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gossypol
Sign in to saveGossypol () is a natural phenol derived from the cotton plant (genus Gossypium). Gossypol is a phenolic aldehyde that permeates cells and acts as an inhibitor for several dehydrogenase enzymes. It is a yellow pigment. The structure exhibits atropisomerism, with the two enantiomers having different biochemical properties.
Chemical data
- Formula
- C30H30O8
- Molecular weight
- 518.6 g/mol
- IUPAC name
- 7-(8-formyl-1,6,7-trihydroxy-3-methyl-5-propan-2-ylnaphthalen-2-yl)-2,3,8-trihydroxy-6-methyl-4-propan-2-ylnaphthalene-1-carbaldehyde
- SMILES
- CC1=CC2=C(C(=C(C(=C2C(C)C)O)O)C=O)C(=C1C3=C(C4=C(C=C3C)C(=C(C(=C4C=O)O)O)C(C)C)O)O
- InChIKey
- QBKSWRVVCFFDOT-UHFFFAOYSA-N
- XLogP
- 6.9
- Polar surface area
- 156 Ų
- H-bond donors
- 6
- H-bond acceptors
- 8
- Formal charge
- 0
via PubChem
Research
2,424 papers- Gossypol: phytoalexin of cotton.Science China. Life sciences · 2016
- Gossypol and Semisynthetic Derivatives: Chemistry, Bioactivities, and Mechanism of Actions.Chemistry & biodiversity · 2025
- Gossypol-hypokalaemia interrelationships.International journal of andrology · 1985
- Natural Product Gossypol and its Derivatives in Precision Cancer Medicine.Current medicinal chemistry · 2019
- Gossypol--a polyphenolic compound from cotton plant.Advances in food and nutrition research · 2009
via PubMed
Wikidata facts
- Mass
- 518.194068
Show 3 more facts
- Commons category
- Gossypol
- chemical formula
- C₃₀H₃₀O₈
- canonical SMILES
- CC1=C(C(=C2C(=C1)C(=C(C(=C2C=O)O)O)C(C)C)O)C3=C(C=C4C(=C3O)C(=C(C(=C4C(C)C)O)O)C=O)C
Sources (3)
via Wikidata · CC0
~6 min read
Article
7 sectionsContents
- History
- Biosynthesis
- Research
- Contraception
- Toxicity
- References
- External links
Gossypol () is a natural phenol derived from the cotton plant (genus Gossypium). Gossypol is a phenolic aldehyde that permeates cells and acts as an inhibitor for several dehydrogenase enzymes. It is a yellow pigment. The structure exhibits atropisomerism, with the two enantiomers having different biochemical properties.
Among other applications, it has been tested as a male oral contraceptive in China. In addition to its putative contraceptive properties, gossypol has also long been known to possess antimalarial properties.