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2-methyl thiophene

Chemical Structure

General Material Information

Preferred name 2-methyl thiophene
Trivial Name 2-Methylthiophene
Short Description thiophene, 2-methyl-
Formula C5 H6 S
CAS Number 554-14-3
FEMA Number 4928
Flavis Number 15.091
ECHA Number 209-063-0
FDA UNII 7115JAP77A
Nikkaji Number J6.459I
Beilstein Number 0103734
MDL MFCD00005451
COE Number 11631
NMR Predictor External link
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
Synonyms
  • alpha- methyl thiophene
  • 2-methylthiophene
  • thiophene, 2-methyl-
  • 2-Methylthiophene
  • α-Methylthiophene
  • 2-Thienylmethane

US / EU / FDA / JECFA / FEMA / Scholar / Patents

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Literature & References

2-methylthiophene
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:554-14-3
Pubchem (cid):11126
Pubchem (sid):134976149
Flavornet:554-14-3
Publications by US Patents
3,931,166 - Certain 2,5-dimethyl-3-thiopyrazines
Publications by PubMed
High-intensity ultrasound production of Maillard reaction flavor compounds in a cysteine-xylose model system.
Mixed-metal chalcogenide tetrahedral clusters with an exo-polyhedral metal fragment.
Green synthesis and anti-inflammatory studies of a series of 1,1-bis(heteroaryl)alkane derivatives.
Product ion distributions for the reactions of NO(+) with some physiologically significant volatile organosulfur and organoselenium compounds obtained using a selective reagent ionization time-of-flight mass spectrometer.
Structural, spectroscopic, and electrochemical properties of tri- and tetradentate N3 and N3S copper complexes with mixed benzimidazole/thioether donors.
Mechanisms for the reaction of thiophene and methylthiophene with singlet and triplet molecular oxygen.
A mechanistic study of the 2-thienylmethyl + HO2 radical recombination reaction.
Metabolomic approach for determination of key volatile compounds related to beef flavor in glutathione-Maillard reaction products.
Practical preparation of ethyl 2-methylthiophene-3-carboxylate.
Effects of lard on the formation of volatiles from the Maillard reaction of cysteine with xylose.
RuCl₃·3H₂O catalyzed reactions: facile synthesis of bis(indolyl)methanes under mild conditions.
Pyrolysis mechanisms of thiophene and methylthiophene in asphaltenes.
On-line measurement of oxidative degradation kinetics for trace gasoline contaminants in aqueous solutions and natural water by membrane introduction tandem mass spectrometry.
Biodesulfurization of dibenzothiophene by a newly isolated Rhodococcus erythropolis strain.
Diastereoselective domino reactions of chiral 2-substituted 1-(2',2',3',3'-tetramethylcyclopropyl)-alkan-1-ols under Friedel-Crafts conditions.
A computational study of photochemical isomerization reactions of thiophenes.
Selectivity in the oxidative addition of C-S bonds of substituted thiophenes to the (C5Me5)Rh(PMe3) fragment: a comparison of theory with experiment.
Highly diastereoselective Friedel-Crafts alkylation reactions via chiral alpha-functionalized benzylic carbocations.
[Determination and distribution of sulfur compounds in coked gasoline by gas chromatography-sulfur chemiluminescence detection].
Aquasonolysis of thiophene and its derivatives.
[Determination of sulfur compounds in fluid catalytic cracking gasoline by gas chromatography with a sulfur chemiluminescence detector].
Aroma extract dilution analysis of Cv. Marion (Rubus spp. hyb) and Cv. Evergreen (R. laciniatus L.) blackberries.
Thiophenes as traps for benzyne. 3. Diaryl sulfides and the role of dipolar intermediates.
One-pot synthesis of C-glycosylic compounds (C-glycosides) from D-glucal, p-tolylsulfenyl chloride and aromatic/heteroaromatic compounds in the presence of Lewis acids.
Lewis Acid Catalysis in the Oxidative Cycloaddition of Thiophenes(1).
Antioxidative activities of heterocyclic compounds formed in brewed coffee.
Surface Enhanced Raman Spectroscopic Study of Isomeric Methylthiophenes in Silver Colloid.
Fabrication of conducting polymer interconnects.

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):HMDB33118
FooDB:FDB011118
YMDB (Yeast Metabolome Database):YMDB01462
Export Tariff Code:2934.99.9000
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 98.167823791504
Specific gravity @ 25 °C
Pounds per Gallon 8.429 to 8.504
Refractive Index 1.516 to 1.523 @ 20 °C
Vapor Pressure 30.964001 mmHg @ 25 °C
Flash Point TCC Value 15 °C TCC
logP (o/w) 2.33
Solubility
water, 112.6 mg/L @ 25 °C (exp) Yes
water, 1212 mg/L @ 25 °C (est) Yes

Organoleptic Properties

Odor Type: Sulfurous
sulfurous, alliaceous, onion, roasted, green
General comment At 0.01 % in propylene glycol. sulfurous alliaceous onion roasted green
Flavor Type: Sulfurous
sulfurous, roasted, green, cabbage, onion, bitter
General comment Sulfurous roasted green cabbage onion bitter

Occurrences

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
Xn - Harmful.
R 11 - Highly flammable.
R 22 - Harmful if swallowed.
S 02 - Keep out of the reach of children.
S 16 - Keep away from sources of ignition - No Smoking.
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 36/37/39 - 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-rat LD50 1000 mg/kg
"Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 87, 1982.

unreported-mammal (species unspecified) LD50 1260 mg/kg
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 51(5), Pg. 61, 1986.

oral-mouse LD50 1460 mg/kg
"Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 87, 1982.

oral-rat LD50 3200 mg/kg
"Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 87, 1982.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
inhalation-mouse LC50 11500 mg/m3/2H
"Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 87, 1982.

Safety in use information

Category:
flavoring agents
Recommendation for 2-methyl thiophene usage levels up to:
not for fragrance use.
Maximised Survey-derived Daily Intakes (MSDI-EU): 0.019 (μg/capita/day)
Modified Theoretical Added Maximum Daily Intake (mTAMDI): 78 (μg/person/day)
Threshold of Concern:540 (μg/person/day)
Structure Class: II
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: 29
Click here to view publication 29
average usual ppmaverage maximum ppm
baked goods: 0.3000010.00000
beverages(nonalcoholic): 0.100005.00000
beverages(alcoholic): 0.100005.00000
breakfast cereal: 0.3000010.00000
cheese: 0.100005.00000
chewing gum: 0.100005.00000
condiments / relishes: 0.100005.00000
confectionery froastings: 0.3000010.00000
egg products: 0.100005.00000
fats / oils: 0.100005.00000
fish products: 0.100005.00000
frozen dairy: 0.100005.00000
fruit ices: 0.100005.00000
gelatins / puddings: 0.100005.00000
granulated sugar: --
gravies: 0.100005.00000
hard candy: 0.3000010.00000
imitation dairy: 0.3000010.00000
instant coffee / tea: 0.100005.00000
jams / jellies: 0.100005.00000
meat products: 0.100005.00000
milk products: 0.100005.00000
nut products: 0.100005.00000
other grains: 0.100005.00000
poultry: 0.100005.00000
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: 0.100005.00000
snack foods: 0.3000010.00000
soft candy: 0.3000010.00000
soups: 0.100005.00000
sugar substitutes: --
sweet sauces: 0.100005.00000
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 (05.3): --
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): 0.100000.50000
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

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 21: Thiazoles, thiophene, thiazoline and thienyl derivatives from chemical group 29. Miscellaneous substances from chemical group 30. (Commission Regulation (EC) No 1565/2000 of 18 July 2000) - Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC)
View page or View pdf

Flavouring Group Evaluation 76, (FGE.76)[1] - Consideration of sulphur-containing heterocyclic compounds evaluated by JECFA (59th meeting) structurally related to thiazoles, thiophene, thiazoline and thienyl derivatives from chemical group 29, miscellaneous substances from chemical group 30 evaluated by EFSA in FGE.21 - Scientific Opinion of the Panel on Food Additives, Flavourings, Processing Aids and Materials in Contact with Food
View page or View pdf

Flavouring Group Evaluation 21, Revision 1 (FGE.21Rev1): Thiazoles, thiophene, thiazoline and thienyl derivatives from chemical group 29 Miscellaneous substances from chemical group 30
View page or View pdf

Flavouring Group Evaluation 93 (FGE.93): Consideration of sulphur heterocyclic evaluated by JECFA (68th meeting) structurally related to thiazoles, thiophene, thiazoline and thienyl evaluated by EFSA in FGE.21Rev1 (2009)
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 21, Revision 2 (FGE.21Rev2): Thiazoles, thiophene, thiazoline and thienyl derivatives from chemical group 29. Miscellaneous substances from chemical group 30.
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 21, Revision 3 (FGE.21Rev3): Thiazoles, thiophenes, thiazoline and thienyl derivatives from chemical groups 29 and 30
View page or View pdf

Statement on List of Representative Substances for Testing. The current Statement lays down a list of substances in sub-groups with representative substances for which additional data are required prior to their evaluation through the Procedure (Regulation (EC) No 1565/2000).
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 21, Revision 4 (FGE.21Rev4): Thiazoles, thiophenes, thiazoline and thienyl derivatives from chemical groups 29 and 30
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 21, Revision 5 (FGE.21Rev5): Thiazoles, thiophenes, thiazoline and thienyl derivatives from chemical groups 29 and 30
View page or View pdf

EPI System: View
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):554-14-3
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :11126
National Institute of Allergy and Infectious Diseases:Data
WISER:UN 1993
WGK Germany:3
2-methylthiophene
Chemidplus:0000554143
RTECS:XM9625000 for cas# 554-14-3