CAS 22255-22-7 Trismethoxyresveratrol (HCID 5388063)

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Basic information

CAS: 22255-22-7
Standard SMILES: COc1ccc(/C=C/c2cc(OC)cc(OC)c2)cc1
InChIKey: GDHNBPHYVRHYCC-SNAWJCMRSA-N
Molecular formula: C17H18O3
Average molar mass: 270.32 g/mol
Monoisotopic mass: 270.12559444

Overview

(E)-3,5,4'-Trimethoxystilbene has been reported in Scirpoides holoschoenus, Dalea versicolor, and other organisms with data available.

Names & identifiers

Preferred name: Trismethoxyresveratrol
IUPAC: 1,3-dimethoxy-5-[(E)-2-(4-methoxyphenyl)ethenyl]benzene
English name: 3,4',5-TRIMETHOXY-TRANS-STILBENE
Molecular formula: C17H18O3
Molecular weight: 270.32

Names & synonyms

TRISMETHOXYRESVERATROL1,3-dimethoxy-5-[(E)-2-(4-methoxyphenyl)ethenyl]benzene1,3-dimethoxy-5-((E)-2-(4-methoxyphenyl)ethenyl)benzeneRefChem:110053922255-22-7trans-Trimethoxyresveratrol(E)-1,3-Dimethoxy-5-(4-methoxystyryl)benzene3,4',5-trimethoxy-trans-stilbene3,4',5-trimethoxystilbeneTRIMETHOXYSTILBENE(E)-3,5,4'-TrimethoxystilbeneMFCD02093500

Show more names

RP201772RP 201772RP-201772TriMethoxystibeneTRISMETHOXY RESVERATROLTri-O-methylresveratrolResveratrol three etherTrimethoxy-trans-stilbene

3,4`,5-Trimethoxy-trans-stilbeneE-Resveratrol trimethyl ether1,3-dimethoxy-5-[(E)-2-(4-methoxyphenyl)vinyl]benzeneCHEMBL2964111,3-Dimethoxy-5-[(1E)-2-(4-methoxyphenyl)ethenyl]benzeneBenzene, 1,3-dimethoxy-5-[(1E)-2-(4-methoxyphenyl)ethenyl]-NSC6313631,3-dimethoxy-5-[2-(4-methoxyphenyl)ethenyl]benzene

Database identifiers

Properties

Computed structural properties

XLogP: 4.1
Topological polar surface area: 27.7 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 3
Rotatable bonds: 5
Heavy atoms: 20
Formal charge: 0
Complexity: 283

Physicochemical properties

Melting point: 57 °C · 57°C
Boiling point: 423.8 · 423.8±35.0 °C(Predicted)
Density: 1.104 · 1.104±0.06 g/cm3(Predicted)
storage temp.: 2 · Sealed in dry,2-8°C
solubility: 34 mg/mL · DMSO: ≥34mg/mL
form: powder to crystal
color: white to tan
InChI: InChI=1S/C17H18O3/c1-18-15-8-6-13(7-9-15)4-5-14-10-16(19-2)12-17(11-14)20-3/h4-12H,1-3H3/b5-4+
InChIKey: GDHNBPHYVRHYCC-SNAWJCMRSA-N
SMILES: C1(OC)=CC(/C=C/C2=CC=C(OC)C=C2)=CC(OC)=C1
CAS DataBase Reference: 22255 · 22255-22-7
Symbol(GHS): 5 · GHS05,GHS07,GHS09
Signal word: Danger
Hazard statements: 315 · H315-H318-H335-H410
Precautionary statements: 261 · P261-P264-P273-P280-P302+P352-P305+P351+P338

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P273, P280, P302+P352, P304+P340, P305+P354+P338, P317, P319, P321, P332+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Safety data

ridadr: UN 3077 9 / PGIII
hs_code: 2909.30.6000
risk_code: 36/37/38-50/53-41-37/38
Signal word: Danger
Symbol(GHS): GHS05,GHS07,GHS09
hazard_code: Xi,N
safety_code: 26-36/37/39-61-60-39
Hazard statements: H315-H318-H335-H410
Precautionary statements: P261-P264-P273-P280-P302+P352-P305+P351+P338

Chemistry & industry

Applications · 4 items

Descriptiontrans-trismethoxy Resveratrol is a polyketide synthase-derived stilbene originally isolated from Virola cuspidata that has diverse biological activities. It is cytotoxic to several cancer cell lines, including PC3, KB, HT-29, SW480, and HL-60 cells (IC50s =3.6, 10.2, 16.1, 54, and 2.5 μM, respectively). trans-trismethoxy Resveratrol (15 μM) inhibits TNF-α-induced activation of NF-κB in HEK293T cells in a reporter assay. It inhibits angiogenesis in zebrafish embryos when used at a concentration of 0.1 μM.

UsesA resveratrol analog with a variety of pharmacology action, including anti-cancer properties, anti-allergic activity, estrogenic activity, antiangiogenic activity, and vascular-targeting activity against microtubule-destabilization

UsesA resveratrol analog with a variety of pharmacology action, including inst microtubule-destabilization

UsesPhenolic compounds, particularly flavonoids, from plant sources have long been observed to have antioxidant activity with potential benefits for human health. Resveratrol is a potent phenolic antioxidant found in grapes and red wine that also has antiproliferative and anti-inflammatory activity. When the three phenolic hydroxyl groups of resveratrol are converted to methyl ethers, the inhibition of cell growth and pro-apoptotic activities of resveratrol are enhanced.