L-Menthyl acetate

Base Information

• Chemical Name: L-Menthyl acetate
• CAS No.: 89-48-5
• Deprecated CAS: 29066-34-0
• Molecular Formula: C₁₂H₂₂O₂
• Molecular Weight: 198.305
• Hs Code.: 2915390090
• European Community (EC) Number: 201-911-8,220-076-0
• NSC Number: 52970,3722
• UNII: W8C5F4H1OA,LF3LEI45OH
• DSSTox Substance ID: DTXSID9041817,DTXSID7051472
• Nikkaji Number: J71.002D
• Wikipedia: Menthyl_acetate
• Wikidata: Q6817577
• RXCUI: 2048710,2282306
• Metabolomics Workbench ID: 49297
• ChEMBL ID: CHEMBL2236867
• Mol file: 89-48-5.mol

Synonyms:L-Menthyl acetate;(-)-Menthyl acetate;(1R)-(-)-Menthyl acetate;2623-23-6;l-Menthol acetate;dl-Menthyl acetate;89-48-5;Menthyl acetate, dl-;(-)-Acetoxy-p-menthane;L-p-Menth-3-yl acetate;(1R,2S,5R)-rel-2-Isopropyl-5-methylcyclohexyl acetate;(dl)-Menthyl acetate;(+/-)-Menthyl acetate;[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] acetate;NSC-3722;Menthyl acetate, (-)-;LF3LEI45OH;UNII-W8C5F4H1OA;W8C5F4H1OA;p-Menth-3-yl acetate, dl-;CHEBI:104;NSC3722;Acetic acid, L-;NSC52970;EINECS 201-911-8;EINECS 249-409-8;NSC-52970;Cyclohexanol, 5-methyl-2-(1-methylethyl)-, acetate, (1R,2S,5R)-rel-;Menthol, acetate, cis-1,3,trans-1,4-;(+-)-Menthol acetate;(+-)-Menthyl acetate;l-Menthyl acetate (natural);dl-5-Methyl-2-(1-methylethyl)cyclohexyl acetate;4-06-00-00153 (Beilstein Handbook Reference);FEMA No. 2668;Cyclohexan-1-ol, acetate, L-;rel-(1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl acetate;(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl acetate;(1R,2S,5R)-5-Methyl-2-(1-methylethyl)cyclohexanol 1-acetate;NSC 3722;EINECS 220-076-0;5-Methyl-2-(1-methylethyl)cyclohexyl acetate, (1alpha,2beta,5alpha)-;Cyclohexanol, 5-methyl-2-(1-methylethyl)-, 1-acetate, (1R,2S,5R)-;NSC 52970;L - menthyl acetate;Cyclohexanol, 5-methyl-2-(1-methylethyl)-, 1-acetate, (1R,2S,5R)-rel-;Cyclohexanol, 5-methyl-2-(1-methylethyl)-, acetate, (1alpha,2beta,5alpha)-;BRN 2208505;WLN: L6TJ AY1&1 BOV1 D1 -L;Menthol, acetate, (1R,3R,4S)-(-)-;UNII-LF3LEI45OH;(5R)-2-Isopropyl-5-methylcyclohexyl acetate;ACETIC ACID, p-MENTH-3-YL ESTER, l-;Cyclohexan-1-ol, 2-isopropyl-5-methyl-, acetate, L-;Cyclohexanol, 5-methyl-2-(1-methylethyl)-, acetate, (1R,2S,5R)-;l-Menthyl acetate (1alpha,2beta,5alpha);L-?Menthyl acetate;Nat.Menthyl Acetate;laevo-menthyl acetate;EC 201-911-8;(-)-?Menthyl acetate;MENTHYL ACETATE, L-;SCHEMBL57397;MENTHYL ACETATE [MI];MENTHYL ACETATE [INCI];MENTHYL ACETATE, RACEMIC;P- MENTH-3-YL ACETATE;CHEMBL2236867;DTXSID7051472;DTXSID9041817;MENTHYL ACETATE [MART.];(+/-)-MENTHOL ACETATE;L-MENTHYL ACETATE [FHFI];CYCLOHEXANOL, 5-METHYL-2-(1-METHYLETHYL)-, ACETATE, (1.ALPHA.,2.BETA.,5.ALPHA.)-;Cyclohexanol, 5-methyl-2-(1-methylethyl)-, acetate, (1R-(1alpha,2beta,5alpha))-;Cyclohexanol, 5-methyl-2-(1-methylethyl)-, acetate, (1theta-(1alpha,2beta,5alpha))-;Cyclohexanol, 5-methyl-2-(1-methylethyl)-, acetate, [1R-(1.alpha.,2.beta.,5.alpha.)]-;HY-N7132;(-)-MENTHYL ACETATE [FCC];MENTHYL ACETATE, (+/-)-;MFCD00001482;MFCD00063644;s5597;(1R)-(-)-Menthyl acetate, 98%;MENTHYL ACETATE RACEMATE [MI];AKOS015913189;CCG-266575;CS-W010530;LS-2351;MENTHYL ACETATE, RACEMIC [FCC];AS-71989;FEMA NO. 2668, (-)-;A1107;M3399;FEMA NO. 2668, (+/-)-;C09870;D88378;F77849;(1R)-(-)-Menthyl acetate, analytical standard;L-Menthyl acetate, natural, >=98%, FCC, FG;A861167;(1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl acetate;Q6817577;W-107187;Cyclohexanol,5-methyl-2-(1-methylethyl)-,1-acetate

Chemical Property of L-Menthyl acetate

Chemical Property:

• Vapor Pressure: 0.0707mmHg at 25°C
• Melting Point: 37 - 38oC
• Refractive Index: n20/D 1.447(lit.)
• Boiling Point: 222.2 °C at 760 mmHg
• Flash Point: 87 °C
• PSA: 26.30000
• Density: 0.932 g/cm³
• LogP: 3.01030
• Storage Temp.: ?20°C
• Water Solubility.: 17mg/L at 25℃
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 198.161979940
• Heavy Atom Count: 14
• Complexity: 199

Purity/Quality:

99% ^*data from raw suppliers

(±)-MenthylAcetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): N
• Hazard Codes: N
• Statements: 51/53
• Safety Statements: 61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC(C(C1)OC(=O)C)C(C)C
• Isomeric SMILES: C[C@@H]1CC[C@H]([C@@H](C1)OC(=O)C)C(C)C
• Description: Menthyl acetate has a fresh odor similar to mint and rose (on dilution). It has a characteristic, fresh, pungent flavor, different from menthol (being much milder). It has a cool mouthfeel with only a trace of mint flavor. May be prepared by reacting acetic anhydride with menthol in the presence of anhydrous sodium acetate.
• Uses: Menthyl acetate may be used in the preparation of 3-amino-2-hydroxyalkanoates via lithium amide-supported Mannich-type reaction of its lithium enolate with PMP-arylaldimines (PMP=p-methoxyphenyl) followed by in situ oxidation with oxaziridine. Menthyl acetate is in perfumery; emphasizes floral notes, especially that of rose, used in toilet waters having a lavender odor. Has been suggested for flavoring extracts having caraway or mint flavors.

Technology Process of L-Menthyl acetate

There total 46 articles about L-Menthyl acetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

menthol (89-78-1) + acetic anhydride (108-24-7) → 2-isopropyl-5-methylcyclohexyl acetate (89-48-5,2230-87-7,2552-91-2,2623-23-6,5157-89-1,16409-45-3,20777-36-0,20777-45-1,29066-34-0,42241-42-9,50539-17-8,55058-46-3,79199-84-1,146502-80-9)

Guidance literature:

With lithium perchlorate; at 25 ℃; for 22h;

DOI:10.1055/s-2001-17483

Reference yield: 97.0%

Isopropenyl acetate (108-22-5) + menthol (89-78-1) → 2-isopropyl-5-methylcyclohexyl acetate (89-48-5,2230-87-7,2552-91-2,2623-23-6,5157-89-1,16409-45-3,20777-36-0,20777-45-1,29066-34-0,42241-42-9,50539-17-8,55058-46-3,79199-84-1,146502-80-9)

Guidance literature:

With P(MeNCH₂CH₂)3N; In tetrahydrofuran; at 50 ℃; for 14h;

DOI:10.1021/jo981819m

Reference yield: 95.0%

menthol (89-78-1) + acetyl chloride (75-36-5) → 2-isopropyl-5-methylcyclohexyl acetate (89-48-5,2230-87-7,2552-91-2,2623-23-6,5157-89-1,16409-45-3,20777-36-0,20777-45-1,29066-34-0,42241-42-9,50539-17-8,55058-46-3,79199-84-1,146502-80-9)

Guidance literature:

With potassium fluoride on basic alumina; In toluene; for 2h;

DOI:10.1016/S0040-4020(01)00677-9

upstream raw materials:

acetic anhydride

menthol

[1-α]-5-methyl-2-[1-methylethyl]-cyclohexanol

vinyl acetate

Downstream raw materials:

menthol

(-)-menthol

(1S,2R,5S)-(+)-menthol

(+/-)-menthone

Refernces

• 1、 -. "A Method For Preparing (Meth)Acrylic Acid Ester Based Compound". Paragraph 0071-0072. . Retrieved 2021/05/07.
• 2、 Belkacemi, Fatima Zohra,Merabet-Khelassi, Mounia,Aribi-Zouioueche, Louisa,Riant, Olivier. "Production of l-menthyl acetate through kinetic resolution by?Candida cylindracea lipase: effects of alkaloids as additives". . p. 6847 - 6860. Retrieved 2018/07/15.