Perillic acid

Base Information

• Chemical Name: Perillic acid
• CAS No.: 7694-45-3
• Molecular Formula: C10H14 O2
• Molecular Weight: 166.22
• Hs Code.: 2916209090
• European Community (EC) Number: 231-709-5
• NSC Number: 641067
• UNII: PKS69DU4ZQ
• DSSTox Substance ID: DTXSID60864105
• Nikkaji Number: J13.588G
• Wikidata: Q27104388
• NCI Thesaurus Code: C64168
• Metabolomics Workbench ID: 75132
• ChEMBL ID: CHEMBL1373981
• Mol file: 7694-45-3.mol

Synonyms:4-(1-methylethenyl)-1-cyclohexene-1-carboxylic acid;4-(2-propenyl)-1-cyclohexane-1-carboxylic acid;4-isopropenylcyclohex-1-ene carboxylic acid;NSC 667676;NSC-667676;perillic acid

Chemical Property of Perillic acid

Chemical Property:

• Appearance/Colour: White solid.
• Vapor Pressure: 0.000746mmHg at 25°C
• Melting Point: 129-131 °C(lit.)
• Refractive Index: 1.4859 (estimate)
• Boiling Point: 284.9 °C at 760 mmHg
• PKA: 4.94±0.40(Predicted)
• Flash Point: 134 °C
• PSA: 37.30000
• Density: 1.068 g/cm³
• LogP: 2.37360
• Storage Temp.: 2-8°C
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 166.099379685
• Heavy Atom Count: 12
• Complexity: 238

Purity/Quality:

99% ^*data from raw suppliers

(S)-(?)-Perillic acid 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=C)C1CCC(=CC1)C(=O)O
• Uses: inhibits posttranslational cys isoprenylation, blocks G-protein

Technology Process of Perillic acid

There total 25 articles about Perillic acid 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: 50.0%

perillaldehyde (2111-75-3) → 4-(prop-1-en-2-yl)cyclohex-1-ene-1-carboxylic acid (7694-45-3)

Guidance literature:

With 1-hydroxycyclohexyl phenyl ketone; sodium hydroxide; In 1,2-dimethoxyethane; at 60 ℃; chemoselective reaction; Sealed tube;

DOI:10.1021/acs.orglett.1c02188

upstream raw materials:

8-bromo-p-menth-1-en-7-oic acid

perillaldehyde

2-hydroxy-6,6-dimethylbicyclo[3.1.1]heptane-2-carboxylic acid

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

Downstream raw materials:

4-isopropyl-3-nitrobenzoic acid

p-menth-8-en-7-oic acid

(-)-sirenin

(S)-4-(1-Hydroxymethyl-vinyl)-cyclohex-1-enecarboxylic acid methyl ester

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.