1-p-Menthene-8-thiol

Base Information

• Chemical Name: 1-p-Menthene-8-thiol
• CAS No.: 71159-90-5
• Deprecated CAS: 161273-20-7,83108-07-0
• Molecular Formula: C10H18S
• Molecular Weight: 170.319
• European Community (EC) Number: 280-191-7,275-223-1
• UNII: 7AT54D0N8R
• DSSTox Substance ID: DTXSID1052458
• Nikkaji Number: J308.725E
• Wikipedia: Grapefruit_mercaptan
• Wikidata: Q26220987
• RXCUI: 1940004
• Metabolomics Workbench ID: 47017
• Mol file: 71159-90-5.mol

Synonyms:p-Menthene-8-thiol;1-p-Menthene-8-thiol;71159-90-5;2-(4-methylcyclohex-3-en-1-yl)propane-2-thiol;1-p-menthen-8-thiol;P-Menth-1-en-8-thiol;FEMA No. 3700;alpha,alpha,4-Trimethylcyclohex-3-ene-1-methanethiol;p-menth-1-ene-8-thiol;UNII-7AT54D0N8R;7AT54D0N8R;3-Cyclohexene-1-methanethiol, .alpha.,.alpha.,4-trimethyl-;grapefruit mercaptan;EINECS 275-223-1;EINECS 280-191-7;alpha,alpha,4-Trimethyl-3-cyclohexene-1-methanethiol;3-Cyclohexene-1-methanethiol, alpha,alpha,4-trimethyl-;(1)-alpha,alpha,4-Trimethylcyclohex-3-ene-1-methanethiol;p-1-Menthen-8-thiol;p-1-Menthene-8-thiol;p-Mentha-1-ene-8-thiol;8-Mercapto-p-menth-1-ene;SCHEMBL114630;DTXSID1052458;FEMA 3700;CHEBI:184430;AKOS006290100;1-P-MENTHENE-8-THIOL [FHFI];(+/-)-1-P-MENTHENE-8-THIOL;1-P-MENTHENE-8-THIOL, (+/-)-;2-(4-methylcyclohex-1-enyl)propane-2-thiol;A9339;FT-0655519;|A,|A,4-trimethylcyclohex-3-ene-1-methanethiol;3-Cyclohexene-1-methanethiol, ?,?,4-trimethyl-;4-(1-Mercapto-1-methylethyl)-1-methylcyclohexene;2-(4-METHYLCYCLOHEX-3-ENYL)PROPANE-2-THIOL;a,a,4-Trimethyl-3-cyclohexene-1-methanethiol, 9CI;Q26220987;(+-)-alpha,alpha,4-trimethylcyclohex-3-ene-1-methanethiol;a,a,4 - trimethylcyclohex - 3 - ene - 1 - methanethiol;.ALPHA.,.ALPHA.,4-TRIMETHYLCYCLOHEX-3-ENE-1-METHANETHIOL;3-Cyclohexene-1-methanethiol, .alpha.,.alpha.,4-trimethyl-,(.+-.)-;83108-07-0

Chemical Property of 1-p-Menthene-8-thiol

Chemical Property:

• Appearance/Colour: Colourless liquid with aroma and taste of grapefruit in dilute solution Visual appearance of the given substance.
• Vapor Pressure: 0.105mmHg at 25°C
• Refractive Index: 1.5
• Boiling Point: 229.4 °C at 760 mmHg
• PKA: 11.12±0.10(Predicted)
• Flash Point: 90.7 °C
• PSA: 38.80000
• Density: 0.938 g/cm³
• LogP: 3.44120
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 170.11292175
• Heavy Atom Count: 11
• Complexity: 168

Purity/Quality:

99% ^*data from raw suppliers

P-MENTHENE-8-THIOL 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CCC(CC1)C(C)(C)S
• Description: 1-p-Menthene-8-thiol, also known as grapefruit mercaptan or thioterpineol, is a p-menthane monoterpenoid compound. Its chemical structure includes a p-menthene backbone with a thiol group (–SH) attached to the eighth carbon atom. 1-p-Menthene-8-thiol is a colorless to light yellow liquid with a sulfurous, onion, acrid odor. In dilute solution, it exhibits an aroma and taste of grapefruit.
• Sources: Exists naturally in grapefruit juice.
• Uses: Widely used in the food industry as a flavoring agent to impart citrus flavors, especially in grapefruit-flavored products. Its FEMA number is 3700, and it is considered generally recognized as safe (GRAS).
• Analysis Method: Identification and quantification can be performed using gas chromatography–olfactometry (GC–O), gas chromatography–sulfur chemiluminescence detection (GC–SCD), and two-dimensional gas chromatography coupled with time-of-flight mass spectrometry (GC × GC–TOF/MS).
• References: [1] Screening for Novel Mercaptans in 26 Fruits and 20 Wines Using a Thiol-Selective Isolation Procedure in Combination with Three Detection Methods; DOI 10.1021/acs.jafc.9b01242; [2] Structure–Odor Activity Studies on Monoterpenoid Mercaptans Synthesized by Changing the Structural Motifs of the Key Food Odorant 1-p-Menthene-8-thiol; DOI 10.1021/acs.jafc.6b01645

Technology Process of 1-p-Menthene-8-thiol

There total 12 articles about 1-p-Menthene-8-thiol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

α-terpinyl thiocyanate (133490-04-7) → 2-(4-methylcyclohex-3-enyl)propane-2-thiol (71159-90-5,83150-77-0,83150-78-1)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; for 1h;

Reference yield: 85.0%

p-menth-1-ene-8-thiolacetate → 2-(4-methylcyclohex-3-enyl)propane-2-thiol (71159-90-5,83150-77-0,83150-78-1)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at 0 - 20 ℃; Solvent; Inert atmosphere;

Reference yield: 20.0%

terpineol (98-55-5,2438-12-2) → 2-(4-methylcyclohex-3-enyl)propane-2-thiol (71159-90-5,83150-77-0,83150-78-1)

Guidance literature:

With Lawessons reagent; In toluene; for 0.5h; Heating;

upstream raw materials:

(-)-α-pinene

terpineol

(1R,5R)-(+)-β-pinene

8,9-epthio-1-p-menthene

Refernces

• 1、 -. "Synthesis process method of p-menon-1-ene-8-thiol". Paragraph 0017; 0019; 0020; 0022; 0023; 0025; 0026; 0028. . Retrieved 2019/04/26.
• 2、 Gurudutt, K. N.,Rao, Sanjay,Srinivas, P.,Srinivas, S.. "Simple synthetic protocols for tertiary alkyl and allyl thiols". . p. 1169 - 1171. Retrieved 2007/10/03.