136954-20-6

Basic information

• Product Name: 3-Mercaptohexyl acetate
• Synonyms: HEXANE-3-THIOL ACETATE;FEMA 3851;3-MERCAPTOHEXYL ACETATE;3-THIOHEXYL ACETATE;3-Sulfanylhexyl acetate;3-mercaptohexyl-acetate,3-mercapto-1-hexanol-1-acetate;Hexane-3-thiol acetate 95%;3-mercapto-1-hexanol acetate
• CAS NO: 136954-20-6
• Molecular Formula: C₈H₁₆O₂S
• Molecular Weight: 176.28
• EINECS: 603-987-1
• Product Categories: Aliphatics;ester Flavor
• Mol File: 136954-20-6.mol

Chemical Properties

• Boiling Point: 235.7 °C at 760 mmHg
• Flash Point: 109.8 °C
• Appearance: /
• Density: 0.987 g/cm³
• Vapor Pressure: 0.0494mmHg at 25°C
• Refractive Index: 1.4560 to 1.4600
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility: Chloroform (Sparingly),Methanol (Slightly)
• PKA: 10.53±0.10(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: 3-Mercaptohexyl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Mercaptohexyl acetate(136954-20-6)
• EPA Substance Registry System: 3-Mercaptohexyl acetate(136954-20-6)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 136954-20-6(Hazardous Substances Data)

Usage

Uses

Used in Flavor and Fragrance Industry:
3-Mercaptohexyl acetate is used as a flavoring agent for its unique taste characteristics, which include sulfurous, fruity, catty, savory meaty, and fried onion notes with a tropical fruity catty aftertaste. It is particularly useful in creating complex and nuanced flavor profiles in the food and beverage industry.
Used in Chemical Synthesis:
3-Mercaptohexyl acetate serves as a precursor for the synthesis of 3-mercaptohexan-1-ol (M225270), a compound found in grape juice. This makes it an essential component in the production of certain chemicals and additives used in various industries, including the food and beverage sector.
Used in Aromatherapy:
Due to its distinct aroma characteristics, 3-Mercaptohexyl acetate can be used in aromatherapy as a component in essential oil blends. Its green sulfurous notes with a sweet meaty background can contribute to creating a relaxing and soothing atmosphere, potentially benefiting mental well-being and stress relief.
Used in the Perfume Industry:
3-Mercaptohexyl acetate's unique scent profile makes it a valuable ingredient in the perfume industry. It can be used to create distinct and long-lasting fragrances, adding depth and complexity to perfume compositions.

InChI:InChI=1/C8H16O2S/c1-3-4-8(11)5-6-10-7(2)9/h8,11H,3-6H2,1-2H3

Upstream product

• 90180-88-4 3-mercapto-1-hexanol 
• 75-36-5 acetyl chloride 
• 136954-25-1 3-(acetylmercapto)hexyl acetate 

Downstream Products

• 90243-48-4 (2R,4R)-2-methyl-4-propyl-1,3-oxathiane 
• 90243-46-2 (2R,4S)-2-methyl-4-propyl-1,3-oxathiane 
• 90243-47-3 (2S,4R)-2-methyl-4-propyl-1,3-oxathiane 
• 90243-45-1 (2S,4S)-2-methyl-4-propyl-1,3-oxathiane 

Relevant articles and documents

Characterization of the aroma-active compounds in pink guava (Psidium guajava, L.) by application of the aroma extract dilution analysis

The volatiles present in fresh, pink-fleshed Colombian guavas (Psidium guajava, L.), variety regional rojo, were carefully isolated by solvent extraction followed by solvent-assisted flavor evaporation, and the aroma-active areas in the gas chromatogram were screened by application of the aroma extract dilution analysis. The results of the identification experiments in combination with the FD factors revealed 4-methoxy-2,5-dimethyl-3(2H)-furanone, 4-hydroxy-2,5-dimethyl-3(2H)-furanone, 3-sulfanylhexyl acetate, and 3-sulfanyl-1-hexanol followed by 3-hydroxy-4,5-dimethyl-2(5H)-furanone, (Z)-3-hexenal, trans-4,5-epoxy-(E)-2-decenal, cinnamyl alcohol, ethyl butanoate, hexanal, methional, and cinnamyl acetate as important aroma contributors. Enantioselective gas chromatography revealed an enantiomeric distribution close to the racemate in 3-sulfanylhexyl acetate as well as in 3-sulfanyl-1-hexanol. In addition, two fruity smelling diastereomeric methyl 2-hydroxy-3- methylpentanoates were identified as the (R,S)- and the (S,S)-isomers, whereas the (S,R)- and (R,R)-isomers were absent. Seven odorants were identified for the first time in guavas, among them 3-sulfanylhexyl acetate, 3-sulfanyl-1-hexanol, 3-hydroxy-4,5-dimethyl-2(5H)-furanone, frans-4,5-epoxy-(E)-2-decenal, and methional were the most odor-active.

Determination and isolation of a thioesterase from passion fruit (Passiflora edulis Sims) that hydrolyzes volatile thioesters

Volatile organosulfur compounds (VOSCs) are high impact aroma chemicals characteristic of tropical fruits which are active as both free thiols and the respective thioesters. Using a simple and sensitive colorimetric enzyme assay, a thioesterase activity toward VOSCs has been identified in ripening purple passion fruit (Passiflora edulis Sims). The assay was based on determining the release of free thiols from 2-methyl-3-furanthiol acetate using Ellman's reagent. The major thioesterase in the fruit was found to be a wall-bound protein in the mesocarp. The extracted enzyme activity was purified 150-fold and shown to be associated with a 43 kDa monomeric serine hydrolase which was selectively labeled with a fluorophosphonate suicide probe. MS-MS sequencing identified the thioesterase as a class 13 glycoside hydrolase, most similar to pectin acetylesterase, an enzyme involved in cell wall modifications in the peel of a number of fruit. Our results suggest that cell wall hydrolases in tropical fruit may have additional useful roles in biotransforming VOSCs.

CHIRALE, SCHWEFELHALTIGE AROMASTOFFE DER GELBEN PASSIONSFRUCHT (PASSIFLORA EDULIS F. FLAVICARPA). DARSTELLUNG DER ENANTIOMEREN UND ABSOLUTE KONFIGURATION

3-Methylthio-hexane-1-ol and 2-methyl-4-propyl-1,3-oxathiane, chiral S-containing aroma substances of the yellow passion fruit are resolved to enantiomers and absolute configurations are elucidated.