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Erianin

HCID 356759
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Basic information

CAS
95041-90-0
Standard SMILES
COc1ccc(CCc2cc(OC)c(OC)c(OC)c2)cc1O
InChIKey
UXDFUVFNIAJEGM-UHFFFAOYSA-N
Molecular formula
C18H22O5
Average molar mass
318.4 g/mol
Monoisotopic mass
318.1467238

Overview

Erianin is a diphenylethane that is 1,2-dihydrostilbene substituted by a hydroxy group at position 3 and by methoxy groups at positions 4, 3', 4', and 5'. It is isolated from Dendrobium species. It has a role as an autophagy inducer, a ferroptosis inducer, an antioxidant, an antibacterial agent, a non-narcotic analgesic, an antipyretic, an antineoplastic agent, an angiogenesis inhibitor, an antipsoriatic, a neuroprotective agent, an anti-inflammatory agent, an apoptosis inducer and a plant metabolite. It is a member of phenols, a diphenylethane and a member of methoxybenzenes. It derives from a hydride of a 1,2-dihydrostilbene.

Names & identifiers

Preferred name
Erianin
IUPAC
2-methoxy-5-[2-(3,4,5-trimethoxyphenyl)ethyl]phenol
English name
Phenol, 2-methoxy-5-[2-(3,4,5-trimethoxyphenyl)ethyl]-
Molecular formula
C18H22O5
Molecular weight
318.36

Names & synonyms

Erianin95041-90-02-methoxy-5-[2-(3,4,5-trimethoxyphenyl)ethyl]phenolDTXSID403267512-methoxy-5-(2-(3,4,5-trimethoxyphenyl)ethyl)phenol2-methoxy-5-(2-(3,4,5-trimethoxyphenyl)-ethyl)-phenol2-methoxy-5-[2-(3,4,5-trimethoxyphenyl)-ethyl]-phenolEri cpdRefChem:921109DTXCID302778643-hydro-4,3',4',5'-quamythloxy-stilbene2-methoxy-5-(3,4,5-trimethoxyphenethyl)phenol
Show more names
Erianin 95041-90-0MolansinErianin-RMErianin (Standard)Erianin, 10 mM in DMSOInhibitor,Erianin,inhibit,Bacterial3'-Hydroxy-3,4,4',5-tetraMethoxybibenzyl2-Methoxy-5-(3,4,5-trimethoxyphenethyl)phenol , Erianin
Phenol, 2-methoxy-5-[2-(3,4,5-trimethoxyphenyl)ethyl]-CHEMBL10557MFCD06795132NSC6137442-Methoxy-5-[2-(3,4,5-trimethoxy-phenyl)-ethyl]-phenolDendroErianin?2-Methoxy-5-[2-(3,4,5-trimethoxyphenyl)ethyl]phenol; NSC 613744

Properties

Computed structural properties

XLogP
3.7
Topological polar surface area
57.2 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
5
Rotatable bonds
7
Heavy atoms
23
Formal charge
0
Complexity
323

Physicochemical properties

Boiling point
439.1 · 439.1±40.0 °C(Predicted)
Density
1.147 · 1.147
storage temp.
2 · 2-8°C
solubility
DMSO:PBS (pH 7.2) (1:8):0.11(Max Conc. mg/mL);0.35(Max Conc. mM)DMF:30.0(Max Conc. mg/mL);94.23(Max Conc. mM)Ethanol:5.0(Max Conc. mg/mL);15.71(Max Conc. mM)
form
A crystalline solid
pka
9.99 · 9.99±0.10(Predicted)
color
White to off-white
Major Application
food and beverages
InChI
InChI=1S/C18H22O5/c1-20-15-8-7-12(9-14(15)19)5-6-13-10-16(21-2)18(23-4)17(11-13)22-3/h7-11,19H,5-6H2,1-4H3
InChIKey
UXDFUVFNIAJEGM-UHFFFAOYSA-N
SMILES
C1(O)=CC(CCC2=CC(OC)=C(OC)C(OC)=C2)=CC=C1OC
UNSPSC Code
41116107 · 41116107
NACRES
24 · NA.24
WGK Germany
3 · WGK 3
HS Code
29089990 · 29089990

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Safety data

wgk
WGK 3
hs_code
29089990
Storage Class
11 - Combustible Solids

Chemistry & industry

Applications

UsesErianin acts as a promising anticancer agent. Cytotoxic compound strongly inhibits tubulin polymerization in cell mitosis.

Upstream & downstream products

Upstream raw materials

Phenol, 2-methoxy-5-[2-(3,4,5-trimethoxyphenyl)ethynyl]-Triphenyl-(3,4,5-trimethoxy-benzyl)-phosphonium, bromide3-tert-Butyldimethylsiloxy-4-methoxybenzaldehyde3,4,5-Trimethoxybenzyl alcoholPhenol, 2-methoxy-5-[(1E)-2-(3,4,5-trimethoxyphenyl)ethenyl]-3,4,5-TrimethoxybenzaldehydeMethanolHydrogenPalladiumActivated carbon

Related reactions

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Compound notes

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Database identifiers

CAS
95041-90-0
PubChem CID
356759
DTXSID
DTXSID40326751
ChEMBL
CHEMBL10557
ChEBI
CHEBI:233659
Nikkaji
J421.340H
Storage Class
11 · 11 - Combustible Solids