Product Name

  • Name

    Paeoniflorin

  • EINECS 245-476-2
  • CAS No. 23180-57-6
  • Article Data2
  • CAS DataBase
  • Density 1.63 g/cm3
  • Solubility
  • 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
  • Appearance White fine powder
  • Safety 24/25
  • Risk Codes R22; R50; R39/23/24/25; R23/24/25
  • Molecular Structure Molecular Structure of 23180-57-6 (Paeoniflorin)
  • 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;
  • PSA 164.37000
  • LogP -1.35750

Synthetic route

C59H58O13

C59H58O13

paeoniflorin
23180-57-6

paeoniflorin

Conditions
ConditionsYield
With hydrogen; palladium dihydroxide In methanol; water; ethyl acetate100%
2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl trichloroacetimidate
74808-09-6

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

paeoniflorin
23180-57-6

paeoniflorin

Conditions
ConditionsYield
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

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

paeoniflorin
23180-57-6

paeoniflorin

Conditions
ConditionsYield
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

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

paeoniflorin
23180-57-6

paeoniflorin

Conditions
ConditionsYield
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

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

paeoniflorin
23180-57-6

paeoniflorin

Conditions
ConditionsYield
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

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

paeoniflorin
23180-57-6

paeoniflorin

Conditions
ConditionsYield
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

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

paeoniflorin
23180-57-6

paeoniflorin

Conditions
ConditionsYield
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
154854-76-9

C20H22O5

paeoniflorin
23180-57-6

paeoniflorin

Conditions
ConditionsYield
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
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

paeoniflorin
23180-57-6

paeoniflorin

Conditions
ConditionsYield
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
154854-73-6

C21H21NO4

paeoniflorin
23180-57-6

paeoniflorin

Conditions
ConditionsYield
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
154854-74-7

C21H22O6

paeoniflorin
23180-57-6

paeoniflorin

Conditions
ConditionsYield
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
C21H21ClO5

C21H21ClO5

paeoniflorin
23180-57-6

paeoniflorin

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

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

paeoniflorin
23180-57-6

paeoniflorin

Conditions
ConditionsYield
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
154854-70-3

(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
23180-57-6

paeoniflorin

Conditions
ConditionsYield
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
C26H25NO5S

C26H25NO5S

paeoniflorin
23180-57-6

paeoniflorin

Conditions
ConditionsYield
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
154854-78-1

C25H24O8

paeoniflorin
23180-57-6

paeoniflorin

Conditions
ConditionsYield
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
154854-77-0

C28H28O7

paeoniflorin
23180-57-6

paeoniflorin

Conditions
ConditionsYield
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
acetic anhydride
108-24-7

acetic anhydride

paeoniflorin
23180-57-6

paeoniflorin

paeoniflorin tetra-O-acetate

paeoniflorin tetra-O-acetate

Conditions
ConditionsYield
With pyridine at 20 - 22℃;83%
3,4,6-tri-O-benzyl-D-glucal epoxide
74372-90-0

3,4,6-tri-O-benzyl-D-glucal epoxide

paeoniflorin
23180-57-6

paeoniflorin

A

C50H56O16

C50H56O16

B

C50H56O16

C50H56O16

Conditions
ConditionsYield
With 4-nitrophenylboronic acid; water In acetonitrile at -10℃; for 6h; Inert atmosphere; regioselective reaction;A 73%
B 7%
...Expand
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
861695-58-1

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
23180-57-6

paeoniflorin

C49H71NO31
1093135-93-3

C49H71NO31

Conditions
ConditionsYield
With endo-β-N-acetylglucosaminidase from Arthrobactor protophormiae In dimethyl sulfoxide at 23℃; for 2h; pH=7.0; aq. phosphate buffer; Enzymatic reaction;60%
benzoyl chloride
98-88-4

benzoyl chloride

paeoniflorin
23180-57-6

paeoniflorin

paeoniflorin tetra-O-benzoate

paeoniflorin tetra-O-benzoate

Conditions
ConditionsYield
With pyridine at 20 - 22℃; for 48h;58%
benzoyl chloride
98-88-4

benzoyl chloride

paeoniflorin
23180-57-6

paeoniflorin

A

C58H48O16

C58H48O16

B

C58H48O16

C58H48O16

Conditions
ConditionsYield
With pyridine at 0 - 22℃;A 49%
B 36%
...Expand
methanol
67-56-1

methanol

paeoniflorin
23180-57-6

paeoniflorin

A

3-O-methylpaeoniflorin

3-O-methylpaeoniflorin

B

4-oxo-9-O-methylpaeoniflorin
209969-75-5

4-oxo-9-O-methylpaeoniflorin

Conditions
ConditionsYield
With cation exchanger KU-2-8 (H+) for 2h; Reflux; Overall yield = 90 %; Overall yield = 296 mg;A 40%
B 42%
...Expand
paeoniflorin
23180-57-6

paeoniflorin

A

7S-paeonimetaboline I
99624-67-6

7S-paeonimetaboline I

B

7R-paeonimetaboline I
112018-99-2

7R-paeonimetaboline I

C

paeonimetaboline II
111950-55-1

paeonimetaboline II

Conditions
ConditionsYield
With Bacteroides fragilis ss. thetaotus In water at 37℃; for 12h; Product distribution;A 12.6%
B 6.2%
C 0.9%
...Expand
paeoniflorin
23180-57-6

paeoniflorin

A

7S-paeonimetaboline I
99624-67-6

7S-paeonimetaboline I

B

7R-paeonimetaboline I
112018-99-2

7R-paeonimetaboline I

Conditions
ConditionsYield
With GAM broth; Lactobacillus brevis In water at 37℃; for 12h; Product distribution;A 11%
B 9.6%
paeoniflorin
23180-57-6

paeoniflorin

8-O-debenzoylpaeoniflorin

8-O-debenzoylpaeoniflorin

Conditions
ConditionsYield
With sodium hydroxide In methanol for 0.166667h; Ambient temperature;124.4 mg
thiobenzoic acid
98-91-9

thiobenzoic acid

paeoniflorin
23180-57-6

paeoniflorin

A

(7S)-8-benzoylthiopaeonimetabolin I
118045-44-6

(7S)-8-benzoylthiopaeonimetabolin I

B

(7R)-8-benzoylthiopaeonimetabolin I
118138-70-8

(7R)-8-benzoylthiopaeonimetabolin I

Conditions
ConditionsYield
With Lactobacillus brevis In phosphate buffer at 37℃; for 6h; pH=7.3;A 20 mg
B 10 mg
...Expand
Cyclohexanethiol
1569-69-3

Cyclohexanethiol

paeoniflorin
23180-57-6

paeoniflorin

A

(7R)-8-cyclohexylthiopaeonimetabolin I

(7R)-8-cyclohexylthiopaeonimetabolin I

B

(7S)-8-cyclohexylthiopaeonimetabolin I

(7S)-8-cyclohexylthiopaeonimetabolin I

Conditions
ConditionsYield
With Lactobacillus brevis In phosphate buffer at 37℃; for 6h; pH=7.3; Title compound not separated from byproducts;
...Expand
1-thiopropane
107-03-9

1-thiopropane

paeoniflorin
23180-57-6

paeoniflorin

A

(7S)-8-(n-propylthio)paeonimetabolin I

(7S)-8-(n-propylthio)paeonimetabolin I

B

(7R)-8-(n-propylthio)paeonimetabolin I

(7R)-8-(n-propylthio)paeonimetabolin I

Conditions
ConditionsYield
With Lactobacillus brevis In phosphate buffer at 37℃; for 6h; pH=7.3; Title compound not separated from byproducts;
...Expand
prop-2-ene-1-thiol
870-23-5

prop-2-ene-1-thiol

paeoniflorin
23180-57-6

paeoniflorin

A

(7S)-8-allylthiopaeonimetabolin I

(7S)-8-allylthiopaeonimetabolin I

B

(7R)-8-allylthiopaeonimetabolin I

(7R)-8-allylthiopaeonimetabolin I

Conditions
ConditionsYield
With Lactobacillus brevis In phosphate buffer at 37℃; for 6h; pH=7.3; Title compound not separated from byproducts;
...Expand
1-methyl-1-propanethiol
513-53-1

1-methyl-1-propanethiol

paeoniflorin
23180-57-6

paeoniflorin

A

(7S)-8-(sec-butylthio)paeonimetabolin I

(7S)-8-(sec-butylthio)paeonimetabolin I

B

(7R)-8-(sec-butylthio)paeonimetabolin I

(7R)-8-(sec-butylthio)paeonimetabolin I

Conditions
ConditionsYield
With Lactobacillus brevis In phosphate buffer at 37℃; for 6h; pH=7.3; Title compound not separated from byproducts;
...Expand
2-methylpropanethiol-1
513-44-0

2-methylpropanethiol-1

paeoniflorin
23180-57-6

paeoniflorin

A

(7R)-8-(iso-butylthio)paeonimetabolin I

(7R)-8-(iso-butylthio)paeonimetabolin I

B

(7S)-8-(iso-butylthio)paeonimetabolin I

(7S)-8-(iso-butylthio)paeonimetabolin I

Conditions
ConditionsYield
With Lactobacillus brevis In phosphate buffer at 37℃; for 6h; pH=7.3; Title compound not separated from byproducts;
...Expand
1-butanethiol
109-79-5

1-butanethiol

paeoniflorin
23180-57-6

paeoniflorin

A

(7S)-8-(n-butylthio)paeonimetabolin I

(7S)-8-(n-butylthio)paeonimetabolin I

B

(7R)-8-(n-butylthio)paeonimetabolin I

(7R)-8-(n-butylthio)paeonimetabolin I

Conditions
ConditionsYield
With Lactobacillus brevis In phosphate buffer at 37℃; for 6h; pH=7.3; Title compound not separated from byproducts;
...Expand
Hexanethiol
111-31-9

Hexanethiol

paeoniflorin
23180-57-6

paeoniflorin

A

(7S)-8-(n-hexylthio)paeonimetabolin I

(7S)-8-(n-hexylthio)paeonimetabolin I

B

(7R)-8-(n-hexylthio)paeonimetabolin I

(7R)-8-(n-hexylthio)paeonimetabolin I

Conditions
ConditionsYield
With Lactobacillus brevis In phosphate buffer at 37℃; for 6h; pH=7.3;A 19 mg
B 10 mg
...Expand
toluene-3-thiol
108-40-7

toluene-3-thiol

paeoniflorin
23180-57-6

paeoniflorin

A

(7S)-8-(m-tolylthio)paeonimetabolin I

(7S)-8-(m-tolylthio)paeonimetabolin I

B

(7R)-8-(m-tolylthio)paeonimetabolin I

(7R)-8-(m-tolylthio)paeonimetabolin I

Conditions
ConditionsYield
With Lactobacillus brevis In phosphate buffer at 37℃; for 6h; pH=7.3; Title compound not separated from byproducts;
...Expand
cyclopentylthiol
1679-07-8

cyclopentylthiol

paeoniflorin
23180-57-6

paeoniflorin

A

(7S)-8-cyclopentylthiopaeonimetabolin I

(7S)-8-cyclopentylthiopaeonimetabolin I

B

(7R)-8-cyclopentylthiopaeonimetabolin I

(7R)-8-cyclopentylthiopaeonimetabolin I

Conditions
ConditionsYield
With Lactobacillus brevis In phosphate buffer at 37℃; for 6h; pH=7.3; Title compound not separated from byproducts;
...Expand
thiophenol
108-98-5

thiophenol

paeoniflorin
23180-57-6

paeoniflorin

A

(7R)-8-phenylthio-paeonimetabolin I

(7R)-8-phenylthio-paeonimetabolin I

B

(7S)-8-phenylthio-paeonimetabolin I

(7S)-8-phenylthio-paeonimetabolin I

Conditions
ConditionsYield
With Lactobacillus brevis In phosphate buffer at 37℃; for 6h; pH=7.3; Title compound not separated from byproducts;
...Expand
2-propanethiol
75-33-2

2-propanethiol

paeoniflorin
23180-57-6

paeoniflorin

A

(7R)-8-(iso-propylthio)paeonimetabolin I

(7R)-8-(iso-propylthio)paeonimetabolin I

B

(7S)-8-(iso-propylthio)paeonimetabolin I

(7S)-8-(iso-propylthio)paeonimetabolin I

Conditions
ConditionsYield
With Lactobacillus brevis In phosphate buffer at 37℃; for 6h; pH=7.3; Title compound not separated from byproducts;
...Expand
para-thiocresol
106-45-6

para-thiocresol

paeoniflorin
23180-57-6

paeoniflorin

A

(7S)-8-(p-tolylthio)paeonimetabolin I

(7S)-8-(p-tolylthio)paeonimetabolin I

B

(7R)-8-(p-tolylthio)paeonimetabolin I

(7R)-8-(p-tolylthio)paeonimetabolin I

Conditions
ConditionsYield
With Lactobacillus brevis In phosphate buffer at 37℃; for 6h; pH=7.3; Title compound not separated from byproducts;
...Expand
phenylmethanethiol
100-53-8

phenylmethanethiol

paeoniflorin
23180-57-6

paeoniflorin

A

(7S)-8-benzylthiopaeonimetabolin I

(7S)-8-benzylthiopaeonimetabolin I

B

(7R)-8-benzylthiopaeonimetabolin I

(7R)-8-benzylthiopaeonimetabolin I

Conditions
ConditionsYield
With Lactobacillus brevis In phosphate buffer at 37℃; for 6h; pH=7.3; Title compound not separated from byproducts;
...Expand
paeoniflorin
23180-57-6

paeoniflorin

2-Naphthalenethiol
91-60-1

2-Naphthalenethiol

A

(7S)-8-(2-naphthylthio)paeonimetabolin I

(7S)-8-(2-naphthylthio)paeonimetabolin I

B

(7R)-8-(2-naphthylthio)paeonimetabolin I

(7R)-8-(2-naphthylthio)paeonimetabolin I

Conditions
ConditionsYield
With Lactobacillus brevis In phosphate buffer at 37℃; for 6h; pH=7.3; Title compound not separated from byproducts;
...Expand
paeoniflorin
23180-57-6

paeoniflorin

thioacetic acid
507-09-5

thioacetic acid

A

(7R)-8-acetylthiopaeonimetabolin I

(7R)-8-acetylthiopaeonimetabolin I

B

(7S)-8-acetylthiopaeonimetabolin I

(7S)-8-acetylthiopaeonimetabolin I

Conditions
ConditionsYield
With Lactobacillus brevis In phosphate buffer at 37℃; for 6h; pH=7.3; Title compound not separated from byproducts;
...Expand
paeoniflorin
23180-57-6

paeoniflorin

2-thiocresol
137-06-4

2-thiocresol

A

(7R)-8-(o-tolylthio)paeonimetabolin I

(7R)-8-(o-tolylthio)paeonimetabolin I

B

(7S)-8-(o-tolylthio)paeonimetabolin I

(7S)-8-(o-tolylthio)paeonimetabolin I

Conditions
ConditionsYield
With Lactobacillus brevis In phosphate buffer at 37℃; for 6h; pH=7.3; Title compound not separated from byproducts;
...Expand
paeoniflorin
23180-57-6

paeoniflorin

C23H26O11

C23H26O11

Conditions
ConditionsYield
With sodium periodate In methanol; water at 20℃; for 1h;
paeoniflorin
23180-57-6

paeoniflorin

paeoniflorigenin

paeoniflorigenin

Conditions
ConditionsYield
With β-glucosidase In dimethyl sulfoxide at 37℃; for 5h;
2-[2-(2-{2-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-ethoxy}-ethoxy)-ethoxy]-4-(3-trifluoromethyl-3H-diazirin-3-yl)-benzoic acid

2-[2-(2-{2-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-ethoxy}-ethoxy)-ethoxy]-4-(3-trifluoromethyl-3H-diazirin-3-yl)-benzoic acid

paeoniflorin
23180-57-6

paeoniflorin

C41H54F3N5O16S

C41H54F3N5O16S

Conditions
ConditionsYield
Multistep reaction;

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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