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cis-carveol
cis-carveol is a naturally occurring monoterpenoid alcohol used for flavor and fragrance applications, noted for its spicy odor and presence in various essential oils.
General Material Description
cis-Carveol, also known as (Z)-carveol or cis-p-mentha-1,8-dien-6-ol, is a monoterpenoid alcohol characterized by the molecular formula C10H16O. It typically occurs as a mixture with undefined chiral purity, possessing a cis stereochemical arrangement relative to the isopropenyl group. The compound features a spicy odor reminiscent of caraway, contributing to its utility in flavor and fragrance formulations. cis-Carveol is a naturally occurring ingredient found as a minor constituent in numerous essential oils derived from plant sources such as caraway seed, blood orange, and various herbal oils. More information can be accessed through the ChEBI database. It is primarily obtained by extraction from natural essential oils or synthesized for use in aroma compositions.
cis-carveol with 6S* as stereochemical center, cis relative to isopropenyl group, in practice it is a mixture or undefined chiral purity.
cis-carveol with 6S* as stereochemical center, cis relative to isopropenyl group, in practice it is a mixture or undefined chiral purity.
Occurrence, Applicability & Potential Uses
cis-Carveol naturally occurs in a variety of essential oils including those from caraway seed, blood orange, spearmint, and eucalyptus species. It is present in concentrations ranging from trace levels to approximately 0.5% in these oils, depending on the botanical source. Its spicy, caraway-like aroma makes it valuable as a flavor additive and fragrance agent. The compound is employed to impart warm, spicy notes in perfumery and flavor formulations, covering applications from food flavorings to personal care product scents. Use guidelines for cis-carveol conform to the International Fragrance Association's (IFRA) Code of Practice (Global), with recommended maximum concentrations around 4% in fragrance concentrates. This regulatory framework ensures appropriate use levels to maintain consumer safety and product performance.
Physico-Chemical Properties Summary
cis-Carveol exhibits physicochemical properties that influence its behavior in formulations. It has a molecular weight of approximately 152.24 g/mol and shows moderate lipophilicity, with an estimated logP around 2.8 indicating solubility in organic solvents and limited water miscibility. The compound's vapor pressure is low, at 0.012 mmHg at 25 °C, reflecting relatively low volatility under ambient conditions. Its flash point, measured by the tagged-cup method, is 196 °F (approximately 91 °C), suggesting stability during common formulation processes. cis-Carveol is soluble in alcohol and has limited solubility in water, which affects its incorporation in aqueous systems. These properties must be considered in fragrance and flavor creation to optimize intensity, stability, and delivery of its characteristic spicy aroma.
FAQ
What is cis-carveol and what are its sensory characteristics?
cis-Carveol is a monoterpenoid alcohol identified by the chemical formula C10H16O, known for its presence in various essential oils such as caraway seed and blood orange. It exhibits a spicy odor reminiscent of caraway and serves as an important flavor and fragrance component. The compound's structure includes a cis configuration relative to its isopropenyl group, contributing to its distinct scent profile.
Where is cis-carveol commonly found and how is it used?
This compound occurs naturally in essential oils from plants including caraway, blood orange, spearmint, and eucalyptus species at varying trace concentrations. cis-Carveol is utilized primarily in flavor and fragrance applications to impart spicy and warm notes. It is incorporated in formulations for products such as perfumes, colognes, and flavor blends in the food industry.
What regulatory standards apply to cis-carveol and how is it sourced?
Sourcing of cis-carveol typically involves extraction from natural essential oils or chemical synthesis. It is regulated under the International Fragrance Association's (IFRA) global Code of Practice, which recommends usage limits to ensure safety—commonly up to 4% concentration in fragrance concentrates. No significant hazard classification applies under OSHA standards, reflecting its general compliance for flavor and fragrance use.
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 |
| (1R,5R)-2-methyl-5-prop-1-en-2-ylcyclohex-2-en-1-ol | |
| NIST Chemistry WebBook: | Search Inchi |
| Pubchem (cid): | 330573 |
| Pubchem (sid): | 10505349 |
| Flavornet: | 1197-06-4 |
| Pherobase: | View |
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 |
| UM BBD: | Search |
| KEGG (GenomeNet): | C11395 |
| HMDB (The Human Metabolome Database): | Search |
| FooDB: | FDB003843 |
| Typical G.C. | |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
General Material Information
| Preferred name | cis-carveol |
| Trivial Name | (Z)-carveol |
| Short Description | cis-2-methyl-5-(1-methylethenyl)-2-cyclohexen-1-ol |
| Formula | C10 H16 O |
| CAS Number | 1197-06-4 |
| FDA UNII | OOZ105PLI9 |
| Nikkaji Number | J9.138C |
| xLogP3-AA | 2.10 (est) |
| Bio Activity Summary | External link |
| NMR Predictor | External link |
| Synonyms |
|
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 152.23672485352 |
| Vapor Pressure | 0.012 mmHg @ 25 °C |
| Flash Point TCC Value | 91.2 °C TCC |
| logP (o/w) | 2.819 est |
| Solubility | |
| alcohol | Yes |
| water, 519.7 mg/L @ 25 °C (est) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Spicy | |
| caraway, spicy | |
| General comment | At 100.00 %. caraway |
Occurrences
| (data available) |
Potential Uses
Safety Information
Safety information
| 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: | |||
| flavor and fragrance agents | |||
| RIFM Fragrance Material Safety Assessment: Search | |||
| IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice | |||
| Recommendation for cis-carveol usage levels up to: | |||
| 4.0000 % in the fragrance concentrate. | |||
Safety references
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :330573 |
| National Institute of Allergy and Infectious Diseases:Data |
| (1R,5R)-2-methyl-5-prop-1-en-2-ylcyclohex-2-en-1-ol |
| Chemidplus:0001197064 |