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
• Article Data: 9

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

• 15356-62-4 L-menthoxyacetyl chloride 
• 7378-38-3 2-(L-menthoxy)ethanol 
• 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 
• 43195-93-3 methyl L-menthoxyacetate 
• 1201651-93-5 (3-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyloxy)prop-1-ynyl)benzene 

Relevant articles and documents

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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 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.