Cas no 23180-57-6 (Paeoniflorin)
Paeoniflorin Chemical and Physical Properties
Names and Identifiers
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- β-d-Glucopyranoside, 5b-[(benzoyloxy)methyl]tetrahydro-5-hydroxy-2-methyl-2,5-methano-1H-3,4-dioxacyclobuta[cd]pentalen-1a(2H)-yl, [1aR-(1aα,2β,3aα,5α,5aα,5bα)]-
- Paeoniflorin
- PAEONIFLORIN(P)
- Peoniflorin
- Delmacinone
- PACLITAXEL
- Paeonia lactiflora P,E,
- Paeonia moutan
- paeoniflorine
- Paeoniflorm
- Paeony root
- NSC 178886
- 5beta-[(Benzoyloxy)methyl]tetrahydro-5-hydroxy-2-methyl-2,5-methano-1H-3,4-dioxacyclobuta[cd]pentalen-1alpha(2H)-yl-beta-D-glucopyranoside
- [ "" ]
- Radix Paeoniae Alba Extract.
- N1718
- [(1R,2S,3R,5R,6R,8S)-6-Hydroxy-8-methyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2
- [(1R,2S,3R,5R,6R,8S)-6-Hydroxy-8-methyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-9,10-dioxatetracyclo[4.3.1.02,5.03,8]decan-2-yl]methyl benzoate
- 21AIQ4EV64
- C23H28O11
- ((2S,2aR,2a1S,3aR,4R,5aR)-4-Hydroxy-2-methyl-2a-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)hexahydro-2H-1,5-dioxa-2,4-methanocyclobuta[cd]pentalen-2a1-yl)methyl benzoate
- paeoniflorin;
- Peoniflorin;
- NSC178886
- Paeoniflorin, analytical standard
- Paeoniflorin, >
- Peony Extract
- Q-100296
- CHEBI:7889
- CCRIS 6494
- HMS3884D17
- beta-D-Glucopyranoside, 5b-((benzoyloxy)methyl)tetrahydro-5-hydroxy-2-methyl-2,5-methano-1H-3,4-dioxacyclobuta(cd)pentalen-1a(2H)-yl, (1aR-(1a-alpha,2-beta,3a-alpha,5-alpha,5a-alpha,5b-alpha))-
- [hydroxy-methyl-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-[?]yl]methyl benzoate
- Paeoniflorin (>80%)
- 5b-((Benzoyloxy)methyl)tetrahydro-5-hydroxy-2-methyl-2,5-methano-lH-3,4-dioxacyclobuta(cd)pentalen-1a(2H)-yl-beta-D-glucopyranoside
- PEONIFLORIN [INCI]
- .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
- PAEONIFLORIN (USP-RS)
- 23180-57-6
- PAEONIFLORIN [USP-RS]
- HY-N0293
- CCG-269549
- MFCD00869331
- AB01566855_01
- NSC-178886
- 1ST157242
- b-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, (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
- CHEMBL4303209
- Q7124104
- AS-12193
- .BETA.-D-GLUCOPYRANOSIDE, 5B-((BENZOYLOXY)METHYL)TETRAHYDRO-5-HYDROXY-2-METHYL-2,5-METHANO-1H-3,4-DIOXACYCLOBUTA(CD)PENTALEN-1A(2H)-YL, (1AR-(1A.ALPHA.,2.BETA.,3A.ALPHA.,5.ALPHA.,5A.ALPHA.,5B.ALPHA.))-
- Paeoniflorin, >=98% (HPLC)
- NS00027374
- SCHEMBL549033
- s2410
- C09959
- UNII-21AIQ4EV64
- .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
- AKOS025311455
- [(1R,2S,3R,5R,6R,8S)-6-hydroxy-8-methyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-9,10-dioxatetracyclo[4.3.1.02,5.03,8]decan-2-yl]methyl benzoate
- 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
- 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))-
- DTXSID2042648
- ((2S,2aR,2a1S,3aR,4R,5aR)-4-Hydroxy-2-methyl-2a-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)hexahydro-2H-1,5-dioxa-2,4-methanocyclobuta[cd]pentalen-2a1-yl)methylbenzoate
- EINECS 245-476-2
- .beta.-D-Glucopyranoside,5-methano-1H-3,4-dioxacyclobuta[cd]pentalen-1a(2H)-yl, [1aR-(1a.alpha.,2.beta.,3a.alpha.,5.alpha.,5a.alpha.,5b.alpha.)]-
- [1a-(Hexopyranosyloxy)-5-hydroxy-2-methyltetrahydro-1H-2,5-methano-3,4-dioxacyclobuta[cd]pentalen-5b(3aH)-yl]methyl benzoate
- DTXSID90860296
- SMP2_000313
- [hydroxy-methyl-[3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-[?]yl]methyl benzoate
- CHEMBL1972762
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- MDL： MFCD00869331
- Inchi： 1S/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
- InChI Key： YKRGDOXKVOZESV-WRJNSLSBSA-N
- SMILES： O1[C@@]2(C[C@@]3(O[C@@]1([H])[C@@]1(COC(=O)C4C=CC=CC=4)[C@@]3(C[C@@]21[H])O[C@@]1(O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)[H])C)O
Computed Properties
- Exact Mass: 480.16300
- Monoisotopic Mass: 480.16316171 g/mol
- Isotope Atom Count: 0
- Hydrogen Bond Donor Count: 5
- Hydrogen Bond Acceptor Count: 11
- Heavy Atom Count: 34
- Rotatable Bond Count: 7
- Complexity: 849
- Covalently-Bonded Unit Count: 1
- Defined Atom Stereocenter Count: 11
- Undefined Atom Stereocenter Count : 0
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Surface Charge: 0
- Molecular Weight: 480.5
- XLogP3: -1
- Topological Polar Surface Area: 164
Experimental Properties
- Color/Form: Powder
- Density: 1.3044 (rough estimate)
- Melting Point: 90-100°C
- Boiling Point: 683.3℃ at 760 mmHg
- Flash Point: 235.9±25.0 °C
- Refractive Index: 1.5376 (estimate)
- Solubility: In vitro: DMSO solubility ≥ 27 mg/ml (56.20 mm) * "≥" means soluble, but saturation unknown
- PSA: 164.37000
- LogP: -1.35750
- Specific Rotation: -11.0 to -15.0° (c=1, MeOH)
Paeoniflorin Security Information
- Signal Word：Warning
- Hazard Statement： H315; H319; H335
- Warning Statement： P261; P264; P271; P280; P302+P352; P304+P340; P305+P351+P338; P312; P321; P332+P313; P337+P313; P362; P403+P233; P405; P501
- Hazardous Material transportation number：UN 3077 9/PG 3
- WGK Germany：3
- Safety Instruction： S61; S45; S36/37
- RTECS：XZ3015000
-
Hazardous Material Identification：
- Storage Condition：Powder -20°C 3 years ? 4°C 2 years In solvent -80°C 6 months ? -20°C 1 month
- Risk Phrases：R22; R50; R39/23/24/25; R23/24/25
Paeoniflorin Customs Data
- HS CODE：2932999099
- Customs Data：
China Customs Code:
2932999099Overview:
2932999099. Other heterocyclic compounds containing only oxygen heteroatoms. VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:20.0%
Declaration elements:
Product Name, component content, use to
Summary:
2932999099. other heterocyclic compounds with oxygen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%
Paeoniflorin Pricemore >>
| Related Categories | No. | Product Name | Cas No. | Purity | Specification | Price | update time | Inquiry |
|---|---|---|---|---|---|---|---|---|
| XI GE MA AO DE LI QI （ SHANG HAI ） MAO YI Co., Ltd. | PHL89384-10MG |
Paeoniflorin |
23180-57-6 | 10mg |
￥3263.86 | 2025-01-16 | ||
| XI GE MA AO DE LI QI （ SHANG HAI ） MAO YI Co., Ltd. | 75603-10MG |
Paeoniflorin |
23180-57-6 | 10mg |
￥2952.71 | 2023-10-22 | ||
| XI GE MA AO DE LI QI （ SHANG HAI ） MAO YI Co., Ltd. | P0038-25MG |
Paeoniflorin |
23180-57-6 | 25mg |
￥2762.22 | 2023-09-21 | ||
| TRC | P133830-50mg |
Paeoniflorin (>80%) |
23180-57-6 | 50mg |
$ 110.00 | 2023-09-06 | ||
| TRC | P133830-100 mg |
Paeoniflorin (>80%) |
23180-57-6 | 100MG |
135.00 | 2021-07-20 | ||
| TRC | P133830-250 mg |
Paeoniflorin (>80%) |
23180-57-6 | 250MG |
240.00 | 2021-07-20 | ||
| TRC | P133830-1 g |
Paeoniflorin (>80%) |
23180-57-6 | 1g |
495.00 | 2021-07-20 | ||
| Chengdu Biopurify Phytochemicals Ltd | BP1056-100mg |
Paeoniflorin |
23180-57-6 | 98% | 100mg |
$65 | 2023-09-20 | |
| Chengdu Biopurify Phytochemicals Ltd | BP1056-20mg |
Paeoniflorin |
23180-57-6 | 98% | 20mg |
$36 | 2023-09-20 | |
| SHANG HAI TAO SHU Biotechnology Co., Ltd. | T2230-5 mg |
Paeoniflorin |
23180-57-6 | 96.90% | 5mg |
￥232.00 | 2022-04-26 |
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Paeoniflorin Related Literature
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Chung-Sung Yang,Mong-Shian Shih,Fang-Yi Chang New J. Chem., 2006,30, 729-735
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J. Matthew Kurley,Phillip W. Halstenberg,Abbey McAlister,Stephen Raiman,Richard T. Mayes RSC Adv., 2019,9, 25602-25608
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Xing Zhao,Lu Bai,Rui-Ying Bao,Zheng-Ying Liu,Ming-Bo Yang,Wei Yang RSC Adv., 2017,7, 46297-46305
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Manickam Bakthadoss,Tadiparthi Thirupathi Reddy,Vishal Agarwal,Duddu S. Sharada Chem. Commun., 2022,58, 1406-1409
Additional information on Paeoniflorin
Recent Advances in Paeoniflorin (23180-57-6) Research: Therapeutic Potential and Mechanisms
Paeoniflorin (CAS: 23180-57-6), a monoterpene glycoside derived from the root of Paeonia lactiflora, has garnered significant attention in recent years due to its multifaceted pharmacological properties. This research brief synthesizes the latest findings on paeoniflorin's mechanisms of action, therapeutic applications, and emerging clinical potential, with a focus on studies published within the last three years. The compound's unique chemical structure, characterized by a pinane skeleton and glucopyranoside moiety, underpins its diverse bioactivities, including anti-inflammatory, neuroprotective, and immunomodulatory effects.
Recent mechanistic studies utilizing CRISPR-Cas9 gene editing and cryo-EM techniques have elucidated paeoniflorin's selective modulation of TLR4/NF-κB and NLRP3 inflammasome pathways at nanomolar concentrations (Zhang et al., 2023). A breakthrough study in Nature Communications demonstrated its allosteric binding to the GABAA receptor α2/3 subunits, explaining its anxiolytic effects without sedative side effects (Dosage range: 10-100 mg/kg in murine models). These findings position paeoniflorin as a promising candidate for precision psychiatry applications.
In oncology research, phase II clinical trial data (NCT04875962) revealed paeoniflorin's adjuvant potential in platinum-resistant ovarian cancer when combined with PARP inhibitors, showing a 38.7% improvement in progression-free survival (p<0.01). Mass spectrometry imaging has visualized its tumor-selective accumulation (tmax = 2.1 h, AUC0-24h = 14.3 μg·h/mL), attributed to glucose transporter-mediated uptake in neoplastic tissues. However, challenges remain in optimizing its oral bioavailability (currently 8-12% in humans) through novel delivery systems like PEGylated nanocrystals.
The compound's immunometabolic effects were highlighted in a 2024 Cell Metabolism study showing paeoniflorin-induced browning of white adipose tissue via UCP1 upregulation (3.2-fold increase, p<0.001). This suggests potential applications in metabolic syndrome management. Concurrently, AI-driven molecular docking simulations have identified previously unknown interactions with PI3Kδ isoform, providing rationale for its anti-fibrotic effects in pulmonary and hepatic fibrosis models (EC50 = 56 nM).
Quality control advancements include the development of a validated UPLC-QTOF-MS method (LOQ = 0.1 ng/mL) for pharmacokinetic studies, addressing previous limitations in metabolite detection. Toxicology assessments across multiple species confirm an excellent safety profile (NOAEL = 500 mg/kg/day in primates). Current research gaps include the need for standardized extraction protocols and larger-scale human trials to establish dose-response relationships across different therapeutic indications.
These collective findings underscore paeoniflorin's transition from traditional medicine to a modern therapeutic agent with pleiotropic actions. Future research directions should prioritize structure-activity relationship studies of its aglycone derivatives and investigation of synergistic combinations with biologics. The establishment of an international paeoniflorin research consortium in 2023 reflects growing recognition of its translational potential across multiple disease domains.
