493-46-9

Basic information

• Product Name: (+)-Protolichesterinic acid
• Synonyms: (+)-Protolichesterinic acid;(-)-Protolichesteric acid;(2S)-2β-Tridecyl-4-methylene-5-oxotetrahydrofuran-3α-carboxylic acid;(2S,3R)-Tetrahydro-4-methylene-5-oxo-2-tridecyl-3-furancarboxylic acid;[2S,3R,(-)]-Tetrahydro-4-methylene-5-oxo-2-tridecyl-3-furancarboxylic acid
• CAS NO: 493-46-9
• Molecular Formula: C₁₉H₃₂O₄
• Molecular Weight: 324.45498
• Mol File: 493-46-9.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 488.4°Cat760mmHg
• Flash Point: 166.7°C
• Appearance: /
• Density: 1.02g/cm³
• CAS DataBase Reference: (+)-Protolichesterinic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-Protolichesterinic acid(493-46-9)
• EPA Substance Registry System: (+)-Protolichesterinic acid(493-46-9)

Safety Data

• Hazardous Substances Data: 493-46-9(Hazardous Substances Data)

Usage

General Description

(+)-Protolichesterinic acid is a natural chemical compound that has been isolated from various lichen species. It has been found to possess a range of biological activities, including antioxidant, anti-inflammatory, and cytotoxic effects. Studies have shown that (+)-Protolichesterinic acid exhibits potent antioxidant properties and may have potential applications in the treatment of oxidative stress-related diseases. In addition, it has also been investigated for its anti-inflammatory activity, showing promising results in reducing inflammation. Furthermore, the compound has been found to have cytotoxic effects on certain cancer cell lines, highlighting its potential as a candidate for anticancer drug development. Overall, (+)-Protolichesterinic acid is a promising natural compound with diverse biological activities and potential therapeutic applications.

Upstream product

• 4861-79-4 magnesium methyl carbonate 
• 244612-58-6 (2R,3S)-5-oxo-2-tridecyl-tetrahydrofuran-3-carboxylic acid 
• 124-25-4 myristylaldehyde 
• 412300-70-0 4-methylene-5-oxo-2-tridecyl-tetrahydro-furan-3-carboxylic acid methyl ester 
• 2765-11-9 n-pentadecanal 
• 897657-65-7 (4S,5R)-5-tridecyl-4-[tris(methylsulfanyl)methyl]-4,5-dihydro-3H-furan-2-one 
• 144071-11-4 (+)-Protolichesterinsaeuremethylester 
• 2170-03-8 itaconic acid anhydride 
• 26735-82-0 2-bromomethylmaleic anhydride 
• 203925-02-4 1-tridecyl-1-(prop-2-ynyloxy)-2,3-epoxypropane 
• 203924-96-3 1-tridecyl-2,3-epoxypropan-1-ol 
• 17642-49-8 rac-hexadecen-3-ol 
• 220344-53-6 tert-butyl-(4-chloro-1-tridecyl-but-2-ynyloxy)-dimethyl-silane 
• 220344-52-5 1-chloro-heptadec-2-yn-4-ol 

Downstream Products

• 144032-09-7 (2R,3S,4S)-5-Oxo-4-(N'-phenyl-hydrazinomethyl)-2-tridecyl-tetrahydro-furan-3-carboxylic acid 
• 144032-06-4 (+)-Dibromprotolichesterinsaeure 
• 19464-85-8 (+)-roccellaric acid 
• 19464-87-0 (+)-dihydroprotolichesterinic acid 
• 70579-62-3 (+)-lichesterinic acid 
• 493-47-0 (+/-)-lichesterinic acid 
• 493-45-8 (+/-)-dihydroprotolichesterinic acid 
• 22800-25-5 (-)-lichesterinic acid 

Relevant articles and documents

Stereodivergent Synthesis of Chiral Paraconic Acids via Dynamic Kinetic Resolution of 3-Acylsuccinimides

A direct N-heterocyclic carbene (NHC) catalysis of maleimides with alkyl aldehydes is established for the synthesis of 3-acylsuccinimides. The first dynamic kinetic resolution of 3-acylsuccinimides is accomplished through asymmetric transfer hydrogenation. These two catalytic methodologies are utilized for the synthesis of each enantiomer of trans-paraconic acids in three steps and cis-paraconic acids in four steps with good yields and high stereoselectivities. This stereodivergent synthetic methodology is applied for the synthesis of seven bioactive paraconic acid natural products.

Design, synthesis and biological evaluation of potential antibacterial butyrolactones

Novel butyrolactone analogues were designed and synthesized based on the known lichen antibacterial compounds, lichesterinic acids (B-10 and B-11), by substituting different functional groups on the butyrolactone ring trying to enhance its activity. All synthesized butyrolactone analogues were evaluated for their in vitro antibacterial activity against Streptococcus gordonii. Among the derivatives, B-12 and B-13 had the lowest MIC of 9.38 μg/mL where they have shown to be stronger bactericidals, by 2–3 times, than the reference antibiotic, doxycycline. These two compounds were then checked for their cytotoxicity against human gingival epithelial cell lines, Ca9–22, and macrophages, THP-1, by MTT and LDH assays which confirmed their safety against the tested cell lines. A preliminary study of the structure–activity relationships unveiled that the functional groups at the C4position had an important influence on the antibacterial activity. An optimum length of the alkyl chain at the C5position registered the best antibacterial inhibitory activity however as its length increased the bactericidal effect increased as well. This efficiency was attained by a carboxyl group substitution at the C4position indicating the important dual role contributed by these two substituents which might be involved in their mechanism of action.

Diastereoselective synthesis of (+)-nephrosterinic acid and (+)-protolichesterinic acid

A diastereoselective synthesis of (+)-nephrosterinic acid and (+)-protolichesterinic acid, common members of the paraconic acids is described. The synthesis is based on a diastereoselective orthoester Johnson-Claisen rearrangement of a (Z)-allyl alcohol with a vicinal dioxolane moiety as key steps. The synthesis is completed in 10 steps and with overall yields of 15.9% for (+)-nephrosterinic acid and 16.4% for (+)-protolichesterinic acid.