7786-67-6

Basic information

• Product Name: ISOPULEGOL, TECH.
• Synonyms: isopulegol, mixture of isomers;PARA-MENTH-8-EN-3-OL;2-Isopropenyl-5-methyl-1-cyclohexanol;3-Methyl-6-isopropenylcyclohexanol;2-Isopropenyl-5-methylcyclohexanol;5-methyl-2-(1-methylethenyl)-cyclohexano;5-methyl-2-(1-methylethenyl)-Cyclohexanol;8(9)-p-Menthen-3-ol
• CAS NO: 7786-67-6
• Molecular Formula: C₁₀H₁₈O
• Molecular Weight: 154.24932
• EINECS: 232-102-8
• Product Categories: Biochemistry;Monocyclic Monoterpenes;Terpenes
• Mol File: 7786-67-6.mol
• Article Data: 98

Chemical Properties

• Boiling Point: 90-92°C 12mm
• Flash Point: 78°C
• Appearance: /
• Density: 0,91 g/cm3
• Vapor Pressure: 0.0993mmHg at 25°C
• Refractive Index: 1.4725
• PKA: 15.11±0.60(Predicted)
• Water Solubility: Slightly soluble in water
• CAS DataBase Reference: ISOPULEGOL, TECH.(CAS DataBase Reference)
• NIST Chemistry Reference: ISOPULEGOL, TECH.(7786-67-6)
• EPA Substance Registry System: ISOPULEGOL, TECH.(7786-67-6)

Safety Data

• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39
• RTECS: OT0190000
• TSCA: Yes
• Hazardous Substances Data: 7786-67-6(Hazardous Substances Data)

Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 7786-67-6 differently. You can refer to the following data:
1. clear colorless to light yellow liquid
2. Similarly to menthol, isopulegol has three asymmetric carbon atoms and, therefore, four stereoisomers, each occurring as a pair of enantiomers. All isomers are colorless liquids with a more or less minty, herbaceous odor. The isopulegols occur in a number of essential oils, often in optically active or partly racemic form. Since citronellal readily cyclizes to isopulegol, the latter occurs frequently in citronellal-containing essential oils, in which it is formed during the isolation of the oil. (1R,3R,4S)-(?)-Isopulegol is produced on a large scale as an intermediate for the production of (?)-menthol.(br/) A huge number of catalysts for the cyclization of citronellal to isopulegol have been described. Newer developments offer advantages in diastereoselectivity and yield through the use of modified silicon dioxides or zeolites. Isopulegol is mainly used in mint-like flavor compositions. Pure (?)-isopulegol is also used to impart cooling sensation effects to cosmetic and pharmaceutical preparations. Terpineols are unsaturated monocyclic terpene alcohols and are formed by acid-catalyzed hydration of pinenes;α-, β-, γ-, and δ-isomers exist: α- and β-Terpineol occur in optically active forms and as racemates. α-Terpineol is an important commercial product. It occurs in a large number of essential oils primarily as (?)-α-terpineol (e.g., in conifer and lavandin oils). Small quantities of (+)- and rac-α-terpineol are found in many other essential oils; β-, γ-, and δ-terpineol do not occur widely in nature.

Uses

Isopulegol is a component of essential and volatile oils extracted from natural sources.

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+/m0/s1

Upstream product

• 2385-77-5 (R)-Citronellal 
• 106-23-0 3,7-dimethyl-oct-6-enal 
• 60-29-7 diethyl ether 
• 529-00-0 (+)-cis-isopulegone 
• 130628-58-9 Dec-9-enylmagnesium bromide 
• 5949-05-3 (S)-Citronellal 
• 106-22-9 Citronellol 
• 5392-40-5 (E/Z)-3,7-dimethyl-2,6-octadienal 
• 50-00-0 formaldehyd 
• 89-79-2 isopulegol 
• 89-79-2 isopulegol 
• 29606-79-9 p-menth-8-en-3-one 
• 5989-27-5 D-limonene 
• 16750-82-6 (S)-isopiperitenone 

Downstream Products

• 166317-78-8 (1R,3R,4S,8R)-9-<(triisopropylsilyl)oxy>-p-menthol 
• 948912-47-8 (2S,5R)-2-((S)-1,4-Dimethyl-pent-4-enyl)-5-methyl-cyclohexanone 
• 2216-51-5 (-)-menthol 
• 29606-79-9 isopulegone 
• 80868-19-5 tert-butyldimethyl(((1R,2S,5R)-5-methyl-2-(prop-1-en-2-yl)cyclohexyl)oxy)silane 
• 103615-41-4 (1R,2R,5R)-5-methyl-2-((R)-2-methyloxiran-2-yl)cyclohexan-1-ol 
• 103615-39-0 (1R,2R,5R)-5-methyl-2-((S)-2-methyloxiran-2-yl)cyclohexanol 
• 593279-34-6 di(-)-isopulegyl fumarate 
• 20549-46-6 (+)-neoisopulegol 
• 84051-32-1 (2S,5R)-2-((R)-1-(benzyloxy)propan-2-yl)-5-methylcyclohexanone 
• 106145-00-0 (6S,1'R)-6-(1'-hydroxy-1',5'-dimethyl-4'-hexenyl)-3-methyl-2-cyclohexenone 
• 95602-94-1 (6S,1'S)-6-(1'-hydroxy-1',5'-dimethyl-4'-hexenyl)-3-methyl-2-cyclohexenone 
• 84051-31-0 <1R>-5(R)-methyl-2(S)-<1(R)-methyl-2-(phenylmethoxy)ethyl>cyclohexanol 
• 13834-16-7 (1R,2S,5R)-2-[(S)-2-hydroxy-1-methylethyl]-5-methylcyclohexan-1-ol 

Relevant articles and documents

Continuous synthesis of menthol from citronellal and citral over Ni-beta-zeolite-sepiolite composite catalyst

One-pot continuous synthesis of menthols both from citronellal and citral was investigated over 5 wt% Ni supported on H-Beta-38-sepiolite composite catalyst at 60–70 °C under 10–29 bar hydrogen pressure. A relatively high menthols yield of 53% and 49% and stereoselectivity to menthol of 71–76% and 72–74% were obtained from citronellal and citral respectively at the contact time 4.2 min, 70 °C and 20 bar. Citral conversion noticeably decreased with time-on-stream under 10 and 15 bar of hydrogen pressure accompanied by accumulation of citronellal, the primary hydrogenation product of citral, practically not affecting selectivity to menthol. A substantial amount of defuctionalization products observed during citral conversion, especially at the beginning of the reaction (ca. 1 h), indicated that all intermediates could contribute to formation of menthanes. Ni/H-Beta-38-sepiolite composite material prepared by extrusion was characterized by TEM, SEM, XPS, XRD, ICP-OES, N2 physisorption and FTIR techniques to perceive the interrelation between the physico-chemical and catalytic properties.

Method for improving optical purity of L-isopulegol through chiral resolution

The invention provides a method for improving the optical purity of L-isopulegol through chiral resolution. The method comprises the following steps: putting D,L-isopulegol and a resolution agent L-linalool into a dispersant and an auxiliary agent and reacting for 3 to 4 hours at 70 to 80 DEG C; after cooling to 10 to 25 DEG C, centrifuging and separating to obtain an intermediate L-isopulegol.L-linalool; carrying out alkali analysis on the intermediate; decomposing the intermediate; then carrying out gel chromatography to obtain the high-purity L-isopulegol. The method has the advantages of low raw material cost and low reaction energy consumption and is applicable to large-scale industrialized production.

Unveiling reactive metal sites in a Pd pincer MOF: Insights into Lewis acid and pore selective catalysis

A porous Zr metal-organic framework, 1-PdBF4 [Zr6O4(OH)4(OAc)2.4{(PNNNP)Pd(MeCN)}2.4(BF4)2.4; PNNNP = 2,6-(HNPAr2)2C5H3N; Ar = p-C6H4CO2-], has been synthesized via postsynthetic oxidative I-/BF4- ligand exchange using NOBF4. 1-PdBF4 enjoys markedly superior catalytic activity and recyclability to its trifluoracetate-exchanged analogue, 1-PdTFA, for the intramolecular cyclization of o-alkynyl anilines and the carbonyl-ene cyclization of citronellal. Moreover, 1-PdBF4 demonstrates a rare example of pore selective catalysis for the cyclization of 2-ethynyl aniline.