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3,7-dimethyl-2,6-octadien-1-yl cyclopropyl carboxamide
3,7-dimethyl-2,6-octadien-1-yl cyclopropyl carboxamide is a synthetic flavoring compound used primarily as a meat flavor enhancer with a cooked, roasted odor.
General Material Description
3,7-dimethyl-2,6-octadien-1-yl cyclopropyl carboxamide, also known as N-3,7-dimethyl-2,6-octadienylcyclopropylcarboxamide, is a synthetic chemical flavoring agent with the molecular formula C14H23NO. It is characterized by a cooked brown roasted, meaty odor when diluted at 0.10% in propylene glycol. This compound is structurally classified as a cyclopropanecarboxamide derivative linked to a terpenoid-like aliphatic chain. Its synonyms include various forms of N-substituted cyclopropanecarboxamides reflecting minor variations in naming conventions used by chemical registries. The compound is sourced primarily through chemical synthesis and is documented under FEMA number 4267 and CAS number 744251-93-2. For more detailed chemical data, refer to its PubChem entry. It is used mainly as a flavoring agent to impart savory, meat-like notes in food formulations.
Occurrence, Applicability & Potential Uses
Although not naturally occurring, this compound is applied extensively in the flavor industry as a synthetic meat flavor enhancer. Its meaty, cooked aroma profile makes it suitable for inclusion in processed foods seeking to simulate or amplify meat flavors. Regulatory bodies such as FEMA (Food & Flavoring Materials Association, US) have assigned it the number 4267, recognizing its safety and permitted usage in flavor compositions. It finds use in diverse applications including baked goods, cheese, condiments, gravies, and meat products at controlled concentrations according to industry guidelines. The European Food Safety Authority and other regulatory entities have also evaluated the compound's safety for human consumption in flavorings, endorsing its controlled use under specified limits.
Physico-Chemical Properties Summary
This compound exhibits a molecular weight of approximately 221.34 g/mol, with a semi-volatile nature demonstrated by a boiling point range between 388 and 389°C at standard atmospheric pressure (760 mm Hg). Its estimated logP value of 3.255 indicates moderate lipophilicity, influencing its solubility profile; it is slightly soluble in water, with an estimated solubility of 8.726 mg/L at 25 °C, and somewhat more soluble in alcohol. The flash point is reported at 456°F, underscoring its combustible nature at high temperatures. These physicochemical properties inform formulation scientists about its behavior in flavor matrices, guiding its handling and incorporation within food systems to optimize stability and sensory performance.
FAQ
What is 3,7-dimethyl-2,6-octadien-1-yl cyclopropyl carboxamide used for?
This compound is mainly used as a synthetic flavor enhancer in the food industry, specifically to impart meaty and roasted notes in various products. It contributes a cooked brown meat aroma that enhances the sensory qualities of processed foods such as baked goods, cheese, sauces, and meat substitutes.
How is 3,7-dimethyl-2,6-octadien-1-yl cyclopropyl carboxamide regulated and where does it apply?
It is regulated under standards like FEMA (US) with FEMA number 4267, and its safety has been evaluated by organizations such as the European Food Safety Authority. Usage levels are controlled to ensure safety in food applications, with maximum permitted concentrations varying by food category. It is approved primarily for use as a flavor additive and not for fragrance purposes.
Where can I find safety and regulatory information about 3,7-dimethyl-2,6-octadien-1-yl cyclopropyl carboxamide?
Comprehensive safety data are available from FEMA GRAS publications and evaluations by EFSA and JECFA. It has been assigned CAS number 744251-93-2 and FDA UNII 0T7H9YA5WZ. Toxicological studies indicate an oral rat LD50 greater than 2000 mg/kg, and no significant hazards are classified under OSHA standards, supporting its safe use within recommended limits.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
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Literature & References
| N-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]cyclopropanecarboximidic acid | |
| NIST Chemistry WebBook: | Search Inchi |
| Pubchem (cid): | 11658617 |
| Pubchem (sid): | 23759374 |
| Publications by US Patents | |
| 7,794,768 - Saturated and unsaturated N-alkamides exhibiting taste and flavor enhancement effect in flavor compositions | |
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 |
| CHEMBL: | View |
| HMDB (The Human Metabolome Database): | HMDB32240 |
| FooDB: | FDB009327 |
| ChemSpider: | View |
General Material Information
| Preferred name | 3,7-dimethyl-2,6-octadien-1-yl cyclopropyl carboxamide |
| Trivial Name | N-[(2E)-3,7-Dimethyl-2,6-octadien-1-yl]cyclopropanecarboxamide |
| Short Description | N-3,7-dimethyl-2,6-octadienylcyclopropylcarboxamide |
| Formula | C14 H23 N O |
| CAS Number | 744251-93-2 |
| FEMA Number | 4267 |
| Flavis Number | 16.095 |
| FDA UNII | 0T7H9YA5WZ |
| xLogP3-AA | 3.40 (est) |
| NMR Predictor | External link |
| JECFA Food Flavoring | 1779 N-3,7-dimethyl-2,6-octadienyl cyclopropylcarboxamide |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 744251-93-2 ; N-3,7-DIMETHYL-2,6-OCTADIENYLCYCLOPROPYLCARBOXAMIDE |
| Synonyms |
|
Suppliers
| Parchem |
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 221.34350585938 |
| Boiling Point | 388 to 389°C @ 760 mm Hg |
| Flash Point TCC Value | 235.7 °C TCC |
| logP (o/w) | 3.255 est |
| Solubility | |
| alcohol, slightly | Yes |
| water, slightly | Yes |
| water, 8.726 mg/L @ 25 °C (est) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Meaty | |
| cooked, brown, roasted, meaty | |
| General comment | At 0.10 % in propylene glycol. cooked brown roasted meaty |
Potential Uses
| Applications | |
| Flavoring purposes | Meat |
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: | |
| oral-rat LD50 > 2000 mg/kg (Merkel, 2004) | |
| Dermal Toxicity: | |
| Not determined | |
| Inhalation Toxicity: | |
| Not determined | |
Safety in use information
| Category: | |||
| flavor enhancers | |||
| Recommendation for 3,7-dimethyl-2,6-octadien-1-yl cyclopropyl carboxamide usage levels up to: | |||
| not for fragrance use. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 61.00 (μg/capita/day) | ||
| Maximised Survey-derived Daily Intakes (MSDI-USA): | 31.00 (μg/capita/day) | ||
| Modified Theoretical Added Maximum Daily Intake (mTAMDI): | 380 (μg/person/day) | ||
| NOEL (No Observed Effect Level): | 92.00 (mg/kg bw per day) | ||
| Threshold of Concern: | 90 (μg/person/day) | ||
| Structure Class: | III | ||
| 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: 23 | |||
| Click here to view publication 23 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | 0.20000 | 1.00000 | |
| beverages(nonalcoholic): | 0.40000 | 2.00000 | |
| beverages(alcoholic): | - | - | |
| breakfast cereal: | - | - | |
| cheese: | 2.00000 | 8.00000 | |
| chewing gum: | - | - | |
| condiments / relishes: | 4.00000 | 20.00000 | |
| confectionery froastings: | - | - | |
| egg products: | 2.00000 | 10.00000 | |
| fats / oils: | - | - | |
| fish products: | 2.00000 | 10.00000 | |
| frozen dairy: | - | - | |
| fruit ices: | - | - | |
| gelatins / puddings: | - | - | |
| granulated sugar: | - | - | |
| gravies: | 4.00000 | 10.00000 | |
| hard candy: | - | - | |
| imitation dairy: | 2.00000 | 10.00000 | |
| instant coffee / tea: | - | - | |
| jams / jellies: | - | - | |
| meat products: | 2.00000 | 10.00000 | |
| milk products: | - | - | |
| nut products: | 1.00000 | 4.00000 | |
| other grains: | - | - | |
| poultry: | 2.00000 | 10.00000 | |
| processed fruits: | - | - | |
| processed vegetables: | 1.00000 | 5.00000 | |
| reconstituted vegetables: | 1.00000 | 4.00000 | |
| seasonings / flavors: | - | - | |
| snack foods: | 5.00000 | 20.00000 | |
| soft candy: | - | - | |
| soups: | 2.00000 | 10.00000 | |
| sugar substitutes: | - | - | |
| sweet sauces: | 2.00000 | 10.00000 | |
| Food categories according to Commission Regulation EC No. 1565/2000 (EC, 2000) in FGE.06 (EFSA, 2002a). According to the Industry the "normal" use is defined as the average of reported usages and "maximum use" is defined as the 95th percentile of reported usages (EFSA, 2002i). | |||
| Note: mg/kg = 0.001/1000 = 0.000001 = 1/1000000 = ppm. | |||
| average usage mg/kg | maximum usage mg/kg | ||
| Dairy products, excluding products of category 02.0 (01.0): | 0.01000 | 0.05000 | |
| Fats and oils, and fat emulsions (type water-in-oil) (02.0): | 0.01000 | 0.05000 | |
| Edible ices, including sherbet and sorbet (03.0): | 0.10000 | 0.50000 | |
| Processed fruit (04.1): | - | - | |
| Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2): | - | - | |
| Confectionery (05.0): | 1.00000 | 5.00000 | |
| Chewing gum (05.3): | - | - | |
| Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0): | - | - | |
| Bakery wares (07.0): | 0.10000 | 0.50000 | |
| Meat and meat products, including poultry and game (08.0): | 0.01000 | 0.05000 | |
| Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0): | 0.01000 | 0.05000 | |
| Eggs and egg products (10.0): | - | - | |
| Sweeteners, including honey (11.0): | - | - | |
| Salts, spices, soups, sauces, salads, protein products, etc. (12.0): | 0.01000 | 0.05000 | |
| Foodstuffs intended for particular nutritional uses (13.0): | - | - | |
| Non-alcoholic ("soft") beverages, excl. dairy products (14.1): | 1.00000 | 5.00000 | |
| Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2): | 1.00000 | 5.00000 | |
| Ready-to-eat savouries (15.0): | 0.01000 | 0.05000 | |
| Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0): | 0.01000 | 0.05000 | |
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): |
| Scientific Opinion on Flavouring Group Evaluation 94: Consideration of aliphatic amines and amides evaluated in addendum to the JECFA group aliphatic and aromatic amines and amides by JECFA View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 300 (FGE.300): One cyclo-aliphatic amide from chemical group 33 View page or View pdf |
| Statement on List of Representative Substances for Testing. The current Statement lays down a list of substances in sub-groups with representative substances for which additional data are required prior to their evaluation through the Procedure (Regulation (EC) No 1565/2000). View page or View pdf |
| (FGE.94Rev1): Consideration of aliphatic amines and amides evaluated in an addendum to the group of aliphatic and aromatic amines and amides evaluated by the JECFA (68th meeting) View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 94, Revision 2 (FGE.94Rev2): Consideration of aliphatic amines and amides evaluated in an addendum to the group of aliphatic and aromatic amines and amides evaluated by the JECFA (68th meeting) 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 :11658617 |
| National Institute of Allergy and Infectious Diseases:Data |
| N-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]cyclopropanecarboximidic acid |
| Chemidplus:0744251932 |