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vanilla carboxylate
Vanilla carboxylate (methyl cyclohexanecarboxylate) is a methyl ester with fruity and vanilla odor used in flavor and fragrance applications.
General Material Description
Vanilla carboxylate, commonly known by its preferred chemical name methyl cyclohexanecarboxylate, is an organic compound classified as a methyl ester. The molecule has the formula C8H14O2 and is structurally a methyl ester of cyclohexanecarboxylic acid. It appears as a clear liquid with a distinctive fruity and vanilla aroma profile that may also include cooling and minty notes. This compound is also identified by several synonyms such as cyclohexanecarboxylic acid methyl ester and methyl hexahydrobenzoate. It is referenced in controlled chemical vocabularies like PubChem (CID 20748). Vanilla carboxylate is mainly sourced synthetically for use in flavor and fragrance formulations, mimicking fruity and vanilla sensory nuances found in natural vanilla. It is a valuable additive in products requiring pleasant aromatic characteristics derived from ester functional groups.
Occurrence, Applicability & Potential Uses
Vanilla carboxylate naturally occurs in vanilla and contributes subtly to its complex aroma. In commercial applications, it is utilized predominantly as a flavor and fragrance agent due to its fruity, minty, and vanilla-like notes. The compound enhances flavors related to banana, grape, mint, and vanilla in various consumer goods. Usage guidelines follow standards such as FEMA (US), where it is listed under FEMA number 3568, and JECFA (International), recognized as flavoring substance 962. These evaluations provide safety thresholds for incorporation in food products and fragrances. Applications include adding characteristic fruity esters to baked goods, beverages, confectionery, and personal care formulations. Its medium odor strength and long substantivity make it suitable for maintaining scent profiles over extended periods in consumer items.
Physico-Chemical Properties Summary
Vanilla carboxylate exhibits physical and chemical properties that influence its performance in formulations. It has a molecular weight of approximately 142.2 g/mol and a methyl ester functional group attached to a cyclohexane ring. The compound displays a moderate estimated log P value around 2.25, suggesting balanced lipophilicity that aids solubility in organic solvents and partial miscibility in water (approximate solubility of 453.8 mg/L at 25 °C). Specific gravity ranges from 0.99 to 0.999 at 25 °C, and the refractive index varies between 1.439 and 1.447 at 20 °C, which are typical for ester liquids. The vapor pressure is low (0.788 mmHg at 25 °C), indicating modest volatility, and the flash point is about 60 °C (140 °F), which is important for handling and safety considerations. Acid value is low (max 2 KOH/g), confirming minimal free acid content. Overall, these characteristics support its use in flavor and fragrance products where controlled volatility and solubility profiles are required.
FAQ
What is vanilla carboxylate and what are its main sensory properties?
Vanilla carboxylate, scientifically known as methyl cyclohexanecarboxylate, is a methyl ester used primarily as a flavor and fragrance compound. It emits a medium-strength fruity aroma with additional notes reminiscent of vanilla, mint, and tropical fruits. Sensory evaluations describe it as cooling and sweet with berry, banana, pineapple, and floral aspects. These properties make it valuable for enhancing fragrances and flavors requiring fruity and vanilla nuances.
Where does vanilla carboxylate occur naturally and how is it applied industrially?
This compound naturally occurs as a minor component of vanilla, contributing to its complex aromatic profile. Industrially, vanilla carboxylate is synthesized for use as a flavor and fragrance agent. It is incorporated into products such as baked goods, beverages, confectionery items, and personal care formulations to impart fruity, minty, and vanilla-like scents and tastes. Regulatory standards from FEMA and JECFA guide its safe usage levels in these applications.
What regulations and safety considerations apply to vanilla carboxylate?
Vanilla carboxylate is regulated under flavor and fragrance safety frameworks including FEMA (US) and JECFA (International), where it holds FEMA number 3568 and JECFA number 962, respectively. It is generally regarded as safe within specified concentration limits, typically up to 1.0% in fragrance concentrates. Safety data classify it as an irritant to skin and eyes under European regulation, necessitating proper handling precautions. Toxicological evaluations report an oral LD50 in rats at 3881 mg/kg. Users must follow established guidelines and wear appropriate protective equipment to mitigate irritation risks.
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 |
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): | HMDB31343 |
| FooDB: | FDB003407 |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
General Material Information
| Preferred name | vanilla carboxylate |
| Trivial Name | Methyl cyclohexanecarboxylate |
| Short Description | methyl cyclohexanecarboxylate |
| Formula | C8 H14 O2 |
| CAS Number | 4630-82-4 |
| FEMA Number | 3568 |
| Flavis Number | 9.536 |
| ECHA Number | 225-050-2 |
| FDA UNII | 96144H696Q |
| Beilstein Number | 1306359 |
| MDL | MFCD00001458 |
| COE Number | 11920 |
| xLogP3-AA | 2.20 (est) |
| NMR Predictor | External link |
| JECFA Food Flavoring | 962 methyl cyclohexanecarboxylate |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 4630-82-4 ; METHYL CYCLOHEXANECARBOXYLATE |
| Synonyms |
|
Suppliers
| BOC Sciences | Frinton Laboratories |
| Penta International | Santa Cruz Biotechnology |
| Synerzine | TCI AMERICA |
| Penta International Corporation |
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 142.19798278809 |
| Specific gravity | @ 25 °C |
| Pounds per Gallon | 8.238 to 8.313 |
| Refractive Index | 1.439 to 1.447 @ 20 °C |
| Acid Value | 2 max KOH/g |
| Vapor Pressure | 0.788 mmHg @ 25 °C |
| Flash Point TCC Value | 60 °C TCC |
| logP (o/w) | 2.248 est |
| Solubility | |
| alcohol | Yes |
| water, 453.8 mg/L @ 25 °C (est) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Fruity | |
| fruity, berry, estery, pineapple, milky, sweet, cooling, minty | |
| Odor strength | medium , recommend smelling in a 10.00 % solution or less |
| Substantivity | 200 hour(s) at 100.00 % |
| Luebke, William tgsc, (1996) | At 10.00 % in dipropylene glycol. fruity berry estery pineapple milk |
| Mosciano, Gerard P&F 18, No. 4, 51, (1993) | Sweet, cooling, minty and fruity |
| Flavor Type: Fruity | |
| cooling, fruity, ethereal, banana, musty, creamy, tropical, floral, sweet | |
| Luebke, William tgsc, (1996) | Cooling fruity ethereal banana musty creamy tropical floral |
| Mosciano, Gerard P&F 18, No. 4, 51, (1993) | At 20.00 ppm. Cooling, sweet, fruity and floral |
Occurrences
| (data available) |
Safety Information
Safety information
| Preferred SDS: View | |
| European information : | |
| Most important hazard(s): | |
| Xi - Irritant | |
| R 36/38 - Irritating to skin and eyes. 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 - 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: | |
| gavage-rat LD50 [sex: M,F] 3881 mg/kg Study acceptable but number of dosage groups has not been referred. (Moran et al., 1980) oral-rat LD50 3881 mg/kg Drug and Chemical Toxicology. Vol. 3, Pg. 249, 1980. | |
| 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 vanilla carboxylate usage levels up to: | |||
| 1.0000 % in the fragrance concentrate. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 0.073 (μg/capita/day) | ||
| Maximised Survey-derived Daily Intakes (MSDI-USA): | 0.01 (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: 11 | |||
| Click here to view publication 11 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | - | 0.10000 | |
| beverages(nonalcoholic): | - | 0.01000 | |
| beverages(alcoholic): | - | - | |
| breakfast cereal: | - | - | |
| cheese: | - | - | |
| chewing gum: | - | - | |
| condiments / relishes: | - | - | |
| confectionery froastings: | - | 0.05000 | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | - | 0.01000 | |
| fruit ices: | - | 0.01000 | |
| gelatins / puddings: | - | 0.10000 | |
| granulated sugar: | - | - | |
| gravies: | - | - | |
| hard candy: | - | - | |
| imitation dairy: | - | 0.01000 | |
| 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 ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :20748 |
| National Institute of Allergy and Infectious Diseases:Data |
| WISER:UN 3272 |
| WGK Germany:2 |
| methyl cyclohexanecarboxylate |
| Chemidplus:0004630824 |
| RTECS:GU8599000 for cas# 4630-82-4 |