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

Different sources of media describe the Description of 89-79-2 differently. You can refer to the following data:
1. Synthesis: Several stereoisomers are possible; only l-isopulegol and d-α-isopulegol have been isolated from mixtures of alcohols obtained by cyclization of d-citronellal.
2. (–)-Isopulegol is a monoterpene that has been found in the essential oils of several aromatic plants, including Cannabis, with diverse biological activities. It has antibacterial activity against S. aureus, E. faecium, E. coli, and M. smegmatis (MICs = 0.78, 12.5, 0.78, and 1.56 μl/ml, respectively, in an agar diffusion assay) and antifungal activity against C. albicans and A. niger (MIC = 1.56 μl/ml for both in an agar diffusion assay). (–)-Isopulegol inhibits C. albicans morphogenesis, adhesion, and biofilm formation (MICs = 0.125, 4, and 0.25 mg/ml, respectively). In vivo, (–)-isopulegol (50 mg/kg, i.p.) increases immobility time in the forced swim and tail suspension tests and increases the number of head dips in a hole board test and time spent in the open arms of the elevated plus maze in mice, indicating depressant- and anxiolytic-like activity. It reduces the size of ulcerated lesions in the stomach in mouse models of ethanol- and indomethacin-induced gastric lesions when administered at a dose of 100 mg/kg.

Chemical Properties

Different sources of media describe the Chemical Properties of 89-79-2 differently. You can refer to the following data:
1. Isopulegol is a cyclic nonaromatic alcohol.
2. Water-white liquid; mint-like odor. Combustible. Available forms: The acetate.

Occurrence

l-Isopulegol has been reported found in the essences of lemongrass, East African geranium and Eucalyptus citriodora; d-isopulegol is present in the oils of Backhousia and Baeckea citriodorae; d-neoisopulegol is found in Mentha rotundifolia. Also reported found in mint, mandarin, orange juice, citrus peel oils, currant bud, ginger, corn mint oil, cognac, rum, buchu oil, lemon balm and mastic gum oil

Uses

Different sources of media describe the Uses of 89-79-2 differently. You can refer to the following data:
1. (?)-Isopulegol can be used as a starting material for the enantioselective preparation of:?????? 8-arylmenthols by Smiles-Truce rearrangement of aryl sulfonates.,·???????? Stereoisomers of 5,9-dimethylpentadecane. Octahydro-2H-chromen-4-ol by Prins cyclization with vanillin in the presence of montmorillonite clay as the catalyst.????? p-menthane-3,8,9-triol by catalytic Sharpless dihydroxylation.
2. Perfumery (geranium and rose compounds), flavoring.

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.

Taste threshold values

Taste characteristics at 30 ppm: minty cooling, herbaceous peppermint nuance.

Synthesis Reference(s)

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

General Description

Isopulegol is monoterpene alcohol, 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.

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

• 106-23-0 3,7-dimethyl-oct-6-enal 
• 2385-77-5 (R)-Citronellal 
• 34212-48-1 (R)-7-hydroxy-3,7-dimethyl-octanal 
• 144-62-7 oxalic acid 
• 623-73-4 diazoacetic acid ethyl ester 
• 108-85-0 1-bromocyclohexane 
• 106-22-9 Citronellol 
• 108-24-7 acetic anhydride 
• 16750-82-6 (S)-isopiperitenone 
• 89-82-7 pulegone 
• 29606-79-9 isopulegone 
• 57396-86-8 C₁₃H₂₆OSi 
• 2216-51-5 (-)-menthol 
• 5949-05-3 (S)-Citronellal 

Downstream Products

• 859181-11-6 isopulegol ether 
• 3058-01-3 3-methyladipic acid 
• 89-83-8 thymol 
• 10458-14-7 (2R,5S)-menthone 
• 1196-31-2 (1R,4R)-(+)-isomenthone 
• 42822-86-6 p-menthane-3,8-diol 
• 130838-61-8 (+)-(1R;3Ξ;4S)-3-chloro-p-menth-8-ene 
• 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 
• 110328-55-7 (1R,2S,5R)-<5-methyl-2-<1-methylene-2-(trimethylsilyl)ethyl>cyclohexyloxy>trimethylsilane 
• 593279-34-6 di(-)-isopulegyl fumarate 
• 820208-73-9 (1R,2R,5R)-5-methyl-2-[(4R)-2,2,4-trimethyl-1,3-dioxolan-4-yl]cyclohexan-1-ol 

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.

Sulfonated Hyper-cross-linked Porous Polyacetylene Networks as Versatile Heterogeneous Acid Catalysts

Two highly sulfonated micro/mesoporous polymers, P(1,3-DEB)-SO3H and P(1,4-DEB)-SO3H, with permanent porosity, the specific surface area about 550 m2 ? g?1 and the content of SO3H groups of 2.7 mmol ? g?1 were prepared as new acid Porous Polymer Catalysts, PPCs. The PPCs were achieved by easy sulfonation of parent hyper-cross-linked micro/mesoporous polyacetylene-type networks resulting from a chain-growth homopolymerization of 1,3- and 1,4-diethynylbenzenes. New PPCs are reported as highly active and reusable heterogeneous catalysts of esterification of fatty acids with methanol and ethanol, Prins cyclization of aldehydes with isoprenol and intramolecular Prins cyclization of citronellal to isopulegol. The catalytic activity of the micro/mesoporous PPCs (TON values up to 522 mol ? mol?1) was higher than that of commercial polymer-based heterogeneous catalyst Amberlyst 15 possessing gel texture without permanent pores and that of p-toluenesulfonic acid applied as a homogeneous catalyst.