CAS Number22139-77-1
Synonyms3,5-dihydroxystilbene; E-3,5-Stilbenediol; 5-Styrylresorcinol; 3,5-TRANS-DIHYDROXYSTILBENE; 5-[(E)-2-Phenylvinyl]-1,3-benzenediol; Pisylvin; 5-[(E)-2-Phényléthènyl]-1,3-benzènediol; 5-[(E)-2-phenylethenyl]benzene-1,3-diol; 5-[(E)-2-Phenylvinyl]benzene-1,3-diol; trans-3,5-Dihydroxystilbene; 5-(2-phenylethenyl)benzene-1,3-diol; (trans)-3,5-stilbenediol; 5-(2-phenylvinyl)benzene-1,3-diol; 5-(2-phenylethenyl)-1,3-benzenediol; Pinosylvin
Molecular FormulaC14H12O2
Molecular Weight212.24
Purity≥97.0 (HPLC)%
Density1.3±0.1 g/cm3
Boiling Point397.6±17.0 °C at 760 mmHg
Melting Point153-157 °C
Appearancesolid
Symbol
Signal WordWarning
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| Chemical & Physical Properties | |
|---|---|
| CAS Number | 22139-77-1 |
| Catalog No. | 2A-9038893 |
| Chinese Name | 赤松素 |
| Synonyms | 3,5-dihydroxystilbene; E-3,5-Stilbenediol; 5-Styrylresorcinol; 3,5-TRANS-DIHYDROXYSTILBENE; 5-[(E)-2-Phenylvinyl]-1,3-benzenediol; Pisylvin; 5-[(E)-2-Phényléthènyl]-1,3-benzènediol; 5-[(E)-2-phenylethenyl]benzene-1,3-diol; 5-[(E)-2-Phenylvinyl]benzene-1,3-diol; trans-3,5-Dihydroxystilbene; 5-(2-phenylethenyl)benzene-1,3-diol; (trans)-3,5-stilbenediol; 5-(2-phenylvinyl)benzene-1,3-diol; 5-(2-phenylethenyl)-1,3-benzenediol; Pinosylvin |
| Molecular Formula | C14H12O2 |
| Molecular Weight | 212.24 |
| Purity | ≥97.0 (HPLC) |
| Density | 1.3±0.1 g/cm3 |
| Boiling Point | 397.6±17.0 °C at 760 mmHg |
| Melting Point | 153-157 °C |
| Appearance | solid |
| Storage Condition | 2-8°C |
| Application | Pinosylvin is a pre-infectious styrenoid toxin with anti-bacterial activity isolated from the heartwood of Pinus spp. Pinosylvin is a resveratrol analogue that can induce apoptosis and autophagy in le |
| PubChem ID | 329758200 |
| MDL Number | MFCD00210544 |
| SMILES | Oc1cc(O)cc(\C=C\c2ccccc2)c1 |
| InChI | 1S/C14H12O2/c15-13-8-12(9-14(16)10-13)7-6-11-4-2-1-3-5-11/h1-10,15-16H/b7-6+ |
| InChI Key | YCVPRTHEGLPYPB-VOTSOKGWSA-N |
| Beilstein/REAXYS | 1870942 |
| NACRES Code | NA.25 |
| UNSPSC | 41116107 |
| Hazard Symbols | transportation |
| MSDS | msds/38893_1_22139_77_1.pdf |
| Bioactivity | Pinosylvin is a pre-infectious stilbenoid toxin isolated from the heartwood of Pinus spp, has anti-bacterial activities[1]. Pinosylvin is a resveratrol analogue, can induce cell apoptosis and autophapy in leukemia cells[2]. Related Catalog Signaling Pathways >> Apoptosis >> Apoptosis Research Areas >> Cancer Research Areas >> Infection Signaling Pathways >> Autophagy >> Autophagy Signaling Pathways >> Anti-infection >> Bacterial In Vitro Pinosylvin (0-100 μM; 24 hours) is cytotoxic to THP‐1 and U937 cells, exhibits an IC50 value of 20-30 μM in leukemia cells, the maximal cytotoxic effect occurred at 100 μM following incubation for 24 hr[3]. Pinosylvin (0-100 μM; 24 hours) enhances the number of annexin V+ and PI+ cells in the U937 population at 50 μM, increases annexin V+ and PI+ cells in the THP‐1 population at 100 μM[3]. Pinosylvin (0-100 μM; 24 hours) promotes autophagy in leukemia cells by enhancing the level of LC3‐II and p62/SQSTM1 degradation in leukemia cells[3]. Cell Viability Assay[3] Cell Line: Leukemia cells Concentration: 0 μM; 0.1 μM; 1 μM; 10 μM; 50 μM; 100 μM Incubation Time: 24 hours Result: Was cytotoxic to leukemia cells at high concentrations. Apoptosis Analysis[3] Cell Line: U937 and THP‐1 cells Concentration: 0 μM; 0.1 μM; 1 μM; 10 μM; 50 μM; 100 μM Incubation Time: 24 hours Result: Induced apoptosis cell number in U937 and THP‐1 cells. Western Blot Analysis[3] Cell Line: U937 and THP‐1 cells Concentration: 0 μM; 0.1 μM; 1 μM; 10 μM; 50 μM; 100 μM Incubation Time: 24 hours Result: Induced autophagy in leukemia cells. In Vivo Pinosylvin (intravenous injection; 10 mg/kg) yields the plasma AUC, urine t , CL and Vd values of 5.23 ± 1.20 mgh mL-1, 13.13 ± 2.05 h, 1.84 ± 0.44 Lh-1kg-1 and 2.29 Lkg-1, respectively in male Sprague-Dawley rats, in a PK study[1]. References [1]. Lee SK, et al. Antibacterial and antifungal activity of pinosylvin, a constituent of pine.Fitoterapia. 2005 Mar;76(2):258-60. [2]. Roupe KA, et al. Pharmacokinetics of selected stilbenes: rhapontigenin, piceatannol and pinosylvin in rats.J Pharm Pharmacol. 2006 Nov;58(11):1443-50. [3]. Song J, et al. Pinosylvin enhances leukemia cell death via down-regulation of AMPKα expression. Phytother Res. 2018 Oct;32(10):2097-2104. Chemical & Physical Properties Density 1.3±0.1 g/cm3 Boiling Point 397.6±17.0 °C at 760 mmHg Melting Point 155.5-156° Molecular Formula C14H12O2 Molecular Weight 212.244 Flash Point 194.9±15.5 °C Exact Mass 212.083725 PSA 40.46000 LogP 3.68 Vapour Pressure 0.0±1.0 mmHg at 25°C Index of Refraction 1.727 InChIKey YCVPRTHEGLPYPB-VOTSOKGWSA-N SMILES Oc1cc(O)cc(C=Cc2ccccc2)c1 Storage condition 2-8°C |
| Use of | Pinosylvin is a pre-infectious stilbenoid toxin isolated from the heartwood of Pinus spp, has anti-bacterial activities[1]. Pinosylvin is a resveratrol analogue, can induce cell apoptosis and autophapy in leukemia cells[2]. Properties Name pinosylvin Synonym More Synonyms Pinosylvin Biological Activity Description Pinosylvin is a pre-infectious stilbenoid toxin isolated from the heartwood of Pinus spp, has anti-bacterial activities[1]. Pinosylvin is a resveratrol analogue, can induce cell apoptosis and autophapy in leukemia cells[2]. Related Catalog Signaling Pathways >> Apoptosis >> Apoptosis Research Areas >> Cancer Research Areas >> Infection Signaling Pathways >> Autophagy >> Autophagy Signaling Pathways >> Anti-infection >> Bacterial References [1]. Lee SK, et al. Antibacterial and antifungal activity of pinosylvin, a constituent of pine.Fitoterapia. 2005 Mar;76(2):258-60. [2]. Roupe KA, et al. Pharmacokinetics of selected stilbenes: rhapontigenin, piceatannol and pinosylvin in rats.J Pharm Pharmacol. 2006 Nov;58(11):1443-50. [3]. Song J, et al. Pinosylvin enhances leukemia cell death via down-regulation of AMPKα expression. Phytother Res. 2018 Oct;32(10):2097-2104. Chemical & Physical Properties Molecular Formula C14H12O2 Exact Mass 212.083725 PSA 40.46000 Index of Refraction 1.727 InChIKey YCVPRTHEGLPYPB-VOTSOKGWSA-N |
| Transport Info | Shipping Name: UN |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Danger Regulations: 3077 International Maritime Transport Danger Regulations: 3077 International Air Transport Danger Regulations: 3077 14.2 United Nations shipping name European land transport hazard regulations: ENVIRONMENTALLY HAZARDOUS SUBSTANCE, SOLID, N.O.S. (Pinosylvin) IMDG Code: ENVIRONMENTALLY HAZARDOUS SUBSTANCE, SOLID, N.O.S. (Pinosylvin) International air transport hazard regulations: Environmentally hazardous substance, solid, n.o.s. (Pinosylvin) 14.3 Transport hazard categories European land transport Dangerous Regulations: 9 International sea transport Dangerous Regulations: 9 International air transport Dangerous Regulations: 9 14.4 Package group European Land Transport Danger Regulations: III International Maritime Transport Danger Regulations: III International Air Transport Danger Regulations: III 14.5 Environmental hazards European Land Transport Dangerous Regulations: Yes International Maritime Transport Dangerous Regulations International Air Transport Dangerous Regulations: Yes Marine Pollutants (Yes/No): Yes 14.6 Special reminder to users further information Dangerous goods are individually packaged, with liquids exceeding 5 liters or solids exceeding 5 kilograms. The outer packaging of each independent package and the combined independent inner package must have EHS on it. Identification (according to European ADR Regulation 2.2.9.1.10, IMDG Regulation 2.10.3), See reverse side of invoice or packing slip. |
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