Grindelic acid

Base Information

• Chemical Name: Grindelic acid
• CAS No.: 1438-57-9
• Molecular Formula: C20H32 O3
• Molecular Weight: 320.4663
• DSSTox Substance ID: DTXSID10878535
• Metabolomics Workbench ID: 129034
• Wikidata: Q104253413
• Mol file: 1438-57-9.mol

Synonyms:grindelic acid

Chemical Property of Grindelic acid

Chemical Property:

• Melting Point: 100-101°
• Boiling Point: 434.7°Cat760mmHg
• Flash Point: 145.8°C
• PSA: 46.53000
• Density: 1.07g/cm³
• LogP: 4.95160
• Storage Temp.: ?20°C
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 320.23514488
• Heavy Atom Count: 23
• Complexity: 549

Purity/Quality:

99% ^*data from raw suppliers

(-)-GrindelicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CCC2C(CCCC2(C13CCC(O3)(C)CC(=O)O)C)(C)C
• Isomeric SMILES: CC1=CCC2[C@@]([C@@]13CC[C@](O3)(C)CC(=O)O)(CCCC2(C)C)C
• Uses: (-)-Grindelic Acid is a natural diterpene with potential pharmaceutical applications including Nox4 inhibition and antitumor activity.

Technology Process of Grindelic acid

There total 2 articles about Grindelic 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:

grindelic acid methyl ester (1438-58-0) → (-)-grindelic acid (1438-57-9)

Guidance literature:

With potassium hydroxide; In methanol; water; for 48h; Ambient temperature;

DOI:10.1021/jo960547p

Reference yield:

→ grindelic acid (1438-57-9)

Guidance literature:

aus Methyl-grindelat 1b durch Hydrolyse;

Reference yield: 97.0%

(-)-grindelic acid (1438-57-9) + Benzyl isocyanide (88333-03-3,10340-91-7) + acetone (67-64-1) + benzylamine (100-46-9)

Guidance literature:

acetone; benzylamine; In methanol; for 3h;

(-)-grindelic acid; Benzyl isocyanide; In methanol; for 24h;

DOI:10.1016/j.ejmech.2013.06.013

upstream raw materials:

grindelic acid methyl ester

Downstream raw materials:

methyl grindelate

(S)-3-Hydroxy-3-methyl-5-((S)-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-pentanoic acid methyl ester

(S)-3-Hydroxy-3-methyl-5-((4aS,8aS)-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-pentanoic acid methyl ester

grindelic acid methyl ester

Refernces

Stereoselective Synthesis of the Novel Bisnorditerpene Grindelistrictic Acid, Isolated from Grindelia stricta

10.1021/jo00364a043

The research focuses on the stereoselective synthesis of the novel bisnorditerpene Grindelistrictic acid, which was isolated from the plant genus Grindelia. The purpose of the study was to confirm the structures of the terpenoids strictanonic acid and Grindelistrictic acid, which were initially proposed based on NMR data, through unambiguous syntheses. The researchers successfully synthesized Grindelistrictic acid (3b) via a series of chemical reactions, including reductive cleavage, methylation, Jones oxidation, and intramolecular ketalization, using a variety of chemicals such as grindelic acid, sodium borohydride, Jones' reagent, sodium hydride, ethyl ether, and diazomethane, among others. The conclusions were supported by the coinciding 'H NMR and mass spectral data of the synthetic 3b with those of the natural product, and the 13C NMR spectrum which showed expected signals supporting the proposed structure.

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