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2',3-dimethyl-3',4-dioxa-2,8-dithiabicyclo(3.3.0)octane spirocyclopentane
2',3-dimethyl-3',4-dioxa-2,8-dithiabicyclo(3.3.0)octane spirocyclopentane is a sulfur-containing bicyclic compound used primarily as a meaty flavoring agent in food applications.
General Material Description
2',3-dimethyl-3',4-dioxa-2,8-dithiabicyclo(3.3.0)octane spirocyclopentane is a bicyclic organic compound characterized by a sulfur heterocyclic structure featuring oxygen and sulfur atoms incorporated into its ring system. It has the molecular formula C10H16O2S2 and exhibits a distinctive spiro-fused ring arrangement, lending it structural uniqueness among flavor compounds. This compound is also known by several trivial and systematic names such as hexahydro-2',3a-dimethylspiro[1,3-dithiolo[4,5-b]furan-2,3'(2'H)-furan] and spirobeef, reflecting its complex structural details. The molecular structure can be explored further via its PubChem entry and ChEBI database identifiers. Synthetically derived, this bicyclic molecule is primarily obtained for use in flavor development, especially in formulations targeting meat-like sensory profiles.
Occurrence, Applicability & Potential Uses
This compound does not naturally occur but is synthetically manufactured for use as a flavoring ingredient, particularly to impart meaty characteristics in various food products. It is recognized by FEMA (US) with the number 3270 and by the Joint FAO/WHO Expert Committee on Food Additives (JECFA) as substance 1296. The compound finds application specifically as a flavor agent in beverages, fats and oils, frozen dairy, fruit ices, gravies, hard candies, and soups according to regulated usage levels. Its inclusion in flavor formulations leverages the compound’s distinct odor profile to enhance the savory notes of products, often mimicking meat flavors. Usage restrictions and levels are controlled to comply with safety evaluations and regulatory standards.
Physico-Chemical Properties Summary
2',3-dimethyl-3',4-dioxa-2,8-dithiabicyclo(3.3.0)octane spirocyclopentane is a bicyclic molecule with sulfur and oxygen heteroatoms contributing to its chemical properties. Its molecular weight is approximately 232.36 g/mol. The compound features a moderate estimated logP value around 2.8, indicating a balanced lipophilicity that affects its solubility and flavor performance in lipid versus aqueous systems. It has a specific gravity ranging from 1.2 to 1.208 at 25°C and a refractive index of approximately 1.56 at 20°C, properties relevant to its identification and quality control in formulations. The boiling point ranges between 135 and 140°C at reduced pressure (3 mm Hg), consistent with its moderate volatility. Its very low vapor pressure at room temperature (5.0E-5 mmHg at 25°C) indicates limited volatility under ambient conditions, which is favorable for controlled flavor release. The compound shows good solubility in alcohol and low but measurable solubility in water (~69 mg/L at 25°C). These physicochemical characteristics influence its application and stability in flavor systems.
FAQ
What is 2',3-dimethyl-3',4-dioxa-2,8-dithiabicyclo(3.3.0)octane spirocyclopentane?
2',3-dimethyl-3',4-dioxa-2,8-dithiabicyclo(3.3.0)octane spirocyclopentane is a bicyclic organosulfur compound used primarily as a flavoring agent. It has a complex sulfur- and oxygen-containing ring system, with a molecular formula of C10H16O2S2. The compound is known for its meaty flavor notes and is utilized to enhance savory characteristics in food products. It is also referred to by multiple systematic and trivial names including hexahydro-2',3a-dimethylspiro[1,3-dithiolo[4,5-b]furan-2,3'(2'H)-furan] and the trade name spirobeef.
How and where is this compound used as a flavoring agent?
This compound is synthetically manufactured and incorporated into flavor formulations to impart meaty, savory notes. It is applied in diverse food categories such as nonalcoholic beverages, fats and oils, frozen dairy products, fruit ices, gravies, hard candy, and soups. The compound's moderate volatility and solubility traits make it suitable for blending into both aqueous and lipid food matrices, enabling controlled flavor release. Regulatory bodies like FEMA (US) specify usage limits to ensure consumer safety while achieving desirable culinary effects.
What regulations and safety evaluations apply to this flavor compound?
The compound is recognized by FEMA (US) with the number 3270 and by JECFA (FAO/WHO) as substance 1296. Safety evaluations classify it within structure class III using Threshold of Concern principles. Usage levels are regulated with detailed maximum levels in various food categories to assure safety, as documented in FEMA GRAS assessments and JECFA reviews. There are no hazard classifications identified under OSHA Hazard Communication Standards, and extensive toxicology data, including genotoxicity and subchronic studies, support its authorized use within regulated limits.
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 |
| FDA Substances Added to Food (formerly EAFUS): | View |
| HMDB (The Human Metabolome Database): | HMDB37809 |
| FooDB: | FDB016954 |
| ChemSpider: | View |
| EFSA Update of results on the monitoring of furan levels in food: | Read Report |
| EFSA Previous report: Results on the monitoring of furan levels in food: | Read Report |
| EFSA Report of the CONTAM Panel on provisional findings on furan in food: | Read Report |
General Material Information
| Preferred name | 2',3-dimethyl-3',4-dioxa-2,8-dithiabicyclo(3.3.0)octane spirocyclopentane |
| Trivial Name | Hexahydro-2′,3a-dimethylspiro[1,3-dithiolo[4,5-b]furan-2,3′(2′H)-furan] |
| Short Description | spiro(2,4-dithia-1-methyl-8-oxabicyclo(3.3.0)octane-3,3'-(1'-oxa-2-methyl)cyclopentane) |
| Formula | C10 H16 O2 S2 |
| CAS Number | 38325-25-6 |
| FEMA Number | 3270 |
| Flavis Number | 15.007 |
| ECHA Number | 253-884-7 |
| FDA UNII | TER5ZXE00D |
| Nikkaji Number | J294.644K |
| COE Number | 2325 |
| xLogP3-AA | 2.10 (est) |
| NMR Predictor | External link |
| JECFA Food Flavoring | 1296 spiro[2,4-dithia-1-methyl-8-oxabicyclo(3.3.0)octane-3,3'-(1'-oxa-2'-methyl)-cyclopentane] |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 38325-25-6 ; SPIRO(2,4-DITHIA-1-METHYL-8-OXABICYCLO(3.3.0)OCTANE-3,3'-(1'-OXA-2'-METHYL)CYCLOPENTANE) |
| Synonyms |
|
Suppliers
| BOC Sciences | Parchem |
| Penta International | Shijiazhuang Donglian Nankai Aroma Chemicals |
| Penta International Corporation |
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 232.36592102051 |
| Specific gravity | @ 25 °C |
| Pounds per Gallon | 9.985 to 10.052 |
| Refractive Index | 1.559 to 1.565 @ 20 °C |
| Boiling Point | 135 to 140°C @ 3 mm Hg |
| Vapor Pressure | 5.0E-5 mmHg @ 25 °C |
| Flash Point TCC Value | 169.44 °C TCC |
| logP (o/w) | 2.832 est |
| Solubility | |
| alcohol | Yes |
| water, 68.67 mg/L @ 25 °C (est) | Yes |
| water | No |
Organoleptic Properties
| Flavor Type: Meaty | |
| meaty | |
| General comment | Meaty |
Potential Uses
| Applications | |
| Flavoring purposes | Meat |
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: | |
| Not determined | |
| Dermal Toxicity: | |
| Not determined | |
| Inhalation Toxicity: | |
| Not determined | |
Safety in use information
| Category: | |||
| flavoring agents | |||
| Recommendation for 2',3-dimethyl-3',4-dioxa-2,8-dithiabicyclo(3.3.0)octane spirocyclopentane usage levels up to: | |||
| not for fragrance use. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 6.10 (μg/capita/day) | ||
| Threshold of Concern: | 90 (μg/person/day) | ||
| Structure Class: | III | ||
| 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: 5 | |||
| Click here to view publication 5 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | - | - | |
| beverages(nonalcoholic): | - | 0.04500 | |
| beverages(alcoholic): | - | - | |
| breakfast cereal: | - | - | |
| cheese: | - | - | |
| chewing gum: | - | - | |
| condiments / relishes: | - | - | |
| confectionery froastings: | - | - | |
| egg products: | - | - | |
| fats / oils: | - | 2.40000 | |
| fish products: | - | - | |
| frozen dairy: | - | 0.25000 | |
| fruit ices: | - | 0.25000 | |
| gelatins / puddings: | - | - | |
| granulated sugar: | - | - | |
| gravies: | - | 0.07000 | |
| hard candy: | - | 0.10000 | |
| imitation dairy: | - | - | |
| instant coffee / tea: | - | - | |
| jams / jellies: | - | - | |
| meat products: | - | 0.07000 | |
| milk products: | - | - | |
| nut products: | - | - | |
| other grains: | - | - | |
| poultry: | - | - | |
| processed fruits: | - | - | |
| processed vegetables: | - | - | |
| reconstituted vegetables: | - | - | |
| seasonings / flavors: | - | - | |
| snack foods: | - | - | |
| soft candy: | - | - | |
| soups: | - | 0.07000 | |
| 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): |
| 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 |
| Scientific Opinion on Flavouring Group Evaluation 08, Revision 5 (FGE.08Rev5): 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 Substance Registry Services (TSCA):38325-25-6 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :61979 |
| National Institute of Allergy and Infectious Diseases:Data |
| 2',3a-dimethylspiro[6,6a-dihydro-5H-[1,3]dithiolo[4,5-b]furan-2,3'-oxolane] |
| Chemidplus:0038325256 |