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Juvabione
Sign in to saveJuvabione, historically known as the paper factor, is the methyl ester of todomatuic acid. Both are sesquiterpenes (C15) found in the wood of true firs of the genus Abies. They occur naturally as part of a mixture of sesquiterpenes based upon the bisabolane scaffold. Sesquiterpenes of this family are known as insect juvenile hormone analogues (IJHA) because of their ability to mimic juvenile activity in order to stifle insect reproduction and growth. These compounds play important roles in conifers as the second line of defense against insect induced trauma and fungal pathogens. none|600px
Chemical data
- Formula
- C16H26O3
- Molecular weight
- 266.38 g/mol
- IUPAC name
- methyl (4R)-4-[(2R)-6-methyl-4-oxoheptan-2-yl]cyclohexene-1-carboxylate
- SMILES
- C[C@H](CC(=O)CC(C)C)[C@@H]1CCC(=CC1)C(=O)OC
- InChIKey
- IIWNDLDEVPJIBT-OLZOCXBDSA-N
- XLogP
- 3.5
- Polar surface area
- 43.4 Ų
- H-bond donors
- 0
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 266.188195
Show 5 more facts
- found in taxon
- Abies lasiocarpa
- chemical formula
- C₁₆H₂₆O₃
- isomeric SMILES
- C[C@H](CC(=O)CC(C)C)[C@@H]1CCC(=CC1)C(=O)OC
- canonical SMILES
- CC(C)CC(=O)CC(C)C1CCC(=CC1)C(=O)OC
- Commons category
- Juvabione
Sources (2)
via Wikidata · CC0
~4 min read
Encyclopedic overview
5 sectionsContents
- History
- Induction of sesquiterpene biosynthesis in conifers
- Biosynthesis of (+)-juvabione and (+)-todomatuic acid
- Notes
- References
Juvabione, historically known as the paper factor, is the methyl ester of todomatuic acid. Both are sesquiterpenes (C15) found in the wood of true firs of the genus Abies. They occur naturally as part of a mixture of sesquiterpenes based upon the bisabolane scaffold. Sesquiterpenes of this family are known as insect juvenile hormone analogues (IJHA) because of their ability to mimic juvenile activity in order to stifle insect reproduction and growth. These compounds play important roles in conifers as the second line of defense against insect induced trauma and fungal pathogens. none|600px
==History== In 1965, Karel Sláma and Carroll Williams made a surprising discovery: paper towels made from the wood of the balsam fir (Abies balsamea, Fig. 1) released vapors that elicited a potent effect on hemipteran bugs of the Pyrrhocoridae family. They named this substance "the paper factor." It was thought to contain a mixture of JH-mimicking sesquiterpenes, but it wasn't until 1966 that (+)-juvabione was first isolated as an active component from the balsam fir by Bowers. none|150px Figure 1. Abies balsamea
Excerpted from Wikipedia’s “Juvabione” article, available under the CC BY-SA 4.0 licence.