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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.
Chemical Structure

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
Publications by PubMed
An immunosensor based on antibody binding fragments attached to gold nanoparticles for the detection of peptides derived from avian influenza hemagglutinin h5.
Macromol. Rapid commun. 15/2014.
Telechelic Poly(disulfide)s and Related Block Copolymer.
A regenerating self-assembled gold nanoparticle-containing electrochemical impedance sensor.
Multiwall carbon nanotube-ionic liquid electrode modified with gold nanoparticles as a base for preparation of a novel impedimetric immunosensor for low level detection of human serum albumin in biological fluids.
Enhanced magneto-optical properties of semiconductor EuS nanocrystals assisted by surface plasmon resonance of gold nanoparticles.
Enhanced wavelength modulation SPR biosensor based on gold nanorods for immunoglobulin detection.
Electrophoretic separation of gold nanoparticles according to bifunctional molecules-induced charge and size.
Thiol-ene chemistry guided preparation of thiolated polymeric nanocomposite for anodic stripping voltammetric analysis of Cd2+ and Pb2+.
Greatly extended storage stability of electrochemical DNA biosensors using ternary thiolated self-assembled monolayers.
A nanostructured piezoelectric immunosensor for detection of human cardiac troponin T.
Synthesis of phthalocyanine conjugates with gold nanoparticles and liposomes for photodynamic therapy.
Microfluidic biosensor for beta-amyloid(1-42) detection using cyclic voltammetry.
Synthesis and photophysical studies of phthalocyanine-gold nanoparticle conjugates.
Highly sensitive disposable nucleic acid biosensors for direct bioelectronic detection in raw biological samples.
Highly active engineered-enzyme oriented monolayers: formation, characterization and sensing applications.
Selective determination of 3,4-dihydroxyphenylacetic acid in the presence of ascorbic acid using 4-(dimethylamino)pyridine capped gold nanoparticles immobilized on gold electrode.
Electrochemical detection of DNA hybridization using a change in flexibility.
Covalent immobilization of cholesterol oxidase on self-assembled gold nanoparticles for highly sensitive amperometric detection of cholesterol in real samples.
Electrochemical real-time detection of L-histidine via self-cleavage of DNAzymes.
Electrochemical impedimetric immunosensor for insulin like growth factor-1 using specific monoclonal antibody-nanogold modified electrode.
Aptamer-based electrochemical approach to the detection of thrombin by modification of gold nanoparticles.
Immunosensor incorporating anti-His (C-term) IgG F(ab') fragments attached to gold nanorods for detection of His-tagged proteins in culture medium.
Electrochemical DNA biosensor fabrication with hollow gold nanospheres modified electrode and its enhancement in DNA immobilization and hybridization.
High-performance glucose amperometric biosensor based on magnetic polymeric bionanocomposites.
Architectures of bilayered gold nanoparticles on UV cross-linked poly(4-vinylpyridine) thin films.
Surface plasmon resonance biosensor based on water-soluble ZnO-Au nanocomposites.
Immobilization of specific monoclonal antibody on Au nanoparticles for hGH detection by electrochemical impedance spectroscopy.
Ultrasensitive electrochemical immunosensor for ochratoxin A using gold colloid-mediated hapten immobilization.
Sensitivity enhancement of SPR biosensor with silver mirror reaction on the Ag/Au film.
Reversible end-to-end assembly of gold nanorods using a disulfide-modified polypeptide.
Immobilization of enzymes through one-pot chemical preoxidation and electropolymerization of dithiols in enzyme-containing aqueous suspensions to develop biosensors with improved performance.
Measurements of stretch lengths of gold mono-atomic wires covered with 1,6-hexanedithiol in 0.1 M NaClO4 with an electrochemical scanning tunneling microscope.
Comparison of electrochemical immunosensors based on gold nano materials and immunoblot techniques for detection of histidine-tagged proteins in culture medium.
Photosystem I/molecular wire/metal nanoparticle bioconjugates for the photocatalytic production of H2.
Accurate determination of multiple sets of single molecular conductance of Au/1,6-hexanedithiol/Au break junctions by ultra-high vacuum-scanning tunneling microscope and analyses of individual current-separation curves.
Enzymatic synthesis of polythioester by the ring-opening polymerization of cyclic thioester.
Chemo-enzymatic preparation of copolymeric polythioesters containing branched-chain thioether groups.
Interpretation of stochastic events in single molecule conductance measurements.
Electrochemical impedance spectroscopy for study of amyloid beta-peptide interactions with (-) nicotine ditartrate and (-) cotinine.
Deposition of gold nanoparticles onto thiol-functionalized multiwalled carbon nanotubes.
Resistance changes due to thermal coalescence in colloidal au/organic linker molecule multilayer films.
Electrochemical and piezoelectric quartz crystal detection of antisperm antibody based on protected Au nanoparticles with a mixed monolayer for eliminating nonspecific binding.
In situ scanning tunneling microscopy of 1,6-hexanedithiol, 1,9-nonanedithiol, 1,2-benzenedithiol, and 1,3-benzenedithiol adsorbed on pt(111) electrodes.
In situ sensing of metal ion adsorption to a thiolated surface using surface plasmon resonance spectroscopy.
Characterization of surface-confined alpha-synuclein by surface plasmon resonance measurements.
Dithiol-mediated immobilization of CdS nanoparticles from reverse micellar system onto Zn-doped silica particles and their high photocatalytic activity.
Electrochemical behavior of Au colloidal electrode through layer-by-layer self-assembly.
1,6-Hexanedithiol monolayer as a receptor for specific recognition of alkylmercury.
Organosulfur-functionalized Au, Pd, and Au-Pd nanoparticles on 1D silicon nanowire substrates: preparation and XAFS studies.
Investigations of step-growth thiol-ene polymerizations for novel dental restoratives.
Copolymeric polythioesters by lipase-catalyzed thioesterification and transthioesterification of alpha,omega-alkanedithiols.
Photoinduced plasticity in cross-linked polymers.
Direct observation of a cooperative mechanism in the adsorption of heavy metal ions to thiolated surface by in-situ surface plasmon resonance measurements.
Enzymatic synthesis of multi-component copolymers and their structural characterization.
Dithiol-mediated incorporation of CdS nanoparticles from reverse micellar system into Zn-doped SBA-15 mesoporous silica and their photocatalytic properties.
Piezoelectric quartz crystal impedance and electrochemical impedance study of HSA-diazepam interaction by nanogold-structured sensor.
Study of the immobilization of alcohol dehydrogenase on Au-colloid modified gold electrode by piezoelectric quartz crystal sensor, cyclic voltammetry, and electrochemical impedance techniques.
In-situ analysis of stepwise self-assembled 1,6-hexanedithiol multilayers by surface plasmon resonance measurements.
Sensitivity enhancement of DNA sensors by nanogold surface modification.
Gold Clustering at the Terminal Functions of Long-Chain Thiols and Amines.

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
  • 1,6-diercaptohexane
  • 1,6-dimercaptohexane
  • hexamethlyene dimercaptan
  • hexamethylene dimercaptan
  • 1,6-hexamethylenedithiol
  • 1,6-hexane dimercaptan
  • hexane-1,6-dithiol
  • 1,6-hexanedimercaptan
  • 1, 6 hexanedithiol
  • 1,6-hexanedithiol
  • USAF uctl-72
  • 1,6-Hexanedithiol
  • 1,6-Dimercaptohexane
  • 1,6-Hexanedimercaptan
  • 1,6-Hexamethylenedithiol
  • NSC 29031
  • NSC 403684

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

Potential Uses

Applications
Flavoring purposes Beef, Meat, Poultry, Soup

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 ppmaverage 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