(S)-4-(1-Methylethenyl)-1-cyclohexene-1-carboxylic acidanion

Base Information

• Chemical Name: (S)-4-(1-Methylethenyl)-1-cyclohexene-1-carboxylic acidanion
• CAS No.: 23635-14-5
• Molecular Formula: C₁₀H₁₄O₂
• Molecular Weight: 166.22
• Hs Code.: 29162000
• DSSTox Substance ID: DTXSID00946454
• Nikkaji Number: J1.187.416I
• Mol file: 23635-14-5.mol

Synonyms:DTXSID00946454;(S)-4-(1-Methylethenyl)-1-cyclohexene-1-carboxylic acidanion

Chemical Property of (S)-4-(1-Methylethenyl)-1-cyclohexene-1-carboxylic acidanion

Chemical Property:

• Vapor Pressure: 0.000746mmHg at 25°C
• Melting Point: 129-131 °C(lit.)
• Boiling Point: 284.9°Cat760mmHg
• PKA: 4.94±0.40(Predicted)
• Flash Point: 134°C
• PSA: 37.30000
• Density: 1.068g/cm³
• LogP: 2.37360
• Storage Temp.: 2-8°C
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 165.091554653
• Heavy Atom Count: 12
• Complexity: 233

Purity/Quality:

98%,99%, ^*data from raw suppliers

PerillicAcid ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=C)C1CCC(=CC1)C(=O)[O-]
• Isomeric SMILES: CC(=C)[C@H]1CCC(=CC1)C(=O)[O-]
• Uses: Perillic Acid is an apoptosis inducing agent via an increase in p21, Bax, and caspase-3 in cells.A possible biomarker of Parkinson’s disease.

Technology Process of (S)-4-(1-Methylethenyl)-1-cyclohexene-1-carboxylic acidanion

There total 15 articles about (S)-4-(1-Methylethenyl)-1-cyclohexene-1-carboxylic acidanion 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: 65.0%

(-)-perillyl alcohol (536-59-4,18457-55-1) → (s)-(-)-perillic acid (23635-14-5,7694-45-3,23635-15-6) + (S)-(-)-perillaldehyde (18031-40-8)

Guidance literature:

With tert-butyl 1-hydroxy-2-methyl-6-trifluoromethyl-1H-indole-3-carboxylate; oxygen; copper(l) chloride; In N,N-dimethyl-formamide; at 50 ℃; for 24h; under 760.051 Torr;

DOI:10.1016/j.tetlet.2011.12.058

Reference yield: 60.0%

(S)-(-)-perillaldehyde (18031-40-8) → (s)-(-)-perillic acid (23635-14-5,7694-45-3,23635-15-6)

Guidance literature:

With sodium chlorite; sodium dihydrogenphosphate; In water; tert-butyl alcohol;

DOI:10.3762/bjoc.10.289

Reference yield: 13.0%

(S)-(-)-perillaldehyde (18031-40-8) → (s)-(-)-perillic acid (23635-14-5,7694-45-3,23635-15-6) + (4S)-8,9-epoxy-p-menth-1-en-7-ol

Guidance literature:

With oxygen; In ethyl acetate; for 5h; Irradiation;

upstream raw materials:

(S)-8-bromo-p-menthen-⁽¹⁾-oic acid-⁽⁷⁾

(S)-(-)-perillaldehyde

perriloside B

(-)-perillyl alcohol

Downstream raw materials:

(S)-1-Isocyanato-4-isopropenyl-cyclohexene

perriloside B

Refernces

• 1、 Chepanova, Arina A.,Dyrkheeva, Nadezhda S.,Ilina, Ekaterina S.,Korchagina, Dina V.,Lavrik, Olga I.,Mozhaitsev, Evgenii S.,Munkuev, Aldar A.,Reynisson, Jóhannes,Salakhutdinov, Nariman F.,Suslov, Evgeniy V.,Volcho, Konstantin P.,Zakharenko, Alexandra L.,Zakharova, Olga D.. "Novel tdp1 inhibitors based on adamantane connected with monoterpene moieties via heterocyclic fragments". . . Retrieved 2021/06/12.
• 2、 Jongedijk, Esmer,van der Klis, Frits,de Zwart, Rozemarijn,van Es, Daan S.,Beekwilder, Jules. "Methyl Perillate as a Highly Functionalized Natural Starting Material for Terephthalic Acid". . p. 201 - 203. Retrieved 2018/03/06.