89-79-2

Basic information

• Product Name: ISOPULEGOL
• Synonyms: 5-methyl-2-(1-methylethenyl)-,[1R-(1.alpha.,2.beta.,5.alpha.)]-Cyclohexanol;cyclohexanol,5-methyl-2-(1-methylethenyl)-,[1theta-(1alpha,2beta,5alpha)];p-Menth-8(9)-en-3-ol;p-Menth-8-en-3-ol, (1R,3R,4S)-(-)-;1-METHYL-4-ISOPROPENYLCYCLOHEXAN-3-OL;(1R,3R,4S)-P-MENTH-8-EN-3-OL;(1R,2S,5R)-2-ISOPROPENYL-5-METHYLCYCLOHEXANOL;(-)-ISOPULEGOL
• CAS NO: 89-79-2
• Molecular Formula: C₁₀H₁₈O
• Molecular Weight: 154.25
• EINECS: 201-940-6
• Mol File: 89-79-2.mol
• Article Data: 125

Chemical Properties

• Melting Point: 78°C
• Boiling Point: 212 °C(lit.)
• Flash Point: 195 °F
• Appearance: /
• Density: 0.912 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0993mmHg at 25°C
• Refractive Index: n20/D 1.471(lit.)
• Storage Temp.: ?20°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 15.11±0.60(Predicted)
• Water Solubility: 3g/L at 21.9℃
• BRN: 1906573
• CAS DataBase Reference: ISOPULEGOL(CAS DataBase Reference)
• NIST Chemistry Reference: ISOPULEGOL(89-79-2)
• EPA Substance Registry System: ISOPULEGOL(89-79-2)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36/37/39
• RIDADR: NA 1993 / PGIII
• WGK Germany: 2
• F: 10-23
• Hazardous Substances Data: 89-79-2(Hazardous Substances Data)

Usage

Description

ISOPULEGOL is a monoterpene alcohol that serves as a useful ingredient for the production of fragrances in perfume industries. It is also used as a starting material in the manufacture of menthol by the hydrogenation process. Menthol is an important component in cosmetics, pharmaceuticals, and toothpaste. ISOPULEGOL is a cyclic nonaromatic alcohol with a water-white liquid appearance and a mint-like odor. It is combustible and available in the form of its acetate.

Uses

Used in Chemical Synthesis:
ISOPULEGOL is used as a starting material for the enantioselective preparation of 8-arylmenthols by Smiles-Truce rearrangement of aryl sulfonates, stereoisomers of 5,9-dimethylpentadecane, and octahydro-2H-chromen-4-ol by Prins cyclization with vanillin in the presence of montmorillonite clay as the catalyst. It is also used in the synthesis of p-menthane-3,8,9-triol by catalytic Sharpless dihydroxylation.
Used in Perfumery:
ISOPULEGOL is used as a component in geranium and rose compounds for perfumery, providing a minty cooling and herbaceous peppermint nuance at a taste threshold value of 30 ppm.
Used in Flavoring:
ISOPULEGOL is used as a flavoring agent, imparting a minty and herbaceous taste to various food products.
Used in Essential Oils:
ISOPULEGOL is found in the essences of lemongrass, East African geranium, Eucalyptus citriodora, Backhousia, Baeckea citriodorae, Mentha rotundifolia, mint, mandarin, orange juice, citrus peel oils, currant bud, ginger, corn mint oil, cognac, rum, buchu oil, lemon balm, and mastic gum oil.
Used in Pharmaceutical Applications:
(–)-Isopulegol exhibits antibacterial activity against S. aureus, E. faecium, E. coli, and M. smegmatis, as well as antifungal activity against C. albicans and A. niger. It also inhibits C. albicans morphogenesis, adhesion, and biofilm formation. In vivo, (–)-isopulegol demonstrates depressantand anxiolytic-like activity in mice and reduces the size of ulcerated lesions in the stomach in mouse models of ethanoland indomethacin-induced gastric lesions when administered at a dose of 100 mg/kg.

Preparation

Several stereoisomers are possible; only l-isopulegol and d-α-isopulegol have been isolated from mixtures of alcohols obtained by cyclization of d-citronellal.

Synthesis Reference(s)

Synthetic Communications, 18, p. 2309, 1988 DOI: 10.1080/00397918808082375

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C10H18O/c1-7(2)9-5-4-8(3)6-10(9)11/h8-11H,1,4-6H2,2-3H3/t8-,9+,10-/m1/s1

Upstream product

• 623-73-4 diazoacetic acid ethyl ester 
• 106-23-0 3,7-dimethyl-oct-6-enal 
• 2385-77-5 (R)-Citronellal 
• 7664-93-9 sulfuric acid 
• 5392-40-5 (E/Z)-3,7-dimethyl-2,6-octadienal 
• 64-18-6 formic acid 
• 42822-86-6 p-menthane-3,8-diol 
• 91951-11-0 p-menth-8-en-3-ylamine; isopulegylamine 
• 7782-77-6 cis-nitrous acid 
• 123366-53-0 N-(3,7-dimethyl-1,6-octadienyl)-piperidine 
• 106-22-9 Citronellol 
• 57576-09-7 (1R,2S,5R)-5-methyl-2-(prop-1-en-2-yl)cyclohexyl acetate 
• 16750-82-6 (S)-isopiperitenone 
• 67392-56-7 (R)-(-)-N,N-diethyl-3,7-dimethyl-1(E),6-octadienylamine 

Downstream Products

• 89-82-7 pulegone 
• 29606-79-9 isopulegone 
• 91633-23-7 2-(2-azidoisopropyl)-5-methylcyclohexan-1-ol 
• 139721-76-9 2-[1-(chloromethyl)ethenyl]-5-methylcyclohexanol 
• 2216-51-5 (-)-menthol 
• 124323-84-8 8-chloro-3,7-dimethyl-6-octenal 
• 74514-24-2 10-chloro-isopulegol 
• 294634-38-1 (1R,2R,5R)-5-Methyl-2-(2-methyl-oxiranyl)-cyclohexanol 
• 529-00-0 (S)-isopulegone 
• 17882-43-8 (?)-trans-isopulegone 
• 29606-79-9 p-menth-8-en-3-one 
• 166317-78-8 (1R,3R,4S,8R)-9-<(triisopropylsilyl)oxy>-p-menthol 
• 13834-14-5 2-<(1S,2R,4R)-2-hydroxy-4-methylcyclohexyl>-2-propen-1-ol 
• 13834-08-7 <1R>-5(R)-methyl-2(S)-<1(S)-methyl-2-hydroxyethyl>cyclohexanol 

Relevant articles and documents

Fe-Modified Zeolite BETA as an Active Catalyst for Intramolecular Prins Cyclization of Citronellal

Abstract: Prins intramolecular cyclization of citronellal giving desired product isopulegol was performed using different modified zeolites BETA (Si/Al ratio 25, 38 and 75 modified with iron or zinc of 1, 5 or 10?wt.% by wet impregnation method). In case of materials BETA Si/Al 38 and 75 led material impregnation with metal to increase of material catalytic activity (accompanied with increase of amount of weak acid sites detected using temperature programmed desorption). Material BETA 38 with loading 1?wt.% of Fe provided 97% citronellal conversion and 94% selectivity of isopulegol formation (90?°C, toluene, 24?h). Graphic Abstract: [Figure not available: see fulltext.]

Synthesis modulation as a tool to increase the catalytic activity of metal-organic frameworks: The unique case of UiO-66(Zr)

The catalytic activity of the zirconium terephthalate UiO-66(Zr) can be drastically increased by using a modulation approach. The combined use of trifluoroacetic acid and HCl during the synthesis results in a highly crystalline material, with partial substitution of terephthalates by trifluoroacetate. Thermal activation of the material leads not only to dehydroxylation of the hexanuclear Zr cluster but also to post-synthetic removal of the trifluoroacetate groups, resulting in a more open framework with a large number of open sites. Consequently, the material is a highly active catalyst for several Lewis acid catalyzed reactions.

Tuning the surface properties of novel ternary iron(iii) fluoride-based catalysts using the template effect of the matrix

Sol-gel prepared ternary FeF3-MgF2 materials have become promising heterogeneous catalysts due to their porosity and surface Lewis/Bronsted acidity (bi-acidity). Despite the good catalytic performance, nanoscopic characterisations of this type of material are still missing and the key factors controlling the surface properties have not yet been identified, impeding both a better understanding and further development of ternary fluoride catalysts. In this study, we characterised the interaction between the bi-acidic component (FeF3) and the matrix (MgF2) on the nano-scale. For the first time, the formation pathway of FeF3-MgF2 was profiled and the template effect of MgF2 during the synthesis process was discovered. Based on these new insights two novel materials, FeF3-CaF2 and FeF3-SrF2, were established, revealing that with decreasing the atomic numbers (from Sr to Mg), the ternary fluorides exhibited increasing surface acidity and surface area but decreasing pore size. These systematic changes gave rise to a panel of catalysts with tuneable surface and bulk properties either by changing the matrix alkaline earth metal fluoride or by adjusting their ratios to Fe or both. The template effect of the alkaline earth metal fluoride matrix was identified as the most probable key factor determining the surface properties and further influencing the catalytic performance in ternary fluoride based catalysts, and paves the way to targeted design of next-generation catalysts with tunable properties. This journal is

Method for preparing L-menthol by adopting modified homogeneous catalyst

The invention discloses a method for preparing L-menthol by adopting a modified homogeneous catalyst. The method comprises the following steps: preparing a modified homogeneous catalyst, preparing isopulegol, preparing D, L-menthol, and preparing L-menthol; wherein a ligand is prepared from 2, 6-dimethylpyridine and a ketone compound by using the modified homogeneous catalyst, the ligand is reacted with alkyl aluminum to obtain an organic aluminum compound, and L-menthol is prepared by chemically inducing chiral resolution of D, L-menthol. According to the method, the organic aluminum compoundis used as the catalyst of the ring-closure reaction of citronellal, so that the yield of isopulegol is increased, the selectivity on product isopulegol is high, and the used organic aluminum catalyst is easy to synthesize, high in stereoselectivity to reaction and easy to crystallize and recover; D, L-menthol is split by a chemical induction method, the method is simple to operate, the reactionyield of each step is high, the reaction conditions are stable, the product cannot be partially racemized, and the product loss is small.

Continuous flow synthesis of menthol: Via tandem cyclisation-hydrogenation of citronellal catalysed by scrap catalytic converters

A continuous flow synthesis of menthol starting from citronellal catalysed by scrap catalytic converters is reported. The reaction was conducted in a tandem system connecting in series two catalytic systems, with the first having Lewis acid properties (favouring the cyclisation of citronellal to isopulegols) and the second having hydrogenation catalytic activity (catalysing the hydrogenation of isopulegols to menthols). A Lewis acid catalyst was prepared by supporting iron oxide nanoparticles over a waste material, i.e. the ceramic core of scrap catalytic converters (SCATs) via a microwave assisted method. Most importantly, SCATs, containing a low residual noble metal content, could be directly employed in the second step as hydrogenation catalysts. The reaction was performed studying the influence on the yield and selectivity to (-)-menthol of various reaction parameters (T, p and flow rate). Under the best reaction conditions (at a flow rate of 0.1 mL min-1 and at 373 K and 413 K for cyclisation and hydrogenation steps respectively) a conversion of >99% of (+)-citronellal to (-)-menthol with 77% final yield was achieved.