L-Menthyl acetate

Base Information

• Chemical Name: L-Menthyl acetate
• CAS No.: 2623-23-6
• Deprecated CAS: 29066-34-0
• Molecular Formula: C12H22O2
• Molecular Weight: 198.305
• Hs Code.: 2915 39 00
• 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: 2623-23-6.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: <25 °C
• Refractive Index: n20/D 1.447(lit.)
• Boiling Point: 229.1 °C at 760 mmHg
• Flash Point: 92.2 °C
• PSA: 26.30000
• Density: 0.92 g/cm³
• LogP: 3.01030
• Storage Temp.: Store below +30°C.
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: 23.2mg/L at 20℃
• 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

L-Menthyl acetate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

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
• Uses: L-Menthyl Acetate, and its derivatives, is used as a penetration enhancers, to enhance the skin permeation of various drugs with differing lipophilicities, such as 5-aminolevulinic acid (ALA), 5-fluorouracil (5-FU), isosorbide dinitrate (ISDN), lidocaine (LD), etc.

Technology Process of L-Menthyl acetate

There total 94 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:

l-menthyl (trimethylsilyl)acetate

Menthane

menthol

(-)-menthol

Refernces

• 1、 Miyazawa, Mitsuo,Kawazoe, Hideki,Sumi, Yuji,Hyakumachi, Mitsuro. "Lytic activity of l-menthol derivatives against the snow blight disease fungus, Micronectriella nivalis". . p. 1880 - 1883. Retrieved 2003.
• 2、 Guncheva, Maya,Dimitrov, Momtchil,Napoly, Francois,Draye, Micheline,Andrioletti, Bruno. "Novel hybrid materials on the basis of nanostructured tin dioxide and a lipase from Rhizopus delemar with improved enantioselectivity". . p. 72 - 80. Retrieved 2014.
• 3、 -. "A Method For Preparing (Meth)Acrylic Acid Ester Based Compound". Paragraph 0071-0072. . Retrieved 2021/05/07.
• 4、 Zaharani, Lia,Khaligh, Nader Ghaffari,Johan, Mohd Rafie,Gorjian, Hayedeh. "Synthesis and characterization of a new acid molten salt and the study of its thermal behavior and catalytic activity in Fischer esterification". . p. 7081 - 7088. Retrieved 2021/05/03.