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cyclohexyl formate
Cyclohexyl formate is a formic acid ester with a sweet, fruity odor widely used in flavor and fragrance formulations.
General Material Description
Cyclohexyl formate is a chemical ester derived from the reaction of cyclohexanol and formic acid. It presents as a clear liquid with the molecular formula C7H12O2 and a molecular weight of approximately 128.17 g/mol. Sensory evaluation notes a sweet, fruity aroma characterized by green banana-like and ethereal qualities. Known also under synonyms such as cyclohexanol formate and formic acid cyclohexyl ester, it is indexed in chemical databases including PubChem. This compound typically occurs naturally in the floral extract of Jasminum sambac and is synthesized for use in flavor and fragrance formulations.
Occurrence, Applicability & Potential Uses
Cyclohexyl formate naturally occurs in plants such as Jasminum sambac, contributing to their characteristic scent profiles. In commercial applications, it serves primarily as a flavor and fragrance agent. Within flavor formulations, it imparts sweet, fruity notes reminiscent of banana, cherry, plum, and saffron. Its use is regulated by standards such as FEMA (US) which classifies it under flavoring substances, supporting limits on concentrations to ensure consumer safety. The IFRA (Global) standards also provide guidelines on use levels in fragrance concentrates. These regulations help maintain its applicability in food products, beverages, and perfumery.
Physico-Chemical Properties Summary
Cyclohexyl formate exhibits physicochemical characteristics relevant to its formulation and handling. The compound has a boiling range of 162 to 163 °C at atmospheric pressure, indicating moderate volatility. Its specific gravity ranges between 1.052 and 1.06 at 25 °C, and the refractive index varies from 1.439 to 1.445 at 20 °C, reflecting its optical properties. The vapor pressure is about 1.785 mmHg at 25 °C, indicative of its tendency to evaporate under ambient conditions. A LogP value of 2.1 suggests moderate lipophilicity, affecting its solubility profile, which includes solubility in acetic acid, alcohols, formic acid, and low estimated solubility in water. The flash point is approximately 49 °C (120 °F), a consideration for safe storage and processing. These properties influence how cyclohexyl formate can be incorporated into flavor and fragrance products.
FAQ
What is cyclohexyl formate and what are its main characteristics?
Cyclohexyl formate is an ester formed from cyclohexanol and formic acid, identified by the molecular formula C7H12O2. It appears as a clear liquid with a distinctive sweet, fruity odor, often described as having green banana and ethereal notes. It is used primarily as a flavor and fragrance ingredient due to these sensory properties.
Where does cyclohexyl formate occur naturally and how is it used in industry?
This compound occurs naturally in the floral extract of Jasminum sambac, contributing to its aroma. Industrially, cyclohexyl formate is used in flavor and fragrance formulations to impart fruity and sweet aromas such as banana, cherry, plum, and saffron. Its physicochemical properties support its use in various product types, including baked goods, beverages, and perfumes.
How is cyclohexyl formate regulated and what guidelines exist for its use?
Cyclohexyl formate is subject to regulation by bodies such as FEMA (Flavor and Extract Manufacturers Association) in the US and IFRA (International Fragrance Association) globally. These organizations establish usage limits and safety assessments to ensure consumer protection. For example, IFRA recommends usage levels up to 4% in fragrance concentrates. Additionally, safety data classify it as an irritant with precautions advised for skin contact.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
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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 |
| HMDB (The Human Metabolome Database): | HMDB31351 |
| FooDB: | FDB003416 |
| Export Tariff Code: | 2915.13.0000 |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
General Material Information
| Preferred name | cyclohexyl formate |
| Trivial Name | Cyclohexyl formate |
| Short Description | formic acid, cyclohexyl ester |
| Formula | C7 H12 O2 |
| CAS Number | 4351-54-6 |
| FEMA Number | 2353 |
| Flavis Number | 9.16 |
| ECHA Number | 224-415-3 |
| FDA UNII | ESO2F2836U |
| Nikkaji Number | J100.653C |
| COE Number | 498 |
| NMR Predictor | External link |
| JECFA Food Flavoring | 1095 cyclohexyl formate |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 4351-54-6 ; CYCLOHEXYL FORMATE |
| Synonyms |
|
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 128.1710357666 |
| Specific gravity | @ 25 °C |
| Pounds per Gallon | 8.754 to 8.82 |
| Refractive Index | 1.439 to 1.445 @ 20 °C |
| Boiling Point | 162 to 163°C @ 760 mm Hg |
| Vapor Pressure | 1.785 mmHg @ 25 °C |
| Flash Point TCC Value | 48.89 °C TCC |
| logP (o/w) | 2.1 |
| Solubility | |
| acetic acid | Yes |
| alcohol | Yes |
| formic acid | Yes |
| water, 1518 mg/L @ 25 °C (est) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Ethereal | |
| ethereal, cooling, sweet, fruity, banana, cherry, jammy | |
| General comment | At 100.00 %. ethereal cooling sweet fruity banana cherry jam |
| Mosciano, Gerard P&F 15, No. 1, 19, (1990) | Ethereal and cooling with sweet fruity banana nuances |
| Flavor Type: Green | |
| cooling, green, fruity, banana | |
| Mosciano, Gerard P&F 15, No. 1, 19, (1990) | At 30.00 ppm. Slightly cooling, green and fruity banana |
| General comment | Green fruity banana |
Occurrences
| (data available) |
Safety Information
Safety information
| European information : | |
| Most important hazard(s): | |
| Xi - Irritant | |
| R 38 - Irritating to skin. S 02 - Keep out of the reach of children. S 24 - Avoid contact with skin. S 36 - Wear suitable protective clothing. | |
| 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 cyclohexyl formate usage levels up to: | |||
| 4.0000 % in the fragrance concentrate. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 0.012 (μg/capita/day) | ||
| Maximised Survey-derived Daily Intakes (MSDI-USA): | 0.20 (μg/capita/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: | 7.00000 | 10.00000 | |
| beverages(nonalcoholic): | - | 11.00000 | |
| beverages(alcoholic): | - | - | |
| breakfast cereal: | - | - | |
| cheese: | - | - | |
| chewing gum: | - | - | |
| condiments / relishes: | - | - | |
| confectionery froastings: | - | - | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | - | 2.80000 | |
| fruit ices: | - | 2.80000 | |
| gelatins / puddings: | - | - | |
| granulated sugar: | - | - | |
| gravies: | - | - | |
| hard candy: | - | 8.00000 | |
| 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): |
| Flavouring Group Evaluation 51, (FGE.51)[1] - Consideration of alicyclic ketones and secondary alcohols and related esters evaluated by JECFA (59th meeting) and structurally related to alicyclic ketones, secondary alcohols and related esters evaluated by EFSA in FGE.09 (2004) - Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in Contact with Food View page or View pdf |
| Flavouring Group Evaluation 9, Revision 1: (FGE.09 Rev1)[1] - Secondary alicyclic saturated and unsaturated alcohols, ketones and esters containing secondary alicyclic alcohols from chemical groups 8 and 30, and an ester of a phenol carboxylic acid from chemical group 25 - Scientific Opinion of the Panel on Food Additives, Flavourings, Processing Aids and Materials in Contact with Food View page or View pdf |
| Flavouring Group Evaluation 9, Revision 2 (FGE.09Rev2): Secondary alicyclic saturated and unsaturated alcohols, ketones and esters containing secondary alicyclic alcohols from chemical group 8 and 30, and an ester of a phenol derivative from chemical group 25 View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 51, Revision 1 (FGE.51Rev1): Consideration of alicyclic ketones and secondary alcohols and related esters evaluated by the JECFA (59th meeting) structurally related to alicyclic ketones secondary alcohols and related esters in FGE.09Rev3 (2011) View page or View pdf |
| Flavouring Group Evaluation 51, Revision 2 (FGE.51Rev2): Consideration of alicyclic ketones and secondary alcohols and related esters evaluated by JECFA (59th meeting) structurally related to alicyclic ketones secondary alcohols and related esters in FGE.09Rev6 (2015) View page or View pdf |
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA Substance Registry Services (TSCA):4351-54-6 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :20358 |
| National Institute of Allergy and Infectious Diseases:Data |
| WISER:UN 1993 |
| WGK Germany:2 |
| cyclohexyl formate |
| Chemidplus:0004351546 |