22139-77-1

Basic information

• Product Name: PINOSYLVIN
• Synonyms: (e)-5-stilbenediol;5-(2-phenylethenyl)-3-benzenedio(e)-;pinosylvine;AKOS 211-07;3,5-DIHYDROXY-STILBENE;3,5-TRANS-DIHYDROXYSTILBENE;5-(2-Phenylethenyl)benzene-1,3-diol;5-[(E)-2-Phenylethenyl]-1,3-benzenediol
• CAS NO: 22139-77-1
• Molecular Formula: C₁₄H₁₂O₂
• Molecular Weight: 212.24
• EINECS: 1312995-182-4
• Product Categories: Stilbenes (substituted)
• Mol File: 22139-77-1.mol

Chemical Properties

• Melting Point: 155.5-156°
• Boiling Point: 312.08°C (rough estimate)
• Flash Point: 195 °C
• Appearance: /
• Density: 1.1035 (rough estimate)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• Storage Temp.: 2-8°C
• PKA: 9.34±0.10(Predicted)
• BRN: 1870942
• CAS DataBase Reference: PINOSYLVIN(CAS DataBase Reference)
• NIST Chemistry Reference: PINOSYLVIN(22139-77-1)
• EPA Substance Registry System: PINOSYLVIN(22139-77-1)

Safety Data

• Hazard Codes: Xn,N
• Statements: 22-36-51/53
• Safety Statements: 26-61
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 3
• RTECS: WJ5580000
• Hazardous Substances Data: 22139-77-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
Pinosylvin is used as a fungitoxin and therapeutic agent for studying its properties and potential applications in medicine.
Used in Biological Research:
Pinosylvin is used as a representative stilbene to study its biological actions and therapeutic value in processes such as cell survival, apoptosis, and cell mobility.

Enzyme inhibitor

This trans-stilbene derivative (FW = 212.25 g/mol; CAS 102-61-4; M.P. = 155.5-156°C; low solubility in water), also known as (E)-3,5-stilbenediol and trans-3,5-dihydroxystilbene and named systematically as 5-[(E)-2- phenylethenyl]benzene-1,3-diol, occurs naturally in the hardwood of pine and other woody plants. Pinosylvin exxhibits micromolar Ki values for specific isozymes of stilbene synthase and chalcone synthase. Target(s): chalcone synthase; stilbene synthase; tyrosinase, or monophenol monooxygenase.

InChI:InChI=1/C15H14O2/c16-14-9-13(10-15(17)11-14)8-4-7-12-5-2-1-3-6-12/h1-7,9-11,16-17H,8H2/b7-4+

Upstream product

• 35302-70-6 3-methoxy-5-[(E)-2-phenylvinyl]phenol 
• 21956-56-9 (E)-3,5-dimethoxystilbene 
• 133156-35-1 (E)-1-<3,5-bis(benzyloxy)phenyl>-2-phenylethene 
• 106325-78-4 5-[(1Z)-2-phenylethenyl]benzene-1,3-diol 
• 107192-05-2 1,3-Bis-(tert-butyl-dimethyl-silanyloxy)-5-((E)-styryl)-benzene 
• 33617-50-4 3.5-Dihydroxy-benzylphosphonsaeurediaethylester 
• 100-52-7 benzaldehyde 
• 5252-43-7 4-Hydroxy-7-((E)-styryl)-pyrano[4,3-b]pyran-2,5-dione 
• 100-39-0 benzyl bromide 
• 1449-46-3 benzyltriphenylphosphonium bromide 
• 103929-83-5 methyl 3,5-bis(tert-butyldimethylsilyloxy)benzoate 
• 24131-32-6 3,5-bis(benzyloxy)benzyl bromide 
• 33617-49-1 diethyl <3,5-bis(benzyloxy)benzyl>phosphonate 
• 107030-46-6 C₂₆H₄₀O₂Si₂ 

Downstream Products

• 71144-79-1 3,5-diacetoxy-(E)-stilbene 
• 21956-56-9 (E)-3,5-dimethoxystilbene 
• 143207-70-9 (E)-3-hydroxy-5-butoxystilbene 
• 143207-67-4 (E)-3-hydroxy-5-ethoxystilbene 
• 143207-73-2 (E)-3-hydroxy-5-heptyloxystilbene 
• 129657-74-5 2,3-dihydro-2,2-dimethyl-7-hydroxy-5-(2-phenylethenyl)-4H-1-benzopyran-4-one 
• 129657-75-6 2,3-dihydro-2,2-dimethyl-5-hydroxy-7-(2-phenylethenyl)-4H-1-benzopyran-4-one 
• 143207-71-0 (E)-3-hydroxy-5-pentyloxystilbene 
• 143207-72-1 (E)-3-hydroxy-5-hexyloxystilbene 
• 143207-74-3 (E)-3-hydroxy-5-octyloxystilbene 
• 143207-75-4 (E)-3-hydroxy-5-decyloxystilbene 
• 14531-52-3 dihydropinosylvin 
• 143207-68-5 (E)-3-hydroxy-5-propoxystilbene 
• 143207-69-6 (E)-5-allyloxy-3-hydroxystilbene 

Relevant articles and documents

Pinosylvine, application of the pinosylvine and preparation method of same

The invention provides pinosylvine which is a crystal compound, and the temperature of the pinosylvine is 153-155 DEG C; EI-MS m/Z: 212(M+). The pinosylvine is used for preparing medicines for treating oligoasthenozoospermia, and can also be used for prep

Electro-Olefination—A Catalyst Free Stereoconvergent Strategy for the Functionalization of Alkenes

Conventional methods carrying out C(sp2)?C(sp2) bond formations are typically mediated by transition-metal-based catalysts. Herein, we conceptualize a complementary avenue to access such bonds by exploiting the potential of electrochemistry in combination with organoboron chemistry. We demonstrate a transition metal catalyst-free electrocoupling between (hetero)aryls and alkenes through readily available alkenyl-tri(hetero)aryl borate salts (ATBs) in a stereoconvergent fashion. This unprecedented transformation was investigated theoretically and experimentally and led to a library of functionalized alkenes. The concept was then carried further and applied to the synthesis of the natural product pinosylvin and the derivatization of the steroidal dehydroepiandrosterone (DHEA) scaffold.

Two resveratrol analogs, pinosylvin and 4,4′-dihydroxystilbene, improve oligoasthenospermia in a mouse model by attenuating oxidative stress via the Nrf2-ARE pathway

Two synthesized resveratrol analogs from our laboratory, namely pinosylvin (3,5-dihydroxy-trans-stilbene, PIN) and 4,4′-dihydroxystilbene (DHS), have been carefully evaluated for treatment of oligoasthenospermia. Recent studies have demonstrated that PIN and DHS improved sperm quality in the mouse. However, the mechanism of action of PIN and DHS on oligoasthenospermia remains unknown. Herein, we investigated the mechanistic basis for improvements in sperm parameters by PIN and DHS in a mouse model of oligoasthenospermia induced by treatment with busulfan (BUS) at 6 mg/kg b.w. Two weeks following busulfan treatment, mice were administered different concentrations of PIN or DHS daily for 2 consecutive weeks. Thereafter, epididymal sperm concentration and motility were determined, and histopathology of the testes was performed. Serum hormone levels including testosterone (T), luteinizing hormone (LH), and follicle stimulating hormone (FSH) were measured using corresponding specific enzyme-linked immunosorbent assay (ELISA) kits. Testicular mRNA expression profiles were determined by RNA sequencing analysis. These findings were validated by quantitative real-time PCR, western blotting and ELISA. Both PIN and DHS improved the epididymal sperm concentration and motility, enhanced testosterone levels, and promoted testicular morphological recovery following BUS treatment. PIN treatment was found to significantly reduce oxidative stress via the nuclear factor erythroid 2-related factor 2 (Nrf2)-antioxidant response element (ARE)-dependent antioxidant, glutathione peroxidase 3. DHS treatment significantly reduced oxidative stress via the Nrf2-ARE-dependent antioxidants glutathione S-transferase theta 2 and glutathione S-transferase omega 2. In summary, PIN and DHS ameliorated oligoasthenospermia in this mouse model by attenuating oxidative stress via the Nrf2-ARE pathway.

Ligand-controlled iridium-catalyzed semihydrogenation of alkynes with ethanol: highly stereoselective synthesis of E- and Z-alkenes

A ligand-controlled iridium-catalyzed semihydrogenation of alkynes to E- and Z-alkenes with ethanol was developed. Effective selectivity control was achieved by ligand regulation. The use of 1,2-bis(diphenylphosphino)ethane (DPPE) and 1,5-cyclooctadiene (COD) was critical for the stereoselective semihydrogenation of alkynes. The general applicability of this procedure was highlighted by the synthesis of more than 40 alkenes, with good stereoselectivities. The value of our approach in practical applications was investigated by studying the effects of pinosylvin and 4,4′-dihydroxystilbene (DHS) on zebrafish as a vertebrate model.

Use and preparation method of pinosylvi

The invention provides use and preparation method of pinosylvin. The pinosylvin is used for preparing a medicine for inhibiting nerve activity, and is also used for preparing an antipsychotic drug. Itis found through the study of the pinosylvi that the pi

Novel Carbazole-Based N-Heterocyclic Carbene Ligands to Access Synthetically Relevant Stilbenes in Pd-Catalyzed Coupling Processes

A series of new carbazole-based N-heterocyclic carbene (NHC) ligands have been synthesized in a simple and facile synthetic route and subsequently used in a Pd/carbazole-based NHC catalytic system, which was found to be effective in catalyzing Heck reactions to provide substituted stilbene derivatives in good yields. Several bioactive stilbenes, including pterostilbene, pinosylvin, trimethoxy resveratrol, and resveratrol, were synthesized in good yields, and a 10 mmol scale-up was also performed for trimethoxy resveratrol. The synthetic application was also extended by performing a double-tandem chemoselective Heck reaction followed by Miyaura borylation in a one-pot procedure to give single-step access to synthetically useful stilbenyl boronate esters. Similarly, a unique triple-tandem protocol of a chemoselective Heck reaction/Miyaura borylation/Suzuki–Miyaura coupling reaction sequence was performed for the one-pot modification of biologically relevant molecules.

Synthesis of resveratrol derivatives as new analgesic drugs through desensitization of the TRPA1 receptor

A series of 31 resveratrol derivatives was designed, synthesized and evaluated for activation and inhibition of the TRPA1 channel. Most acted as activators and desensitizers of TRPA1 channels like resveratrol or allyl isothiocyanate (AITC). Compound 4z (HUHS029) exhibited higher inhibitory activity than resveratrol with an IC50 value of 16.1?μM. The activity of 4z on TRPA1 was confirmed in TRPA1-expressing HEK293 cells, as well as in rat dorsal root ganglia neurons by a whole cell patch clamp recording. Furthermore, pretreatment with 4z exhibited an analgesic effect on AITC-evoked TRPA1-related pain behavior in vivo.

Method for synthesizing artificially all-trans-resveratrol and derivative thereof

The invention discloses a method for synthesizing artificially all-trans-resveratrol and a derivative thereof. In the method, the precursors of all-trans-resveratrol and the derivative thereof are prepared by means of constructing a conjugated fused ring, thus the all-trans-spatial structure of resveratrol and the derivative thereof is restricted completely, to prepare all-trans-resveratrol and the derivative thereof. The resulting product of the preparation method of 1,2-stilbene or the derivative thereof in the invention is of all-trans configuration, so as to meet the demand of biologically active substance chemicals. Compared to the previous processes, the method provided by the invention has the advantages of simple processes and mild conditions, thereby meeting the green chemistry concept.

A method for the synthesis of hydroxy [...] composition of the new method (by machine translation)

The present invention discloses a new method for the synthesis of hydroxy [...] compound. The claimed method is: in the organic solvent, under a certain temperature, ammonium formate/through the palladium catalytic removal of benzyl protecting group system, to obtain hydroxyl [...] compound. The method has the mild reaction conditions, the operation is simple, small reagent toxicity, safety, high yield, wide range of application, low cost, relatively suitable for mass production and the like. (by machine translation)

A facile and rapid access to resveratrol derivatives and their radioprotective activity

A facile and rapid access to resveratrol derivatives has been achieved based on palladium-catalyzed oxidative Heck reaction of aryl boronic acids with styrenes followed by demethylation in moderate to good yields. A series of resveratrol derivatives with various functional groups has been synthesized easily. The radioprotective activity of synthesized compounds has also been evaluated using rat thymocytes. The results revealed that some resveratrol derivatives efficiently protected the thymocytes from radiation-induced apoptosis.