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gamma-thiobutyrolactone
Gamma-thiobutyrolactone is a sulfur heterocyclic compound with a burnt and garlic-like odor, commonly used as a flavoring agent and found in roasted coffee.
General Material Description
Gamma-thiobutyrolactone is a sulfur-containing heterocyclic compound characterized by a molecular formula of C4H6OS. It appears as a colorless liquid known for its distinct burnt and garlic organoleptic notes. This compound belongs to the class of thiolactones and has numerous synonyms, including 4-butyrothiolactone and thiolan-2-one, reflecting its structural variants. As listed in authoritative chemical databases such as ChEBI, gamma-thiobutyrolactone is notable for its sulfur heterocycle, which plays a significant role in its sensory properties. It is typically derived by chemical synthesis and occurs naturally in some roasted coffee products, contributing to their characteristic aroma profiles.
Occurrence, Applicability & Potential Uses
Gamma-thiobutyrolactone naturally occurs in roasted coffee, where it contributes to the complex flavor profile with its burnt and garlic-like notes. It is utilized primarily as a flavoring agent due to these distinctive sensory properties. Regulatory bodies such as FEMA (US) recognize gamma-thiobutyrolactone under FEMA number 4570 for flavor use, with specified maximum use levels in various food categories including baked goods, chewing gum, fats and oils, and frozen dairy products. Its application requires adherence to safety and concentration guidelines to achieve desired flavor effects without exceeding acceptable limits.
Physico-Chemical Properties Summary
Gamma-thiobutyrolactone is a moderately polar liquid with a specific gravity between 1.175 and 1.185 at 20°C. It displays a refractive index range of 1.518 to 1.528 at the same temperature, indicating its optical density. Its boiling point varies from 195 to 197°C at standard atmospheric pressure and reduces significantly under reduced pressure, boiling at 39 to 40°C at 1 mm Hg. The compound exhibits a vapor pressure of approximately 0.38 mmHg at 25°C and has an estimated log P value of about 1.039, reflecting limited lipophilicity. It is soluble in alcohols and moderately soluble in water (approx. 35.25 g/L at 25°C). These properties facilitate its handling and formulation in flavor applications, influencing volatility, solubility, and sensory impact. Thermal stability is evidenced by a flashpoint near 87°C (189°F).
FAQ
What is gamma-thiobutyrolactone and what are its primary characteristics?
Gamma-thiobutyrolactone is a sulfur-containing heterocyclic compound with the molecular formula C4H6OS. It features a lactone ring containing sulfur and exhibits a distinct burnt and garlic-like odor. The compound exists as a colorless liquid and is known for contributing specific sensory qualities, particularly in flavoring contexts. It has several synonyms, such as thiolan-2-one and 4-butyrothiolactone, underscoring its chemical structure and variations.
Where does gamma-thiobutyrolactone occur naturally and how is it used industrially?
This compound naturally occurs in roasted coffee, imparting part of its complex aroma with burnt and sulfurous notes. Industrially, gamma-thiobutyrolactone is used primarily as a flavoring agent. Its inclusion in various food products follows regulatory guidelines, given its potent sensory effects. Usage levels are specified for applications like baked goods, chewing gum, and frozen dairy to ensure flavor consistency and safety.
What safety regulations apply to gamma-thiobutyrolactone and how is it controlled for use?
Gamma-thiobutyrolactone is regulated as a flavoring substance by bodies including FEMA (US), where it holds FEMA number 4570. Its use is subject to recommended maximum concentration limits in different food categories to maintain safe consumption levels. Safety data indicate it is harmful if swallowed and appropriate handling precautions should be observed. No fragrance uses are recommended. Information is available through regulatory databases such as ECHA (EU) and FDA (US), ensuring compliance with relevant chemical safety standards.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
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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 |
| HMDB (The Human Metabolome Database): | HMDB31253 |
| FooDB: | FDB003286 |
| Export Tariff Code: | 2932.29.5050 |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
| FAO: | 2-Oxothiolane |
General Material Information
| Preferred name | gamma-thiobutyrolactone |
| Trivial Name | Thiobutyrolactone |
| Short Description | 2-oxothiolane |
| Formula | C4 H6 O S |
| CAS Number | 1003-10-7 |
| FEMA Number | 4570 |
| ECHA Number | 213-700-8 |
| FDA UNII | A3ERZ734SN |
| Nikkaji Number | J36.541F |
| Beilstein Number | 0105273 |
| MDL | MFCD00005479 |
| xLogP3-AA | 0.70 (est) |
| Bio Activity Summary | External link |
| NMR Predictor | External link |
| JECFA Food Flavoring | 1923 2-oxothiolane |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 1003-10-7 ; 2-OXOTHIOLANE |
| Synonyms |
|
Suppliers
| BOC Sciences | Endeavour Specialty Chemicals |
| Robinson Brothers | Santa Cruz Biotechnology |
| Sigma-Aldrich: Aldrich |
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 102.15602111816 |
| Specific gravity | @ 20 °C |
| Pounds per Gallon | 9.789 to 9.872 |
| Refractive Index | 1.518 to 1.528 @ 20 °C |
| Boiling Point | 195 to 197°C @ 760 mm Hg |
| Boiling Point | 39 to 40°C @ 1 mm Hg |
| Vapor Pressure | 0.38 mmHg @ 25 °C |
| Flash Point TCC Value | 87.22 °C TCC |
| logP (o/w) | 1.039 est |
| Solubility | |
| alcohol | Yes |
| water, 3.525e+004 mg/L @ 25 °C (est) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Garlic | |
| burnt, garlic | |
| General comment | At 0.01 % in propylene glycol. burnt garlic |
| Flavor Type: Burnt | |
| burnt, chemical | |
| General comment | Burnt chemical |
Occurrences
| (data available) |
Safety Information
Safety information
| Preferred SDS: View | |
| European information : | |
| Most important hazard(s): | |
| Xn - Harmful. | |
| R 22 - Harmful if swallowed. S 02 - Keep out of the reach of children. S 20/21 - When using do not eat, drink or smoke. 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 36/39 - Wear suitable clothing 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 199 mg/kg BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Journal of Medicinal Chemistry. Vol. 14, Pg. 846, 1971. oral-mouse LD50 1860 mg/kg Drug and Chemical Toxicology. Vol. 3, Pg. 249, 1980. | |
| Dermal Toxicity: | |
| Not determined | |
| Inhalation Toxicity: | |
| Not determined | |
Safety in use information
| Category: | |||
| flavoring agents | |||
| Recommendation for gamma-thiobutyrolactone usage levels up to: | |||
| not for fragrance use. | |||
| 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: 24 | |||
| Click here to view publication 24 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | 0.00200 | 0.02000 | |
| beverages(nonalcoholic): | 0.00030 | 0.00300 | |
| beverages(alcoholic): | - | - | |
| breakfast cereal: | - | - | |
| cheese: | - | - | |
| chewing gum: | 0.02000 | 0.20000 | |
| condiments / relishes: | - | - | |
| confectionery froastings: | - | - | |
| egg products: | - | - | |
| fats / oils: | 0.02000 | 0.20000 | |
| fish products: | - | - | |
| frozen dairy: | 0.00060 | 0.00600 | |
| fruit ices: | - | - | |
| gelatins / puddings: | - | - | |
| granulated sugar: | - | - | |
| gravies: | - | - | |
| hard candy: | 0.00200 | 0.02000 | |
| 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):1003-10-7 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :13852 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:3 |
| thiolan-2-one |
| Chemidplus:0001003107 |
| RTECS:XN1930000 for cas# 1003-10-7 |