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carotol
Sign in to saveCarotol was first isolated by scientists Asahina and Tsukamoto in 1925. It is one of the primary components found in carrot seed oil comprising approximately 40% of this essential oil. This sesquiterpene alcohol is thought to be formed in carrot seeds (Daucus carota L., Umbelliferae) during the vegetation period. Additionally, studies have shown that carotol may be involved in allelopathic interactions expressing activity as an antifungal, herbicidal and insecticidal agent.
Chemical data
- Formula
- C15H26O
- Molecular weight
- 222.37 g/mol
- IUPAC name
- (3R,3aS,8aR)-6,8a-dimethyl-3-propan-2-yl-1,2,3,4,5,8-hexahydroazulen-3a-ol
- SMILES
- CC1=CC[C@]2(CC[C@@H]([C@]2(CC1)O)C(C)C)C
- InChIKey
- XZYQCFABZDVOPN-ILXRZTDVSA-N
- XLogP
- 3.6
- Polar surface area
- 20.2 Ų
- H-bond donors
- 1
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 222.198365
Show 3 more facts
- chemical formula
- C₁₅H₂₆O
- canonical SMILES
- CC1=CCC2(CCC(C2(CC1)O)C(C)C)C
- isomeric SMILES
- CC1=CC[C@]2(CC[C@@H]([C@]2(CC1)O)C(C)C)C
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Encyclopedic overview
2 sectionsContents
- Biosynthesis
- References
Carotol was first isolated by scientists Asahina and Tsukamoto in 1925. It is one of the primary components found in carrot seed oil comprising approximately 40% of this essential oil. This sesquiterpene alcohol is thought to be formed in carrot seeds (Daucus carota L., Umbelliferae) during the vegetation period. Additionally, studies have shown that carotol may be involved in allelopathic interactions expressing activity as an antifungal, herbicidal and insecticidal agent.
==Biosynthesis== It has been proposed that there is a direct cyclisation of farnesyl pyrophosphate (FPP) to the carotol (carotane backbone). This type of cyclisation is unconventional for the typical chemistry of sesquiterpenes. The only other proposed mechanism requires a complex ten-membered ring with a methyl migration. This latter reaction, regardless of how plausible it may appear to be on paper, is energetically undesired, and through the diligent work of M. Soucek and coworkers, it was shown that the cyclization from FPP to carotol is the most probable biosynthesis route.
Excerpted from Wikipedia’s “carotol” article, available under the CC BY-SA 4.0 licence.