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absinthin
Sign in to saveAlso known as Absynthin, (+)-absinthin
Absinthin is a naturally produced triterpene lactone from the plant Artemisia absinthium (Wormwood). It constitutes one of the most bitter chemical agents responsible for absinthe's distinct taste. The compound shows biological activity and has shown promise as an anti-inflammatory agent, and should not be confused with thujone, a neurotoxin also found in Artemisia absinthium.
Chemical data
- Formula
- C30H40O6
- Molecular weight
- 496.6 g/mol
- IUPAC name
- (1R,2R,5S,8S,9S,12S,13R,14S,15S,16R,17S,20S,21S,24S)-12,17-dihydroxy-3,8,12,17,21,25-hexamethyl-6,23-dioxaheptacyclo[13.9.2.01,16.02,14.04,13.05,9.020,24]hexacosa-3,25-diene-7,22-dione
- SMILES
- C[C@H]1[C@@H]2CC[C@]([C@@H]3[C@H]4[C@H]5C=C([C@@]6([C@H]4C(=C3[C@H]2OC1=O)C)[C@@H]5[C@@](CC[C@@H]7[C@@H]6OC(=O)[C@H]7C)(C)O)C)(C)O
- InChIKey
- PZHWYURJZAPXAN-ILOFNVQHSA-N
- XLogP
- 2.2
- Polar surface area
- 93.1 Ų
- H-bond donors
- 2
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Wikidata facts
- Named after
- Artemisia absinthium
- Mass
- 496.282489
Show 6 more facts
- Commons category
- Absinthin
- found in taxon
- Artemisia carvifolia
- chemical formula
- C₃₀H₄₀O₆
- canonical SMILES
- CC1C2CCC(C3C4C5C=C(C6(C4C(=C3C2OC1=O)C)C5C(CCC7C6OC(=O)C7C)(C)O)C)(C)O
- isomeric SMILES
- C[C@H]1[C@@H]2CC[C@]([C@@H]3[C@H]4[C@H]5C=C([C@@]6([C@H]4C(=C3[C@H]2OC1=O)C)[C@@H]5[C@@](CC[C@@H]7[C@@H]6OC(=O)[C@H]7C)(C)O)C)(C)O
- has characteristic
- bitterness
via Wikidata · CC0
~5 min read
Encyclopedic overview
5 sectionsContents
- Chemical structure
- Total synthesis
- Biosynthesis
- References
- External links
Absinthin is a naturally produced triterpene lactone from the plant Artemisia absinthium (Wormwood). It constitutes one of the most bitter chemical agents responsible for absinthe's distinct taste. The compound shows biological activity and has shown promise as an anti-inflammatory agent, and should not be confused with thujone, a neurotoxin also found in Artemisia absinthium.
==Chemical structure== Absinthin's (1) complex structure is classified as a sesquiterpene lactone, meaning it belongs to a large category of natural products chemically derived from 5-carbon "building blocks" (3) derived from isoprene (4). The complete structure consists of two identical monomers (2) that are attached via a suspected naturally occurring Diels Alder reaction occurring at the alkenes on the 5-membered ring of the guaianolide.
Excerpted from Wikipedia’s “absinthin” article, available under the CC BY-SA 4.0 licence.