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1,2-dithiane

1,2-dithiane is a sulfur-containing cyclic compound with a characteristic sulfurous and garlic-like odor.
Chemical Structure

General Material Description

1,2-dithiane, known also as 1,2-dithiacyclohexane and tetramethylene disulfide, is a heterocyclic organosulfur compound with the molecular formula C4H8S2. This compound has a cyclic structure containing a six-membered ring with two adjacent sulfur atoms. Its sensory profile includes sulfurous and garlic-like odor notes, making it distinctive among sulfur compounds. 1,2-dithiane appears as a liquid under standard conditions, characterized by a boiling point near 173 to 174°C at atmospheric pressure. The compound's chemistry and usage are detailed in chemical databases such as ChEBI. It is typically obtained through synthetic routes rather than directly isolated from natural sources.

Occurrence, Applicability & Potential Uses

Although 1,2-dithiane is a sulfur-containing compound structurally related to other dithiacyclohexanes, its biological occurrence is limited or not well-documented. Its typical application lies strictly in informational contexts, with no current approved uses in flavor or fragrance formulations. Despite its garlic and vegetable-like flavor attributes, it is not employed as a flavoring agent due to regulatory and safety considerations. Regulatory standards such as FEMA (US) do not list 1,2-dithiane for direct use, and its status reflects its role as a chemical of interest rather than a functional additive.

Physico-Chemical Properties Summary

1,2-dithiane exhibits physicochemical characteristics influenced by its cyclic sulfur-containing structure. It has a boiling point range of approximately 173 to 174°C at standard atmospheric pressure and a flash point estimated near 95°C (206°F). The compound’s predicted log P value around 2.5 suggests moderate lipophilicity, impacting solubility profiles. It demonstrates limited solubility in water, approximately 455 mg/L at 25°C, while being more soluble in hot alcohol. Vapor pressure at room temperature is low, near 1.669 mmHg at 25°C, indicating restricted volatility. These properties influence its handling and formulation considerations in laboratory and industrial settings.

FAQ

What is 1,2-dithiane and what are its key characteristics?
1,2-dithiane is an organosulfur compound with the molecular formula C4H8S2, featuring a six-membered ring containing two adjacent sulfur atoms. It possesses sulfurous and garlic-like odors and is known by synonyms such as tetramethylene disulfide and 1,2-dithiacyclohexane. The compound is a liquid with a boiling point near 173 to 174°C and moderate lipophilicity, reflected by its estimated log P. It is primarily of chemical interest rather than commercial use.
How is 1,2-dithiane used and where does it occur naturally?
1,2-dithiane is not commonly found in nature and has limited biological occurrence. It has distinctive sulfurous sensory properties but is not utilized commercially for flavoring or fragrance purposes. Instead, it serves informational and research roles in chemical science. Regulatory assessments classify it as a compound without recognized hazard classifications, but it does not have approved applications in flavors or perfumes.
What are the regulatory considerations and sourcing information for 1,2-dithiane?
1,2-dithiane is subject to chemical safety reviews but lacks specific hazard classifications under standards such as OSHA’s hazard communication program (29 CFR 1910) in the US. It is recommended for informational use only, with no authorized flavor or fragrance usage levels recommended by FEMA (US). Procurement typically occurs through chemical suppliers for research purposes, and comprehensive data can be accessed via listings such as CAS 505-20-4 and FDA’s Unique Ingredient Identifier.

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Literature & References

dithiane
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):136335
Pubchem (sid):135091995
Pherobase:View
Publications by PubMed
A theoretical investigation of internal conversion in 1,2-dithiane using non-adiabatic multiconfigurational molecular dynamics.
Synthesis of a novel 1,2-dithianenucleoside via Pummerer-like reaction, followed by Vorbruggen glycosylation between a 1,2-dithiane derivative and uracil.
Solution phase photolysis of 1,2-dithiane alone and with single-walled carbon nanotubes.
Identification of a 2-cys peroxiredoxin as a tetramethyl benzidine-hydrogen peroxide stained protein from the thylakoids of the extreme halophyte Arthrocnemum macrostachyum L.
Modulating the endoplasmic reticulum stress response with trans-4,5-dihydroxy-1,2-dithiane prevents chemically induced renal injury in vivo.
Endoplasmic reticulum stress due to altered cellular redox status positively regulates murine hepatic CYP2A5 expression.
Synthesis, resolution, and determination of the absolute configuration of the enantiomers of cis-4,5-dihydroxy-1,2-dithiane 1,1-dioxide, an HIV-1NCp7 inhibitor.
Protection of renal epithelial cells against oxidative injury by endoplasmic reticulum stress preconditioning is mediated by ERK1/2 activation.
Effect of ring strain on the thiolate-disulfide exchange. A computational study.
Effect of polyamine-induced compaction and aggregation of DNA on the formation of radiation-induced strand breaks: quantitative models for cellular radiation damage.
Reduction of trans-4,5-dihydroxy-1,2-dithiane by cellular oxidoreductases activates gadd153/chop and grp78 transcription and induces cellular tolerance in kidney epithelial cells.
Endoplasmic reticulum chaperones GRP78 and calreticulin prevent oxidative stress, Ca2+ disturbances, and cell death in renal epithelial cells.
Reaction of dithiothreitol and para-nitroacetophenone with different radical precursors of .OH radical-induced strand break formation of single-stranded DNA in anoxic aqueous solution.
Thiol-mediated oxidation of nonphenolic lignin model compounds by manganese peroxidase of Phanerochaete chrysosporium.
The nonenzymatic oxidation of glutathione in the presence of plasmalike concentrations of disulfides and copper ions.
[Thermal decomposition of cysteine, cystine, N-acetylcysteine, 4-thiazolidinecarboxylic acid and cysteine methyl ester in soy bean oil (authors transl)].

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
CHEBI:View
HMDB (The Human Metabolome Database):Search
ChemSpider:View
Wikipedia:View

General Material Information

Preferred name 1,2-dithiane
Trivial Name 1,2-Dithiane
Short Description tetramethylene disulfide
Formula C4 H8 S2
CAS Number 505-20-4
FDA UNII Search
Nikkaji Number J101.092A
Beilstein Number 102504
xLogP3-AA 1.40 (est)
NMR Predictor External link
Synonyms
  • 1,2-dithiacyclohexane
  • dithiane
  • o- dithiane
  • ortho- dithiane
  • tetramethylene disulfide
  • o-Dithiane
  • 1,2-Dithiacyclohexane
  • NSC 521078

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 120.23776245117
Boiling Point 173 to 174°C @ 760 mm Hg
Vapor Pressure 1.669 mmHg @ 25 °C
Flash Point TCC Value 96.9 °C TCC
logP (o/w) 2.532 est
Solubility
alcohol, hot Yes
water, 455.1 mg/L @ 25 °C (est) Yes
water No

Organoleptic Properties

Odor Type: Sulfurous
General comment At 0.01 % in propylene glycol. sulfurous
Flavor Type: Garlic
garlic, metallic, sulfurous
General comment Garlic metallic sulfurous

Potential Uses

Applications
Flavoring purposes Horseradish , Vegetable

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:
information only not used for fragrances or flavors
Recommendation for 1,2-dithiane usage levels up to:
not for fragrance use.
Recommendation for 1,2-dithiane flavor usage levels up to:
not for flavor use.

Safety references

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 :136335
National Institute of Allergy and Infectious Diseases:Data
dithiane
Chemidplus:0000505204