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(R)-(-)-2-octanol
(R)-(-)-2-octanol is a chiral secondary alcohol known for its creamy cucumber odor, primarily used for research and informational purposes rather than in fragrances or flavorings.
General Material Description
(R)-(-)-2-octanol is a chiral secondary alcohol with the molecular formula C8H18O and a molecular weight of approximately 130.23 g/mol. This compound is characterized by a unique creamy cucumber-like odor when diluted in dipropylene glycol at 1.00%. It appears as a colorless liquid under standard conditions. Known by several synonyms including (2R)-octan-2-ol, L-octan-2-ol, and (R)-(-)-hexylmethylcarbinol, it has stereospecific chemical properties arising from its chirality. It is sourced primarily through chemical synthesis and is registered under CAS number 5978-70-1 or within chemical inventories such as ECHA REACH (227-777-0). For detailed chemical information, (R)-(-)-2-octanol is indexed in public databases like PubChem. Although its sensory attributes are distinctive, this compound is not used commercially in fragrances or flavorings but mainly serves informational and research roles in chemical contexts.
Occurrence, Applicability & Potential Uses
(R)-(-)-2-octanol occurs as a synthetic chiral secondary alcohol and is not commonly present in significant biological sources. Its application is largely informational, with no authorized use in fragrances or flavor additives. Regulatory frameworks such as REACH (EU) recognize this compound, but restrictions apply due to its absence from typical consumer product formulations. In industrial or research settings, it may be studied for its chiral properties or physicochemical behavior rather than for direct use as an odorant. This specialized status positions (R)-(-)-2-octanol away from widespread commercial use, aligning instead with chemical characterization and analytical investigations.
Physico-Chemical Properties Summary
(R)-(-)-2-octanol features a moderate molecular weight and exhibits a specific gravity of about 0.838 at 25°C. The compound boils within a narrow temperature range between 177°C and 178°C at atmospheric pressure (760 mm Hg). It displays relatively low vapor pressure around 0.306 mmHg at 25°C, indicating low volatility at room temperature. The estimated octanol-water partition coefficient (logP) is 2.72, suggesting moderate lipophilicity. Its solubility profile includes good miscibility with alcohol solvents and limited water solubility — approximately 990.9 mg/L estimated at 25°C. The flash point measured by the Tag Closed Cup method is 160°F (approximately 71°C). These properties influence handling and usage considerations in laboratory or industrial environments, supporting stability yet limiting applications in aqueous formulations.
FAQ
What is (R)-(-)-2-octanol and what are its main characteristics?
(R)-(-)-2-octanol is a chiral secondary alcohol with the formula C8H18O. It is distinguished by a creamy cucumber-like odor when diluted in dipropylene glycol at 1%. The compound appears as a colorless liquid with a moderate boiling point near 177–178°C and has several synonyms reflecting its stereochemistry. It is mainly used for informational and research purposes and is not common in commercial fragrance or flavor products.
Where does (R)-(-)-2-octanol occur naturally, and what are its typical applications?
(R)-(-)-2-octanol is primarily obtained through chemical synthesis and does not have significant natural biological sources. Its applications are limited almost exclusively to informational or research contexts due to the lack of registration for fragrance or flavor use. It serves as a subject for chemical studies involving chirality and physicochemical property evaluations rather than as an active ingredient in consumer products.
What regulations or safety considerations exist for (R)-(-)-2-octanol usage?
(R)-(-)-2-octanol is recognized under regulatory frameworks such as REACH (EU) with specific identifiers including CAS number 5978-70-1 and ECHA registration 227-777-0. Safety documentation indicates no classified hazards under OSHA (29 CFR 1910), and there are no established precautionary statements. Current recommendations advise against use in fragrances or flavor formulations due to the lack of authorized safety evaluations for these purposes. The substance's handling follows typical chemical safety practices with no defined oral, dermal, or inhalation toxicity data.
What is (R)-(-)-2-octanol and how is it characterized?
(R)-(-)-2-octanol is a chiral secondary alcohol with the molecular formula C8H18O, known for its specific stereochemistry at the carbon bearing the hydroxyl group. It features a creamy cucumber-like odor at dilute concentration in solvents. Various synonyms, such as (2R)-octan-2-ol and L-(−)-octan-2-ol, represent the same enantiomer. It is typically a colorless liquid with moderate boiling point and low volatility.
Where does (R)-(-)-2-octanol occur and what are its main applications?
(R)-(-)-2-octanol is generally synthetic and not a major natural product, although trace amounts might occur in some botanical extracts. It is mainly utilized in chemical research for stereochemical and analytical purposes rather than in commercial products. Its characteristic cucumber odor has been studied but it is not approved or commonly employed in flavor or fragrance applications. Regulatory bodies document it primarily for information and safety assessment.
What regulatory considerations and sourcing information apply to (R)-(-)-2-octanol?
(R)-(-)-2-octanol is catalogued under CAS number 5978-70-1 and registered in databases such as ECHA (EC number 227-777-0). According to REACH (EU) and other regional authorities, it is not authorized for use in flavors or fragrances and is classified primarily as an informational substance without specific hazard labeling under OSHA HCS (US). Suppliers typically provide it for research and industrial chemical applications rather than consumer products.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
| Google Scholar | Start search |
| Google Books | Start search |
| Google Patents | Start search |
| Perfumer & Flavorists | Start search |
| EU Patents | Start search |
| PubMeb | Start search |
| NCBI | Start search |
Literature & References
| Leffingwell: | Chirality or Article |
| (2R)-octan-2-ol | |
| NIST Chemistry WebBook: | Search Inchi |
| Canada Domestic Sub. List: | 5978-70-1 |
| Pubchem (cid): | 80080 |
| Pubchem (sid): | 135039391 |
Other Information
| (IUPAC): | Atomic Weights of the Elements 2011 (pdf) |
| Videos: | The Periodic Table of Videos |
| tgsc: | Atomic Weights use for this web site |
| (IUPAC): | Periodic Table of the Elements |
| CHEBI: | View |
| HMDB (The Human Metabolome Database): | Search |
| Export Tariff Code: | 2905.16.0010 |
| ChemSpider: | View |
General Material Information
| Preferred name | (R)-(-)-2-octanol |
| Trivial Name | (R)-2-Octanol |
| Short Description | 2-octanol, (2R)- |
| Formula | C8 H18 O |
| CAS Number | 5978-70-1 |
| ECHA Number | 227-777-0 |
| FDA UNII | 2SHB67XF6H |
| Nikkaji Number | J10.699B |
| Beilstein Number | 1719324 |
| MDL | MFCD00064284 |
| NMR Predictor | External link |
| Synonyms |
|
Suppliers
| BOC Sciences | Changzhou Longo Chemical |
| EMD Millipore | Santa Cruz Biotechnology |
| Sigma-Aldrich: Aldrich | TCI AMERICA |
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 130.23066711426 |
| Specific gravity | @ 25 °C |
| Pounds per Gallon | |
| Boiling Point | 177 to 178°C @ 760 mm Hg |
| Vapor Pressure | 0.306 mmHg @ 25 °C |
| Flash Point TCC Value | 71.1 °C TCC |
| logP (o/w) | 2.721 est |
| Solubility | |
| alcohol | Yes |
| water, 990.9 mg/L @ 25 °C (est) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Cucumber | |
| creamy, cucumber, fatty, sour | |
| General comment | At 1.00 % in dipropylene glycol. creamy cucumber fatty sour |
Safety Information
Safety information
| Preferred SDS: View | |
| Hazards identification | |
| Classification of the substance or mixture | |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) | |
| None found. | |
| GHS Label elements, including precautionary statements | |
| Pictogram | |
| Hazard statement(s) | |
| None found. | |
| Precautionary statement(s) | |
| None found. | |
| Oral/Parenteral Toxicity: | |
| Not determined | |
| Dermal Toxicity: | |
| Not determined | |
| Inhalation Toxicity: | |
| Not determined | |
Safety in use information
| Category: | |||
| information only not used for fragrances or flavors | |||
| Recommendation for (R)-(-)-2-octanol usage levels up to: | |||
| not for fragrance use. | |||
| Recommendation for (R)-(-)-2-octanol flavor usage levels up to: | |||
| not for flavor use. | |||
Safety references
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA Substance Registry Services (TSCA):5978-70-1 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :80080 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:3 |
| (2R)-octan-2-ol |
| Chemidplus:0005978701 |