Structure via PubChem · Public domain (PubChem)
L-hydrastine
Sign in to saveAlso known as (3S)-6,7-dimethoxy-3-[(5R)-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-3H-2-benzofuran-1-one, hydrastine
Hydrastine is an isoquinoline alkaloid which was discovered in 1851 by Alfred P. Durand. Nitric acid induced hydrolysis of hydrastine yields hydrastinine, which was patented by Bayer as a haemostatic drug in the early 1900s. It is present in Hydrastis canadensis (thus the name) and other plants of the family Ranunculaceae.
Chemical data
- Formula
- C21H21NO6
- Molecular weight
- 383.4 g/mol
- IUPAC name
- (3S)-6,7-dimethoxy-3-[(5R)-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-3H-2-benzofuran-1-one
- SMILES
- CN1CCC2=CC3=C(C=C2[C@@H]1[C@@H]4C5=C(C(=C(C=C5)OC)OC)C(=O)O4)OCO3
- InChIKey
- JZUTXVTYJDCMDU-MOPGFXCFSA-N
- XLogP
- 2.7
- Polar surface area
- 66.5 Ų
- H-bond donors
- 0
- H-bond acceptors
- 7
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 383.136887
Show 5 more facts
- found in taxon
- Artemisia maritima
- isomeric SMILES
- CN1CCC2=CC3=C(C=C2[C@@H]1[C@@H]4C5=C(C(=C(C=C5)OC)OC)C(=O)O4)OCO3
- chemical formula
- C₂₁H₂₁NO₆
- canonical SMILES
- CN1CCC2=CC3=C(C=C2C1C4C5=C(C(=C(C=C5)OC)OC)C(=O)O4)OCO3
- described by source
- Encyclopædia Britannica 11th edition
Sources (2)
via Wikidata · CC0
~2 min read
Encyclopedic overview
5 sectionsContents
- Total synthesis
- Biological action
- See also
- References
- External links
Hydrastine is an isoquinoline alkaloid which was discovered in 1851 by Alfred P. Durand. Nitric acid induced hydrolysis of hydrastine yields hydrastinine, which was patented by Bayer as a haemostatic drug in the early 1900s. It is present in Hydrastis canadensis (thus the name) and other plants of the family Ranunculaceae.
==Total synthesis==
Excerpted from Wikipedia’s “L-hydrastine” article, available under the CC BY-SA 4.0 licence.
Gallery (2)
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