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
• Article Data: 3

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

Occurrence

Reported found in yellow passion fruit.

Uses

3-Sulfanylhexyl Acetate is a precursor of 3-mercaptohexan-1-ol (M225270) found in grape juice.

Definition

ChEBI: An acetate ester obtained by formal O-acetylation of 3-mercaptohexanol.

Aroma threshold values

Aroma characteristics at 0.001%: green sulfurous with a sweet meaty background, slightly caramelized onion-like and with a catty dry out.

Taste threshold values

Taste characteristics at 0.0005 ppm: sulfurous, fruity, catty, savory meaty, fried onion, with a tropical fruity catty aftertaste.

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

Upstream product

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

Downstream Products

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

Relevant articles and documents

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.