220621-22-7

Basic information

• Product Name: Pentanedioic acid, 1-[(1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl] ester
• Synonyms: Pentanedioic acid, 1-[(1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl] ester;L-MONOMENTHYLGLUTARATE;L-menthylglutaric acid; Pentanedioic acid,L-Monomenthyl glutarate;laevo-monomenthyl glutarate
• CAS NO: 220621-22-7
• Molecular Formula: C₁₅H₂₆O₄
• Molecular Weight: 270.36
• Mol File: 220621-22-7.mol

Chemical Properties

• Boiling Point: 393.4±25.0 °C(Predicted)
• Appearance: /
• Density: 1.0318
• Refractive Index: 1.478
• PKA: 4.61±0.10(Predicted)
• CAS DataBase Reference: Pentanedioic acid, 1-[(1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl] ester(CAS DataBase Reference)
• NIST Chemistry Reference: Pentanedioic acid, 1-[(1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl] ester(220621-22-7)
• EPA Substance Registry System: Pentanedioic acid, 1-[(1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl] ester(220621-22-7)

Safety Data

• Hazardous Substances Data: 220621-22-7(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
Pentanedioic acid, 1-[(1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl] ester is used as an intermediate in the synthesis of various complex organic compounds. Its unique structure and stereochemistry make it a valuable building block for creating novel molecules with potential applications in different industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Pentanedioic acid, 1-[(1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl] ester is used as a precursor for the development of new drugs. Its specific stereochemistry and functional groups can be exploited to design molecules with targeted therapeutic effects, potentially leading to the discovery of new medications.
Used in Flavor and Fragrance Industry:
Pentanedioic acid, 1-[(1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl] ester is used as a component in the creation of unique fragrances and flavors. Its polar nature and potential odor or flavor properties make it a candidate for use in the development of new scents and tastes for consumer products.
Used in Material Science:
In material science, Pentanedioic acid, 1-[(1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl] ester is used as a component in the development of new materials with specific properties. Its inclusion in polymers or other materials can influence their physical and chemical characteristics, leading to innovative applications in various fields.

InChI:InChI=1/C15H26O4/c1-10(2)12-8-7-11(3)9-13(12)19-15(18)6-4-5-14(16)17/h10-13H,4-9H2,1-3H3,(H,16,17)/t11-,12+,13-/m1/s1

Upstream product

• 108-55-4 glutaric anhydride, 
• 2216-51-5 (-)-menthol 

Downstream Products

• 106161-14-2 4-Chlorocarbonyl-butyric acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 106140-99-2 4-(2-Vinyl-[1,3]dioxolan-2-yl)-butyric acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 

Relevant articles and documents

The effect of the position of chiral (?)-menthyl on the formation of blue phase and mesophase behavior in biphenyl-benzoate liquid crystals

Eight new chiral liquid crystal compounds 4-(4-menthyloxy-n-oxoalkanoyloxy) biphenyl-4′-yl 4-butoxybenzoates MnB4OB (n = 1–8), were prepared by modifying the position of chiral (?)-menthyl in the menthol based liquid crystal compounds through gradually increasing the alkyl chain length of the dicarboxylic spacer. All compounds were characterized by FT-IR and NMR spectroscopy in order to prove their chemical structures. Differential scanning calorimetry (DSC), polarized optical microscopy (POM) and X-ray diffraction were carried out to systematically investigate their phase transition behaviors. The position of chiral (?)-menthyl in relation to the core has a great effect on the formation of BPs and mesomorphic behaviors. Only CLCs M1B4OB and M2B4OB with short spacer chains presented blue phases. Furthermore, the length and parity of the flexible spacers have a profound influence on phase structures and phase transition behaviors. An odd-even effect is observed for these chiral liquid crystal compounds.

A single acid preparation fifth heavenly stem method of L-menthyl ester

The invention discloses a feeding manner for preparing L-monomenthyl glutarate with glutaric anhydride and menthol and belongs to the field of organic chemical synthesis. According to the method takes the glutaric anhydride and the menthol as the raw materials and artificial zeolite as the catalyst and comprises adding in solvent for dissolution, and after the temperature rises, reducing temperature and removing the solvent to achieve solvent-less reaction and further to obtain the L-monomenthyl glutarate. The feeding manner for preparing the L-monomenthyl glutarate mainly solves the problem that, during the process of preparing the L-monomenthyl glutarate through solvent-less reaction, the menthol can easily sublimate to result in low conversion ratio, so that the material cost for preparing the L-monomenthyl glutarate can be reduced, the shortcoming of high viscosity and stirring difficulty at the beginning of the solvent-less reaction can be avoided, subsequent processes can be facilitated, and a series of problems caused by sublimation of the menthol can be eliminated. The feeding manner for preparing the L-monomenthyl glutarate can improve the conversion rate of the menthol from originally 73% to more than 87%.

COOLING SENSATION AGENT COMPOSITION, SENSORY STIMULATION AGENT COMPOSITION AND USE OF THE SAME

Disclosed is a cooling sensation agent composition or sensory stimulation agent composition which contains at least one of diester compounds of dicarboxylic acid represented by the formula (1) wherein A represents CH2 or CH═CH, n represents an integer of 0 to 4 when A is CH2, or 1 when A is CH═CH, B is an alcohol residue having 10 to 18 carbon atoms and containing a para-menthane skeleton, which may have a substituent, and C is an alcohol residue having 6 to 18 carbon atoms, which may have a substituent as well as a flavor or fragrance composition, a beverage, a food product, a perfume or cosmetic product, a toiletry product, daily utensil products or groceries, a fiber, a fiber product, clothes, clothing or a medicine, wherein the cooling sensation agent composition or the sensory stimulation agent composition is compounded.

Process for making monomenthyl esters

A process for making monomenthyl esters of dicarboxylic acids is disclosed. Menthol reacts with a saturated, cyclic anhydride in the presence of a base catalyst under conditions effective to produce a mixture of mono- and bis-menthyl esters in which the molar ratio of mono- to bis-menthyl esters is enhanced compared with the ratio of esters produced in a similar uncatalyzed process.

Synthetic routes to the stereoisomers of 2,4-dimethylpentane-1,5-diol derivatives

Five different routes to every stereoisomer of non-symmetric derivatives of 2,4-dimethylpentanedioic acid and/or of O-monoprotected 2,4-dimethylpentane- 1,5-diols, which are common building blocks for the total synthesis of many polypropionates, have been investigated. Alkylation of the lithium enolate of N-propanoylpseudoephedrine turned out to be the most appropriate method, in connection with the synthesis of fragment C1-C5 of amphidinolide K.