3,5-DIHYDROXY-4'-BROMOSTILBENE Property

storage temp. 

2-8°C

solubility 

DMSO: soluble20mg/mL, clear

form 

powder

color 

white to yellow to brown

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26

WGK Germany 

3

HazardClass 

IRRITANT

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

3,5-DIHYDROXY-4'-BROMOSTILBENE Chemical Properties,Usage,Production

Biological Activity

4'-bromo-resveratrol is a sirt1 and sirt3 inhibitor.sirtuins are protein deacetylases regulating aging processes and many physiological functions. resveratrol activates human sirt1 and inhibits sirt3, and can mimic calorie restriction effects including lifespan extension in lower organisms.

in vitro

sirtuin modulation was studied by using 4’-bromo-resveratrol in a previous study. 4’-bromo-resveratrol inhibited sirt3 with much higher potency than resveratrol, and it also inhibited rather than activated sirt1. crystal structures of human sirt3/peptide complexes of 4’ -bromo-resveratrol identified two binding sites. an internal site caused the potent inhibitory effect. 4’-bromo-resveratrol interfered with nad+ and substrate peptide binding, and it extended its bromo-phenyl group in a unrecognized site pocket. the second binding site for 4’-bromo-resveratrol was found to be located on the surface of sirt3 and connected via two helices to peptide-binding active site loops. in sirt1, this site appeared to comprise a residue that was essential for its activation by small molecules and 4’-bromo-resveratrol therefore constituted a candidate for the long-sought allosteric sirt1 activator binding site [1].

References

[1] nguyen gt, gertz m, steegborn c. crystal structures of sirt3 complexes with 4'-bromo-resveratrol reveal binding sites and inhibition mechanism. chem biol. 2013 nov 21;20(11):1375-85.