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1,6-hexane dithiol
1,6-Hexane dithiol is a sulfur-based compound known for its burnt, fatty, and meaty odor and flavor, often used to enhance savory notes in food products such as meat and soups.
General Material Description
1,6-Hexane dithiol is an organic compound characterized by two thiol (-SH) groups attached to a six-carbon alkane chain, making it a dithiol molecule with the molecular formula C6H14S2. It appears as a clear liquid with a distinct burnt, fatty, and meaty odor. Known under various synonyms including hexane-1,6-dithiol and 1,6-dimercaptohexane, it belongs chemically to the sulfur compound class. This compound is primarily sourced through synthetic chemical processes and is recognized for its role as a flavoring agent. Its PubChem entry (CID 14491) provides detailed chemical data. 1,6-Hexane dithiol finds applications as a potent flavor ingredient in savory food formulations due to its unique organoleptic characteristics.
Occurrence, Applicability & Potential Uses
1,6-Hexane dithiol occurs naturally in cooked beef, contributing to the characteristic meaty aroma of this food. Its presence is linked to sulfur-containing biochemicals generated during cooking processes. This compound is predominantly employed as a flavoring additive in the food industry, particularly in products aiming to replicate or enhance meaty, fatty, or burnt flavor notes. Typical uses include poultry, meat preparations, soups, and savory flavors. Regulatory frameworks such as FEMA (US) number 3495 govern its application levels, recommending that total dithiols added to foodstuffs do not exceed 1.0 ppm to ensure safety and quality. Its sensory contribution is valued for imparting a robust burnt and fatty-meaty profile at very low concentrations.
Physico-Chemical Properties Summary
1,6-Hexane dithiol is a sulfur-containing liquid with moderate volatility, displaying a boiling point near 242 to 243 °C at atmospheric pressure and reduced boiling at 118 to 119 °C under low pressure (15 mm Hg). Its specific gravity ranges narrowly around 0.995 to 0.998 at 20 °C, indicating a density close to water. The compound is partially soluble in water, with an estimated solubility of 146.9 mg/L at 25 °C, and exhibits good solubility in alcohols and fats, facilitating its use in various flavor matrices. The estimated logP value of approximately 3.2 suggests a moderate hydrophobic character, influencing its behavior in formulations. The flash point is about 90.5 °C (195 °F), implying it requires careful handling under warming conditions. These properties impact how 1,6-hexane dithiol disperses and persists in flavor systems, affecting stability and aroma delivery.
FAQ
What is 1,6-hexane dithiol and what are its main uses?
1,6-Hexane dithiol is a sulfur-containing organic compound with the formula C6H14S2, featuring two thiol groups on a six-carbon chain. It is primarily used as a flavoring agent in the food industry, especially to impart burned, fatty, and meaty notes to products such as meat, poultry, and soups. Its distinctive odor and flavor profile contribute to enhancing savory characteristics in various culinary applications.
Where does 1,6-hexane dithiol naturally occur and how is it applied in food products?
This compound naturally arises in cooked beef, where it contributes to the characteristic aroma profile developed during cooking. In food production, it is added intentionally at low levels, typically between 0.005 and 0.2 parts per million, to recreate or intensify meaty and burnt flavor notes in products like soups, meat dishes, and poultry preparations. The use levels are strictly controlled to maintain flavor balance and ensure consumer safety according to flavor industry standards.
What regulations apply to 1,6-hexane dithiol and how is its safety assessed?
1,6-Hexane dithiol is regulated under FEMA (US) flavor standards with FEMA number 3495, which includes usage limits for food applications. Safety assessments include considerations of its irritant properties and toxicity data obtained from animal studies. The recommended maximum concentration in food products is governed to be below 1.0 ppm total dithiols. Regulatory bodies such as EFSA (European Food Safety Authority) have also evaluated related sulfur compounds for their flavoring use. Manufacturers follow established guidelines to avoid potential irritancy and ensure safe consumer exposure.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
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Literature & References
| hexane-1,6-dithiol | |
| NIST Chemistry WebBook: | Search Inchi |
| Canada Domestic Sub. List: | 1191-43-1 |
| Pubchem (cid): | 14491 |
| Pubchem (sid): | 134980816 |
| 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 |
| HMDB (The Human Metabolome Database): | HMDB31709 |
| FooDB: | FDB008372 |
| Export Tariff Code: | 2930.90.9190 |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
| FAO: | 1,6-Hexanedithiol |
General Material Information
| Preferred name | 1,6-hexane dithiol |
| Trivial Name | 1,6-Hexanedithiol |
| Short Description | 1,6-hexanedithiol |
| Formula | C6H14S2 |
| CAS Number | 1191-43-1 |
| FEMA Number | 3495 |
| Flavis Number | 12.067 |
| ECHA Number | 214-735-1 |
| FDA UNII | RWN7RM884E |
| Nikkaji Number | J40.600G |
| Beilstein Number | 1732507 |
| MDL | MFCD00004910 |
| COE Number | 11486 |
| xLogP3-AA | 2.20 (est) |
| NMR Predictor | External link |
| JECFA Food Flavoring | 540 1,6-hexanedithiol |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 1191-43-1 ; 1,6-HEXANEDITHIOL |
| Synonyms |
|
Suppliers
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 150.05 |
| Specific gravity | @ 20 °C |
| Pounds per Gallon | 8.289 to 8.314 |
| Refractive Index | 1.511 to 1.515 @ 20 °C |
| Boiling Point | 118 to 119°C @ 15 mm Hg |
| Boiling Point | 242 to 243°C @ 760 mm Hg |
| Vapor Pressure | 0.051 mmHg @ 25 °C |
| Flash Point TCC Value | 90.56 °C TCC |
| logP (o/w) | 3.195 est |
| Solubility | |
| alcohol | Yes |
| fats | Yes |
| water, 146.9 mg/L @ 25 °C (est) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Burnt | |
| burnt, fatty, meaty, fungal, sulfurous | |
| General comment | At 0.10 % in propylene glycol. burnt fatty meaty fungal sulfurous |
| Flavor Type: Burnt | |
| burnt, fatty, meaty | |
| General comment | Burnt fatty meaty |
| Used in Poultry, meat, soup and other savoury flavours. Normal levels in end use: 0.005-0.2ppm. FEMA specifies that total dithiols added to a foodstuff should not exceed 1.0ppm. | Burnt; fatty-meaty, on dilution |
Occurrences
| (data available) |
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 36/37/39 - Wear suitable clothing, 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. | |
| Oral/Parenteral Toxicity: | |
| intraperitoneal-mouse LD50 100 mg/kg National Technical Information Service. Vol. AD277-689 intravenous-cat LD50 83 mg/kg BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: MUSCLE WEAKNESS BEHAVIORAL: ATAXIA Journal of Pharmacology and Experimental Therapeutics. Vol. 87(Suppl), Pg. 6, 1946. | |
| Dermal Toxicity: | |
| Not determined | |
| Inhalation Toxicity: | |
| inhalation-mouse LC > 1490 mg/m3/10 National Defense Research Committee, Office of Scientific Research and Development, Progress Report.Vol. NDCrc-132, Pg. Aug, 1942. | |
Safety in use information
| Category: | |||
| flavoring agents | |||
| Recommendation for 1,6-hexane dithiol usage levels up to: | |||
| not for fragrance use. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 1.60 (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: 10 | |||
| Click here to view publication 10 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | - | 0.20000 | |
| beverages(nonalcoholic): | - | - | |
| beverages(alcoholic): | - | - | |
| breakfast cereal: | - | - | |
| cheese: | - | - | |
| chewing gum: | - | - | |
| condiments / relishes: | - | - | |
| confectionery froastings: | - | - | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | - | - | |
| fruit ices: | - | - | |
| gelatins / puddings: | - | - | |
| granulated sugar: | - | - | |
| gravies: | - | 0.20000 | |
| hard candy: | - | - | |
| imitation dairy: | - | - | |
| instant coffee / tea: | - | - | |
| jams / jellies: | - | - | |
| meat products: | - | 0.20000 | |
| milk products: | - | - | |
| nut products: | - | - | |
| other grains: | - | - | |
| poultry: | - | - | |
| processed fruits: | - | - | |
| processed vegetables: | - | - | |
| reconstituted vegetables: | - | - | |
| seasonings / flavors: | - | - | |
| snack foods: | - | - | |
| soft candy: | - | - | |
| soups: | - | 0.20000 | |
| 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): |
| Flavouring Group Evaluation 8 (FGE.08)[1]: Aliphatic and alicyclic mono-, di-, tri-, and polysulphides with or without additional oxygenated functional groups from chemical group 20 View page or View pdf |
| Flavouring Group Evaluation 8, Revision 1 (FGE.08Rev1): Aliphatic and alicyclic mono-, di-, tri-, and polysulphides with or without additional oxygenated functional groups from chemical groups 20 and 30 View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 8, Revision 3 (FGE.08Rev3): Aliphatic and alicyclic mono-, di-, tri-, and polysulphides with or without additional oxygenated functional groups from chemical groups 20 and 30 View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 08, Revision 4 (FGE.08Rev4): Aliphatic and alicyclic mono-, di-, tri-, and polysulphides with or without additional oxygenated functional groups from chemical groups 20 and 30 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 :14491 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:3 |
| hexane-1,6-dithiol |
| Chemidplus:0001191431 |
| RTECS:MO3500000 for cas# 1191-43-1 |