tetrahydrothiophene
thiophene, tetrahydro-
 
Notes:
Flavouring compound [Flavornet]
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      20-19600 TETRAHYDROTHIOPHENE
       
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      T0114 Tetrahydrothiophene
       
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CAS Number: 110-01-0Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg: 203-728-9
FDA UNII: 744EHT13FM
Nikkaji Web: J2.444I
Beilstein Number: 0102392
MDL: MFCD00005476
XlogP3-AA: 1.40 (est)
Molecular Weight: 88.17276000
Formula: C4 H8 S
NMR Predictor: Predict (works with chrome or firefox)
Category: flavoring agents
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar: Search
Google Books: Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Perfumer and Flavorist: Search
Google Patents: Search
US Patents: Search
EU Patents: Search
Pubchem Patents: Search
PubMed: Search
NCBI: Search
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Physical Properties:
Appearance: pale yellow clear liquid (est)
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Specific Gravity: 0.99500 to 1.00100 @  25.00 °C.
Pounds per Gallon - (est).: 8.279 to  8.329
Refractive Index: 1.49900 to 1.50500 @  20.00 °C.
Boiling Point: 120.00 °C. @ 760.00 mm Hg
Vapor Pressure: 17.452000 mmHg @ 25.00 °C. (est)
Vapor Density: 3.04 ( Air = 1 )
Flash Point: 55.00 °F. TCC ( 12.78 °C. )
logP (o/w): 1.610 (est)
Soluble in:
 alcohol
 water, 3730 mg/L @ 25 °C (est)
Insoluble in:
 water
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Organoleptic Properties:
 
Odor Type: sulfurous
 
 cabbage  
Odor Description:
at 0.01 % in propylene glycol. 
cabbage
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
Arkema
THT
Odor: characteristic
Use: We have developed a unique expertise on gas odorization, having a dedicated R&D laboratory and a focus group composed of trained people to measure odor intensity.
Chevron Phillips
Tetrahydrothiophene
Penta International
TETRAHYDROTHIOPHENE
Sigma-Aldrich: Aldrich
For experimental / research use only.
Tetrahydrothiophene 99%
TCI AMERICA
For experimental / research use only.
Tetrahydrothiophene
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Safety Information:
Preferred SDS: View
European information :
Most important hazard(s):
Xn N - Harmful, Dangerous for the environment.
R 11 - Highly flammable.
R 20/21/22 - Harmful by inhalation, in contact with skin and if swallowed.
R 36/38 - Irritating to skin and eyes.
R 52/53 - Harmful to qauatic organisms, may cause long-term adverse effects in the aquatic environment.
S 01/02 - Keep locked up and out of the reach of children.
S 16 - Keep away from sources of ignition - No Smoking.
S 23 - Do not breath vapour.
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.
S 61 - Avoid release to the environment. Refer to special instructions/safety data sheet.
 
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:
gavage-rat LD50  [sex: M,F (5/sex/group)] M:2000 F:1750 mg/kg
(Auletta & Daly, 1985)

oral-rat LD50  1200 (100% survival rate), 3000 (100% fatality rate) mg/kg
(Dow Chemical Company, 1992a)

oral-rat LD50  1750 mg/kg
BEHAVIORAL: ATAXIA BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: TREMOR
National Technical Information Service. Vol. OTS0555157

Dermal Toxicity:
Not determined
Inhalation Toxicity:
inhalation-mouse LC50 27 gm/m3/2hours
National Technical Information Service. Vol. OTS0555157

inhalation-mouse LC50 27000 mg/m3/2H
"Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 1088, 1986.

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Safety in Use Information:
Category: flavoring agents
Recommendation for tetrahydrothiophene usage levels up to:
 not for fragrance use.
 
Maximised Survey-derived Daily Intakes (MSDI-EU): 0.024 (μg/capita/day)
Modified Theoretical Added Maximum Daily Intake (mTAMDI): 78 (μg/person/day)
Threshold of Concern:540 (μg/person/day)
Structure Class: II
 
Food categories according to Commission Regulation EC No. 1565/2000 (EC, 2000) in FGE.06 (EFSA, 2002a). According to the Industry the "normal" use is defined as the average of reported usages and "maximum use" is defined as the 95th percentile of reported usages (EFSA, 2002i).
Note: mg/kg = 0.001/1000 = 0.000001 = 1/1000000 = ppm.
 average usage mg/kgmaximum usage mg/kg
Dairy products, excluding products of category 02.0 (01.0): 0.200001.00000
Fats and oils, and fat emulsions (type water-in-oil) (02.0): 0.100000.50000
Edible ices, including sherbet and sorbet (03.0): 0.200001.00000
Processed fruit (04.1): 0.200001.00000
Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2): --
Confectionery (05.0): 0.200001.00000
Chewing gum (05.0): --
Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0): 0.100000.50000
Bakery wares (07.0): 0.200001.00000
Meat and meat products, including poultry and game (08.0): 0.100000.20000
Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0): 0.100000.20000
Eggs and egg products (10.0): --
Sweeteners, including honey (11.0): --
Salts, spices, soups, sauces, salads, protein products, etc. (12.0): 0.100000.50000
Foodstuffs intended for particular nutritional uses (13.0): 0.200001.00000
Non-alcoholic ("soft") beverages, excl. dairy products (14.1): 0.100000.30000
Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2): 0.200001.00000
Ready-to-eat savouries (15.0): 0.400002.00000
Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0): 0.100000.50000
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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 74 (FGE.74)[1]: Consideration of Simple Aliphatic Sulphides and Thiols evaluated by JECFA (61st meeting) Structurally related to Aliphatic and Alicyclic Mono-, Di-, Tri-, and Polysulphides with or without Additional Oxygenated Functional Groups from Chemical Group 20 evaluated by EFSA in FGE.08 (2008)
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
Flavouring Group Evaluation 91 (FGE.91): Consideration of simple aliphatic and aromatic sulphides and thiols evaluated by JECFA (53rd and 68th meetings) structurally related to aliphatic and alicyclic mono-, di-, tri-, and polysulphides with or without additional oxygenated functional groups evaluated by EFSA in FGE.08Rev1 (2009)
View page or View pdf
Flavouring Group Evaluation 08 Rev2 (FGE.08 Rev2): 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
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
NIOSH International Chemical Safety Cards: search
AIDS Citations: Search
Cancer Citations: Search
Toxicology Citations: Search
EPA Substance Registry Services (TSCA): 110-01-0
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 1127
National Institute of Allergy and Infectious Diseases: Data
WISER: UN 2412
WGK Germany: 2
 thiolane
Chemidplus: 0000110010
EPA/NOAA CAMEO: hazardous materials
RTECS: 110-01-0
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References:
 thiolane
NIST Chemistry WebBook: Search Inchi
Canada Domestic Sub. List: 110-01-0
Pubchem (cid): 1127
Pubchem (sid): 134974017
Flavornet: 110-01-0
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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
CHEBI: View
CHEMBL: View
HMDB (The Human Metabolome Database): Search
FooDB: FDB029635
Export Tariff Code: 2934.90.5000
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 tea black tea
Search Trop  Picture
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Synonyms:
 tetrahydrothiophene [UN2412] [Flammable liquid]
 tetramethylene sulfide
 thiacyclopentane
 thilane
 thiocylopentane
 thiolane
 thiophane
 thiophene, tetrahydro-
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Articles:
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PubMed: OH···X (X = O, S) hydrogen bonding in thetrahydrofuran and tetrahydrothiophene.
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PubMed: Sodium-mediated magnesiation of thiophene and tetrahydrothiophene: structural contrasts with furan and tetrahydrofuran.
PubMed: Study of the coordination abilities of stibine ligands to gold(I).
PubMed: A straightforward and generalizable synthetic methodology for the synthesis of ruthenium(II) complexes with thioether ligands from either Ru(III) or Ru(0) precursors.
PubMed: Interactions between tetrahydrothiophene (THT) and silver species in AgNa-Y.
PubMed: Facile synthesis of 3-nitro-2-substituted thiophenes.
PubMed: Synthesis of gold phosphido complexes derived from bis(secondary) phosphines. structure of tetrameric [Au(MesP(CH(2))(3)PMes)Au](4).
PubMed: Spectroscopic and luminescence studies on square-planar platinum(II) complexes with anionic tridentate 3-bis(2-pyridylimino)isoindoline derivatives.
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PubMed: Determination of busulfan in human plasma using an ELISA format.
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PubMed: Synthesis of carbosilane dendrimers containing up to four metal layers.
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PubMed: Synthesis of C60-fused tetrahydrothiophene derivatives via nucleophilic cycloaddition of thiocyanates.
PubMed: Revisiting the determination of langmuir parameters--application to tetrahydrothiophene adsorption onto activated carbon.
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PubMed: Volume of reaction, energetics, and kinetics of tetrahydrothiophene displacement of solvent from Mo(CO)5(alkane).
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PubMed: A model system study of the inhibition of heterocyclic aromatic amine formation by organosulfur compounds.
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PubMed: Synthesis and reactivity of the monocarbon molybdenacarborane anion [1,2-mu-NHBu(t)-2,2,2-(CO)(3)-closo-2,1-MoCB(10)H(10)](-).
PubMed: Mechanism of the Uncatalyzed Dissociative Cis-Trans Isomerization of Bis(pentafluorophenyl)bis(tetrahydrothiophene): A Refinement.
PubMed: Structural Diversity in Monomeric Cadmium Phenoxides.
PubMed: Gold(I) Complexes with N-Donor Ligands. 2.(1) Reactions of Ammonium Salts with [Au(acac-kappaC(2))(PR(3))] To Give [Au(NH(3))L](+), [(AuL)(2)(&mgr;(2)-NH(2))](+), [(AuL)(4)(&mgr;(4)-N)](+), or [(AuL)(3)(&mgr;(3)-O)](+). A New and Facile Synthesis of [Au(NH(3))(2)](+) Salts. Crystal Structure of [{AuP(C(6)H(4)OMe-4)(3)}(3)(&mgr;(3)-O)]CF(3)SO(3).
PubMed: Single-molecule vibrations, conformational changes, and electronic conductivity of five-membered heterocycles.
PubMed: Two-, three-, and four-coordination at gold(I) supported by the bidentate selenium ligand [Ph2P(Se)NP(Se)Ph2](-).
PubMed: Infrared matrix-assisted laser desorption/ionization of polycyclic aromatic hydrocarbons with a sulfolane matrix.
PubMed: Carbanion-induced base-catalyzed synthesis of 1H-isothiochromenes, benzo[c]thiochromenes through ring-transformation reactions of 6-aryl-2H-pyran-2-ones.
PubMed: Ab-initio molecular geometry and normal coordinate analysis of tetrahydrothiophene molecule.
PubMed: The first acetimine gold(I) and gold(III) complexes and the first acetonine complexes.
PubMed: Molecular addition compounds. 17. Borane and chloroborane adducts with organic sulfides for hydroboration
PubMed: Sulfolane degradation by mixed cultures and a bacterial isolate identified as a Variovorax sp.
PubMed: Heteropolynuclear complexes with the ligand Ph2PCH2SPh: theoretical evidence for metallophilic Au-M attractions
PubMed: Polysulfonylamines. CXX. Bis(tetrahydrothiophene-S)gold(I) benzene-1,2-disulfonimidate
PubMed: On the performance and inertness of different materials used for the enrichment of sulfur compounds from air and gaseous samples.
PubMed: X-ray structures of small ligand-FKBP complexes provide an estimate for hydrophobic interaction energies.
PubMed: Gas chromatographic-mass spectrometric determination of sulfolane in wetland vegetation exposed to sour gas-contaminated groundwater.
PubMed: Determination of tetrahydrothiophene formation as a probe of in vitro busulfan metabolism by human glutathione S-transferase A1-1: use of a highly sensitive gas chromatographic-mass spectrometric method.
PubMed: Synthesis and Characterization of Molybdenum Based Colloidal Particles.
PubMed: Characterization of Five-Coordinate Ruthenium(II) Phosphine Complexes by X-ray Diffraction and Solid-State (31)P CP/MAS NMR Studies and Their Reactivity with Sulfoxides and Thioethers.
PubMed: Insertion of Fluoroalkenes into Activated C-H Bonds for the Preparation of Polyfluorinated Sulfanes, Alcohols, and Acyclic and Cyclic Ethers.
PubMed: Dimethyl disulfide derivatization of ethyl (9Z,12Z)-9, 12-octadecadienoate and ethyl (9E,12E)-9,12-octadecadienoate.
PubMed: Busulfan conjugation by glutathione S-transferases alpha, mu, and pi.
PubMed: Naturally occurring diallyl disulfide inhibits the formation of carcinogenic heterocyclic aromatic amines in boiled pork juice.
PubMed: The ionized methylene transfer from the distonic radical cation (+)CH 2-O-CH 2 to heterocyclic compounds. A pentaquadrupole mass spectrometric study.
PubMed: Effects of Maillard reaction products on mutagen formation in boiled pork juice.
PubMed: Synthesis, absolute configuration, and enantioselectivity of antiretroviral effect of (R)-(-)- and (S)-(+)-cytallene. Lipase-catalyzed enantioselective acylations of (+/-)-N4-acylcytallenes.
PubMed: Phytogrowth-inhibitory activities of sulfur-containing compounds. II. The inhibitory activities of thiosalicylic acid and dihydro-2(3H)-thiophenone-related compounds on plant growth.
PubMed: Tetronothiodin, a novel cholecystokinin type-B receptor antagonist produced by Streptomyces sp. NR0489. III. Structural elucidation.
PubMed: Tetronothiodin, a novel CCKB receptor ligand, antagonizes cholecystokinin-induced Ca2+ mobilization in a pituitary cell line.
PubMed: Preparations of cyclic sulfoxide derivatives and their evaluation as transdermal penetration enhancers.
PubMed: Biosynthesis and urinary excretion of methyl sulfonium derivatives of the sulfur mustard analog, 2-chloroethyl ethyl sulfide, and other thioethers.
PubMed: Thiophene-degrading Escherichia coli mutants possess sulfone oxidase activity and show altered resistance to sulfur-containing antibiotics.
PubMed: Structures of two diastereomers of the tetrahydrobenzothiophene moiety of breynolide.
PubMed: The inducible trimethylamine N-oxide reductase of Escherichia coli K12: its localization and inducers.
PubMed: Synthesis and D2 dopaminergic activity of pyrrolidinium, tetrahydrothiophenium, and tetrahydrothiophene analogues of sulpiride.
PubMed: Pharmacokinetic and metabolic studies of high-dose busulphan in adults.
PubMed: Pharmacokinetic and metabolic studies of busulfan in rat plasma and brain.
PubMed: Microbial degradation of n-alkyl tetrahydrothiophenes found in petroleum.
PubMed: Thermoregulatory responses of the rabbit to subcutaneous injection of sulfolane.
PubMed: Biliary excretion of a glutathione conjugate of busulfan and 1,4-diiodobutane in the rat.
PubMed: Beta-substituted cysteines as sequestering agents for ethanol-derived acetaldehyde in vivo.
PubMed: Tetrahydrothiophene 1-oxide as an electron acceptor for Escherichia coli.
PubMed: Urinary metabolites of busulfan in the rat.
PubMed: Synthesis and antisecretory and antiulcer activities of derivatives and analogues of 2-(2-pyridyl)tetrahydrothiophene-2-carbothioamide.
PubMed: Effect of 40749 RP on basal and sham feeding stimulated gastric secretion in man.
PubMed: Acute sulfolane exposure produces temperature-independent and dependent changes in visual evoked potentials.
PubMed: Biotransformation and quantitative determination of sulfur-containing metabolites of 1,4-dibromobutane in the rat.
PubMed: Sulfolane-induced hypothermia enhances survivability in mice.
PubMed: Effects of single daily doses of a pyridil-2-tetrahydrothiophene derivative (40749 RP) on 24 hour H+ activity, nocturnal acid output, gastrin and pepsinogen I profiles in duodenal ulcer patients.
PubMed: Increased effect of multiple doses of 40 749 RP a new long acting gastric antisecretory agent.
PubMed: Glutathione S-transferases catalyzed conjugation of 1,4-disubstituted butanes with glutathione in vitro.
PubMed: Synthesis and antitumor activity of a series of ftorafur analogues: the effect of varying electronegativity at the 1'-position.
PubMed: Effect of sulfolane on behavioral and autonomic thermoregulation in the rat.
PubMed: Inhibition of pentagastrin-stimulated gastric secretion by pyridyl-2-tetrahydrothiophene derivative (RP 40749)
PubMed: The coordinating properties of d-biotin.
PubMed: Properties of the biotin transport system in Bifidobacterium breve N4.
PubMed: Dimethyl sulfoxide as an electron acceptor for anaerobic growth.
PubMed: The inhalation toxicity of sulfolane (tetrahydrothiophene-1,1-dioxide).
PubMed: Gas chromatographic determination of sulphur compounds in town gas.
PubMed: Sulfolane-induced convulsions in rodents.
PubMed: Sulphydryl inhibition by ethyl 2-(substituted benzylidene)-3-oxo-2,3,4,5-tetrahydrothiophene-4-carboxylates.
PubMed: Nasal decongestant properties of some tetrahydrothiophene-1,1-dioxide derivatives.
PubMed: [CHEMOTHERAPEUTIC STUDIES ON SCHISTOSOMIASIS. X. SOME AMIDES DERIVED FROM THIOPHENE-2-CARBOXYLIC, THIOPHENE-2-SULPHONIC ACID AND TETRAHYDROTHIOPHENE-2,5- DICARBOXYLIC ACID].
PubMed: Pharmacology of some monohalogenated derivatives of sulfolane (tetrahydrothiophene-1,1-dioxide).
PubMed: Tetrahydrothiophene (thiophane) derivatives.
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