO2-C6H4COCl, Et3N, DMAP / 1.) CH2Cl2, -78 deg C, 2.) CH2Cl2 13: 67 percent / BF3*Et2O / toluene / -78 °C 14: 100 percent / H2 / Pd(OH)2 / methanol; ethyl acetate; H2O View Scheme |
paeoniflorin
Conditions | Yield |
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Multi-step reaction with 5 steps 1: 1.) O2, 2.) (MeO)3P / 1.) toluene, 80 deg C, 2.) toluene 2: 71 percent / Et3N, DMAP / CH2Cl2 3: 1.) O3, MeOH, 2.) p-NO2-C6H4COCl, Et3N, DMAP / 1.) CH2Cl2, -78 deg C, 2.) CH2Cl2 4: 67 percent / BF3*Et2O / toluene / -78 °C 5: 100 percent / H2 / Pd(OH)2 / methanol; ethyl acetate; H2O View Scheme |
C25H24O8
paeoniflorin
Conditions | Yield |
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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 |
C28H28O7
paeoniflorin
Conditions | Yield |
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Multi-step reaction with 3 steps 1: 1.) O3, MeOH, 2.) p-NO2-C6H4COCl, Et3N, DMAP / 1.) CH2Cl2, -78 deg C, 2.) CH2Cl2 2: 67 percent / BF3*Et2O / toluene / -78 °C 3: 100 percent / H2 / Pd(OH)2 / methanol; ethyl acetate; H2O View Scheme |
Conditions | Yield |
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With pyridine at 20 - 22℃; | 83% |
Conditions | Yield |
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With 4-nitrophenylboronic acid; water In acetonitrile at -10℃; for 6h; Inert atmosphere; regioselective reaction; | A 73% B 7% |
O-[(α-D-mannopyranosyl)-(1->6)-(α-D-mannopyranosyl)-(1->3)-β-D-mannopyranosyl]-(1->4)-(1,2-dideoxy-α-D-glucopyrano)-[2,1-d]-2-methyloxazoline
paeoniflorin
C49H71NO31
Conditions | Yield |
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With endo-β-N-acetylglucosaminidase from Arthrobactor protophormiae In dimethyl sulfoxide at 23℃; for 2h; pH=7.0; aq. phosphate buffer; Enzymatic reaction; | 60% |
Conditions | Yield |
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With pyridine at 20 - 22℃; for 48h; | 58% |
Conditions | Yield |
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With pyridine at 0 - 22℃; | A 49% B 36% |
Conditions | Yield |
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With cation exchanger KU-2-8 (H+) for 2h; Reflux; Overall yield = 90 %; Overall yield = 296 mg; | A 40% B 42% |
paeoniflorin
A
7S-paeonimetaboline I
B
7R-paeonimetaboline I
C
paeonimetaboline II
Conditions | Yield |
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With Bacteroides fragilis ss. thetaotus In water at 37℃; for 12h; Product distribution; | A 12.6% B 6.2% C 0.9% |
Conditions | Yield |
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With GAM broth; Lactobacillus brevis In water at 37℃; for 12h; Product distribution; | A 11% B 9.6% |
paeoniflorin
Conditions | Yield |
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With sodium hydroxide In methanol for 0.166667h; Ambient temperature; | 124.4 mg |
thiobenzoic acid
paeoniflorin
A
(7S)-8-benzoylthiopaeonimetabolin I
B
(7R)-8-benzoylthiopaeonimetabolin I
Conditions | Yield |
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With Lactobacillus brevis In phosphate buffer at 37℃; for 6h; pH=7.3; | A 20 mg B 10 mg |
Cyclohexanethiol
paeoniflorin
Conditions | Yield |
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With Lactobacillus brevis In phosphate buffer at 37℃; for 6h; pH=7.3; Title compound not separated from byproducts; |
1-thiopropane
paeoniflorin
Conditions | Yield |
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With Lactobacillus brevis In phosphate buffer at 37℃; for 6h; pH=7.3; Title compound not separated from byproducts; |
prop-2-ene-1-thiol
paeoniflorin
Conditions | Yield |
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With Lactobacillus brevis In phosphate buffer at 37℃; for 6h; pH=7.3; Title compound not separated from byproducts; |
1-methyl-1-propanethiol
paeoniflorin
Conditions | Yield |
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With Lactobacillus brevis In phosphate buffer at 37℃; for 6h; pH=7.3; Title compound not separated from byproducts; |
2-methylpropanethiol-1
paeoniflorin
Conditions | Yield |
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With Lactobacillus brevis In phosphate buffer at 37℃; for 6h; pH=7.3; Title compound not separated from byproducts; |
1-butanethiol
paeoniflorin
Conditions | Yield |
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With Lactobacillus brevis In phosphate buffer at 37℃; for 6h; pH=7.3; Title compound not separated from byproducts; |
Hexanethiol
paeoniflorin
Conditions | Yield |
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With Lactobacillus brevis In phosphate buffer at 37℃; for 6h; pH=7.3; | A 19 mg B 10 mg |
toluene-3-thiol
paeoniflorin
Conditions | Yield |
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With Lactobacillus brevis In phosphate buffer at 37℃; for 6h; pH=7.3; Title compound not separated from byproducts; |
cyclopentylthiol
paeoniflorin
Conditions | Yield |
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With Lactobacillus brevis In phosphate buffer at 37℃; for 6h; pH=7.3; Title compound not separated from byproducts; |
thiophenol
paeoniflorin
Conditions | Yield |
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With Lactobacillus brevis In phosphate buffer at 37℃; for 6h; pH=7.3; Title compound not separated from byproducts; |
2-propanethiol
paeoniflorin
Conditions | Yield |
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With Lactobacillus brevis In phosphate buffer at 37℃; for 6h; pH=7.3; Title compound not separated from byproducts; |
para-thiocresol
paeoniflorin
Conditions | Yield |
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With Lactobacillus brevis In phosphate buffer at 37℃; for 6h; pH=7.3; Title compound not separated from byproducts; |
phenylmethanethiol
paeoniflorin
Conditions | Yield |
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With Lactobacillus brevis In phosphate buffer at 37℃; for 6h; pH=7.3; Title compound not separated from byproducts; |
paeoniflorin
2-Naphthalenethiol
Conditions | Yield |
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With Lactobacillus brevis In phosphate buffer at 37℃; for 6h; pH=7.3; Title compound not separated from byproducts; |
paeoniflorin
thioacetic acid
Conditions | Yield |
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With Lactobacillus brevis In phosphate buffer at 37℃; for 6h; pH=7.3; Title compound not separated from byproducts; |
paeoniflorin
2-thiocresol
Conditions | Yield |
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With Lactobacillus brevis In phosphate buffer at 37℃; for 6h; pH=7.3; Title compound not separated from byproducts; |
paeoniflorin
Conditions | Yield |
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With sodium periodate In methanol; water at 20℃; for 1h; |
paeoniflorin
Conditions | Yield |
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With β-glucosidase In dimethyl sulfoxide at 37℃; for 5h; |
paeoniflorin
Conditions | Yield |
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Multistep reaction; |
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