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neoisomenthol
Neoisomenthol is a cyclohexanol derivative with a mentholic odor used mainly in flavor and fragrance applications.
General Material Description
Neoisomenthol is a monoterpenoid cyclohexanol characterized by the molecular formula C10H20O and a distinctive menthol-like aroma. It appears as a colorless to pale liquid and is structurally identified as (1R,2R,5R)-5-methyl-2-(1-methylethyl)cyclohexanol. This compound shares several synonyms including dl-neoisomenthol and all-cis-2-isopropyl-5-methylcyclohexanol. As a naturally occurring constituent, it can be found at varying concentrations in essential oils such as cornmint, pennyroyal, and peppermint. Synthetic routes also exist, supplying material for its primary roles as a flavor and fragrance agent. The PubChem database (CID 1254) provides a controlled vocabulary resource for chemical information on neoisomenthol. This compound's sensory contribution is noted for its mentholic odor profile, valued in various aromatic applications.
Occurrence, Applicability & Potential Uses
Neoisomenthol occurs naturally in certain essential oils including cornmint oil and pennyroyal oil, where it can be present from trace amounts up to approximately 20% depending on the source. Additionally, it is found in small proportions within peppermint oil varieties. Its principal applications are as a flavor and fragrance agent, imparting a mentholic and refreshing note to consumer products. Regulatory frameworks such as IFRA (Global) provide guidance on its safe usage concentrations in perfumes and scents. The compound's sensory properties and chemical stability make it suitable for incorporation in flavorings, cosmetic products, and aromatic formulations, where its menthol-like effect serves specific olfactory purposes.
Physico-Chemical Properties Summary
Neoisomenthol is a cyclohexanol derivative displaying moderate hydrophobicity with an estimated logP of 3.2, indicating appreciable oil solubility. Its vapor pressure at 25 °C is 0.032 mmHg, classifying it as a low-volatility compound. The substance has a water solubility approximated at 434.5 mg/L at 25 °C, suggesting limited but noteworthy aqueous miscibility. Its flash point measured at 200 °F (approximately 93 °C) indicates a moderate flammability hazard under standard handling conditions. Physicochemical characteristics like these influence neoisomenthol's performance in formulations, affecting evaporation rate, solubility balance, and compatibility with other aromatic ingredients. These parameters are essential for product developers aiming to optimize scent release and stability.
FAQ
What is neoisomenthol and what are its main characteristics?
Neoisomenthol is a stereoisomer of menthol, specifically a cyclohexanol compound with the molecular formula C10H20O. It is known for its mentholic odor and occurs naturally in essential oils such as cornmint and pennyroyal. The compound appears as a colorless liquid and is primarily used for its aromatic properties in flavor and fragrance applications.
Where is neoisomenthol typically found and how is it used?
Neoisomenthol is found in natural sources including cornmint oil, pennyroyal oil, and peppermint oil at varying concentrations. Its sensory profile makes it valuable as a flavor and fragrance agent, adding a refreshing mentholic note to products. It is utilized in perfumery, flavor formulations, and other aromatic consumer goods where such a cooling, minty character is desired.
What regulations apply to neoisomenthol and how is its safety assessed?
Neoisomenthol’s usage is subject to standards such as the IFRA Code of Practice (Global), which sets guidelines for safe concentration levels in fragrances. The substance currently has no classification under OSHA's Hazard Communication Standard in the United States, indicating no identified major hazards in handling. Safety assessments by organizations like RIFM provide additional evaluation, but specific oral, dermal, and inhalation toxicity data remain undetermined or limited.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
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| PubMeb | Start search |
| NCBI | Start search |
Literature & References
| 5-methyl-2-propan-2-ylcyclohexan-1-ol | |
| NIST Chemistry WebBook: | Search Inchi |
| Pubchem (cid): | 1254 |
| Pubchem (sid): | 135059303 |
| Flavornet: | 491-02-1 |
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 |
| CHEMBL: | View |
| KEGG (GenomeNet): | D04849 |
| HMDB (The Human Metabolome Database): | HMDB41628 |
| FooDB: | FDB021834 |
| Typical G.C. | |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
| Formulations/Preparations: •some synthetic menthols are not chemical individuals but...mixtures of various isomers...these are designated...l-menthol, dl-menthol, l-isomenthol, d-isomenthol, dl-isomenthol, l-neomenthol, d-neomenthol, l-neoisomenthol, d-neoisomenthol and dl-neoisomenthol. •when mixed with about equal wt of camphor, chloral hydrate, phenol, or thymol, menthol forms "eutectic" mixt liquifying @ room temp. •menthol, usp drug marketed under generic name. •grades: technical; usp; fcc •synthetic menthol is available as the optically active levo-menthol with a purity of 99.9%. synthetic menthol is also commercially available as the racemic mixture •present in cigarettes and pipe tobacco (0.1-0.45%) shaving creams, pre- and aftershave lotions (0.2-0.3%); toothpastes (0.5%); mouthwashes (1-2%); chewing gums (0.5%); cough drops (0.1%); refreshing towels (1%); rubbing alcohol (1-1.2%); and shampoos (2-0.5%) •mentholatum deep heating rub contains 5.9% menthol; mentholatum ointment, 1.35%; mentholatum deep heating lotion, 6% | |
General Material Information
| Preferred name | neoisomenthol |
| Trivial Name | (±)-Neoisomenthol |
| Short Description | cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1R,2R,5R)- |
| Formula | C10 H20 O |
| CAS Number | 491-02-1 |
| Deleted CAS Number | 3623-53-8 |
| ECHA Number | 207-724-8 |
| FDA UNII | 1JE64OEH7Y |
| Nikkaji Number | J2.129F |
| MDL | MFCD01941448 |
| xLogP3-AA | 3.00 (est) |
| NMR Predictor | External link |
| Synonyms |
|
Suppliers
| Carbosynth |
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 156.26860046387 |
| Vapor Pressure | 0.032 mmHg @ 25 °C |
| Flash Point TCC Value | 93.3 °C TCC |
| logP (o/w) | 3.216 est |
| Solubility | |
| water, 434.5 mg/L @ 25 °C (est) | Yes |
Organoleptic Properties
| Odor Type: Mentholic | |
| mentholic | |
| General comment | At 10.00 % in dipropylene glycol. mentholic |
Occurrences
| (data available) |
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 | |||
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 :1254 |
| National Institute of Allergy and Infectious Diseases:Data |
| 5-methyl-2-propan-2-ylcyclohexan-1-ol |
| Chemidplus:0000491021 |