Synthesis of trans-10-hydroxydec-2-enoic acid and related compounds

Fray, G. I.; Jaeger, R.H.; Morgan, E. David; Robinson, Robert; Sloan, A. D. B.

doi:10.1016/0040-4020(61)80003-3

Cited by 26 publications

(7 citation statements)

References 20 publications

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“…Among them, the most abundant MCFA is 10-HDA, amounting to 70% of lipid extracts from royal jelly and more than 50% of free fatty acids in royal jelly (Li et al, 2013). This MCFA is considered a characteristic constituent of lipids in royal jelly and serves as an index for estimating quality of royal jelly (Chiron, 1982;Fray, Jaeger, Morgan, Robinson, & Sloan, 1961;Genç & Aslan, 1999).…”

Section: Introductionmentioning

confidence: 99%

Standard methods for Apis mellifera royal jelly research

Bíliková

Casabianca

et al. 2017

Journal of Apicultural Research

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Royal jelly, a honey bee secretion, plays a critical role in caste determination in honey bees because it serves as the source of nutrition for young larvae destined to become queens. It is also fed to adult queens. Royal jelly possesses numerous functional properties and thus has been used as a medication, health food, and cosmetic in many countries. In this paper, we first introduce a traditional method for producing royal jelly by artificial larvae grafting and a newly developed method that does not require grafting of larvae. We describe protocols for the storage and freeze-drying of royal jelly to preserve its biological properties. Routine methods for determination of two important quality criteria, water content and trans-10-hydroxy-2-decenoic acid content, are outlined. On a dry basis, protein, carbohydrate, and fatty acids were found to be the 3 most abundant components of royal jelly. Methods for their isolation, identification, and quantification are described. Because royal jelly is susceptible to contamination with veterinary drugs and acaricides, we also describe methods for detection and quantification of some veterinary drugs and acaricides in royal jelly.Mé todos estándar para la investigació n de la jalea real de Apis mellifera La jalea real, una secreció n de abejas, desempeña un papel crítico en la determinació n de castas en la abeja melífera, ya que sirve como fuente de nutrició n para larvas jó venes destinadas a convertirse en reinas. También alimenta a las reinas adultas. La jalea real posee numerosas propiedades funcionales y por lo tanto se ha utilizado como un medicamento, alimento saludable y cosmético en muchos países. En este artículo, introducimos un método tradicional para producir jalea real mediante el injerto artificial de larvas y un método recientemente desarrollado que no requiere injerto de larvas. Describimos protocolos para el almacenamiento y la liofilizació n de la jalea real para preservar sus propiedades bioló gicas. Se describen métodos rutinarios para la determinació n de dos importantes criterios de calidad, el contenido de agua y el de ácido trans-10-hidroxi-2-decenoico. En una base seca, proteínas, carbohidratos y ácidos grasos fueron los tres componentes más abundantes de la jalea real. Se describen métodos para su aislamiento, identificació n y cuantificació n. Debido a que la jalea real es susceptible a la contaminació n con medicamentos veterinarios y acaricidas, también describimos métodos para la detecció n y cuantificació n de algunos medicamentos veterinarios y acaricidas en jalea real.

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Section: Introductionmentioning

confidence: 99%

Standard methods for Apis mellifera royal jelly research

Bíliková

Casabianca

et al. 2017

Journal of Apicultural Research

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“…(E)-10-hydroxy-2-decenoic acid (10H2DA) is a biologically active fatty acid found in the royal jelly of honey bees that possesses a range of noteworthy pharmacological effects including anti-tumour [1], antibacterial [2], neurogenesis [3][4], angiogenesis inhibition [5], and oestrogen receptor modulation [6]. The synthesis of 10H2DA has been reported by several synthetic routes [7][8][9][10][11][12][13].…”

Section: Introductionmentioning

confidence: 99%

“…In many cases, the α,β-unsaturated carbonyl component is formed through the Wittig or Horner-Wittig olefination reactions with 8-(hydroxy or acetyloxy)octanal to give the ester form of 10H2DA, which after hydrolysis yields the free acid (10H2DA). Synthesis of the 8-(hydroxy or acetyloxy)octanal precursor is a vital component of the whole process and involves a multistep procedure starting from compounds including 1,8-octanediol [8], cyclooctanone [7,13], oleic acid [10], and 6-chlorohexanol [12]. In this work, the one-pot synthesis of (E)-10-hydroxy-2-decenoic acid ethyl ester (10H2DA-EE) and (E)-10-hydroxy-2decenoic acid (10H2DA) were achieved.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of (E)-10-hydroxy-2-decenoic acid ethyl ester via a one-pot tandem oxidation-Wittig process

Heppell¹,

Boon²,

Al‐Rawi³

2018

Org.Commun.

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“…Moreover, it can be used on a large scale. Indeed, Doebner-Knoevenagel reaction has been widely reported for the synthesis of 10-HDA 5,7,8 . However, literature is quite ambiguous.…”

Section: Scheme 3 Preparation Of Aldehydementioning

confidence: 99%

“…3 As a result, in recent years, several synthetic approaches for 10-HDA 9-ODA have been reported. [4][5][6][7][8] However, in general these methodologies employ expensive and toxic reagents, or require procedures that are difficult to handle on a large scale. In this work, we report for the first time a cost-effective and metal-free strategy for the selective preparation of compounds 1 and 2 in multigram scale.…”

Section: Introductionmentioning

confidence: 99%

Straightforward, metal-free, and stereoselective synthesis of 9-oxo- and 10-hydroxy-2(E)-decenoic acids, important components of honeybee (Apis mellifera) secretions

et al. 2012

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Abstract10-hydroxy-2E-decenoic (10-HDA) and 9-oxo-2E-decenoic (9-ODA) acids, two components identified in honeybees secretions, have both received considerable recent interest due to their involvement in caste switch and maintenance. Herein we report for the first time a metal-free, gram scale, and stereoselective synthesis of these honeybee secretion components by TEMPO catalyzed oxidation of readily available alcohols and subsequent Doebner-Knoevenagel reaction between the resulting aldehydes and malonic acid. Mechanistic investigations undertaken highlighted the crucial role of the Doebner-Knoevenagel reaction in the high yielding and selective preparation of the α,β-unsaturated acids 10-HDA and 9-ODA.The combination of inexpensive and environmental friendly reagents with simple synthetic procedures render this approach a valuable green strategy for the gram scale preparation of these biologically relevant natural molecules. Graphical abstract

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Synthesis of trans-10-hydroxydec-2-enoic acid and related compounds

Cited by 26 publications

References 20 publications

Standard methods for Apis mellifera royal jelly research

Standard methods for Apis mellifera royal jelly research

Synthesis of (E)-10-hydroxy-2-decenoic acid ethyl ester via a one-pot tandem oxidation-Wittig process

Straightforward, metal-free, and stereoselective synthesis of 9-oxo- and 10-hydroxy-2(E)-decenoic acids, important components of honeybee (Apis mellifera) secretions

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