1(3H)-Isobenzofuranone, 6,7-dimethoxy-3-(5,6,7,8-tetrahydro-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl)-, [S-(R*,S*)]-
Basic information
- CAS
118-08-1- Standard SMILES
COc1ccc2c(c1OC)C(=O)OC2C1c2cc3c(cc2CCN1C)OCO3- InChIKey
JZUTXVTYJDCMDU-UHFFFAOYSA-N- Molecular formula
- C21H21NO6
- Average molar mass
- 383.4 g/mol
- Monoisotopic mass
- 383.13688739
Overview
See also: (-)-Hydrastine (annotation moved to); beta-Hydrastine (annotation moved to).
Names & identifiers
- Preferred name
- 1(3H)-Isobenzofuranone, 6,7-dimethoxy-3-(5,6,7,8-tetrahydro-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl)-, [S-(R*,S*)]-
- IUPAC
- 6,7-dimethoxy-3-(6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-3H-2-benzofuran-1-one
- English name
- (-)-BETA-HYDRASTINE
- Molecular formula
- C21H21NO6
- Molecular weight
- 383.39
Names & synonyms
1(3H)-Isobenzofuranone, 6,7-dimethoxy-3-(5,6,7,8-tetrahydro-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl)-, [S-(R*,S*)]-1(3H)-Isobenzofuranone, 6,7-dimethoxy-3-(5,6,7,8-tetrahydro-6-methyl-1,3-dioxolo(4,5-g)isoquinolin-5-yl)-, (S-(R*,S*))-RefChem:40885460594-55-06,7-Dimethoxy-3-(6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-2-benzofuran-1(3H)-one73554-66-2(-)-beta-Hydrastine;(1R,9S)-beta-HydrastinePhthalide, 6,7-dimethoxy-3-(5,6,7,8-tetrahydro-6-methyl-1,3-dioxolo(4,5-g)isoquinolin-5-yl)-(-)-HydrastinOprea1_165991Oprea1_763992MLS001210424
Show more names
HYDRASTINE(-)-β-Hydrastinel-hydrastineHydrastine-RMHydrastinebase(-)-Hydrastine(+/-)-Nor-βquinolin-5-yl)-(-)--Hydrastine9S)-β-Hydrastine
MEGxp0_001472SCHEMBL1649584CHEMBL1256868DTXSID40859216JZUTXVTYJDCMDU-UHFFFAOYSA-NHMS1679F22HMS2847F12HMS3373A08
Properties
Computed structural properties
- XLogP
- 2.7
- Topological polar surface area
- 66.5 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 3
- Heavy atoms
- 28
- Formal charge
- 0
- Complexity
- 601
Physicochemical properties
- Melting point
- 132 ℃ · 132℃
- alpha
- 20 · D20 -50° (c = 0.3 in abs alc)
- Boiling point
- 510.32 °C · 510.32°C (rough estimate)
- Density
- 1.339 · 1.339±0.06 g/cm3 (20 ºC 760 Torr)
- refractive index
- 1.5614 · 1.5614 (estimate)
- storage temp.
- 20 °C · −20°C
- solubility
- 10 mg/ml; · DMF: 10 mg/ml; DMSO: 10 mg/ml
- form
- A crystalline solid
- pka
- 7.8 · 7.8(at 25℃)
- color
- White to light yellow
- Water Solubility
- 30 mg/L · 30mg/L(20 ºC)
- CAS DataBase Reference
- 118 · 118-08-1(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 8890 V3217X · 8890V3217X
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Hazard information
Regulatory InformationChemical: 1(3H)-Isobenzofuranone, 6,7-dimethoxy-3-(5,6,7,8-tetrahydro-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl)-, [S-(R*,S*)]-
Other Safety InformationEvaluation - Chemicals not considered for in depth evaluation - Not commercially active in Australia
Safety data
- wgk
- 3
- rtecs
- MU6030000
- ridadr
- 1544
- hs_code
- 2939800000
- risk_code
- 20/21/22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- safety_code
- 36
- hazard_class
- 6.1(b)
- packing_group
- III
- Hazard statements
- H302
- Precautionary statements
- P301+P312+P330
Chemistry & industry
Applications
Description(1R,9S)-(–)-β-Hydrastine is an enantiomer of the alkaloid hydrastine that inhibits dopamine biosynthesis (IC50 = 20.7 μM in PC12 cells) by inhibiting tyrosine hydroxylase activity. It inhibits dopamine release with an IC50 value of 66.5 μM in the presence of high extracellular K+ levels. It also inhibits L-type and caffeine-activated store-operated Ca2+ channels and prevents Ca2+ leakage from intracellular stores.
Usesanesthetic (local), antiarrhythmic
Uses(-)-β-Hydrastine is an inhibitor of Dopamine biosynthesis.
Additional notes
DefinitionChEBI: A natural product found in Hydrastis canadensis.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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