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22139-77-1

22139-77-1 structure
22139-77-1 structure
  • Name: Pinosylvin
  • Chemical Name: pinosylvin
  • CAS Number: 22139-77-1
  • Molecular Formula: C14H12O2
  • Molecular Weight: 212.244
  • Catalog: Natural product Phenols
  • Create Date: 2018-03-12 08:00:00
  • Modify Date: 2025-08-20 10:52:26
  • 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].

Name pinosylvin
Synonyms 3,5-dihydroxystilbene
E-3,5-Stilbenediol
5-Styrylresorcinol
3,5-TRANS-DIHYDROXYSTILBENE
5-[(E)-2-Phenylvinyl]-1,3-benzenediol
Pisylvin
1,3-Benzenediol, 5-(2-phenylethenyl)-
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
1,3-Benzenediol, 5-[(E)-2-phenylethenyl]-
Pinosylvin
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
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.

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
Storage condition 2-8°C

CHEMICAL IDENTIFICATION

RTECS NUMBER :
WJ5580000
CHEMICAL NAME :
3,5-Stilbenediol, (E)-
CAS REGISTRY NUMBER :
22139-77-1
BEILSTEIN REFERENCE NO. :
1870942
LAST UPDATED :
199612
DATA ITEMS CITED :
2
MOLECULAR FORMULA :
C14-H12-O2
MOLECULAR WEIGHT :
212.26
WISWESSER LINE NOTATION :
QR CQ E1U1R -T

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
20 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :
DNA inhibition
TEST SYSTEM :
Human Lymphocyte
DOSE/DURATION :
30 mg/L
REFERENCE :
EXPEAM Experientia. (Birkhaeuser Verlag, POB 133, CH-4010 Basel, Switzerland) V.1- 1945- Volume(issue)/page/year: 42,568,1986
Hazard Codes Xn,N
Risk Phrases 22-36-51/53
Safety Phrases 26-61
RIDADR UN 3077 9 / PGIII
RTECS WJ5580000
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