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Tetrahydrothiophen-3-one, also known as 4,5-Dihydro-3(2H)-thiophenone, is a heterocyclic nonaromatic ketone with a distinct garlic meaty, green vegetable, and buttery odor. It is a volatile organic sulfur compound (VOSC) produced by basidiomycetous yeasts and is found in various cooked foods such as beef, coffee, roasted filberts, and roasted peanuts.

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  • 1003-04-9 Structure
  • Basic information

    1. Product Name: Tetrahydrothiophen-3-one
    2. Synonyms: 3-Oxotetrahydrothiophene;3-Thiacyclopentanone;dihydro-3(2h)-thiophenon;Dihydro-3-Thiophenone;Thiolan-3-one;4,5-DIHYDRO-3(2H)-THIOPHENONE;3-THIOPHANONE;dihydrothiophen-3(2h)-one
    3. CAS NO:1003-04-9
    4. Molecular Formula: C4H6OS
    5. Molecular Weight: 102.15
    6. EINECS: 213-698-9
    7. Product Categories: Thiophene&Benzothiophene;thiophene Flavor;Thiophen flavors
    8. Mol File: 1003-04-9.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 175 °C(lit.)
    3. Flash Point: 171 °F
    4. Appearance: Colorless to pale yellow/Liquid
    5. Density: 1.194 g/mL at 25 °C(lit.)
    6. Vapor Density: >1 (vs air)
    7. Vapor Pressure: 1.16mmHg at 25°C
    8. Refractive Index: n20/D 1.528(lit.)
    9. Storage Temp.: 2-8°C
    10. Solubility: N/A
    11. BRN: 105201
    12. CAS DataBase Reference: Tetrahydrothiophen-3-one(CAS DataBase Reference)
    13. NIST Chemistry Reference: Tetrahydrothiophen-3-one(1003-04-9)
    14. EPA Substance Registry System: Tetrahydrothiophen-3-one(1003-04-9)
  • Safety Data

    1. Hazard Codes: Xi
    2. Statements: 36/37/38
    3. Safety Statements: 26-36-36/37/39
    4. RIDADR: UN 3334
    5. WGK Germany: 3
    6. RTECS:
    7. F: 8-13
    8. TSCA: Yes
    9. HazardClass: N/A
    10. PackingGroup: N/A
    11. Hazardous Substances Data: 1003-04-9(Hazardous Substances Data)

1003-04-9 Usage

Uses

1. Used in Flavor Industry:
Tetrahydrothiophen-3-one is used as a flavoring agent for blending soft drinks, beverages, meat products, confectionery, and milk product flavors. Its unique taste characteristics, such as onion, garlic, and cooked meaty notes with vegetable nuances at 15 ppm, make it a valuable addition to the flavor industry.
2. Used in Food Industry:
Tetrahydrothiophen-3-one is used as a food flavoring agent, enhancing the taste and aroma of various cooked foods. Its natural occurrence in cooked beef, coffee, roasted filberts, and roasted peanuts makes it a suitable choice for replicating and enhancing these flavors in the food industry.
3. Used in Organic Synthesis:
Tetrahydrothiophen-3-one is a valuable organic substance that serves as a key compound for the synthesis of numerous thiophene derivatives. Its chemical properties, such as being a clear light yellow liquid with a garlic meaty, green vegetable, and buttery odor, make it an important building block in the development of new compounds and materials.

Preparation

From 4-methoxycarboxyl-3-oxothiophane treated with 10% sulfuric acid.

Synthesis Reference(s)

Journal of the American Chemical Society, 68, p. 2229, 1946 DOI: 10.1021/ja01215a034

References

[1] George A. Burdock (2010) Fenaroli's Handbook of Flavor Ingredients, Sixth Edition [2] https://pubchem.ncbi.nlm.nih.gov [3] Patent 0127121 A1: Process for the preparation of tetrahydro-thiophen-3-one

Check Digit Verification of cas no

The CAS Registry Mumber 1003-04-9 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,0,0 and 3 respectively; the second part has 2 digits, 0 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 1003-04:
(6*1)+(5*0)+(4*0)+(3*3)+(2*0)+(1*4)=19
19 % 10 = 9
So 1003-04-9 is a valid CAS Registry Number.
InChI:InChI=1/C4H6OS/c5-4-1-2-6-3-4/h1-3H2

1003-04-9 Well-known Company Product Price

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  • (Code)Product description
  • CAS number
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  • Alfa Aesar

  • (A11002)  Tetrahydrothiophen-3-one, 97%   

  • 1003-04-9

  • 5g

  • 233.0CNY

  • Detail
  • Alfa Aesar

  • (A11002)  Tetrahydrothiophen-3-one, 97%   

  • 1003-04-9

  • 10g

  • 421.0CNY

  • Detail
  • Alfa Aesar

  • (A11002)  Tetrahydrothiophen-3-one, 97%   

  • 1003-04-9

  • 25g

  • 961.0CNY

  • Detail
  • Alfa Aesar

  • (A11002)  Tetrahydrothiophen-3-one, 97%   

  • 1003-04-9

  • 250g

  • 7995.0CNY

  • Detail
  • Aldrich

  • (264784)  4,5-Dihydro-3(2H)-thiophenone  98%

  • 1003-04-9

  • 264784-5G

  • 443.43CNY

  • Detail
  • Aldrich

  • (264784)  4,5-Dihydro-3(2H)-thiophenone  98%

  • 1003-04-9

  • 264784-25G

  • 1,519.83CNY

  • Detail

1003-04-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name Tetrahydrothiophen-3-one

1.2 Other means of identification

Product number -
Other names Dihydrothiophen-3(2H)-one

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1003-04-9 SDS

1003-04-9Relevant articles and documents

Investigation of the aroma-active compounds formed in the maillard reaction between glutathione and reducing sugars

Lee, Sang Mi,Jo, Ye-Jin,Kim, Young-Suk

, p. 3116 - 3124 (2010)

Aroma-active compounds formed during the thermal reaction between glutathione (GSH) and reducing sugars were analyzed by gas chromatography-mass spectrometry (GC-MS) and GC-olfactometry (GC-O) with aroma extract dilution analysis (AEDA). Application of AEDA to glutathione Maillard reaction products (GSH MRPs) led to the identification of 19 aroma-active compounds in the thermal reaction of glutathione with glucose or fructose. In addition, the carbohydrate module labeling (CAMOLA) approach was also employed to elucidate the formation pathways for selected target sulfur aroma compounds, such as 5-methylthiophene-2-carbaldehyde and 3-methylthiophene-2-carbaldehyde, which have not been reported previously. The intact carbon skeleton of glucose via 3-deoxyhexosone is incorporated into 5-methylthiophene-2-carbaldehyde with the hydrogen sulfide of GSH. On the other hand, the formation of 3-methylthiophene2-carbaldehyde may occur via the recombination of a C-4 sugar fragment and mercaptoacetaldehyde.

Preparation method of substituted thiophene-3-one compound

-

Paragraph 0054; 0062; 0067; 0072; 0077; 0082; 0087; 0092, (2018/08/04)

The invention provides a preparation method of a substituted thiophene-3-one compound, comprising: subjecting material A and material B to Michael addition reaction to obtain an addition product; subjecting the addition product to Dieckmann condensation reaction to obtain a substituted thiophene-3-one compound having a structure shown as formula (IV) that is shown in the description. The preparation method provided by the application has the advantages that using solvents and strong bases is not required, reaction materials are low in price and easy to obtain, no wastewater is produce, and therefore, the preparation method has good environmental friendliness; compared with existing preparation methods, the preparation method has a short synthetic route, can be performed under mild conditions and features good yield stability and good repeatability, which is helpful for greatly increasing total yield of the substituted thiophene-3-one compound and helpful for industrial popularization.

Method for preparing chiral diphosphines

-

, (2008/06/13)

The invention concerns a method for preparing a compound of formula (1) wherein: A represents naphthyl or phenyl optionally substituted; and Ar1, Ar2independently represent a saturated or aromatic carbocyclic group, optionally substituted.

Thio-sugars. Part 10. The Nucleoside from 5-Fluoroacil and 2-Amino-2,3-dideoxy-4-thio-DL-glycero-tetrofuranose and Related Compounds

Jones, John O.,McElhinney, R. Stanley

, p. 1501 - 1517 (2007/10/02)

Another molecular combination of a chloroethylnitrosourea and a pyrimidine antimetabolite (5-fluorouracil) linked through a sugar or sugar-like moiety has been synthesised for biological testing.In this case 2-amino-2,3-dideoxy-4-thio-DL-glycero-tetrofuranose was derived from thiolan-3-one, nitrogen being introduced as azide in preference to the route involving oxime and phthalimide.Some derivatives of 3-amino-3-deoxy-4-thio-DL-erythrofuranose were prepared from trans-4-aminothiolan-3-ol, inverted by way of a fused oxazoline, but although a (5-iodouracil) nucleoside ester was obtained it proved difficult to remove the protecting groups.

Enzymes in organic syntheses. 19. Evaluation of the stereoselectivities of horse liver alcohol dehydrogenase; catalyzed oxidoreductions of hydroxy- and ketothiolanes, -thianes, and -thiepanes

Jones, J. Bryan,Schwartz, Harold M.

, p. 1574 - 1579 (2007/10/02)

The specificity of horse liver alcohol dehydrogenase (HLADH) with respect to unsubstituted five-, six-, and seven-membered ring 3- and 4-thiaketone and -thiaalcohol substrates has been examined.The enzyme is found to have a broad tolerance of the structural variations within this series.HLADH also exhibits encouraging (up to 46percent) enantiotopic and enantiomeric specifity in preparative-scale reduction and oxidation reactions of the heterocyclic ketones and alcohols respectively.

REACTIONS OF α-DIAZO KETONES. IV. S-5 PARTICIPATION AND β-ELIMINATION IN THE ACETOLYSIS OF 4-ARYLTHIO- AND 4-ARALKYLTHIO-1-DIAZO-2-BUTANONES

Rosnati, Vittorio,Saba, Antonio

, p. 211 - 214 (2007/10/02)

The acetolyses of α-diazo ketones 2a-d, bearing a thioether group on the β'-carbon have been studied in neat AcOH and in the presence of acetate.All these reactions lead to products arising from the 1,4-shift of the thioether group, normal substitution being only a secondary pathway, particularly in the case of 2d, which almost exclusively undergoes fragmentation to benzhydryl acetate and 3-oxotetrahydrothiophene.The mechanisms involved are discussed.

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