Citronellic Acid Research Articles

Biodegradation of acyclic isoprenoids by Pseudomonas species.

The ability of various pseudomonads to utilize acyclic isoprenoids as a sole carbon source was investigated. Tests for utilization of acyclic isoprenols such as citronellol and geraniol were complicated by toxic effects of these alcohols, and most species tested were killed by exposure to citronellol or geraniol (0.1%, vol/vol) in liquid culture. In the case of Pseudomonas citronellolis, sensitivity to isoprenols is reduced by prior induction of the isoprenoid degradative pathway via either growth on succinate in the presence of citronellol or growth on citronellic acid. For this species, citronellic acid proved to be the best isoprenoid growth substrate tested. Geraniol utilization as a taxonomic indicator for different subgroups of pseudomonads is discussed. Only a few of the species tested were able to utilize acyclic isoprenoids. Two species which utilize C10 acyclic isoprenoids, P. aeruginosa and P. mendocina, were shown to contain the inducible enzyme geranyl-coenzyme A carboxylase, one of the unique enzymes in the isoprenol degradative pathway known to occur in P. citronellolis. Of the species which utilized geranitol, none showed definite growth on the homologous C15 and C20 isoprenols.

Absolute configuration of (−)-4-methylheptan-3-ol, a pheromone of the smaller european elm bark beetle, as determined by the synthesis of its (3 R,4 R)-(+)- and (3 S,4 R)-(+)-isomers

Nerol and geraniol were stereoselectively converted to (±)- threo- and (±)- erythro-4-methylheptan-3-ol respectively. ( R)-(+)-Citronellic acid was converted to a mixture of (3 R,4 R)-(+)- threo- and (3 S,4 R)-(+)- erythro-isomers which was separable by GLC. These syntheses established the absolute configuration of the naturally occurring (−)-4-methylheptan-3-ol to be 3 S,4 S.

ChemInform Abstract: DIRECT DETERMINATIONS OF R S ENANTIOMER RATIOS OF CITRONELLIC ACID AND RELATED SUBSTANCES BY NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY AND HIGH PRESSURE LIQUID CHROMATOGRAPHY

Chemischer InformationsdienstVolume 7, Issue 14 Preparative Organic Chemistry ChemInform Abstract: DIRECT DETERMINATIONS OF R S ENANTIOMER RATIOS OF CITRONELLIC ACID AND RELATED SUBSTANCES BY NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY AND HIGH PRESSURE LIQUID CHROMATOGRAPHY D. JUN. VALENTINE, D. JUN. VALENTINESearch for more papers by this authorK. K. CHAN, K. K. CHANSearch for more papers by this authorC. G. SCOTT, C. G. SCOTTSearch for more papers by this authorK. K. JOHNSON, K. K. JOHNSONSearch for more papers by this authorK. TOTH, K. TOTHSearch for more papers by this authorG. SAUCY, G. SAUCYSearch for more papers by this author D. JUN. VALENTINE, D. JUN. VALENTINESearch for more papers by this authorK. K. CHAN, K. K. CHANSearch for more papers by this authorC. G. SCOTT, C. G. SCOTTSearch for more papers by this authorK. K. JOHNSON, K. K. JOHNSONSearch for more papers by this authorK. TOTH, K. TOTHSearch for more papers by this authorG. SAUCY, G. SAUCYSearch for more papers by this author First published: April 6, 1976 https://doi.org/10.1002/chin.197614126Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat No abstract is available for this article. Volume7, Issue14April 6, 1976 RelatedInformation

Direct determinations of R/S enantiomer ratios of citronellic acid and related substances by nuclear magnetic resonance spectroscopy and high pressure liquid chromatography

Direct determinations of R/S enantiomer ratios of citronellic acid and related substances by nuclear magnetic resonance spectroscopy and high pressure liquid chromatography

Oxidative degradation of squalene by Arthrobacter species.

An organism isolated from soil and identified as Arthrobacter sp. was studied for its squalene degradation. The degradation product from squalene, which accumulated in the culture broth, was isolated and identified as trans-geranylacetone by mass spectrometry, gas chromatography, infrared spectrometry, and nuclear magnetic resonance spectrometry. Addition of a high concentration of K2HPO4 to the culture medium resulted in accumulation of fairly large amounts of carboxylic acids in addition to geranylacetone. These carboxylic acids were identified as isovaleric, beta,beta'-dimethylacrylic, geranic, and (plus)-(R)-citronellic acids. Among these acids, alpha,beta-saturated carboxylic acids were found to be predominant in quantity.

Oxidative Degradation of Squalene by Arthrobacter Species

An organism isolated from soil and identified as Arthrobacter sp. was studied for its squalene degradation. The degradation product from squalene, which accumulated in the culture broth, was isolated and identified as trans-geranylacetone by mass spectrometry, gas chromatography, infrared spectrometry, and nuclear magnetic resonance spectrometry. Addition of a high concentration of K2HPO4 to the culture medium resulted in accumulation of fairly large amounts of carboxylic acids in addition to geranylacetone. These carboxylic acids were identified as isovaleric, beta,beta'-dimethylacrylic, geranic, and (plus)-(R)-citronellic acids. Among these acids, alpha,beta-saturated carboxylic acids were found to be predominant in quantity.

Microbial transformation of terpenoids. I. Identification of metabolites produced by a pseudomonad from citronellal and citral.

A bacterium capable of utilizing citronellal or citral as the sole source of carbon and energy has been isolated from soil by the enrichment culture technique. It metabolizes citronellal to citronellic acid (65%), citronellol (0.6%), dihydrocitronellol (0.6%), menthol (0.75%), and 3,7-dimethyl-1,7-octane diol (1.7%). The metabolites of citral were geranic acid (62%), 6-methyl-5-heptanoic acid (0.5%), 3-methyl-2-butenoic acid (1%), and 1-hydroxy-3, 7-dimethyl-6-octen-2-one (0.75%).

Microbial Transformation of Terpenoids. I. Indentification of Metabolites Produced by a Pseudomonad from Citronellal and Citral

A bacterium capable of utilizing citronellal or citral as the sole source of carbon and energy has been isolated from soil by the enrichment culture technique. It metabolizes citronellal to citronellic acid (65%), citronellol (0.6%), dihydrocitronellol (0.6%), menthol (0.75%), and 3,7-dimethyl-1,7-octane diol (1.7%). The metabolites of citral were geranic acid (62%), 6-methyl-5-heptanoic acid (0.5%), 3-methyl-2-butenoic acid (1%), and 1-hydroxy-3, 7-dimethyl-6-octen-2-one (0.75%).

PERMANGANATE–PERIODATE OXIDATION: PART VII. THE OXIDATION OF SOME ACYCLIC MONOTERPENES

The reaction of permanganate–periodate with 1-decene and 1-octadecene in aqueous suspension or media containing tert-butanol has been studied. C10-compounds are oxidized almost quantitatively with the aqueous reagent. Myrcene, cis-ocimene, citronellol, citronellal, citronellic acid, geraniol, nerol, linalool, and linalyl acetate are all oxidized in high yield to the predicted products. These can serve conveniently for chemical identification of the aliphatic terpenes when isolated from mixtures by gas–liquid chromatography. The reaction may also be useful in locating the 14C-label in tracer studies.

Studies on Citronellic Acid and Its Derivatives. III

Studies on Citronellic Acid and Its Derivatives. III

Studies on Citronellic Acid and Its Derivatives. II

シトロネル酸が所謂リモネン型とテルピノレン型との混合物ならば何等かの方法により分離し得ずやと考へ,その一手段として餘りに平凡な方法ではあるが反復蒸溜法を試みて得た最前溜分と最後溜分とにつき物理的恒數を檢し又それぞれのアミドの融點を測定したが全然差異を認め得なかつた.次にシトロネル酸を加里熔融したところその大部分は異性化するらしく生成せる酸の物理的恒數は原酸のそれに比し僅微ながら差異あり且つそのアミドの融點は原酸のものより約2°高き事を認めた.

Studies on Citronellic Acid and Its Derivatives. I

Studies on Citronellic Acid and Its Derivatives. I