3aalpha(1H)-Azulenol, 2,3,4,5,8,8a-hexahydro-3alpha-isopropyl-6,8aalpha-dimethyl-, (+)-
PubChem CID: 287687
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| Compound Synonyms | cis-Dauc-8-en-5.beta.-ol, 3-Isopropyl-6,8a-dimethyl-2,3,4,5,8,8a-hexahydro-3a(1H)-azulenol #, SCHEMBL11031851, DTXSID70871643, XZYQCFABZDVOPN-UHFFFAOYSA-N, 3a.alpha.(1H)-Azulenol, 2,3,4,5,8,8a-hexahydro-3.alpha.-isopropyl-6,8a.alpha.-dimethyl-, (+)-, NSC147750, NSC403111, cis-Dauc-8-en-5beta -ol (Carotol), NSC-147750, NSC-403111, 6,8a-Dimethyl-3-(propan-2-yl)-2,3,4,5,8,8a-hexahydroazulen-3a(1H)-ol |
|---|---|
| Topological Polar Surface Area | 20.2 |
| Hydrogen Bond Donor Count | 1.0 |
| Heavy Atom Count | 16.0 |
| Description | Constituent of Daucus carota (carrot) 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 a antifungal, herbicidal and insecticidal agent., 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 later 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. |
| Isotope Atom Count | 0.0 |
| Molecular Complexity | 305.0 |
| Database Name | cmaup_ingredients;fooddb_chem_all;hmdb_chem_all;pubchem |
| Defined Atom Stereocenter Count | 0.0 |
| Iupac Name | 6,8a-dimethyl-3-propan-2-yl-1,2,3,4,5,8-hexahydroazulen-3a-ol |
| Prediction Hob | 0.0 |
| Class | Prenol lipids |
| Xlogp | 3.6 |
| Superclass | Lipids and lipid-like molecules |
| Subclass | Sesquiterpenoids |
| Molecular Formula | C15H26O |
| Prediction Swissadme | 1.0 |
| Inchi Key | XZYQCFABZDVOPN-UHFFFAOYSA-N |
| Fcsp3 | 0.8666666666666667 |
| Logs | -4.302 |
| Rotatable Bond Count | 1.0 |
| State | Solid |
| Logd | 3.679 |
| Synonyms | (+)-carotol, Carotol, Carotol, (+)-, cis-Dauc-8-en-5&beta, -ol (Carotol), cis-Dauc-8-en-5beta -ol (carotol), (+)-Carotol |
| Compound Name | 3aalpha(1H)-Azulenol, 2,3,4,5,8,8a-hexahydro-3alpha-isopropyl-6,8aalpha-dimethyl-, (+)- |
| Kingdom | Organic compounds |
| Prediction Hob Swissadme | 0.0 |
| Exact Mass | 222.198 |
| Formal Charge | 0.0 |
| Monoisotopic Mass | 222.198 |
| Hydrogen Bond Acceptor Count | 1.0 |
| Molecular Weight | 222.37 |
| Covalent Unit Count | 1.0 |
| Total Atom Stereocenter Count | 3.0 |
| Total Bond Stereocenter Count | 0.0 |
| Molecular Framework | Aliphatic homopolycyclic compounds |
| Esol | -3.4081063999999994 |
| Inchi | InChI=1S/C15H26O/c1-11(2)13-7-9-14(4)8-5-12(3)6-10-15(13,14)16/h5,11,13,16H,6-10H2,1-4H3 |
| Smiles | CC1=CCC2(CCC(C2(CC1)O)C(C)C)C |
| Nring | 2.0 |
| Defined Bond Stereocenter Count | 0.0 |
| Taxonomy Direct Parent | Sesquiterpenoids |
- 1. Outgoing r'ship
FOUND_INto/from Capsicum Annuum (Plant) Rel Props:Source_db:cmaup_ingredients - 2. Outgoing r'ship
FOUND_INto/from Chrysanthemum Indicum (Plant) Rel Props:Source_db:cmaup_ingredients - 3. Outgoing r'ship
FOUND_INto/from Cnidium Officinale (Plant) Rel Props:Source_db:cmaup_ingredients - 4. Outgoing r'ship
FOUND_INto/from Daucus Carota (Plant) Rel Props:Source_db:cmaup_ingredients;fooddb_chem_all - 5. Outgoing r'ship
FOUND_INto/from Glehnia Littoralis (Plant) Rel Props:Source_db:cmaup_ingredients - 6. Outgoing r'ship
FOUND_INto/from Ligusticum Sinense (Plant) Rel Props:Source_db:cmaup_ingredients - 7. Outgoing r'ship
FOUND_INto/from Petroselinum Crispum (Plant) Rel Props:Source_db:fooddb_chem_all