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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: 2024-01-02 18:19:02
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	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.

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

Precursor 9
21956-56-9 133156-35-1 71144-79-1 106325-78-4
7311-34-4 24131-32-6 33617-49-1 1080-32-6
705-76-0
DownStream 2
14531-52-3 78916-50-4