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heptanoic acid
Heptanoic acid is a seven-carbon saturated fatty acid with a distinctive cheesy, waxy odor, used mainly as a flavor and fragrance agent.
General Material Description
Heptanoic acid, also known by the synonym enanthic acid, is a saturated fatty acid characterized by the molecular formula C7H14O2. It appears as a colorless liquid with a distinctive cheesy, waxy, and slightly fruity odor. This compound is naturally present in various fruits and essential oils, including apple, banana, cardamom, and bay laurel. Heptanoic acid is used extensively as a flavoring and fragrance agent due to its characteristic sensory qualities. It is well-documented in chemical databases such as ChEBI. The acid is typically derived through natural extraction from plant sources or synthesized for industrial applications.
Occurrence, Applicability & Potential Uses
Heptanoic acid occurs naturally in a variety of fruits such as apple, banana, kiwi, and passion fruit, as well as in spices including cardamom and cassia. It is found in essential oils and flavor extracts like cedarwood oil and osmanthus absolute. Its applications encompass flavor and fragrance formulations, where it imparts waxy, cheesy, and fruity notes aligning with its odor characteristics. The compound's use in foods and cosmetics adheres to standards such as FEMA (US), which provides regulatory guidance on flavoring substances. In fragrance products, compliance with IFRA (Global) codes ensures safe usage levels. Heptanoic acid also features in formulations targeting cheese and vinegar flavor profiles, emphasizing its versatility in organoleptic enhancement.
Physico-Chemical Properties Summary
Heptanoic acid is a liquid at room temperature with a melting point between -11 and -9 °C and a boiling point around 222 to 223 °C under standard atmospheric pressure. Its specific gravity ranges from 0.91 to 0.93 at 25 °C, and it has a refractive index near 1.417 to 1.427 at 20 °C. The compound exhibits moderate vapor pressure of 0.058 mmHg at 25 °C, indicating a low volatility suitable for flavor and fragrance applications. With a logP value of approximately 2.42, it possesses moderate lipophilicity, compatible with formulation in both aqueous and alcoholic matrices, as it is moderately soluble in alcohol and possesses limited water solubility. Its flash point is about 230 °F, reflecting reasonable stability under standard usage conditions.
FAQ
What is heptanoic acid and what are its main characteristics?
Heptanoic acid is a saturated fatty acid with a molecular formula C7H14O2. It is known for its distinctive cheesy, waxy, and fruity odor notes, occurring naturally in various fruits such as apple and banana, and in essential oils. It appears as a colorless liquid and is commonly employed as a flavor and fragrance ingredient.
Where is heptanoic acid found naturally and how is it used industrially?
Heptanoic acid naturally occurs in fruits including kiwi, passion fruit, and mandarin, as well as in spices like cardamom and cassia. Industrially, it is utilized as a flavoring and perfuming agent, contributing characteristic cheesy and waxy notes in foods and fragrances. Its applications must adhere to regulatory standards such as FEMA for flavorings and IFRA for fragrances.
What safety and regulatory considerations are associated with heptanoic acid?
Heptanoic acid is classified as corrosive with hazard statements requiring appropriate handling precautions. It is recognized by FEMA (US) as generally safe within specified use levels in foods. IFRA (Global) provides guidelines for fragrance usage to ensure safety in perfumery. Comprehensive safety data and risk assessments are accessible through regulatory agencies and scientific panels, guiding safe industrial and consumer applications.
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 |
Literature & References
| heptanoic acid | |
| NIST Chemistry WebBook: | Search Inchi |
| Canada Domestic Sub. List: | 111-14-8 |
| Pubchem (cid): | 8094 |
| Pubchem (sid): | 134974864 |
| Pherobase: | View |
| Publications by Info | |
| Volatile Flavor Components in Bogyojosaeng and Suhong Cultivars of Strawberry (Fragaria ananassa Duch.) | |
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 |
| FDA Indirect Additives used in Food Contact Substances: | View |
| CHEBI: | View |
| CHEMBL: | View |
| Golm Metabolome Database: | Search |
| KEGG (GenomeNet): | C17714 |
| HMDB (The Human Metabolome Database): | HMDB00666 |
| FooDB: | FDB008051 |
| YMDB (Yeast Metabolome Database): | YMDB01705 |
| Export Tariff Code: | 2915.90.1800 |
| Typical G.C. | |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
| Wikipedia: | View |
General Material Information
| Preferred name | heptanoic acid |
| Trivial Name | Heptanoic acid |
| Short Description | oenanthic acid |
| Formula | C7 H14 O2 |
| CAS Number | 111-14-8 |
| FEMA Number | 3348 |
| Flavis Number | 8.028 |
| ECHA Number | 203-838-7 |
| FDA UNII | THE3YNP39D |
| Nikkaji Number | J1.985B |
| Beilstein Number | 1744723 |
| MDL | MFCD00004426 |
| COE Number | 28 |
| Bio Activity Summary | External link |
| NMR Predictor | External link |
| JECFA Food Flavoring | 96 heptanoic acid |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 111-14-8 ; HEPTANOIC ACID |
| Synonyms |
|
Suppliers
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 130.18698120117 |
| Specific gravity | @ 25 °C |
| Pounds per Gallon | 7.572 to 7.739 |
| Refractive Index | 1.417 to 1.427 @ 20 °C |
| Melting Point | -11 to -9°C @ 760 mm Hg |
| Boiling Point | 222 to 223°C @ 760 mm Hg |
| Vapor Pressure | 0.058 mmHg @ 25 °C |
| Vapor Density | 4.4 |
| Flash Point TCC Value | 110 °C TCC |
| logP (o/w) | 2.42 |
| Solubility | |
| alcohol | Yes |
| water, 2820 mg/L @ 25 °C (exp) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Cheesy | |
| rancid, sour, cheesy, sweaty, waxy, fermented, pineapple, fruity | |
| General comment | At 1.00 % in propylene glycol. rancid sour cheesy sweat |
| Mosciano, Gerard P&F 22, No. 4, 75, (1997) | Cheesy, waxy, sweaty, fermented, pineapple and fruity |
| Flavor Type: Waxy | |
| waxy, cheesy, fruity, dirty, fatty | |
| Mosciano, Gerard P&F 22, No. 4, 75, (1997) | At 5.00 ppm. Waxy, cheesy, fruity, dirty and fatty |
Occurrences
| (data available) |
Potential Uses
| Applications | |
| Odor purposes | Banana , Fruit , Passion fruit |
| Flavoring purposes | Cheese , Vinegar |
| Other purposes | Sweaty |
| Cosmetic purposes | Perfuming agents |
Safety Information
Safety information
| Preferred SDS: View | |
| European information : | |
| Most important hazard(s): | |
| C - Corrosive. | |
| R 34 - Causes burns. S 02 - Keep out of the reach of children. S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S 28 - After contact with skin, wash immediately with plenty of water. S 36/37/39 - Wear suitable clothing, gloves and eye/face protection. S 45 - In case of accident or if you feel unwell seek medical advice immediately. | |
| 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 7000 mg/kg Food & Drug Research Laboratories, Inc., Papers. Vol. 123, Pg. -, 1976. oral-mouse LD50 6400 mg/kg Biochemical Journal. Vol. 34, Pg. 1196, 1940. intravenous-mouse LD50 1200 mg/kg BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Acta Pharmacologica et Toxicologica. Vol. 18, Pg. 141, 1961. | |
| 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 | |||
| 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: 6. Update in publication number(s): 7 | |||
| Click here to view publication 6 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | - | 8.00000 | |
| beverages(nonalcoholic): | - | 2.00000 | |
| beverages(alcoholic): | - | - | |
| breakfast cereal: | - | - | |
| cheese: | - | - | |
| chewing gum: | - | - | |
| condiments / relishes: | - | - | |
| confectionery froastings: | - | - | |
| egg products: | - | - | |
| fats / oils: | - | 6.00000 | |
| fish products: | - | - | |
| frozen dairy: | - | 2.00000 | |
| fruit ices: | - | 2.00000 | |
| gelatins / puddings: | - | 2.00000 | |
| granulated sugar: | - | - | |
| gravies: | - | - | |
| hard candy: | - | 6.00000 | |
| imitation dairy: | - | - | |
| instant coffee / tea: | - | - | |
| jams / jellies: | - | 2.00000 | |
| 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 Authority (EFSA) reference(s): |
| Flavouring Group Evaluation 6, Revision 1 (FGE.06Rev1) - Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC) View page or View pdf |
| Flavouring Group Evaluation 2, Revision 1 (FGE.02) : Branched- and straight-chain aliphatic saturated primary alcohols and related esters of primary alcohols and straight-chain carboxylic acids and one straight-chain aldehyde from chemical groups 1 and 2 (Commission Regulation (EC) No 1565/2000 of 18 July 2000) - Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC) View page or View pdf |
| Scientific Opinion on the safety and efficacy of straight-chain primary aliphatic alcohols/aldehydes/acids, acetals and esters with esters containing saturated alcohols and acetals containing saturated aldehydes (chemical group 1) when used as flavourings for all animal species View page or View pdf |
| EPI System: View |
| Daily Med:search |
| NIOSH International Chemical Safety Cards:search |
| Chemical Carcinogenesis Research Information System:Search |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA Substance Registry Services (TSCA):111-14-8 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :8094 |
| National Institute of Allergy and Infectious Diseases:Data |
| WISER:UN 3265 |
| WGK Germany:1 |
| heptanoic acid |
| Chemidplus:0000111148 |
| EPA/NOAA CAMEO:hazardous materials |
| RTECS:111-14-8 |