23180-57-6

Basic information

• Product Name: Paeoniflorin
• Synonyms: 5beta-[(benzoyloxy)methyl]tetrahydro-5-hydroxy-2-methyl-2,5-methano-1h-3,4-dioxacyclobuta[cd]pentalen-1alpha(2h)-yl-beta-d-glucopyranoside;PAEONIFLORIN;5-alpha,5a-alpha,5b-alpha))-a-alph;5-methano-1h-3,4-dioxacyclobuta(cd)pentalen-1a(2h)-yl,(1ar-(1a-alpha,2-beta,3;beta-d-glucopyranoside,5b-((benzoyloxy)methyl)tetrahydro-5-hydroxy-2-methyl-2,;peoniflorin;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)]-;PAEONIFLORIN 98+% BY HPLC
• CAS NO: 23180-57-6
• Molecular Formula: C₂₃H₂₈O₁₁
• Molecular Weight: 480.46
• EINECS: 245-476-2
• Product Categories: Heterocycles;Natural Plant Extract;The group of Paeoniflorin;Veterinaries;Steroids;API's;reference substance;Plant extract;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Inhibitors
• Mol File: 23180-57-6.mol
• Article Data: 2

Chemical Properties

• Melting Point: approximate 124℃ (dec.)
• Boiling Point: 498.51°C (rough estimate)
• Flash Point: 235.9 °C
• Appearance: white/
• Density: 1.3044 (rough estimate)
• Vapor Pressure: 1.07E-19mmHg at 25°C
• Refractive Index: 1.5376 (estimate)
• Storage Temp.: room temp
• Solubility: Methanol (Slightly, Sonicated), Pyridine (Slightly)
• PKA: 11.52±0.70(Predicted)
• CAS DataBase Reference: Paeoniflorin(CAS DataBase Reference)
• NIST Chemistry Reference: Paeoniflorin(23180-57-6)
• EPA Substance Registry System: Paeoniflorin(23180-57-6)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• RTECS: RT1200000
• Hazardous Substances Data: 23180-57-6(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Uses

Different sources of media describe the Uses of 23180-57-6 differently. You can refer to the following data:
1. antiinflammatory, antispasmodic, antihypertensive, antidiuretic
2. Paeoniflorin is a herbal constituent extracted from the root of Paeonia albiflora Pall. Paeoniflorin has broad pharmacological effects, such as analgesic, anti-diuretic，anti-inflammatory，anti-convulsant, vasodilatic, and etc. In a study, paeoniflorin effe
3. Paeoniflorin is an active compound of the Paeonia root. Paeoniflorin inhibits Aβ25-35-induced mitochondrial dysfunction, which includes decreased mitochondrial membrane potential, increased Bax/Bcl-2 ratio, cytochrome c release and activity of caspase-3 and caspase-9. Paeoniflorin could attenuate or restore the viability loss, apoptotic increase, and ROS production induced by Aβ25-35 in SH-SY5Y cells.

General Description

Paeoniflorin has been demonstrated to exert anti-inflammatory and immunomodulatory effects.

Biochem/physiol Actions

Herbal constituent of peony root. It is used in Chinese traditional medicine for its spasmolytic and pain-relieving properties. Exhibits anticoagulant, neuromuscular blocking, cognition-enhancing, immunoregulating, and antihyperglycemic effects.

Safety Profile

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

InChI:InChI=1/C23H30O11/c1-21-8-7-14-22(20(33-21)34-23(14,29)10-21,11-30-18(28)12-5-3-2-4-6-12)32-19-17(27)16(26)15(25)13(9-24)31-19/h2-6,13-17,19-20,24-27,29H,7-11H2,1H3/t13-,14-,15-,16+,17-,19+,20?,21+,22-,23-/m1/s1

Synthetic route

C59H58O13 → paeoniflorin (23180-57-6)

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

2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl trichloroacetimidate (74808-09-6) → paeoniflorin (23180-57-6)

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 → paeoniflorin (23180-57-6)

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

(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)

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

(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)

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

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)

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

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)

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 (154854-76-9) → paeoniflorin (23180-57-6)

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 (154854-72-5) → paeoniflorin (23180-57-6)

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 (154854-73-6) → paeoniflorin (23180-57-6)

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

C21H22O6 (154854-74-7) → paeoniflorin (23180-57-6)

Conditions	Yield
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 → paeoniflorin (23180-57-6)

Conditions	Yield
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 → paeoniflorin (23180-57-6)

Conditions

Yield

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) → paeoniflorin (23180-57-6)

Conditions

Yield

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 → paeoniflorin (23180-57-6)

Conditions	Yield
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) → paeoniflorin (23180-57-6)

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

C28H28O7 (154854-77-0) → paeoniflorin (23180-57-6)

Conditions	Yield
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) + paeoniflorin (23180-57-6) → paeoniflorin tetra-O-acetate

Conditions	Yield
With pyridine at 20 - 22℃;	83%

3,4,6-tri-O-benzyl-D-glucal epoxide (74372-90-0) + paeoniflorin (23180-57-6) → C50H56O16 + C50H56O16

Conditions	Yield
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 (861695-58-1) + paeoniflorin (23180-57-6) → C49H71NO31 (1093135-93-3)

Conditions	Yield
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) + paeoniflorin (23180-57-6) → paeoniflorin tetra-O-benzoate

Conditions	Yield
With pyridine at 20 - 22℃; for 48h;	58%

benzoyl chloride (98-88-4) + paeoniflorin (23180-57-6) → C58H48O16 + C58H48O16

Conditions	Yield
With pyridine at 0 - 22℃;	A 49% B 36%

methanol (67-56-1) + paeoniflorin (23180-57-6) → 3-O-methylpaeoniflorin + 4-oxo-9-O-methylpaeoniflorin (209969-75-5)

Conditions	Yield
With cation exchanger KU-2-8 (H+) for 2h; Reflux; Overall yield = 90 %; Overall yield = 296 mg;	A 40% B 42%

paeoniflorin (23180-57-6) → 7S-paeonimetaboline I (99624-67-6) + 7R-paeonimetaboline I (112018-99-2) + paeonimetaboline II (111950-55-1)

Conditions	Yield
With Bacteroides fragilis ss. thetaotus In water at 37℃; for 12h; Product distribution;	A 12.6% B 6.2% C 0.9%

paeoniflorin (23180-57-6) → 7S-paeonimetaboline I (99624-67-6) + 7R-paeonimetaboline I (112018-99-2)

Conditions	Yield
With GAM broth; Lactobacillus brevis In water at 37℃; for 12h; Product distribution;	A 11% B 9.6%

paeoniflorin (23180-57-6) → 8-O-debenzoylpaeoniflorin

Conditions	Yield
With sodium hydroxide In methanol for 0.166667h; Ambient temperature;	124.4 mg

thiobenzoic acid (98-91-9) + paeoniflorin (23180-57-6) → (7S)-8-benzoylthiopaeonimetabolin I (118045-44-6) + (7R)-8-benzoylthiopaeonimetabolin I (118138-70-8)

Conditions	Yield
With Lactobacillus brevis In phosphate buffer at 37℃; for 6h; pH=7.3;	A 20 mg B 10 mg

Cyclohexanethiol (1569-69-3) + paeoniflorin (23180-57-6) → (7R)-8-cyclohexylthiopaeonimetabolin I + (7S)-8-cyclohexylthiopaeonimetabolin I

Conditions	Yield
With Lactobacillus brevis In phosphate buffer at 37℃; for 6h; pH=7.3; Title compound not separated from byproducts;

1-thiopropane (107-03-9) + paeoniflorin (23180-57-6) → (7S)-8-(n-propylthio)paeonimetabolin I + (7R)-8-(n-propylthio)paeonimetabolin I

Conditions	Yield
With Lactobacillus brevis In phosphate buffer at 37℃; for 6h; pH=7.3; Title compound not separated from byproducts;

prop-2-ene-1-thiol (870-23-5) + paeoniflorin (23180-57-6) → (7S)-8-allylthiopaeonimetabolin I + (7R)-8-allylthiopaeonimetabolin I

Conditions	Yield
With Lactobacillus brevis In phosphate buffer at 37℃; for 6h; pH=7.3; Title compound not separated from byproducts;

1-methyl-1-propanethiol (513-53-1) + paeoniflorin (23180-57-6) → (7S)-8-(sec-butylthio)paeonimetabolin I + (7R)-8-(sec-butylthio)paeonimetabolin I

Conditions	Yield
With Lactobacillus brevis In phosphate buffer at 37℃; for 6h; pH=7.3; Title compound not separated from byproducts;

2-methylpropanethiol-1 (513-44-0) + paeoniflorin (23180-57-6) → (7R)-8-(iso-butylthio)paeonimetabolin I + (7S)-8-(iso-butylthio)paeonimetabolin I

Conditions	Yield
With Lactobacillus brevis In phosphate buffer at 37℃; for 6h; pH=7.3; Title compound not separated from byproducts;

1-butanethiol (109-79-5) + paeoniflorin (23180-57-6) → (7S)-8-(n-butylthio)paeonimetabolin I + (7R)-8-(n-butylthio)paeonimetabolin I

Conditions	Yield
With Lactobacillus brevis In phosphate buffer at 37℃; for 6h; pH=7.3; Title compound not separated from byproducts;

Hexanethiol (111-31-9) + paeoniflorin (23180-57-6) → (7S)-8-(n-hexylthio)paeonimetabolin I + (7R)-8-(n-hexylthio)paeonimetabolin I

Conditions	Yield
With Lactobacillus brevis In phosphate buffer at 37℃; for 6h; pH=7.3;	A 19 mg B 10 mg

toluene-3-thiol (108-40-7) + paeoniflorin (23180-57-6) → (7S)-8-(m-tolylthio)paeonimetabolin I + (7R)-8-(m-tolylthio)paeonimetabolin I

Conditions	Yield
With Lactobacillus brevis In phosphate buffer at 37℃; for 6h; pH=7.3; Title compound not separated from byproducts;

cyclopentylthiol (1679-07-8) + paeoniflorin (23180-57-6) → (7S)-8-cyclopentylthiopaeonimetabolin I + (7R)-8-cyclopentylthiopaeonimetabolin I

Conditions	Yield
With Lactobacillus brevis In phosphate buffer at 37℃; for 6h; pH=7.3; Title compound not separated from byproducts;

thiophenol (108-98-5) + paeoniflorin (23180-57-6) → (7R)-8-phenylthio-paeonimetabolin I + (7S)-8-phenylthio-paeonimetabolin I

Conditions	Yield
With Lactobacillus brevis In phosphate buffer at 37℃; for 6h; pH=7.3; Title compound not separated from byproducts;

2-propanethiol (75-33-2) + paeoniflorin (23180-57-6) → (7R)-8-(iso-propylthio)paeonimetabolin I + (7S)-8-(iso-propylthio)paeonimetabolin I

Conditions	Yield
With Lactobacillus brevis In phosphate buffer at 37℃; for 6h; pH=7.3; Title compound not separated from byproducts;

para-thiocresol (106-45-6) + paeoniflorin (23180-57-6) → (7S)-8-(p-tolylthio)paeonimetabolin I + (7R)-8-(p-tolylthio)paeonimetabolin I

Conditions	Yield
With Lactobacillus brevis In phosphate buffer at 37℃; for 6h; pH=7.3; Title compound not separated from byproducts;

phenylmethanethiol (100-53-8) + paeoniflorin (23180-57-6) → (7S)-8-benzylthiopaeonimetabolin I + (7R)-8-benzylthiopaeonimetabolin I

Conditions	Yield
With Lactobacillus brevis In phosphate buffer at 37℃; for 6h; pH=7.3; Title compound not separated from byproducts;

paeoniflorin (23180-57-6) + 2-Naphthalenethiol (91-60-1) → (7S)-8-(2-naphthylthio)paeonimetabolin I + (7R)-8-(2-naphthylthio)paeonimetabolin I

Conditions	Yield
With Lactobacillus brevis In phosphate buffer at 37℃; for 6h; pH=7.3; Title compound not separated from byproducts;

paeoniflorin (23180-57-6) + thioacetic acid (507-09-5) → (7R)-8-acetylthiopaeonimetabolin I + (7S)-8-acetylthiopaeonimetabolin I

Conditions	Yield
With Lactobacillus brevis In phosphate buffer at 37℃; for 6h; pH=7.3; Title compound not separated from byproducts;

paeoniflorin (23180-57-6) + 2-thiocresol (137-06-4) → (7R)-8-(o-tolylthio)paeonimetabolin I + (7S)-8-(o-tolylthio)paeonimetabolin I

Conditions	Yield
With Lactobacillus brevis In phosphate buffer at 37℃; for 6h; pH=7.3; Title compound not separated from byproducts;

paeoniflorin (23180-57-6) → C23H26O11

Conditions	Yield
With sodium periodate In methanol; water at 20℃; for 1h;

paeoniflorin (23180-57-6) → paeoniflorigenin

Conditions	Yield
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 + paeoniflorin (23180-57-6) → C41H54F3N5O16S

Conditions	Yield
Multistep reaction;

Upstream product

• 154854-77-0 C₂₈H₂₈O₇ 
• 154854-78-1 C₂₅H₂₄O₈ 
• 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 
• 154854-74-7 C₂₁H₂₂O₆ 
• 154854-73-6 C₂₁H₂₁NO₄ 
• 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 
• 154854-76-9 C₂₀H₂₂O₅ 
• 74808-09-6 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl trichloroacetimidate 

Downstream Products

• 91402-45-8 6'-hemiglutaryl paeoniflorin 
• 209969-75-5 4-oxo-9-O-methylpaeoniflorin 
• 1093135-93-3 C₄₉H₇₁NO₃₁ 
• 91402-40-3 6'-hemiglutaryl paeoniflorin tetraacetate 
• 91402-39-0 6'-hemisuccinyl paeoniflorin tetraacetate 
• 697300-41-7 paeoniflorigenin 

Relevant articles and documents

The structure of lactiflorin, an artefact during isolation?

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