Juvenile Hormone Analogs in Conifers. II. Isolation, Identification, and Biological Activity of cis-4-[1′(R)-5′-Dimethyl-3′-oxohexyl]-cyclohexane-1-carboxylic Acid and (+)-4(R)-[1′(R)-5′-Dimethyl-3′-oxohexyl]-1-cyclohexene-1-carboxylic Acid from Douglas-fir Wood

1974 ◽  
Vol 52 (7) ◽  
pp. 1192-1199 ◽  
Author(s):  
I. H. Rogers ◽  
J. F. Manville ◽  
T. Sahota
Keyword(s):  
Carboxylic Acid ◽  
Methyl Ester ◽  
Juvenile Hormone ◽  
Methyl Esters ◽  
Petroleum Ether Extract ◽  
Douglas Fir ◽  
Ether Extract ◽  
Biological Assays ◽  
Hormone Analogs ◽  
Derivatives Of

The petroleum ether extract from the whole-wood meal of a number of British Columbia Interior-Intermediate variety Douglas-fir trees have yielded two carboxylic acids (+)-todomatuic acid (3b) and cis-dihydrotodomatuic acid (4b) which as their methyl esters are potentially useful juvenile hormone analogs. These compounds possess the R,R and R stereoconfigurations, respectively. The configuration at C-1′ is opposite to that reported by others for "(+)-juvabione" isolated from Abiesbalsamea grown in Czechoslovakia. Whereas (+)-juvabione naturally occurs as and is the methyl ester of (+)-todomatuic acid (4b), in this variety of Douglas-fir these compounds appear as the free acids. Results of biological assays on certain insects indicate that the methyl ester derivatives of these acids are effective ovicides and juvenilizing hormones.

Juvenile Hormone Mimics in Conifers. I. Isolation of (−)-cis-4-[1′(R)-5′-Dimethyl-3′-oxohexyl]-cyclohexane-1-carboxylic Acid from Douglas-fir Wood

1972 ◽  
Vol 50 (14) ◽  
pp. 2380-2382 ◽  
Author(s):  
I. H. Rogers ◽  
J. F. Manville
Keyword(s):  
Carboxylic Acid ◽  
Juvenile Hormone ◽  
Free Acid ◽  
Petroleum Ether Extract ◽  
Douglas Fir ◽  
Balsam Fir ◽  
Ether Extract ◽  
Juvenile Hormone Mimic ◽  
Steric Configuration ◽  
Juvenile Hormone Mimics

The petroleum ether extract from the whole-wood meal of a British Columbia Interior variety of Douglas-fir has yielded a new and potentially useful juvenile hormone mimic, (−)-cis-4-[1′(R)-5′-dimethyl-3′-oxohexyl]-cyclohexane-1-carboxylic acid (3a). This compound possesses the opposite steric configuration at C-1′ to that of (+)-juvabione (1a), which has been isolated by others from balsam fir. Also, it occurs exclusively as the free acid. Not all Douglas-firs contain this compound and the biological consequences of its formation are being explored.

Derivate des Benzo[1.3]dioxols, 431 Über Benzo [1.3] dioxolcarbonsäuren / Derivatives of 1,3-Benzodioxoles, 43 1,3-Benzodioxolecarboxylic Acids

1978 ◽  
Vol 33 (7-8) ◽  
pp. 465-471
Author(s):  
Franz Daliacker ◽  
Volker Mues ◽  
In-O Kim
Keyword(s):  
Carboxylic Acid ◽  
Methyl Ester ◽  
Benzoic Acid ◽  
Myristic Acid ◽  
Good Yield ◽  
Acid Ester ◽  
Acid Methyl Ester ◽  
Acid Methyl ◽  
Derivatives Of

Abstract We describe the possibilities of formation and preparation of the “natural” 1,3-benzodioxolecarboxylic acids 1, 2, 4, 6 b, and 7, already mentioned in literature. Myristic acid (3e) was prepared in good yield from 3-methoxy-4,5-dihydroxy-benzoic acid ester (3c) , which could be easily made from 3-methoxy-2,3-carbonyldioxy-benzoic acid methylester (3b). Myristicic acid methylester (3d) could be subjected to methylation and hydrolysis leading to 3e without any difficulties. 4.6-dimethoxy-1,3-benzodioxole-5-carboxylic acid (5b) was prepared in good yields by oxidation of 4,6-dimethoxy-1,3-benzodioxole-5-aldehyde (5a). 5.7-dimethoxy-1,3-benzodioxole-carboxylic acid (13f), one of the “unnatural” 1,3-benzodioxolecarboxylic acids, derivatives of o-ipiperonylic acid (8), was prepared from 5-amino-7-methoxy-1,3- benzodioxole-4carboxylic acid methyl ester (13b) by diazotisation, elimination of nitrogen, methylation, and hydrolysis. A comparison of our measured pkA-values showed the strongest acidity belonging to 5,6-dimethoxy-1,3-benzodioxole-4-carbocylic acid (11).

scholarly journals Synthetic Studies on Potent Marine Drugs: Synthesis and the Crystal Structure of 6-tert-butyl-4-phenyl-4H-chromene-2-carboxylic Acid

2013 ◽  
Vol 2013 ◽  
pp. 1-9 ◽  
Author(s):  
Hui-Jing Li ◽  
Jun-Li Wang ◽  
Rui Wang ◽  
Dong-Hui Luo ◽  
Yan-Chao Wu
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bond ◽  
Carboxylic Acid ◽  
Methyl Ester ◽  
Crystallographic Analysis ◽  
Antitumor Antibiotic ◽  
Stacking Interactions ◽  
X Ray ◽  
Structural Activity Relationship ◽  
Derivatives Of

4H-Chromene-2-carboxylic acid ester derivatives of renieramycin M might be of use for the structural-activity relationship studies of antitumor antibiotic tetrahydroisoquinoline natural products. Accordingly, 6-tert-butyl-4-phenyl-4H-chromene-2-carboxylic acid, one key intermediate, was synthesized via the condensation of (3E)-2-oxo-4-phenylbut-3-enoate methyl ester with 4-tert-butylphenol in the presence of AuCl3/3AgOTf (5 mol%), followed by cyclodehydration and aqueous hydrolysis. The product was unambiguously shown to the 4H-chromene-2-carboxylic acid by spectroscopy and X-ray crystallographic analysis. A packing diagram of the crystal structure shows that aromaticπ-stacking interactions and O–H⋯O hydrogen bond stabilize the structure in the solid.

Insect juvenile hormone analogs in conifers. III. Variability of Douglas-fir wood extractives with geographical location

1977 ◽  
Vol 7 (2) ◽  
pp. 429-434 ◽  
Author(s):  
John F. Manville ◽  
Ian H. Rogers
Keyword(s):  
Juvenile Hormone ◽  
Lignin Content ◽  
Geographical Location ◽  
Douglas Fir ◽  
Extractive Content ◽  
Hybrid Index ◽  
Strong Negative Correlation ◽  
Juvenile Hormones ◽  
Hormone Analogs ◽  
Branch Wood

Cores, branch wood, and foliage samples were taken from five healthy Douglas-fir trees at each of 20 sites across southern British Columbia, ranging from central Vancouver Island to the western slopes of the Rocky Mountains. Hybridization values for each tree were established by von Rudloff, based on the composition of the foliage essential oil. Branch wood samples and cores from bole wood were analyzed for lipophilic extractives content; the presence of juvabione-type insect juvenile hormone analogs (IJHA) was noted. A strong negative correlation was noted between lignin content and a hybrid index and a strong positive association between lignin content and diameter. There was a strong positive relationship between extractive content and age. Juvenile hormones were most commonly found in trees of the coastal and coastal intermediate subvariants. Branch wood and bole wood samples usually gave comparable results for the presence of the juvenile hormones.

scholarly journals Isolation of oligomers of 5,6-dihydroxyindole-2-carboxylic acid from the eye of the catfish

1974 ◽  
Vol 143 (1) ◽  
pp. 207-217 ◽  
Author(s):  
Shosuke Ito ◽  
J. A. Colin Nicol
Keyword(s):  
Carboxylic Acid ◽  
Methyl Ester ◽  
Methyl Esters ◽  
Tricarboxylic Acid ◽  
Oxidation Products ◽  
Molecular Weight Determination ◽  
Mushroom Tyrosinase ◽  
Natural Pigment ◽  
Elemental Analyses ◽  
Tapetum Lucidum

The reflecting material of the tapetum lucidum of the sea catfish (Arius felis) was chromatographed on Sephadex LH-20 in methanol–dimethyl sulphoxide–formic acid. Two components were present: one, showing an absorption maximum at 330nm, was tapetal pigment; the other, at 257nm, was an associated nucleoside. The tapetal pigment was extracted in methanol–HCl and isolated by adsorption chromatography on Sephadex LH-20. It yielded a methoxy methyl ester on treatment with diazomethane, and permanganate oxidation gave pyrrole-2,3,5-tricarboxylic acid. From the information provided by u.v. and i.r. spectra of the pigment and its methoxy methyl ester, from elemental analyses and from the oxidation products, we suggest that the tapetal pigment is derived from oxidative coupling of 5,6-dihydroxyindole-2-carboxylic acid. A molecular-weight determination and chromatography of the methoxy methyl ester indicate that the pigment is a mixture of oligomers, among which the tetramers probably predominate. We consider that the monomers are joined mainly by C-C linkages at positions 4 and 7. A synthetic pigment having spectral properties nearly identical with those of the natural pigment was prepared by enzymic oxidation of 5,6-dihydroxyindole-2-carboxylic acid with mushroom tyrosinase. The identity of the tapetal pigment with the synthetic pigment was further confirmed by comparing u.v. and i.r. spectra of their methoxy methyl esters. Formation of the tapetal pigment from tyrosine and relationships of the tapetal pigment to melanin are discussed.

New Cyclodimerization Reaction of (3,5-Di-tert-butyl-4-oxocyclohexa-2,5-dienylidene)acetic Acid

2001 ◽  
Vol 66 (8) ◽  
pp. 1250-1256 ◽  
Author(s):  
Peter Nesvadba ◽  
Piotr Rzadek ◽  
Günther Rist
Keyword(s):  
Acetic Acid ◽  
Sulfuric Acid ◽  
Carboxylic Acid ◽  
Methyl Ester ◽  
Structure Elucidation ◽  
Methyl Esters ◽  
Tert Butyl ◽  
Isomeric Methyl

(3,5-Di-tert-butyl-4-oxocyclohexa-2,5-dienylidene)acetic acid 1a underwent on heating a new cyclodimerization reaction affording a 1 : 1 mixture of the racemic cis- and trans-isomeric lactone-acids 2. The decisive structure elucidation of 2 was carried out after its mild esterification with diazomethane and separation of the racemic isomeric methyl esters 3a and 3b. The attempted esterification of 2 with methanol and sulfuric acid gave only the methyl diarylacetate 4. In contrast to 1a, which contains the carboxylic acid functionality no cyclodimerization was observed with the corresponding methyl ester 1b or nitrile 1c.

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