9.10- Dihydrojasmonic acid

There are few reports on metabolism of jasmonic acid in plants (Fig. 4). Studies on the isolation and structural elucidation of the metabolites of 9,10-dihydrojasmonic acid (DJA) have been reported. [2- C] ( ) DJA (racl) was prepared by treating diethyl [2- C] malonate with 2-pentylcyclopent-2-enone [41] and applying this to six-day-old barley seedlings [42,43]. After a feeding period of 72 hr, about 90% of ( )DJA (racl) was taken up by excised barley shoots. Subsequently the radioactivity was almost completely extracted from the plant material by 80% methanol. 

The results suggest that the conjugation with isoleucine and valine, hydroxylation preferentially at C-11, and hydrogenation at C-6 are important steps in the metabolism of ( + )-9,10-dihydrojasmonic acid in barley shoots. 

Dihydrojasmonic acid (9) has been isolated from culture filtrates of B. theobromae [14] and the amide with isoleucine from G. fujikuroi [11],... 

B. theobromae produces four additional derivatives of dihydrojasmonic acid two carry propionic acid (10) or butyric acid (11) instead of the acetic acid chain on the cyclopentane ring [25] two more are 1 -hydroxy (12) and 4 -hhydroxy (13) derivatives of (11) [24],... 

Cell-free extracts from cell suspension cultures of Lycopersicon peruvianum were found to catalyse the glucosylation of [U- H]dihydrojasmonic acid in the presence of UDP-glucose. The products of the enzymatic reactions were identified as glucosyl esters of dihydrojasmonic acid [45]. 

Fig. 4. Metabolic pathway of ( ) dihydrojasmonic acid in barley shoots. Major route...

Conjugation with amino acids, preferentially isoleucine, of the non-me-tabolized dihydrojasmonic acid and jasmonic acid, their 11-OH and 12-OH metabolites and the cyclopentanol metabolites. 

Dihydrohaematinic acid, T22 f/Txm-dihydrohaematinimide, Y23 Dihydrohomopterocarpin, Y3 Dihydrojasmonic acid, methyl ester, A36... 

Decenoic acid (143), easily prepared from the same telomer 142, was cyclized via acid chloride using A1C13 to give 2-pentyl-2-cyclopentenone (144). Michael addition of methyl malonate followed by removal of one ester group produced methyl dihydrojasmonate (145) (129) ... 

The chemical structures of the majority of FMs that have been studied in wastewater treatment are given in Figs. 1-3. Figure 1 shows a variety of FM structures that include alcohols, aldehydes, and ketones, including benzyl acetate (phenylmethyl ester acetic acid), methyl salicylate (2-hydroxy-methyl ester benzoic acid), methyl dihydrojasmonate (3-oxo-2-pentyl-methyl ester cyclopentaneacetic acid), terpineol (4-trimethyl-3-cyclohexene-1-methanol), benzyl salicylate (2-hydroxy-phenylmethyl ester benzoic acid), isobornyl acetate... 

DIETHYLPHOSPHONOMETHYL-2,2-DIHETHYL-l, 3-DI0XEN-4-0NE, 66, 194-196, 202 Diethyl phthalimidomethylphosphonate Phosphonic acid, (phthalimidomethyl)-, diethyl ester Phosphonic acid, [(1,3-dihydro-l,3-d1oxo-2H-iso1ndol-2-yl)-methyl]-, diethyl ester (33512-26-4), 65, 119 DIHYDROJASMONE, 65, 26... 

Of the four possible optical isomers, the (+)-( I )-cw-isomer possesses the most characteristic jasmin odor. Methyl dihydrojasmonate is prepared by Michael addition of malonic acid esters to 2-pentyl-2-cyclopenten-l-one, followed by hydrolysis and decarboxylation of the resulting (2-pentyl-3-oxocyclopentyl) malonate, and esterification of the (2-pentyl-3-oxocyclopentyl)acetic acid [136]. 

A new acyl anion equivalent derived from an aldehyde, a secondary amine and diphenylalkylphos-phine oxide, e.g. (N-morpholinomethyl)diphenylphosphine oxide, reacts with aldehydes or ketones to form enamines, which on acid hydrolysis afford aldehydes or ketones (Scheme 32). The usefulness of this acyl anion equivalent is demonstrated by the synthesis of dihydrojasmone and (Z)-6-henicosen-11-one. ... 

Thus, dihydrojasmone, " cw-jasmone, a precursor of methylenomycine B, dicran-enone A, a member of a new class of fatty acids having a cyclopentenone ring structurally similar to prostanoids and jasmonoids, have been synthesized from the 1-hydroxycyclopro-panecarbaldehyde derivatives, either via thermal C3 Cj or acid induced C3 -> C4 C5 ring expansions. ... 

Of all possible isomers, the (+)-(lR)-cis isomer possesses the most characteristic and intensive jasmine odor. Therefore, an industrially feasible process for the production of a methyl dihydrojasmonate with a high portion of this isomer has been developed. The process comprises the catalytic hydrogenation of the corresponding cyclopenteneacetic acid in the presence of a ruthenium(II) complex with chiral ligands and subsequent esterification [138]. 

Acetic acid, 2-pentyl-3-oxo-1-cyclopentyl-, methyl ester methyl dihydrojasmonate 172a, 174b, 1053, 3266 ... 

Oxidative decarboxyiation of dihydroaromatic acids. Some years ago Birch mentioned that 1-substituted 1,4-dihydrobenzoic acids are decarboxylated to arenes by LTA. The starting materials are readily available by a one-step Birch reduction (Li-NHo) and alkylation from benzoic acids. Birch and Slobbe have now extended the early work and shown that this process is useful synthetically. One example is the synthesis of olivetol dimethyl ether (equation I), liquation II formulates the synthesis of a useful intermediate to dihydrojasmone. 

IR)-trans-Jasmonic acid) 62653-85-4 ((IR)-cis jasmonic acid) 24851-98-7 (methyl dihydrojasmonate)]... 

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