Tetrahydro-3,4-dipiperonylfuran-2-ol
Basic information
- CAS
18423-69-3- Standard SMILES
OC1OCC(Cc2ccc3c(c2)OCO3)C1Cc1ccc2c(c1)OCO2- InChIKey
DIYWRNLYKJKHAM-UHFFFAOYSA-N- Molecular formula
- C20H20O6
- Average molar mass
- 356.4 g/mol
- Monoisotopic mass
- 356.12598835
Overview
3,4-bis(2H-1,3-benzodioxol-5-ylmethyl)oxolan-2-ol has been reported in Piper cubeba and Piper guineense with data available.
Names & identifiers
- Preferred name
- Tetrahydro-3,4-dipiperonylfuran-2-ol
- IUPAC
- 3,4-bis(1,3-benzodioxol-5-ylmethyl)oxolan-2-ol
- English name
- CUBEBIN
- Molecular formula
- C20H20O6
- Molecular weight
- 356.37
Names & synonyms
rac-CubebinCubebineC20H20O61242843-00-0b-CubebinTetrahydro-3,4-dipiperonylfuran-2-olSCHEMBL590751DIYWRNLYKJKHAM-UHFFFAOYSA-NSZB84300NSC147747AKOS024323386Tetrahydro-3,4-dipiperonyl-2-Furanol
Show more names
CUBEBINAids002469Aids-002469CUBEBIN(RG).beta.-Cubebin2-Furanol, tetrahydro-3,4-dipiperonyl-3,4-Bis[(1,3-benzodioxol-5-yl)methyl]tetrahydrofuran-2-ol2-Furanol, 3,4-bis(1,3-benzodioxol-5-ylmethyl)tetrahydro-, (2S,3R,4R)-
NSC-147747NS000517333,4-Bis(1,3-benzodioxol-5-ylmethyl)tetrahydro-2-Furanol3,4-Bis(1,3-benzodioxol-5-ylmethyl)tetrahydro-2-furanol, 9CI3,4-bis(benzo[d][1,3]dioxol-5-ylmethyl)-tetrahydrofuran-2-ol
Database identifiers
- CAS
18423-69-3- PubChem CID
- 287685
- Nikkaji
Properties
Computed structural properties
- XLogP
- 3.4
- Topological polar surface area
- 66.4 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 4
- Heavy atoms
- 26
- Formal charge
- 0
- Complexity
- 487
Experimental & physicochemical properties
Melting Point131 - 132 °C
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 131 · 131-132°C
- alpha
- 14 · D14 -17° (acetone)
- Boiling point
- 409.21 °C · 409.21°C (rough estimate)
- Density
- 1.2029 · 1.2029 (rough estimate)
- refractive index
- 1.445 · 1.4450 (estimate)
- pka
- 13.04 · 13.04±0.60(Predicted)
- LogP
- 3.34 · 3.340 (est)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 237078 S8A · J237078S8A
Chemistry & industry
Pharmacology
Cellular LocationsMembrane
Applications
UsesCubebin is a dibenzylbutyrolactone lignan isolated from the crude hexane extract of the leaves of Zanthoxyllum naranjillo. Cubebin shows a significant anti-inflammatory activity[1].
Additional notes
DefinitionChEBI: A lignan that consists of tetrahydrofuran-2-ol substituted by two 1,3-benzodioxol-5-ylmethyl groups at positions 3 and 4 respectively (the 2S,3R,4R stereoisomer). It is isolated from the leaves of Pi er nigrum and exhibits analgesic, anti-inflammatory, antimicrobial and trypanocidal activities.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
Loading…