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3-octanol
3-octanol is a secondary alcohol known for its earthy, musty aroma and is used extensively as a flavor and fragrance agent in various natural extracts and essential oils.
General Material Description
3-octanol, also referred to as octan-3-ol or amyl ethyl carbinol, is a clear liquid secondary alcohol with the molecular formula C8H18O. It exhibits an earthy, mushroom-like odor with musty and creamy dairy nuances, lending complexity to natural flavor and fragrance profiles. This compound occurs naturally in numerous plants and fruits, including basil, bay leaf, and coffee, as well as various fruits such as banana and blackberry. The chemical structure includes an eight-carbon chain with a hydroxyl group on the third carbon, which influences its sensory characteristics. The controlled-vocabulary link for 3-octanol is available at ChEBI:80945. It is typically sourced from these essential oils or synthesized for use in flavoring and perfuming applications due to its distinctive aroma.
Occurrence, Applicability & Potential Uses
3-octanol naturally occurs in diverse botanical sources such as basil flower oil, bay leaf oil, peppermint oil, and various fruits including banana, cherry, and passion fruit. Its earthy and musty odor profile makes it valuable in flavoring and fragrance applications. It is applied as a flavoring agent in blue and Swiss cheeses, tropical flavors, and enhances fatty or leek notes. In fragrances, it is utilized to introduce herbal, woody, and minty nuances. The compound’s usage adheres to regulatory frameworks such as FEMA (US), where it is recognized as GRAS (Generally Recognized As Safe) with FEMA number 3581. Further, IFRA (Global) guidelines define usage levels in perfuming agents to ensure safe incorporation into consumer products.
Physico-Chemical Properties Summary
3-octanol is a clear liquid with a molecular weight of 130.23 g/mol, exhibiting a boiling point range between 173 to 175°C at standard atmospheric pressure. It possesses a specific gravity near 0.816 to 0.821 at 25°C and a refractive index of 1.425 to 1.429 at 20°C. The compound displays moderate vapor pressure of approximately 0.512 mmHg at 25°C and a vapor density around 4.5, suggesting relatively low volatility compared to lighter alcohols. It is soluble in alcohols, fixed oils, and water at an estimated concentration of 1379 mg/L at 25°C. The estimated log P value of 2.72 indicates moderate hydrophobicity, influencing its behavior in formulations and its partitioning between aqueous and lipid phases. Its flash point is about 150°F (65.6°C), which impacts handling and storage conditions.
FAQ
What is 3-octanol and what are its key characteristics?
3-octanol is a secondary alcohol with the chemical formula C8H18O, known for its earthy, musty, and creamy odor profile. It is found naturally in various plants, essential oils, and fruits such as basil, bay leaf, and banana. This compound is widely used in food flavoring and perfumery due to its characteristic sensory notes.
Where does 3-octanol commonly occur and how is it used in industry?
3-octanol occurs naturally in numerous essential oils including basil, bay leaf, peppermint, and lavender, as well as certain fruits like cherry, blackberry, and passion fruit. It serves as a flavoring agent in cheeses and tropical flavor formulations and is employed in fragrances to impart herbal, minty, and woody notes.
What regulatory standards govern the use and safety of 3-octanol?
3-octanol is recognized as Generally Recognized As Safe (GRAS) under the FEMA (US) system with FEMA number 3581. Usage levels in fragrances are guided by IFRA (Global) standards, which recommend maximum concentrations to ensure consumer safety. It is classified as an irritant with standard precautions for handling to avoid eye, skin, and respiratory contact.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
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| NCBI | Start search |
Literature & References
| octan-3-ol | |
| NIST Chemistry WebBook: | Search Inchi |
| Canada Domestic Sub. List: | 589-98-0 |
| Pubchem (cid): | 11527 |
| Pubchem (sid): | 134976731 |
| Flavornet: | 589-98-0 |
| Pherobase: | View |
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 |
| CHEBI: | View |
| CHEMBL: | View |
| KEGG (GenomeNet): | C17144 |
| HMDB (The Human Metabolome Database): | HMDB30070 |
| FooDB: | FDB003343 |
| Export Tariff Code: | 2905.16.0050 |
| Typical G.C. | |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
| Wikipedia: | View |
General Material Information
| Preferred name | 3-octanol |
| Trivial Name | 3-Octanol |
| Short Description | octan-3-ol |
| Formula | C8 H18 O |
| CAS Number | 589-98-0 |
| Deleted CAS Number | 20296-29-1 |
| FEMA Number | 3581 |
| Flavis Number | 2.098 |
| ECHA Number | 209-667-4 |
| FDA UNII | 73DZ0U3U1E |
| Nikkaji Number | J43.433G |
| Beilstein Number | 1719310 |
| MDL | MFCD00004590 |
| COE Number | 11715 |
| NMR Predictor | External link |
| JECFA Food Flavoring | 291 3-octanol |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 589-98-0 ; 3-OCTANOL |
| Synonyms |
|
Suppliers
PhysChem Properties
| Material listed in food chemical codex | Yes |
| Molecular weight | 130.23066711426 |
| Specific gravity | @ 25 °C |
| Pounds per Gallon | 6.79 to 6.832 |
| Refractive Index | 1.425 to 1.429 @ 20 °C |
| Boiling Point | 173 to 175°C @ 760 mm Hg |
| Vapor Pressure | 0.512 mmHg @ 25 °C |
| Vapor Density | 4.5 |
| Flash Point TCC Value | 65.56 °C TCC |
| logP (o/w) | 2.721 est |
| Solubility | |
| alcohol | Yes |
| fixed oils | Yes |
| water, 1379 mg/L @ 25 °C (est) | Yes |
Organoleptic Properties
| Odor Type: Earthy | |
| earthy, mushroom, herbal, melon, citrus, woody, spicy, minty, dairy, musty, creamy, waxy, fermented, green | |
| General comment | At 10.00 % in dipropylene glycol. earthy mushroom herbal melon citrus woody spicy minty |
| Mosciano, Gerard P&F 23, No. 5, 49, (1998) | At 5.00 %. Earthy, mushroom, dairy, musty, creamy, waxy with a slight fermented green minty nuance |
| Flavor Type: Musty | |
| musty, mushroom, earthy, creamy, dairy | |
| Mosciano, Gerard P&F 23, No. 5, 49, (1998) | At 5.00 ppm. Musty, mushroom, earthy, creamy dairy |
Occurrences
| (data available) |
Potential Uses
| Applications | |
| Odor purposes | Banana , Blackberry , Cherry , Coffee , Cranberry , Fungus , Grape , Herbal , Huckleberry , Lavender , Lemon , Marjoram , Mint , Passion fruit , Plum , Spearmint , Strawberry |
| Flavoring purposes | Cheese blue cheese , Cheese swiss cheese , Fat , Leek , Marjoram , Tropical |
| Other purposes | Soybean , Truffle |
| Cosmetic purposes | Perfuming agents |
Safety Information
Safety information
| Preferred SDS: View | |
| European information : | |
| Most important hazard(s): | |
| Xi - Irritant | |
| R 36/37/38 - Irritating to eyes, respiratory system, and skin. 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 37/39 - Wear suitable gloves and eye/face protection. | |
| 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. | |
| Human Experience: | |
| 12 % solution: no irritation or sensitization. | |
| Oral/Parenteral Toxicity: | |
| oral-rat LD50 > 5000 mg/kg Food and Cosmetics Toxicology. Vol. 17, Pg. 881, 1979. | |
| Dermal Toxicity: | |
| skin-rabbit LD50 > 5000 mg/kg Food and Cosmetics Toxicology. Vol. 17, Pg. 881, 1979. | |
| 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 3-octanol usage levels up to: | |||
| 8.0000 % in the fragrance concentrate. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 4.70 (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: 11 | |||
| Click here to view publication 11 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | - | 4.80000 | |
| beverages(nonalcoholic): | - | 4.00000 | |
| beverages(alcoholic): | - | 1.00000 | |
| breakfast cereal: | - | - | |
| cheese: | - | - | |
| chewing gum: | - | 11.20000 | |
| condiments / relishes: | - | - | |
| confectionery froastings: | - | - | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | - | 4.00000 | |
| fruit ices: | - | - | |
| gelatins / puddings: | - | 4.00000 | |
| granulated sugar: | - | - | |
| gravies: | - | - | |
| hard candy: | - | - | |
| 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: | - | 10.00000 | |
| soft candy: | - | 4.00000 | |
| 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 7 (FGE.07): Saturated and unsaturated aliphatic secondary alcohols, ketones and esters of secondary alcohols and saturated linear or branched-chain carboxylic acids from chemical group 5 View page or View pdf |
| Flavouring Group Evaluation 7, Revision 1 (FGE.07Rev1): Saturated and unsaturated aliphatic secondary alcohols, ketones and esters of secondary alcohols and saturated linear or branched-chain carboxylic acids from chemical group 5 (Commission Regulation (EC) No 1565/2000 of 18 July 2000) - Scientific opinion of the Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC) on a request from the Commission View page or View pdf |
| Flavouring Group Evaluation 7, Revision 2 (FGE.07Rev2) : Saturated and unsaturated aliphatic secondary alcohols, ketones and esters of secondary alcohols and saturated linear or branched-chain carboxylic acids from chemical group 5 View page or View pdf |
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA Substance Registry Services (TSCA):589-98-0 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :11527 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:2 |
| octan-3-ol |
| Chemidplus:0000589980 |
| RTECS:RH0855000 for cas# 589-98-0 |