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Name	Paeoniflorin	EINECS	245-476-2
CAS No.	23180-57-6	Density	1.63 g/cm³
PSA	164.37000	LogP	-1.35750
Solubility	N/A	Melting Point	approximate 124℃ (dec.)
Formula	C₂₃H₂₈O₁₁	Boiling Point	683.3 °C at 760 mmHg
Molecular Weight	480.469	Flash Point	235.9 °C
Transport Information	N/A	Appearance	White fine powder
Safety	24/25	Risk Codes	R22; R50; R39/23/24/25; R23/24/25
Molecular Structure		Hazard Symbols	Xn,N,T,F
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;	Article Data	2

Paeoniflorin Synthetic route

: C59H58O13

: 23180-57-6
paeoniflorin

Conditions

Conditions	Yield
With hydrogen; palladium dihydroxide In methanol; water; ethyl acetate	100%

: 74808-09-6
2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl trichloroacetimidate

: 23180-57-6
paeoniflorin

Conditions

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

: (1R,3aS,5R,6R,7aR)-1-Hydroxymethyl-7a-isopropenyl-3a-methyl-octahydro-3-oxa-1,6-cyclo-inden-5-ol

: 23180-57-6
paeoniflorin

Conditions

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-6MeCN / 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 / BF3Et2O / toluene / -78 °C 13: 100 percent / H2 / Pd(OH)2 / methanol; ethyl acetate; H2O View Scheme

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

: (1S,3aS,5R,6R,7aR)-5-Hydroxy-7a-isopropenyl-3a-methyl-hexahydro-3-oxa-1,6-cyclo-indene-1-carboxylic acid methyl ester

: 23180-57-6
paeoniflorin

Conditions

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-6MeCN / 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 / BF3Et2O / toluene / -78 °C 15: 100 percent / H2 / Pd(OH)2 / methanol; ethyl acetate; H2O View Scheme

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

: (1S,3aS,6R,7aR)-7a-Isopropenyl-3a-methyl-5-oxo-hexahydro-3-oxa-1,6-cyclo-indene-1-carboxylic acid methyl ester

: 23180-57-6
paeoniflorin

Conditions

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-6MeCN / 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 / BF3Et2O / toluene / -78 °C 16: 100 percent / H2 / Pd(OH)2 / methanol; ethyl acetate; H2O View Scheme

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

: Benzoic acid (1S,3aS,5R,6R,7aR)-5-hydroxy-7a-isopropenyl-3a-methyl-hexahydro-3-oxa-1,6-cyclo-inden-1-ylmethyl ester

: 23180-57-6
paeoniflorin

Conditions

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-6MeCN / 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 / BF3Et2O / toluene / -78 °C 12: 100 percent / H2 / Pd(OH)2 / methanol; ethyl acetate; H2O View Scheme

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

: Benzoic acid (1S,3aS,6R,7aR)-7a-isopropenyl-3a-methyl-5-oxo-hexahydro-3-oxa-1,6-cyclo-inden-1-ylmethyl ester

: 23180-57-6
paeoniflorin

Conditions

Conditions	Yield
Multi-step reaction with 11 steps 1: KCN, 18-crown-6MeCN / 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 / BF3Et2O / toluene / -78 °C 11: 100 percent / H2 / Pd(OH)2 / methanol; ethyl acetate; H2O View Scheme

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

: 154854-76-9
C20H22O5

: 23180-57-6
paeoniflorin

Conditions

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

: 154854-72-5
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

: 23180-57-6
paeoniflorin

Conditions

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

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

: 154854-73-6
C21H21NO4

: 23180-57-6
paeoniflorin

Conditions

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

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

Paeoniflorin Chemical Properties

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

Paeoniflorin Toxicity Data With Reference

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.

Paeoniflorin Safety Profile

Moderately toxic by intravenous route. Mildly toxic by intraperitoneal route. When heated to decomposition it emits acrid smoke and irritating fumes.

Paeoniflorin Specification

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 .

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