Dibenzylbutyrolactone

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Basic information

CAS: 34444-37-6
Standard SMILES: COc1cc(CC2COC(=O)C2(O)Cc2ccc(O)c(OC)c2)ccc1O
InChIKey: ZITBJWXLODLDRH-UHFFFAOYSA-N
Molecular formula: C20H22O7
Average molar mass: 374.4 g/mol
Monoisotopic mass: 374.13655304

Overview

dibenzylbutyrolactone has been reported in Stellera chamaejasme, Selaginella doederleinii, and Bupleurum salicifolium with data available.

Names & identifiers

Preferred name: Dibenzylbutyrolactone
IUPAC: 3-hydroxy-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one
English name: (-)-NORTRACHELOGENIN
Molecular formula: C20H22O7
Molecular weight: 374.38

Names & synonyms

Dibenzylbutyrolactone(-)-Nortrachelogenin(-)-Wikstromol3-Hydroxy-3,4-bis(4-hydroxy-3-methoxybenzyl)dihydrofuran-2(3H)-oneNSC6988022(3H)-Furanone, dihydro-3-hydroxy-3,4-bis((4-hydroxy-3-methoxyphenyl)methyl)-2(3H)-Furanone, dihydro-3-hydroxy-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]-Wikstroemia SP.I(+)-WikstromolWIKSTROEMIA FOETIDA B641599K027Arbo 6B641599K027

Show more names

Nsc 271296PinopalustrinrtrachelogeninNormetholite aglycone34444-37-6 (-)-NORTRACHELOGENINNortrachelogenin, 10 mM in DMSO

3-hydroxy-3,4-bis[(4-hydroxy-3-methoxy-phenyl)methyl]tetrahydrofuran-2-oneMLS000863658MEGxp0_001440orb1990307SCHEMBL4382924CHEMBL1483370SCHEMBL30751576ACon1_001559

Database identifiers

CAS: 34444-37-6

Properties

Computed structural properties

XLogP: 2.5
Topological polar surface area: 105 Å²
Hydrogen bond donors: 3
Hydrogen bond acceptors: 7
Rotatable bonds: 6
Heavy atoms: 27
Formal charge: 0
Complexity: 513

Physicochemical properties

Boiling point: 609.1 · 609.1±50.0 °C(Predicted)
Density: 1.37 · 1.370±0.06 g/cm3(Predicted)
pka: 10.02 · 10.02±0.20(Predicted)
form: Solid
color: White to off-white
InChI: InChI=1S/C20H22O7/c1-25-17-8-12(3-5-15(17)21)7-14-11-27-19(23)20(14,24)10-13-4-6-16(22)18(9-13)26-2/h3-6,8-9,14,21-22,24H,7,10-11H2,1-2H3/t14-,20-/m0/s1
InChIKey: ZITBJWXLODLDRH-XOBRGWDASA-N
SMILES: O1C[C@H](CC2=CC=C(O)C(OC)=C2)[C@@](O)(CC2=CC=C(O)C(OC)=C2)C1=O
LogP: 0.92 · 0.920 (est)
Symbol(GHS): 9 · GHS09
Signal word: Warning
Hazard statements: 400 · H400
Precautionary statements: 273 · P273
Hazard Codes: N
Risk Statements: 50 · 50
Safety Statements

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

ridadr: UN 3077 9 / PGIII
risk_code: 50
Signal word: Warning
Symbol(GHS): GHS09
hazard_code: N
safety_code: 61
Hazard statements: H400
Precautionary statements: P273

Chemistry & industry

Pharmacology

Cellular LocationsCytoplasm

Applications

UsesNortrachelogenin ((-)-Wikstromol) from Partrinia scabiosaefolia elicits an apoptotic response in Candida albicans[1].

Additional notes

DefinitionChEBI: Nortrachelogenin is a lignan.

Related reactions

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Compound notes

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