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heptanal glyceryl acetal
Heptanal glyceryl acetal is a cyclic acetal flavor and fragrance compound notable for its earthy and fungal odor characteristics.
General Material Description
Heptanal glyceryl acetal, also known by its trivial name 2-hexyl-1,3-dioxolane-4-methanol, is a cyclic acetal derivative formed from heptanal and glycerol. Its molecular formula is C10H20O3 with a molecular weight of approximately 188.27 g/mol. This compound typically appears as a colorless to pale liquid and manifests an earthy, fungal, mossy, and sweet aroma profile. Synonyms include aldehyde C-7 glyceryl acetal and heptanal glyceryl acetal (mixed 1,2 and 1,3 acetals), reflecting variations in its acetal linkages. It is principally obtained via synthetic pathways involving the acetalization of heptanal with glycerol. Comprehensive chemical data and related information can be found through recognized databases such as PubChem. The material is primarily used in flavor and fragrance industries.
Occurrence, Applicability & Potential Uses
Heptanal glyceryl acetal is not commonly found as a natural product but is primarily synthesized for use in flavor and fragrance applications. It is especially valued for imparting earthy, fungal, and gardenia-like aroma notes. Regulatory bodies including FEMA (US) have assigned it the number 2542, recognizing it as a flavoring agent with defined usage parameters. The compound is applied in perfuming agents, contributing complexity and depth to fragrance formulations. Its role in food and beverage flavorings is established with assigned maximum usage levels to ensure consumer safety. The IFRA Code of Practice (Global) provides guidelines on its concentration limits in fragrance concentrates, supporting safe application in consumer products.
Physico-Chemical Properties Summary
Heptanal glyceryl acetal exhibits a boiling point range of approximately 271 to 272°C at atmospheric pressure, suggesting moderate volatility appropriate for olfactory delivery. Its specific gravity ranges between 0.99 and 1.003 at 25°C, nearly matching water density, while refractive index values from 1.445 to 1.455 at 20°C indicate optical clarity. The estimated logP of around 2.2 reflects a moderate hydrophobic character, favoring solubility in alcohol but only very slight solubility in water, estimated at about 1540 mg/L at 25°C. Vapor pressure is minimal at ambient temperature, measuring 0.001 mmHg, indicating low evaporation rate under storage conditions. The compound's flash point is approximately 132°C (270°F), classifying it as having moderate flammability risk. An acid value capped at 1 KOH/g confirms low acidity, supporting formulation stability. These properties influence its behavior in flavor and fragrance formulations and storage.
FAQ
What is heptanal glyceryl acetal and what are its primary characteristics?
Heptanal glyceryl acetal is a synthetic cyclic acetal compound derived from heptanal and glycerol. It is characterized by an earthy and fungal aroma with additional sweet and mossy nuances. The chemical structure includes dioxolane rings formed by reaction with glycerol, contributing to its stability and scent profile. This compound is liquid at room temperature, has moderate volatility, and serves as a flavor and fragrance ingredient.
How is heptanal glyceryl acetal used and where is it typically applied?
This compound is mainly utilized as a flavoring and perfuming agent due to its distinctive earthy and gardenia-like notes. It finds application in fragrances and food flavorings, where it enhances complexity and naturalness in scent and taste profiles. Usage levels are controlled by regulatory standards to ensure safety. It is soluble in alcohol, which facilitates its incorporation into various formulations, but it has limited water solubility. The compound is typically synthetic rather than naturally occurring.
What regulations and safety guidelines apply to heptanal glyceryl acetal?
Heptanal glyceryl acetal is recognized by FEMA (US) with number 2542 as a flavoring substance, and its use is subject to concentration limits. The IFRA Code of Practice (Global) recommends maximum levels up to 2.0% in fragrance concentrates to ensure safe exposure. Toxicological evaluations indicate no GHS hazard classification under OSHA standards, though an intraperitoneal LD50 in mice is documented at 439 mg/kg. It is listed in various regulatory databases including ECHA and FDA. Proper handling and formulation according to these guidelines support its safe use in consumer products.
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 |
| HMDB (The Human Metabolome Database): | Search |
| FooDB: | FDB009545 |
| ChemSpider: | View |
General Material Information
| Preferred name | heptanal glyceryl acetal |
| Trivial Name | 2-Hexyl-1,3-dioxolane-4-methanol |
| Short Description | heptanal glyceryl acetal (mixed 1,2 and 1,3 acetals) |
| Formula | C10 H20 O3 |
| CAS Number | 1708-35-6 |
| FEMA Number | 2542 |
| ECHA Number | 216-960-0 |
| FDA UNII | 63ZBP77DDC |
| Nikkaji Number | J42.147B |
| Beilstein Number | 0108185 |
| COE Number | 2016 |
| xLogP3-AA | 2.10 (est) |
| NMR Predictor | External link |
| JECFA Food Flavoring | 912 heptanal glyceryl acetal (mixed 1,2 and 1,3 acetals) |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 977043-66-5 ; HEPTANAL GLYCERYL ACETAL (MIXED 1,2 AND 1,3 ACETALS) |
| Synonyms |
|
Suppliers
| BOC Sciences | Ernesto Ventós |
| Penta International | Penta International Corporation |
| Ernesto Ventós S.A. |
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 188.26699829102 |
| Specific gravity | @ 25 °C |
| Pounds per Gallon | 8.238 to 8.346 |
| Refractive Index | 1.445 to 1.455 @ 20 °C |
| Boiling Point | 271 to 272°C @ 760 mm Hg |
| Acid Value | 1 max KOH/g |
| Vapor Pressure | 0.001 mmHg @ 25 °C |
| Flash Point TCC Value | 132.22 °C TCC |
| logP (o/w) | 2.207 est |
| Solubility | |
| alcohol | Yes |
| water, very slightly | Yes |
| water, 1540 mg/L @ 25 °C (est) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Earthy | |
| earthy, fungal, mossy, green, sweet | |
| General comment | At 100.00 %. earthy fungal mossy green sweet |
Potential Uses
| Applications | |
| Odor purposes | Earth , Fungus , Gardenia |
| Cosmetic purposes | Perfuming agents |
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: | |
| intraperitoneal-mouse LD50 439 mg/kg intraperitoneal-mouse LD50 439 mg/kg PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE) Archives Internationales de Pharmacodynamie et de Therapie. Vol. 85, Pg. 474, 1951. | |
| 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 heptanal glyceryl acetal usage levels up to: | |||
| 2.0000 % in the fragrance concentrate. | |||
| 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: | - | 10.00000 | |
| beverages(nonalcoholic): | - | 5.00000 | |
| beverages(alcoholic): | - | - | |
| breakfast cereal: | - | - | |
| cheese: | - | - | |
| chewing gum: | - | - | |
| condiments / relishes: | - | 100.00000 | |
| confectionery froastings: | - | - | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | - | 10.00000 | |
| fruit ices: | - | 10.00000 | |
| gelatins / puddings: | - | - | |
| granulated sugar: | - | - | |
| gravies: | - | - | |
| hard candy: | - | 10.00000 | |
| 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
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA Substance Registry Services (TSCA):1708-35-6 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :15571 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:2 |
| (2-hexyl-1,3-dioxolan-4-yl)methanol |
| Chemidplus:0001708356 |