Lambertianic acid
From Wikipedia, the free encyclopedia
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| IUPAC name
methyl (1S,4aR,5S,8aR)-5-[2-(furan-3-yl)ethyl]-4a-methyl-6-methylidene-1,2,3,4,5,7,8,8a-octahydronaphthalene-1-carboxylate | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
PubChem CID |
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CompTox Dashboard (EPA) |
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| Properties | |
| C20H28O3 | |
| Molar mass | 316.441 g·mol−1 |
| Density | 1.09 g/cm3 |
| Melting point | 213 °C (415 °F; 486 K) |
| Boiling point | 428 °C (802 °F; 701 K) |
| insoluble | |
| Solubility | soluble in chloroform, methanol, ethyl acetate, DMSO |
| Hazards | |
| Flash point | 213 °C[1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Lambertianic acid is a naturally occurring organic compound classified as a diterpenoid with the molecular formula C20H28O3. This is a tricyclic carboxylic acid first isolated from the oleoresin of the Lambert pine (Pinus lambertiana), from which it derives its name. The acid is a member of the abietane family of diterpenes, characterized by its aromatic C-ring.[2]
Lambertianic acid was first reported by Dauben and German[3] in the mid-20th century as a major acidic constituent of the oleoresin (a mixture of resin acids and terpenes) of the sugar pine (Pinus lambertiana).[4] The acid is biosynthesized in pine trees from geranylgeranyl pyrophosphate via the diterpenoid pathway and serves as a defensive compound against insects and pathogens. The compound has also been found, often in smaller quantities, in other Pinus species and some species of the Lamiaceae family.[5]
Structure
Lambertianic acid is based on the abietane carbon skeleton. Its structure consists of three fused six-membered rings (phenanthrene framework) with a carboxylic acid (–COOH) group at the C-18 position (the fourth carbon of the original abietane side chain) and three conjugated double bonds in rings B and C at the positions 8, 11, and 13. This conjugated system contributes to its reactivity and spectroscopic properties.[6] Lambertianic acid is an optical isomer of daniellic acid.[7]