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cyclohexyl acetic acid
Cyclohexyl acetic acid is an alicyclic organic acid with a sharp, fatty, musty odor, used primarily as a flavor and fragrance ingredient.
General Material Description
Cyclohexyl acetic acid is an alicyclic carboxylic acid characterized by the molecular formula C8H14O2. It appears as a clear liquid exhibiting a sharp acidic odor with fatty, musty, powdery and caramel-like nuances. This compound is also referred to by synonyms including cyclohexaneacetic acid, cyclohexyl ethanoic acid, and 2-cyclohexylacetic acid. Structurally, it comprises a cyclohexyl ring attached to an acetic acid moiety. It is sourced primarily via synthetic organic processes and is documented in controlled-vocabulary databases such as ChEBI. Due to its distinctive sensory characteristics, it finds specialized applications in flavor and fragrance industries.
Occurrence, Applicability & Potential Uses
Cyclohexyl acetic acid occurs predominantly as a synthetic compound rather than a natural product. It has found application as a flavoring and fragrance agent, contributing sharp acidic notes with underlying fatty and caramel elements reminiscent of honey and cocoa. Its inclusion in flavor formulations typically relates to enhancing caramel, chocolate, coffee, honey, and maple flavor profiles. Regulatory frameworks such as FEMA (US) recognize it under the FEMA number 2347 and classify it among substances generally recognized as safe (GRAS) at specified usage levels. IFRA (Global) provides guidance on safe use concentrations within fragrance blends to ensure consumer safety and product compliance.
Physico-Chemical Properties Summary
Cyclohexyl acetic acid possesses a molecular weight of approximately 142.2 g/mol and exhibits moderate lipophilicity, with a logarithmic partition coefficient (log P) near 2.85, indicating balanced solubility between aqueous and lipid phases. It melts between 28 and 33 °C and boils in the range of 242 to 243 °C at atmospheric pressure. Its specific gravity is close to 1.001–1.009 at 25 °C, and the refractive index ranges from 1.459 to 1.467 at 20 °C. The compound has a relatively low vapor pressure of 0.029 mmHg at 25 °C, signifying low volatility under ambient conditions. It dissolves moderately in water (up to approximately 2880 mg/L) and is soluble in alcohol. Its flash point is around 110 °C (230 °F). These properties influence its handling, formulation, and stability in flavor and fragrance preparations.
FAQ
What is cyclohexyl acetic acid and what are its sensory characteristics?
Cyclohexyl acetic acid is an organic acid featuring a cyclohexyl ring attached to an acetic acid group. It has a sharp, acidic odor with fatty, musty, and powdery notes combined with honey and caramel-like nuances. In flavor terms, it imparts sweet aspects reminiscent of honey, caramel, maple, and cocoa at typical usage concentrations.
How is cyclohexyl acetic acid used and where is it typically applied?
This compound is used predominantly in flavor and fragrance formulations to enhance or impart notes associated with caramel, chocolate, coffee, honey, and maple. It is employed in food flavorings regulated under FEMA GRAS status and in fragrance formulations governed by IFRA guidelines, providing nuanced acidic and fatty sensory components.
What regulatory standards and safety information apply to cyclohexyl acetic acid?
Cyclohexyl acetic acid is listed under the FEMA number 2347 and evaluated as a generally recognized as safe (GRAS) flavoring substance by the FEMA Expert Panel. IFRA (Global) regulates its use levels in fragrances to ensure consumer safety. Toxicological data indicate irritant potential to eyes, respiratory system, and skin, recommending appropriate handling precautions. It is subject to registration and classification under EU REACH regulations and documented in multiple safety databases including ECHA and FDA sources.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
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| Perfumer & Flavorists | Start search |
| EU Patents | Start search |
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| NCBI | Start search |
Literature & References
| 2-cyclohexylacetic acid | |
| NIST Chemistry WebBook: | Search Inchi |
| Canada Domestic Sub. List: | 5292-21-7 |
| Pubchem (cid): | 21363 |
| Pubchem (sid): | 134985135 |
| Publications by PubMed | |
| Propionibacterium cyclohexanicum sp. nov., a new acid-tolerant omega-cyclohexyl fatty acid-containing propionibacterium isolated from spoiled orange juice. | |
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 |
| FDA Substances Added to Food (formerly EAFUS): | View |
| CHEBI: | View |
| HMDB (The Human Metabolome Database): | HMDB31403 |
| FooDB: | FDB003477 |
| Export Tariff Code: | 2916.35.1500 |
| ChemSpider: | View |
General Material Information
| Preferred name | cyclohexyl acetic acid |
| Trivial Name | Cyclohexaneacetic acid |
| Short Description | cyclohexaneacetic acid |
| Formula | C8 H14 O2 |
| CAS Number | 5292-21-7 |
| FEMA Number | 2347 |
| Flavis Number | 8.034 |
| ECHA Number | 226-132-0 |
| FDA UNII | V43K3TO0HN |
| Nikkaji Number | J48.532B |
| Beilstein Number | 2041326 |
| MDL | MFCD00001518 |
| COE Number | 34 |
| xLogP3-AA | 2.50 (est) |
| NMR Predictor | External link |
| JECFA Food Flavoring | 965 cyclohexaneacetic acid |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 5292-21-7 ; CYCLOHEXANEACETIC ACID |
| Synonyms |
|
Suppliers
| BOC Sciences | Penta International |
| Santa Cruz Biotechnology | Sigma-Aldrich |
| Synerzine | TCI AMERICA |
| WholeChem | Penta International Corporation |
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 142.19798278809 |
| Specific gravity | @ 25 °C |
| Pounds per Gallon | 8.329 to 8.396 |
| Refractive Index | 1.459 to 1.467 @ 20 °C |
| Melting Point | 28 to 33°C @ 760 mm Hg |
| Boiling Point | 242 to 243°C @ 760 mm Hg |
| Boiling Point | 116 to 117°C @ 4 mm Hg |
| Vapor Pressure | 0.029 mmHg @ 25 °C |
| Flash Point TCC Value | 110 °C TCC |
| logP (o/w) | 2.85 |
| Solubility | |
| alcohol | Yes |
| water, 753.2 mg/L @ 25 °C (est) | Yes |
| water, 2880 mg/L @ 25 °C (exp) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Acidic | |
| sharp, acetic, fatty, cheesy, musty, powdery, honey, caramellic, acidic | |
| General comment | Sharp acetic fatty cheese musty powdery honey caramel |
| Mosciano, Gerard P&F 14, No. 6, 47, (1989) | Sharp acidic, fatty cheesy, musty, powdery, honey and caramellic |
| Flavor Type: Sweet | |
| honey, caramellic, maple, cocoa | |
| Mosciano, Gerard P&F 14, No. 6, 47, (1989) | At 100.00 ppm. Honey, caramallic, maple and cocoa |
Potential Uses
| Applications | |
| Flavoring purposes | Caramel , Chocolate cocoa , Coffee , Honey , Maple |
Safety Information
Safety information
| Preferred SDS: View | |
| European information : | |
| Most important hazard(s): | |
| Xi - Irritant | |
| R 36/37/38 - Irritating to eyes, respiratory system, and skin. S 02 - Keep out of the reach of children. S 24/25 - Avoid contact with skin and eyes. S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S 36/37/39 - Wear suitable clothing, gloves and eye/face protection. | |
| 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: | |
| intravenous-mouse LD50 178 mg/kg U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#00770 | |
| 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 | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 0.12 (μg/capita/day) | ||
| Maximised Survey-derived Daily Intakes (MSDI-USA): | 0.40 (μg/capita/day) | ||
| Threshold of Concern: | 1800 (μg/person/day) | ||
| Structure Class: | I | ||
| Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS). | |||
| The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library | |||
| publication number: 3 | |||
| Click here to view publication 3 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | - | 2.00000 | |
| beverages(nonalcoholic): | - | 1.00000 | |
| beverages(alcoholic): | - | - | |
| breakfast cereal: | - | - | |
| cheese: | - | - | |
| chewing gum: | - | - | |
| condiments / relishes: | - | - | |
| confectionery froastings: | - | - | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | - | 2.00000 | |
| fruit ices: | - | 2.00000 | |
| gelatins / puddings: | - | - | |
| granulated sugar: | - | - | |
| gravies: | - | - | |
| hard candy: | - | 2.00000 | |
| imitation dairy: | - | - | |
| instant coffee / tea: | - | - | |
| jams / jellies: | - | - | |
| meat products: | - | - | |
| milk products: | - | - | |
| nut products: | - | - | |
| other grains: | - | - | |
| poultry: | - | - | |
| processed fruits: | - | - | |
| processed vegetables: | - | - | |
| reconstituted vegetables: | - | - | |
| seasonings / flavors: | - | - | |
| snack foods: | - | - | |
| soft candy: | - | - | |
| soups: | - | - | |
| sugar substitutes: | - | - | |
| sweet sauces: | - | - | |
Safety references
| European Food Safety Athority(EFSA):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies... |
| European Food Safety Authority (EFSA) reference(s): |
| Opinion of the Scientific Panel on food additives, flavourings, processing aids and materials in contact with food (AFC) related to Flavouring Group Evaluation 12 (FGE.12); Primary saturated or unsaturated alicyclic alcohol, aldehyde, and esters from chemical group 7 (Commission Regulation (EC) No 1565/2000 of 18 July 2000) View page or View pdf |
| Primary saturated or unsaturated alicyclic alcohol, aldehyde, and esters from chemical group 7 - Flavouring Group Evaluation 12, Revision 1 - Scientific Opinion of the Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC) View page or View pdf |
| Flavouring Group Evaluation 73, (FGE.73)[1] - Consideration of alicyclic primary alcohols, aldehydes, acids and related esters evaluated by JECFA (59th meeting) structurally related to primary saturated or unsaturated alicyclic alcohol, aldehyde and esters evaluated by EFSA in FGE.12 (2005) - Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in Contact with Food View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 73, Revision 1 (FGE.73Rev1): Consideration of alicyclic primary alcohols, aldehydes, acids and related esters evaluated by JECFA (59th meeting) structurally related to primary saturated or unsaturated alicyclic alcohol, aldehyde, and esters evaluated by EFSA in FGE.12Rev2 (2011) View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 73, Revision 2 (FGE.73Rev2): Consideration of alicyclic primary alcohols, aldehydes, acids and related esters evaluated by JECFA (59th meeting) structurally related to primary saturated or unsaturated alicyclic alcohols, aldehydes, acids and esters evaluated by EFSA in FGE.12Rev3 (2012) View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 73, Revision 3 (FGE.73Rev3): Consideration of alicyclic alcohols, aldehydes, acids and related esters evaluated by JECFA (59th and 63rd meeting) structurally related to primary saturated or unsaturated alicyclic alcohols, aldehydes, acids and esters evaluated by EFSA in FGE.12Rev4 (2013) View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 73, Revision 4 (FGE.73Rev4): consideration of alicyclic alcohols, aldehydes, acids and related esters evaluated by JECFA (59th and 63rd meeting) structurally related to primary saturated or unsaturated alicyclic alcohols, aldehydes, acids and esters evaluated by EFSA in FGE.12Rev5 View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 73, Revision 5 (FGE.73Rev5): consideration of alicyclic alcohols, aldehydes, acids and related esters evaluated by JECFA (59th, 63rd and 86th meeting) and structurally related to substances evaluated in FGE.12Rev5 View page or View pdf |
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA Substance Registry Services (TSCA):5292-21-7 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :21363 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:3 |
| 2-cyclohexylacetic acid |
| Chemidplus:0005292217 |
| RTECS:GU6490000 for cas# 5292-21-7 |