23635-14-5

Basic information

• Product Name: (-)-PERILLIC ACID
• Synonyms: (S)-4-(1-Methylethenyl)-1-cyclohexene-1-carboxylic acid;(S)-4-Isopropenylcyclohexene-1-carboxylic acid;L(-)-Perillic acid,95%;(S)-(-)-Perillic acid 95%
• CAS NO: 23635-14-5
• Molecular Formula: C₁₀H₁₄O₂
• Molecular Weight: 166.22
• Mol File: 23635-14-5.mol

Chemical Properties

• Melting Point: 129-131 °C(lit.)
• Boiling Point: 284.9°Cat760mmHg
• Flash Point: 134°C
• Appearance: /
• Density: 1.068g/cm³
• Vapor Pressure: 0.000746mmHg at 25°C
• Storage Temp.: 2-8°C
• PKA: 4.94±0.40(Predicted)
• CAS DataBase Reference: (-)-PERILLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-PERILLIC ACID(23635-14-5)
• EPA Substance Registry System: (-)-PERILLIC ACID(23635-14-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 23635-14-5(Hazardous Substances Data)

Usage

Uses

1. Used in Anticancer Applications:
In the pharmaceutical industry, (-)-Perillic Acid is used as an apoptosis-inducing agent for its ability to increase the levels of p21, Bax, and caspase-3 in cells. This makes it a promising candidate for the development of new cancer treatments, particularly for solid tumors.
2. Used as a Biomarker for Parkinson's Disease:
In the field of medical research, (-)-Perillic Acid serves as a potential biomarker for Parkinson's disease. Its identification as a biomarker can aid in the early diagnosis and monitoring of the disease, leading to better patient outcomes and more effective treatment strategies.
3. Used in Antimicrobial Applications:
Due to its potent antimicrobial activity, (-)-Perillic Acid can be utilized in the development of new antimicrobial agents, particularly in the pharmaceutical and healthcare industries. This can help in the fight against antibiotic-resistant bacteria and contribute to the development of novel treatments for various infections.
4. Used in Drug Synthesis:
In the chemical industry, (-)-Perillic Acid can be employed as a key intermediate in the synthesis of various drugs and pharmaceutical compounds. Its unique chemical properties make it a valuable building block for the development of new medications with potential applications in various therapeutic areas.

Biochem/physiol Actions

Interferes with activity of p21ras and other small G proteins by inhibiting post-translational cysteine isoprenylation.

InChI:InChI=1/C10H14O2/c1-7(2)8-3-5-9(6-4-8)10(11)12/h5,8H,1,3-4,6H2,2H3,(H,11,12)/p-1/t8-/m1/s1

Upstream product

• 536-59-4 (-)-perillyl alcohol 
• 6931-54-0 trans-2,10-epoxypinane 
• 852920-51-5 β-pinene α-oxide 
• 127-91-3 (1R,5R)-(+)-β-pinene 
• 7785-70-8 (+)-α-pinene 
• 18172-67-3 beta-pinene 
• 146763-95-3 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl (-)-perillate 
• 146763-93-1 perriloside B 
• 18031-40-8 (S)-(-)-perillaldehyde 
• 76509-36-9 (S)-8-bromo-p-menthen-⁽¹⁾-oic acid-⁽⁷⁾ 

Downstream Products

• 117919-42-3 (S)-4-Isopropenyl-cyclohex-1-enecarbonyl azide 
• 92525-48-9 1-isocyanato-4-(2-(2-propenyl))-1-cyclohexene 
• 26460-67-3 (S)-methylperillate 
• 146763-93-1 perriloside B 

Relevant articles and documents

Novel tdp1 inhibitors based on adamantane connected with monoterpene moieties via heterocyclic fragments

Tyrosyl-DNA phosphodiesterase 1 (Tdp1) is a promising target for anticancer therapy due to its ability to counter the effects topoisomerase 1 (Top1) poison, such as topotecan, thus, decreasing their efficacy. Compounds containing adamantane and monoterpenoid residues connected via 1,2,4-triazole or 1,3,4-thiadiazole linkers were synthesized and tested against Tdp1. All the derivatives exhibited inhibition at low micromolar or nanomolar concentrations with the most potent inhibitors having IC50 values in the 0.35–0.57 μM range. The cytotoxicity was determined in the HeLa, HCT-116 and SW837 cancer cell lines; moderate CC50 (μM) values were seen from the mid-teens to no effect at 100 μM. Furthermore, citral derivative 20c, α-pinene-derived compounds 20f, 20g and 25c, and the citronellic acid derivative 25b were found to have a sensitizing effect in conjunction with topotecan in the HeLa cervical cancer and colon adenocarcinoma HCT-116 cell lines. The ligands are predicted to bind in the catalytic pocket of Tdp1 and have favorable physicochemical properties for further development as a potential adjunct therapy with Top1 poisons.

Perilla acid methyl ester derivatives containing nitrogen and its preparation and use

The invention belongs to the technical field of medicines and relates to a purple perilla methyl rosmarinate nitrogen-containing derivative as well as a preparation method and application thereof, wherein the purple perilla methyl rosmarinate nitrogen-containing derivative has structural characteristics shown in a formula I described in the specification. The invention also relates to pharmaceutically acceptable salt and solvate of the purple perilla methyl rosmarinate nitrogen-containing derivative and a pharmaceutical composition containing the purple perilla methyl rosmarinate nitrogen-containing derivative or pharmaceutically acceptable salt of the purple perilla methyl rosmarinate nitrogen-containing derivative as active ingredients, wherein the pharmaceutically acceptable salt and solvate and the pharmaceutical composition can be used for treating cancer. The purple perilla methyl rosmarinate nitrogen-containing derivative and pharmaceutical salt thereof have good antitumour activities, the preparation method is simple and feasible, and operation is easy.

Methyl Perillate as a Highly Functionalized Natural Starting Material for Terephthalic Acid

Renewable commodity chemicals can be generated from plant materials. Often abundant materials such as sugars are used for this purpose. However, these lack appropriate functionalities and, therefore, they require extensive chemical modifications before they can be used as commodity chemicals. The plant kingdom is capable of producing an almost endless variety of compounds, including compounds with highly appropriate functionalities, but these are often not available in high quantities. It has been demonstrated that it is possible to produce functionalized plant compounds on a large scale by fermentation in microorganisms. This opens up the potential to exploit plant compounds that are less abundant, but functionally resemble commodity chemicals more closely. To elaborate this concept, we demonstrate the suitability of a highly functionalized plant compound, methyl perillate, as a precursor for the commodity chemical terephthalic acid.

Oxidative Transformations of Biosourced Alcohols Catalyzed by Earth-Abundant Transition Metals

The catalytic acceptorless dehydrogenative oxidation of biosourced alcohols into carboxylic acid salts was achieved using earth-abundant Fe and Mn complexes that feature aliphatic PNP pincer ligands in good to excellent yields. The Fe derivatives were characterized by using 57Fe NMR spectroscopy. Mn pincer catalysts are catalytically more efficient than their Fe counterparts thanks to their robustness under basic conditions. Attempts to generate aldehydes from alcohols were not successful using the Fe and Mn species, but a commercially available Ru analogue achieves this transformation selectively under very mild conditions in the presence of a large excess of acetone as a hydrogen acceptor.

Stereoselective synthesis of perillaldehyde-based chiral β-amino acid derivatives through conjugate addition of lithium amides

The Michael addition of dibenzylamine to (+)- tert-butyl perillate ( 3) and to (+)- tert-butyl phellandrate (6), derived from ( S)-(-)-perillaldehyde (1 ), resulted in diastereomeric β-amino esters 7A-D in a moderately stereospecific reaction in a ratio of 76:17:6:1. After separation of the diastereoisomers, the major product, cis isomer 7A, was quantitatively isomerized to the minor component, trans-amino ester 7D. All four isomers were transformed to the corresponding β-amino acids 10A-D, which are promising building blocks for the synthesis of β-peptides and 1,3-heterocycles in three steps. The steric effects of the isopropyl group at position 4 and of the α-methyl substituent of (R)-N-benzyl-N-α-methylbenzylamine on the reactivity were also studied, upon application of a chiral amine, excellent stereoselectivity of the conjugate addition was observed. Amino ester 11 was obtained as a single product and transformed to the corresponding amino acids 10A and 10D in good yields on the gram scale.

Selective aerobic oxidation of allylic and benzylic alcohols catalyzed by N-hydroxyindole and copper(I) chloride

In the presence of copper(I) chloride, tert-butyl 1-hydroxy-2-methyl-6- trifluoromethyl-1H-indole-3-carboxylate acted as a catalyst for the chemoselective aerobic oxidation of allylic and benzylic alcohols. A variety of primary and secondary allylic and benzylic alcohols were oxidized into the corresponding α,β-unsaturated carbonyl compounds in good yields without affecting non-allylic alcohols.

One-pot chemoenzymatic synthesis of aldoximes from primary alcohols in water

A new synthetic method for the one-pot preparation of aldoximes in water was developed; the method is based on the combination of the enzymatic oxidation of primary alcohols to aldehydes using different acetic acid bacteria and in situ condensation of the aldehydes with hydroxylamine.

MONOTERPENE GLUCOSIDES AND OTHER CONSTITUENTS FROM PERILLA FRUTESCENS

Three new monoterpene glucosides named perilloside B-D have been isolated from the fresh leaves of Perilla frutescens.The structures were determined on the basis of spectral and chemical evidence.

Enantioselective synthesis of chiral liquid crystalline compounds from monoterpenes

Chiral liquid crystalline compounds 1-9 have been synthesized enantioselectively from monoterpenes. The optical purities of (S)-(-)- and (R)-(+)-perillalcohol (16, 27), (S)-(-)- and (R)-(+)-1-pentyl-4-hydroxymethyl-1-cyclohexene (33, 34) and (2S,5S)-2-pentyl-5-hydroxymethyl-1-cyclohexanone (53) have been determined by 1H NMR analysis using chiral shift reagents. The mesomorphic phases and transition temperatures of compounds 2,3,5,6,7,8 and 9 have been characterized.

Photochemical Reaction of Perillaldehyde under Various Conditions

(-)-Perillaldehyde (1) was photoirradiated by a 400 W high-pressure mercury lamp under various conditions.In MeOH, 1 was degraded to give two new MeOH adducts (2 and 3) and a new methyl ether (4) under an N2 stream, while 1 was converted to a dimethyl acetal (5) and oxidation product (6) in additon to 2 and 3 under O2 stream.In EtOAc, 1 disappeared to afford two new dimers (7 and 8) under an N2 stream, while 1 was changed to two oxygenated products (9 and 10) including a new compound under an O2 stream.In the presence of rose bengal (RB), 1 was converted to 5 by visible light in MeOH under an N2 stream.Photosensitization of RB was observed under an O2 stream, and two new oxygenated products (11 and 12) were formed.Perillaldehyde was relatively stable in n-hexane under N2 stream or in the presence of RB under an O2 stream.