Pinocembrin

Base Information

• Chemical Name: Pinocembrin
• CAS No.: 480-39-7
• Deprecated CAS: 36052-36-5,58904-42-0
• Molecular Formula: C₁₅H₁₂O₄
• Molecular Weight: 256.258
• Hs Code.: 29329990
• European Community (EC) Number: 817-146-3
• UNII: 8T7C8CH791
• DSSTox Substance ID: DTXSID3075412
• Nikkaji Number: J12.347A
• Wikipedia: Pinocembrin
• Wikidata: Q76005702
• Pharos Ligand ID: AKSVRLMWM5J6
• Metabolomics Workbench ID: 27378
• ChEMBL ID: CHEMBL399910
• Mol file: 480-39-7.mol

Synonyms:(+)-pinocoembrin;5,7-dihydroxy-flavanone;5,7-dihydroxyflavanone;pinocembrin;pinocembrine

Chemical Property of Pinocembrin

Chemical Property:

• Vapor Pressure: 1.85E-11mmHg at 25°C
• Melting Point: 202 °C
• Refractive Index: 1.661
• Boiling Point: 511.1 °C at 760 mmHg
• PKA: 7.50±0.40(Predicted)
• Flash Point: 199.3 °C
• PSA: 66.76000
• Density: 1.386 g/cm³
• LogP: 2.80430
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 256.07355886
• Heavy Atom Count: 19
• Complexity: 337

Purity/Quality:

98%,99%, ^*data from raw suppliers

(S)-Pinocembrin ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(OC2=CC(=CC(=C2C1=O)O)O)C3=CC=CC=C3
• Isomeric SMILES: C1[C@H](OC2=CC(=CC(=C2C1=O)O)O)C3=CC=CC=C3
• Recent ClinicalTrials: Phase ⅡStudy of Pinocembrin Injection to Treat Ischemic Stroke
• Description: Pinocembrin is a flavonoid that has been found in Eucalyptus, and has diverse biological activities. It induces apoptosis in, and inhibits the migration of, SKOV3 ovarian cancer cells when used at a concentration of 200 μM. Pinocembrin (5 mg/kg) reduces lesion volume, as well as brain microglial activation and production of IL-1β, IL-6, and TNF-α in a mouse model of collagenase-induced intracerebral hemorrhage (ICH). It prevents increases in plasma and kidney malondialdehyde (MDA) levels, glomeruli lobulation, mesangial expansion, and tubule vacuolization and occlusion, and it decreases hepatic cholesterol, triglyceride, and LDL levels in a rat model of diabetic nephropathy. Pinocembrin (20 and 50 mg/kg) reduces pulmonary edema, as well as neutrophil, lymphocyte, and macrophage infiltration in a mouse model of LPS-induced lung injury.
• Uses: Pinocembrin is a flavanoid with antioxidant activity found in damiana, honey, and propolis. Recent studies show that Pinocembrin maybe be a therapeutic option in reducing cerebral ischemia/reperfusion injury as a result of its anti-oxidative and anti-apoptotic effects. Pinocembrin displayed neuroprotective effects in glutamate injury model partly by inhibiting p53 expression causing a lower Bax-Bc l-2 ratio and by inhibiting the release of cytochrome c. Pinocembrin is a flavanoid with antioxidant activity found in damiana, honey, and propolis. Recent studies show that Pinocembrin maybe be a therapeutic option in reducing cerebral ischemia/reperfusion injury as a result of its anti-oxidative and anti-apoptotic effects. Pinocembrin displayed neuroprotective effects in glutamate injury model partly by inhibiting p53 expression causing a lower Bax-Bcl-2 ratio and by inhibiting the release of cytochrome c.

Technology Process of Pinocembrin

There total 40 articles about Pinocembrin 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: 90.0%

2',4',6'-trihydroxychalcone (82451-30-7) → pinocembrin (480-39-7,61490-55-9,68745-38-0)

Guidance literature:

With potassium hydroxide; In methanol; at 25 ℃;

DOI:10.1080/00397911.2016.1228110

Reference yield: 90.0%

5,7-bis(methoxymethoxy)-2-phenylchroman-4-one (873070-89-4) → pinocembrin (480-39-7,61490-55-9,68745-38-0)

Guidance literature:

With hydrogenchloride; In methanol; for 0.5h; Heating;

DOI:10.1021/ol052269z

Reference yield: 76.0%

5,7-dihydroxy-2-phenyl-chromen-4-one (480-40-0) → pinocembrin (480-39-7,61490-55-9,68745-38-0)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In 1,4-dioxane; methanol; at 20 ℃; for 24h;

upstream raw materials:

benzaldehyde

1-[2-hydroxy-4,6-bis-(tetra-O-acetyl-β-D-glucopyranosyloxy)-phenyl]-ethanone

C₂₂H₁₈O₄

5,7-dihydroxy-2-phenyl-chromen-4-one

Downstream raw materials:

2'.4'.6'-triacetoxy-trans-chalcone

7-acetylpinocembrine

pinostrobin Acetate

(+/-)-7-acetoxy-5-hydroxy-2-phenyl-chroman-4-one

Refernces

• 1、 Xu, Xinya,Xie, Haihui,Hao, Jing,Jiang, Yueming,Wei, Xiaoyi. "Flavonoid glycosides from the seeds of litchi chinensis". . p. 1205 - 1209. Retrieved 2011.
• 2、 -. "Novel chromenone derivatives having substituted biphenyl group and a pharmaceutical composition for prevention or treatment of allergic diseases compring the same". Paragraph 0157-0164. . Retrieved 2020/11/26.
• 3、 Zaki, Mohamed A.,Nanayakkara, N. P. Dhammika,Hetta, Mona H.,Jacob, Melissa R.,Khan, Shabana I.,Mohammed, Rabab,Ibrahim, Mohamed A.,Samoylenko, Volodymyr,Coleman, Christina,Fronczek, Frank R.,Ferreira, Daneel,Muhammad, Ilias. "Bioactive Formylated Flavonoids from Eugenia rigida: Isolation, Synthesis, and X-ray Crystallography". . p. 2341 - 2349. Retrieved 2016/10/04.