fragranol
cyclobutaneethanol, 1-methyl-2-(1-methylethenyl)-, (1R,2R)-
Identification
| Name | fragranol |
| IUPAC | 2-[(1R,2R)-2-isopropenyl-1-methylcyclobutyl]ethanol |
| Molecular Formula | C10 H18 O |
| Molecular Weight | 154.25266000 |
| Nikkaji Number | J237.971F |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 209.90 °C. @ 760.00 mm Hg (est) |
| Flash Point | 173.00 °F. TCC ( 78.50 °C. ) (est) |
| logP (o/w) | 2.920 (est) |
| Soluble in | water, 287.6 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for fragranol usage levels up to | not for fragrance use. |
| Recommendation for fragranol flavor usage levels up to | not for flavor use. |
No supplier data available
Potential Uses
Natural Occurrence
Synonyms
cyclobutaneethanol, 1-methyl-2-(1-methylethenyl)-, (1R,2R)-
cyclobutaneethanol, 2-isopropenyl-1-methyl-, cis-(+)-
grandisol
2-[(1R,2R)-2-iso
propenyl-1-methylcyclobutyl]ethanol
PubMed:
Toxic essential oils: anxiolytic, antinociceptive and antimicrobial properties of the yarrow Achillea umbellata Sibth. et Sm. (Asteraceae) volatiles.
PubMed:
Identification of male-produced aggregation pheromone of the curculionid beetle Sternechus subsignatus.
PubMed:
Transannular Claisen rearrangement reactions for the synthesis of vinylcyclobutanes: formal synthesis of (±)-grandisol.
PubMed:
A versatile synthetic approach to grandisol monoterpene pheromone.
PubMed:
Synthesis of grandisol, the sexual attracting insect pheromone.
PubMed:
(1R,2S,6R)-2-Hydroxymethyl-2,6-dimethyl-3-oxabicyclo[4.2.0]octane, a new volatile released by males of the papaya borer Pseudopiazurus obesus (Col.: Curculionidae).
PubMed:
An efficient synthesis of (+/-)-grandisol featuring 1,5-enyne metathesis.
PubMed:
Comparative study of the essential oils and extracts of Achillea fragrantissima (Forssk.) Sch. Bip. and Achillea santolina L. (Asteraceae) from Egypt.
PubMed:
C2-Symmetric enantiopure ethanotethered bis(alpha,beta-butenolides) as templates for asymmetric synthesis. Application to the synthesis of (+)-grandisol.
PubMed:
Preparative chiral liquid chromatography for enantiomeric separation of pheromones.
PubMed:
Strategies of a bark beetle, Pityogenes bidentatus, in an olfactory landscape.
PubMed:
An asymmetric synthesis of (+)-grandisol, a constituent of the aggregation pheromone of the cotton boll weevil, via a kinetic resolution.
PubMed:
Highly efficient, enantioselective synthesis of (+)-grandisol from a C2-symmetric bis(alpha,beta-butenolide).
PubMed:
Semiochemicals from bark beetles: New results, remarks, and reflections.
PubMed:
Enantiomeric composition of grandisol and grandisal produced byPissodes strobi andP. nemorensis and their electroantennogram response to pure enantiomers.
PubMed:
Receptor chirality and behavioral specificity of the boll weevil,Anthonomus grandis Boh. (Coleoptera: Curculionidae), for its pheromone, (+)-grandisol.
PubMed:
Extreme sensitivity of grandisal to acids.
PubMed:
Interspecific activity of semiochemicals among sibling species ofPissodes (Coleoptera: Curculionidae).
PubMed:
Aggregation pheromone of the deodar weevll,Pissodes nemorensis (Coleoptera: Curculionidae): Isolation and activity of grandisol and grandisal.
PubMed:
Aggregation pheromone components of two species ofPissodes weevils (Coleoptera: Curculionidae) Isolation, identification, and field activity.
PubMed:
Studies on terpenes. 4. Synthesis of optically active grandisol, the boll weevil pheromone.