71159-90-5

Basic information

• Product Name: p-Menthene-8-thiol
• Synonyms: GRAPEFRUIT MERCAPTAN;FEMA 3700;ALPHA, ALPHA,4-TRIMETHYL-3-CYCLOHEXENE-1-METHANETHIOL;P-MENTHENE-8-THIOL;P-1-MENTHEN-8-THIOL;.alpha.,.alpha.-4-Trimethylcyclohex-3-ene-1-methanethiol;1-p-menthene-8-thiol;alpha,alpha,4-trimethyl-3-cyclohexene-1-methanethio
• CAS NO: 71159-90-5
• Molecular Formula: C₁₀H₁₈S
• Molecular Weight: 170.31
• EINECS: 275-223-1
• Product Categories: thiol Flavor
• Mol File: 71159-90-5.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 229.4 °C at 760 mmHg
• Flash Point: 90.7 °C
• Appearance: /
• Density: 0.938 g/cm³
• Vapor Pressure: 0.105mmHg at 25°C
• Refractive Index: 1.5
• PKA: 11.12±0.10(Predicted)
• CAS DataBase Reference: p-Menthene-8-thiol(CAS DataBase Reference)
• NIST Chemistry Reference: p-Menthene-8-thiol(71159-90-5)
• EPA Substance Registry System: p-Menthene-8-thiol(71159-90-5)

Safety Data

• Hazardous Substances Data: 71159-90-5(Hazardous Substances Data)

Usage

Description

p-Menthene-8-thiol is a naturally occurring organic sulfur compound found in grapefruit juice. It is a liquid with a powerful, obnoxious odor, but when diluted, it exhibits the typical aroma of fresh grapefruit juice. Its odor threshold value is extremely low, making it a potent contributor to the flavor profile of grapefruit.

Uses

Used in Flavor and Fragrance Industry:
p-Menthene-8-thiol is used as a flavoring agent for its characteristic grapefruit aroma and taste. Its low odor threshold value allows it to be used in small quantities to impart a strong grapefruit flavor to food products and beverages.
Used in Perfumery:
Due to its powerful and distinctive aroma, p-Menthene-8-thiol can be used as a fragrance ingredient in the perfumery industry. Its unique combination of grapefruit, sulfurous, and citrus notes can contribute to the creation of complex and long-lasting scents.
Used in Cosmetics and Personal Care Products:
p-Menthene-8-thiol can be incorporated into cosmetics and personal care products for its refreshing and invigorating grapefruit scent. It can be used in products such as body lotions, shower gels, and hair care products to provide a pleasant and uplifting sensory experience.
Used in Aromatherapy:
The natural and powerful aroma of p-Menthene-8-thiol can be utilized in aromatherapy for its potential mood-enhancing and stress-relieving properties. Its citrus and fresh notes may help to create a sense of relaxation and well-being when inhaled or used in massage oils.

InChI:InChI=1/C10H18S/c1-8-4-6-9(7-5-8)10(2,3)11/h4,9,11H,5-7H2,1-3H3

Synthetic route

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether for 1h; Reduction;	90%

→ 2-(4-methylcyclohex-3-enyl)propane-2-thiol (71159-90-5)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether at 0 - 20℃; Solvent; Inert atmosphere;	85%

terpineol (98-55-5) → 2-(4-methylcyclohex-3-enyl)propane-2-thiol (71159-90-5)

Conditions	Yield
With Lawessons reagent In toluene for 0.5h; Heating;	20%
With tetraphosphorus decasulfide In tetrahydrofuran at 50℃; for 1h; Solvent; Reagent/catalyst; Temperature; Large scale;	500 g

(1R,5R)-(+)-β-pinene (127-91-3) → 2-(4-methylcyclohex-3-enyl)propane-2-thiol (71159-90-5) + trans-Pinane-2-thiol (88600-02-6) + 4-Methyl-2,4-di(4-methyl-3-cyclohexenyl)pentane-2-thiol (88600-04-8)

Conditions	Yield
With aluminum tri-bromide; hydrogen sulfide In chloroform at 20℃; for 0.5h; Yields of byproduct given;	A n/a B n/a C 13%
With aluminum tri-bromide; hydrogen sulfide In chloroform at 20℃; for 0.5h; Product distribution; EtAlClBr as reagent.;

(-)-α-pinene (7785-26-4) → 2-(4-methylcyclohex-3-enyl)propane-2-thiol (71159-90-5) + trans-Pinane-2-thiol (88600-02-6) + 4-Methyl-2,4-di(4-methyl-3-cyclohexenyl)pentane-2-thiol (88600-04-8)

Conditions	Yield
With aluminum tri-bromide; hydrogen sulfide In chloroform at 20℃; for 0.5h; Product distribution; EtAlClBr as reagent.;
With aluminum tri-bromide; hydrogen sulfide In chloroform

8,9-epthio-1-p-menthene (83108-08-1) → 2-(4-methylcyclohex-3-enyl)propane-2-thiol (71159-90-5)

Conditions	Yield
With lithium aluminium tetrahydride; 2-neopentoxyphenol; water 1.) THF, reflux, 1 h; 2.) 10 min; Yield given. Multistep reaction;

2-(4-methylcyclohex-3-enyl)propane-2-thiol (71159-90-5) → 1,8-epithio-p-menthane

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 70℃; for 1h;	97%

2-(4-methylcyclohex-3-enyl)propane-2-thiol (71159-90-5) → 2,8-epithio-cis-p-menthene

Conditions	Yield
With azobisisobutyronitrile In hexane at 70℃; for 2h;	65%

Upstream product

• 7785-26-4 (-)-α-pinene 
• 98-55-5 terpineol 
• 127-91-3 (1R,5R)-(+)-β-pinene 
• 83108-08-1 8,9-epthio-1-p-menthene 
• 133490-04-7 α-terpinyl thiocyanate 
• 39864-10-3 α-terpinyl chloride 
• 5989-27-5 D-limonene 
• 7783-06-4 hydrogen sulfide 
• 138-86-3 limonene. 
• 586-62-9 Terpinolene 

Relevant articles and documents

Method for preparing 1-poxlene -8-thiol

The invention belongs to the technical field of fine chemistry, and provides a method for preparing 1-poxlene-8-thiol, wherein a-terpineol is used as a raw material, and the a-terpineol reacts with athioreagent to obtain the 1-poxlene -8-thiol, the method comprises the following steps: dissolving the a-terpineol in an organic solvent; adding the thioreagent in batches to carry out a thioreaction;the system after reaction is cooled to room temperature, the solvent is removed through rotating evaporation, and sodium hydroxide aqueous solution is slowly added until the pH value is more than orequal to 12; extracting the water phase with methyl tert-ether twice, combining the organic phase, washing with saturated brine once, drying with anhydrous sodium sulfate, concentrating, and distilling under reduced pressure to obtain the product 1-poxlene-8-thiol. The method solves the problems that in the prior art, the synthesis route of the 1-poxlene-8-thiol is complex, the lithium aluminum tetrahydrate in the raw material is expensive, the danger is high, and the prior method is not suitable for industrial production.

ADDITION OF H2S TO TERPENES FOR PRODUCING NOVEL MOLAR MASS REGULATORS FOR RADICAL POLYMERISATIONS

The present invention relates to a method for producing thiols through addition of hydrogen sulfide onto at least one unsaturated terpene, where the reaction is carried out in the presence of at least one organic ion exchanger, and to the use of thiols derived from terpinolene as molar mass regulator in the polymerization of monomers.

Direct Conversion of Alcohols into Thiols

A simple one-pot reaction between alcohols and 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide (Lawesson's reagent, LR) affords the corresponding thiols, accompanied by dehydration products, alkenes.Treatment of acyclic 1,4-diols with LR gives the 1,3-dienes. o-(Dihydroxymethyl)benzene derivatives yield the 1,3-dihydrobenzothiophenes when treated with LR.