Hinokinin
Basic information
- CAS
26543-89-5- Standard SMILES
O=C1OC[C@H](Cc2ccc3c(c2)OCO3)[C@H]1Cc1ccc2c(c1)OCO2- InChIKey
DDWGQGZPYDSYEL-LSDHHAIUSA-N- Molecular formula
- C20H18O6
- Average molar mass
- 354.4 g/mol
- Monoisotopic mass
- 354.11033829
Overview
Hinokinin is a lignan that is dihydrofuran-2(3H)-one (gamma-butyrolactone) substituted by a 3,4-methylenedioxybenzyl group at positions 3 and 4 (the 3R,4R-diastereoisomer). It has a role as a trypanocidal drug. It is a lignan, a gamma-lactone and a member of benzodioxoles.
Names & identifiers
- Preferred name
- Hinokinin
- IUPAC
- (3R,4R)-3,4-bis(1,3-benzodioxol-5-ylmethyl)oxolan-2-one
- English name
- Cubebinolide
- Molecular formula
- C20H18O6
- Molecular weight
- 354.35
Names & synonyms
Hinokinin26543-89-5(3R,4R)-3,4-Bis(benzo[d][1,3]dioxol-5-ylmethyl)dihydrofuran-2(3H)-one(3R,4R)-3,4-bis(1,3-benzodioxol-5-ylmethyl)oxolan-2-oneCHEBI:5722(3R,4R)-3,4-bis(benzo(d)(1,3)dioxol-5-ylmethyl)dihydrofuran-2(3H)-oneRefChem:146441(-)-HinokininCubebinolideCHEMBL242011(3R,4R)-3,4-bis(1,3-benzodioxol-5-ylmethyl)dihydrofuran-2(3H)-one2(3H)-Furanone, 3,4-bis(1,3-benzodioxol-5-ylmethyl)dihydro-, (3R,4R)-
Show more names
Hinokinin-RMDihydroisohibalactone3α,4β-Dipiperonyltetrahydrofuran-2-one(3R)-3α,4β-Bis(1,3-benzodioxole-5-ylmethyl)tetrahydrofuran-2-one2(3H)-Furanone,3,4-bis(1,3-benzodioxol-5-ylmethyl)dihydro-, (3R,4R)-
(3R-trans)-3,4-bis(1,3-benzodioxol-5-ylmethyl)dihydrofuran-2(3H)-onehinoquinin(-)-hinoquininMFCD29918433Hinokinin (Standard)Epitope ID:116880orb2283376orb3139495
Database identifiers
Properties
Computed structural properties
- XLogP
- 3.7
- Topological polar surface area
- 63.2 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 4
- Heavy atoms
- 26
- Formal charge
- 0
- Complexity
- 524
Experimental & physicochemical properties
SpringerMaterials PropertiesChemical shift
Physicochemical properties
- Melting point
- 63 · 63-64 °C
- Boiling point
- 549 · 549.0±19.0 °C(Predicted)
- Density
- 1.388 · 1.388±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · Store at -20°C
- form
- Solid
- color
- White to off-white
- InChI
- 1S/C20H18O6/c21-20-15(6-13-2-4-17-19(8-13)26-11-24-17)14(9-22-20)5-12-1-3-16-18(7-12)25-10-23-16/h1-4,7-8,14-15H,5-6,9-11H2/t14-,15+/m0/s1
- InChIKey
- DDWGQGZPYDSYEL-LSDHHAIUSA-N
- SMILES
- O1C[C@@H]([C@H](C1=O)Cc4cc5c(cc4)OCO5)Cc2cc3c(cc2)OCO3
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 7 · GHS07
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]
P261, P272, P280, P302+P352, P321, P333+P317, P362+P364, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesSkin Sens. 1 (100%)
Safety data
- wgk
- WGK 3
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H317
- Hazard Classifications
- Skin Sens. 1
- Precautionary statements
- P261-P272-P280-P302+P352-P333+P313-P362+P364
Chemistry & industry
Applications
UsesHinokinin (Standard) is the analytical standard of Hinokinin. This product is intended for research and analytical applications. Hinokinin (Compound 1) is a compound isolated from the stems of Hypoestes aristate. Hinokinin exhibits moderate activity of HIV-1 protease enzyme.
Additional notes
DefinitionChEBI: A lignan that is dihydrofuran-2(3H)-one (gamma-butyrolactone) substituted by a 3,4-methylenedioxybenzyl group at positions 3 and 4 (the 3R,4R-diastereoisomer).
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