Metalation of limonene. Novel method for the synthesis of bisabolane sesquiterpenes

Crawford, Robert J.; Erman, William F.; Broaddus, C. D.

doi:10.1021/ja00767a044

Cited by 119 publications

(59 citation statements)

References 6 publications

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“…Authentic standards of FaOH, FaDOH, and FaDOAc were isolated from carrots following the procedure of Kidmose et al 4 Authentic aroma reference compounds of α-phellandrene, β-myrcene, α-terpinene, ρ-cymene, β-caryophyllene, and α-humulene were obtained from Fluka Chemie GmbH (Buchs, Switzerland), α-pinene, camphene, β-pinene, sabinene, limonene, β-phellandrene, and γ-terpinene from Sigma-Aldrich (St. Louis, MO), α-thujene and β-farnesene from Wako Chemicals Ltd. (Tokyo, Japan), terpinolene from Carl Roth GmbH (Karlsruhe, Germany), and γ-bisabolene from TCI Tokyo Organic Chemicals Ltd. (Tokyo, Japan). β-Bisabolene was synthesized using the method of Crawford et al 30 Production of Carrots. Carrots (Daucus carota L. cv.…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

Eating Quality of Carrots (Daucus carota L.) Grown in One Conventional and Three Organic Cropping Systems over Three Years

Bach

Kidmose

Kristensen

et al. 2015

J. Agric. Food Chem.

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The eating quality of carrots (Daucus carota L.) was investigated to evaluate the impact of cropping systems (one conventional and three organic systems) and growing years (2007, 2008, and 2009) on root size, chemical composition, and sensory quality. The content of dry matter, sugars, polyacetylenes, and terpenes as well as the sensory quality and root size were related to the climate during the three growing years. A higher global radiation and a higher temperature sum in 2009 as compared to 2007 and 2008 resulted in larger roots, higher contents of dry matter, sucrose, total sugars, and total polyacetylenes, and lower contents of terpenes, fructose, and glucose. No differences were found between conventional and organic carrots with regard to the investigated parameters. This result shows that organically grown carrots have the same eating quality as conventionally grown carrots, while being produced in a more sustainable way. KEYWORDS: Daucus carota L., organic, conventional, polyacetylenes, terpenes, sugar, dry matter, sensory descriptive analysis, climateCarrot (Daucus carota L.) is an important food crop with a low sensitivity to cropping system, 1 which makes it well-suited for organic production. Carrots are consumed both raw and cooked or processed into frozen products or juice. The eating quality of carrots is determined by cultivar, fertilization, geographical location, and climate.2−5 The cultivar and the year-to-year variation in climate has a bigger influence on the quality of carrots than the cropping system. 6 Paoletti et al. 7 also reported that year had a greater effect on carrot quality than conventional and organic cropping, but they did not take variation in climate into consideration.Consumers expect organic foods to be healthier and safer than conventional foods and to taste better, but the scientific literature is contradictionary and it has been shown that there is no difference in eating quality between organic and conventional foods. 6,8,9 A recent meta-analysis, however, showed that organic foods have higher contents of antioxidants and lower contents of cadmium, nitrate, nitrite, and pesticide residues than the similar conventional food.10 Only a few studies have compared the sensory quality of conventionally and organically grown carrots under comparable conditions. 7,11 Haglund et al. 12 found that organically grown carrots were more bitter and had less carrot flavor than conventional carrots, but the results were presented as averages across several cultivars and growing sites. Studies comparing chemical composition of conventionally and organically grown vegetables have mainly focused on nutrients, 8,9,13 and selected secondary metabolites such as carotenoids, polyacetylenes, and phenolic acids. 6,14,15 However, studies are lacking which compare the eating quality of conventionally and organically grown vegetables under comparable field conditions. 11In organic vegetable production, synthetic pesticides are banned and the type and intensity of fertilization is restrict...

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Section: ■ Materials and Methodsmentioning

confidence: 99%

Eating Quality of Carrots (Daucus carota L.) Grown in One Conventional and Three Organic Cropping Systems over Three Years

Bach

Kidmose

Kristensen

et al. 2015

J. Agric. Food Chem.

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“…Since the optical rotation of 13a showed a negative value, the (S) stereochemistry at C-6 is proposed, similarly to other analogous (S)-(E)-bisabolene derivatives. 7,8 Therefore, compound 13a was characterized as the methyl ester of lanceolic acid 13. These two compounds were previously obtained by synthesis and only incomplete 1 H NMR assignments have been published for 13a.…”

Section: Resultsmentioning

confidence: 99%

Indole alkaloid and other constituents from Ocotea minarum

Garcez¹,

Garcez²,

Silva³

et al. 2005

J. Braz. Chem. Soc.

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Dos frutos deA new alkyl phenol, 3-(1,4-dihydroxypentyl)-5-methoxyphenol, was obtained from the heartwood in addition to 5-propylresorcinol, trans-asarone, lyonyresinol, 3-O-β-D-glucopyranosyl stigmasterol and stigmasta-4,22-dien-3-one, whereas from the trunk bark the sesquiterpene lanceolic acid (as its methyl ester derivative after methylation procedures) and β-sitosterol were isolated. 5-propylresorcinol and lanceolic acid are reported for the first time as natural products.

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“…The enantiomers of limonene were individually submitted to metallation at the propenyl side chain 123 and the resulting species were subjected to treatment with oxygen, leading to hydroperoxydic intermediates, which were reduced in situ to the corresponding allyl alcohols 208. In turn, these were converted into the required allylic chlorides 193 by reaction with the PPh 3 /CCl 4 reagent.…”

Section: Synthesis and Evaluation Of Acd-ring Analoguesmentioning

confidence: 99%

Isolation, synthesis and complement inhibiting activity of the naturally occurring K-76, its analogues and derivatives

Larghi¹,

Kaufman²

2011

Arkivoc

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The Complement inhibitor K-76 was isolated from the supernatant of the culture broth of the fungus Stachybotrys complementi, nov. sp. K-76. The natural product is a sesquiterpenic dialdehyde which can be partially oxidized to the monocarboxylic acid derivative (K-76 COOH, MX-1), the sodium salt of which is more soluble and less toxic than the natural product. Both, K-76 and K-76 COOH inhibit Complement activation by the classical and alternative pathways, mainly at the C5 level. Reviewed here are the isolation and total syntheses of the natural product as well as aspects of its Complement inhibitory activity. Approaches to the synthesis of grisan, which bears the BCD skeleton of the natural product, as well as the synthesis of CD-, BCD-and ACD-ring structural analogues of K-76, including the use of natural products as starting materials, and evaluation of their biological activity as Complement inhibitors, are also discussed.

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Metalation of limonene. Novel method for the synthesis of bisabolane sesquiterpenes

Cited by 119 publications

References 6 publications

Eating Quality of Carrots (Daucus carota L.) Grown in One Conventional and Three Organic Cropping Systems over Three Years

Eating Quality of Carrots (Daucus carota L.) Grown in One Conventional and Three Organic Cropping Systems over Three Years

Indole alkaloid and other constituents from Ocotea minarum

Isolation, synthesis and complement inhibiting activity of the naturally occurring K-76, its analogues and derivatives

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