40248-63-3

Basic information

• Product Name: (-)-MENTHOXYACETIC ACID
• Synonyms: Acetic acid, [[5-methyl-2-(1-methylethyl)cyclohexyl]oxy]-, [1R-(1alpha,2beta,5alpha)]-;(-)-MENTHYLOXYACETIC ACID;(-)-MENTHOXYACETIC ACID;L-MENTHOXYACETIC ACID;2-[(2-ISOPROPYL-5-METHYLCYCLOHEXYL)OXY]ACETIC ACID;L-p-menth-3-yloxyacetic acid;(-)-MENTHYLOXYACETIC ACID ABOUT 98%;(-)-MENTHOXYACETIC ACID 98+%
• CAS NO: 40248-63-3
• Molecular Formula: C₁₂H₂₂O₃
• Molecular Weight: 214.3
• EINECS: 254-857-2
• Product Categories: chiral;Biochemistry;for Resolution of Alcohols & Thiols;Monocyclic Monoterpenes;Optical Resolution;Synthetic Organic Chemistry;Terpenes
• Mol File: 40248-63-3.mol

Chemical Properties

• Melting Point: 52-55 °C(lit.)
• Boiling Point: 163-164 °C10 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: yellow/liquid
• Density: 1.01 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.000423mmHg at 25°C
• Refractive Index: n20/D 1.4672(lit.)
• Storage Temp.: 2-8°C
• PKA: 3.47±0.10(Predicted)
• BRN: 2444474
• CAS DataBase Reference: (-)-MENTHOXYACETIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-MENTHOXYACETIC ACID(40248-63-3)
• EPA Substance Registry System: (-)-MENTHOXYACETIC ACID(40248-63-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 40248-63-3(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powde

InChI:InChI=1/C12H22O3/c1-8(2)10-5-4-9(3)6-11(10)15-7-12(13)14/h8-11H,4-7H2,1-3H3,(H,13,14)/t9-,10-,11-/m1/s1

Upstream product

• 79-11-8 chloroacetic acid 
• 568598-78-7 (-)-menthoxyacetic acid 2-oxo-1,2,2-triphenylethyl ester 
• 3926-62-3 sodium monochloroacetic acid 
• 2216-51-5 (-)-menthol 

Downstream Products

• 43195-93-3 methyl L-menthoxyacetate 
• 15356-62-4 L-menthoxyacetyl chloride 
• 7378-38-3 2-(L-menthoxy)ethanol 
• 36143-11-0 6β-(2-(1R)-menthyloxy-acetylamino)-penicillanic acid 
• 88663-66-5 norethisterone menthyloxyacetate 
• 85891-96-9 ((1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexyloxy)-acetic acid (1R,2R)-2-[2-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-acetoxy]-1,2-diphenyl-ethyl ester 
• 85891-96-9 ((1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexyloxy)-acetic acid (1S,2S)-2-[2-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-acetoxy]-1,2-diphenyl-ethyl ester 
• 440369-60-8 3-[2-((1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexyloxy)-acetoxy]-2-[2-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-acetoxymethyl]-2-methyl-propionic acid benzyl ester 

Relevant articles and documents

Shape Similarity by Fractal Dimensionality: An Application in the de novo Design of (?)-Englerin A Mimetics

Molecular shape and pharmacological function are interconnected. To capture shape, the fractal dimensionality concept was employed, providing a natural similarity measure for the virtual screening of de novo generated small molecules mimicking the structurally complex natural product (?)-englerin A. Two of the top-ranking designs were synthesized and tested for their ability to modulate transient receptor potential (TRP) cation channels which are cellular targets of (?)-englerin A. Intracellular calcium assays and electrophysiological whole-cell measurements of TRPC4 and TRPM8 channels revealed potent inhibitory effects of one of the computer-generated compounds. Four derivatives of this identified hit compound had comparable effects on TRPC4 and TRPM8. The results of this study corroborate the use of fractal dimensionality as an innovative shape-based molecular representation for molecular scaffold-hopping.

New copper(II) 2-(alkylamino)troponates

The copper aminotropones Cu[ON(R′)C7H4R-4] 2 [R = H, R′ = Me (13), Et (14), n-Pr (15), n-Bu (16), Bz (17), MenOCH2CH2 (20); R = i-Pr, R′ = Me (18), n-Pr (19), MenOCH2CH2 (21)] have been prepared from the corresponding aminotropones HN(R′)OC7H4R-4 (1-7) by reacting with copper(II) acetate in aqueous ethanol. 20, 21 contain the flavourant, menthol, as part of the ligand. The structures of 5 (R = H, R′ = Bz), a hydrogen-bonded dimer, 14 and 20, both incorporating square-planar, four-coordinate copper centres, have been determined by X-ray crystallography. The antibacterial activities of complexes 13, 17, 20 and 21 have been assayed against Staphylococcus waneri, an in vitro model of plaque inhibition effects, and found to be more active than a commercial toothpaste formulation, but less active than the O,O-chelated copper(II) complex of ethylmaltol.

Synthesis, structure, and properties of chiral liquid crystal monomers and polymers based on menthol

To study structure-mesomorphism relationships of the monomers and polymers based on menthol, four new chiral monomers (M1-M4) and the corresponding homopolymers (P1-P4) with menthyl group were synthesized. Their chemical structures, formula, phase behavior, and thermal stability were characterized by FTIR, 1H NMR, 13C NMR, elemental analyses, differential scanning calorimetry, polarizing optical microscopy, X-ray diffraction, and thermogravimetric analysis. The selective reflection of light was investigated with ultraviolet/visible spectrometer. The influence of the mesogenic core rigidity, spacer length, and menthyl steric effect on the mesomorphism of M1-M4 and P 1-P4 was examined. By inserting a flexible spacer between the mesogenic core and the terminal menthyl groups, four target monomers and polymers could form the expected mesophase. Moreover, their melting temperature (Tm), glass transition temperature (Tg), clearing temperature (Ti), and mesophase range (δT) increased with increasing the mesogenic core rigidity; whereas the Tm and T g decreased, Ti and δT increased with an increase of the spacer length. M1 and M2 showed monotropic and enantiotropic cholesteric phase, respectively, whereas M3 and M 4 all revealed chiral smectic C (SmC*), cholesteric and cubic blue phases. In addition, with increasing temperature, the selective reflection of light shifted to the long wavelength region at the SmC* phase range and to the short wavelength region at the cholesteric range, respectively. P 1 and P2 only showed a smectic A (SmA) phase, whereas P3 and P4 exhibited the SmC* and SmA phases. All the obtained polymers had very good thermal stability.

Chemical resolution of (±)-calanolide A, (±)-cordatolide A and their 11-demethyl analogues

The chemical resolution of (±)-calanolide A and (±)-cordatolide A into their corresponding optically active enantiomers is described. Their inhibitory activities against HIV-1 are tested in vitro.

Synthesis of alkynyl ethers and low-temperature sigmatropic rearrangement of allyl and benzyl alkynyl ethers

(Chemical Equation Presented) α-Alkoxy ketones 3 can be transformed into 1-alkynyl ethers 5 by a two-step procedure involving formation of the enol triflate or phosphate and base-induced elimination. Performing the same reaction sequence with allylic alcohols (R2OH, R2 = allyl) furnishes instead γ,δ-unsaturated carboxylic acid derivatives 6, derived from [3,3]-sigmatropic rearrangement of the intermediate allyl alkynyl ethers at -78 °C and trapping of the subsequently formed ketene with nucleophiles (Nu-H). Benzyl alkynyl ether 5 (R2 = benzyl) rearranges to indanone 7 upon heating to 60 °C.

2-Hydroxy-1,2,2-triphenylethanone as an efficient photolabile protecting group for carboxylic acids

The synthesis is reported of 2-hydroxy-1,2,2-triphenylethanone esters of carboxylic acids by the reaction between 2-chloro-1,2,2-triphenylethanone and a carboxylic acid in the presence of silver carbonate and silver tetrafluoroborate. Photolysis of the esters occurs rapidly on irradiation with a medium-pressure mercury lamp through quartz or Pyrex to return the carboxylic acid. The side product of the photolysis is benzo[b]phenanthro[9,10-d]furan, formed through a tandem process involving initial generation of 2,3-diphenylbenzofuran, photochemical cyclisation and re-aromatisation by aerial oxidation.

Studies on fused β-lactams: Synthesis, stereochemistry and antimicrobial activity of some new cepham analogues

β-Lactam ring has been conveniently grafted onto 2-phenyl-5,6-dihydro-1,3-thiazine 1 by annelating it with in situ prepared ketenes to furnish cepham analogues 6-9. A variety of acids such as menthoxy acetic acid 2, butylthioacetic acid 3, chloroacetic acid 4 and benzotriazole acetic acid 5 have been used as mixed sulphonic acid anhydrides for the cycloaddition reaction. All the compounds have been screened for their antibacterial activities.

Synthesis of chiral O-functionalized isobornyloxy, menthyloxy and fenchyloxy cyclopentadienyl ligands

Natural (+)-camphene was used as the starting material for the preparation of an isobornyloxy-substituted cyclopentadienyl ligand in a simple two-step procedure. (-)-Menthol and (+)-fenchol were converted to analogous chiral cyclopentadienyl ligands in a four-step procedure. The new ligands contain an ether linkage suitable for bidentate chelation to a transition metal.

SYNTHESIS OF (+)-2R,3R,11R,12R- AND (-)-2S,3S,11S,12S-TETRAPHENYL-18-CROWN-6

The synthesis of the title crown ethers starting from optically active hydrobenzoins is described.R(+)-1, in CDCl3, preferentially extracts R(+)-phenylglycine methyl ester hydroperchlorate from an aqueous solution of the racemate with a chiral recognition factor of 1.5 as shown by nmr measurements.