Paeoniflorin

Base Information

• Chemical Name: Paeoniflorin
• CAS No.: 23180-57-6
• Molecular Formula: C23H28O11
• Molecular Weight: 480.469
• Hs Code.: 29389090
• European Community (EC) Number: 245-476-2
• UNII: 21AIQ4EV64
• DSSTox Substance ID: DTXSID2042648
• Nikkaji Number: J39.219G
• Wikipedia: Paeoniflorin
• Wikidata: Q7124104
• ChEMBL ID: CHEMBL4303209
• Mol file: 23180-57-6.mol

Synonyms:paeoniflorin;peoniflorin;peoniflorin sulfonate

Chemical Property of Paeoniflorin

Chemical Property:

• Appearance/Colour: White fine powder
• Vapor Pressure: 1.07E-19mmHg at 25°C
• Melting Point: approximate 124℃ (dec.)
• Refractive Index: 1.649
• Boiling Point: 683.3 °C at 760 mmHg
• PKA: 11.52±0.70(Predicted)
• Flash Point: 235.9 °C
• PSA: 164.37000
• Density: 1.63 g/cm³
• LogP: -1.35750
• Storage Temp.: room temp
• Solubility.: Methanol (Slightly, Sonicated), Pyridine (Slightly)
• XLogP3: -1
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 7
• Exact Mass: 480.16316171
• Heavy Atom Count: 34
• Complexity: 849

Purity/Quality:

99% ^*data from raw suppliers

Paeoniflorin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,N,T,F
• Hazard Codes: Xn,N,T,F
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC12CC3(C4CC1(C4(C(O2)O3)COC(=O)C5=CC=CC=C5)OC6C(C(C(C(O6)CO)O)O)O)O
• Isomeric SMILES: C[C@]12C[C@@]3([C@@H]4C[C@]1([C@@]4([C@H](O2)O3)COC(=O)C5=CC=CC=C5)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)O
• Recent ClinicalTrials: Paeoniflorin Combination of Hepatoprotective Drugs Versus Hepatoprotective Drugs Only for Auto-immune Hepatitis
• Uses: antiinflammatory, antispasmodic, antihypertensive, antidiuretic 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 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.

Technology Process of Paeoniflorin

There total 18 articles about Paeoniflorin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

C59H58O13 → paeoniflorin (23180-57-6)

Guidance literature:

With hydrogen; palladium dihydroxide; In methanol; water; ethyl acetate;

DOI:10.1021/ja00088a055

Reference yield:

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

Guidance literature:

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

With boron trifluoride diethyl etherate; hydrogen; palladium dihydroxide; In methanol; water; ethyl acetate; toluene;

DOI:10.1021/ja00088a055

Reference yield:

(1R,3aS,5R,6R,7aR)-1-Hydroxymethyl-7a-isopropenyl-3a-methyl-octahydro-3-oxa-1,6-cyclo-inden-5-ol → paeoniflorin (23180-57-6)

Guidance literature:

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

With pyridine; hydrogenchloride; methanol; dmap; potassium cyanide; oxalyl dichloride; [bis(acetoxy)iodo]benzene; boron trifluoride diethyl etherate; hydrogen; iodine; oxygen; 4-nitro-benzoyl chloride; ozone; dimethyl sulfoxide; 18-crown-6 complexed with acetonitrile; triethylamine; N,N-dimethyl-formamide; phosphorous acid trimethyl ester; palladium dihydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; ethyl acetate; toluene; acetonitrile; benzene;

DOI:10.1021/ja00088a055

upstream raw materials:

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

C₂₀H₂₂O₅

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

C₂₁H₂₁NO₄

Downstream raw materials:

6'-hemisuccinyl paeoniflorin

6'-hemiglutaryl paeoniflorin

paeoniflorin pentaacetate

7S-Paeonimetabolin-I

Refernces

• 1、 Hatakeyama,Kawamura,Takano. "Total synthesis of (-)-paeoniflorin". . p. 4081 - 4082. Retrieved 2007/10/02.