- A new approach to the synthesis of royal jelly acid
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A new approach to the synthesis of royal jelly acid (trans-10-hydroxy-2- decenoic acid) was proposed starting from 1,8-octanediol, which included selective monoprotection of 1,8-octanediol with acetic anhydride, oxidation, Wittig-Horner reaction, and hydrolysis and acidification, four steps in total, to yield the product. Overall yield is 80.2%.
- Zong, Qian-Shou,Wu, Jian-Yi
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- Synthesis of 10-hydroxy- and 9-oxo-2E-decenoic acids from oleic acid
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A practical synthesis of biologically active 10-hydroxy- and 9-oxo-2E-decenoic acids, components of mandibular gland secretion of honeybee (Apis mellifera L.), is developed using ozonolysis - reduction of oleic acid and 1,9-diacetoxynon-1-ene in the key steps.
- Kharisov,Botsman,Botsman,Ishmuratova,Ishmuratov,Tolstikov
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- LA REACTION DE WITTIG-HORNER EN MILIEU HETEROGENE VI. SELECTIVITE DE LA REACTION SUR DES COMPOSES BIFONCTIONNELS
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Heterogenous media of low basicity (K2CO3 or KHCO3), liquid-liquid or solid-liquid allow the Wittig-Horner reaction of fragile and unprotected aldehydes (hydroxyaldehydes, nitroaldehyde and ketoaldehydes) with excellent yields.The reaction is applied to the synthesis of Royal Jelly acid and Queen Substance of Honey bee.
- Villieras, Jean,Rambaud, Monique,Graff, Micheline
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- A preparation method of the inventioin
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The invention discloses a method for preparing a product yield, which belongs to the field of chemical synthesis. Its to propiolic acid methyl ester and 7 - bromo heptanol as the starting material, in the solvent, under the action of the strong alkali sodium amide, get the 10 - hydroxy - 2 - [...] acid dimethyl ester; in liquid ammonia in the solvent, the use of sodium metal to trans-reduction, shall (E)- 10 - hydroxy - 2 - decene acid dimethyl ester, then under the action of the alkali hydrolysis, then acidification, to obtain the target product jelly acid. The invention jelly acid preparation method, the technical route has the short route, the operation is simple, and easy for industrial production characteristics, is a very economic, simple and convenient synthetic Royal jelly acid.
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- Method for synthesizing royal jelly acid
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The invention discloses a method for synthesizing royal jelly acid. 1,8-octanediol from a wide variety of sources, used as a starting material, sequentially undergoes an addition reaction, an oxidation reaction and Knoevenagel reaction-hydrolysis. The method has the advantages of few steps, less byproducts, increase of the yield and reduction of the production cost.
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Paragraph 0023; 0026; 0029; 0032; 0035
(2018/11/27)
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- Lithiated anions derived from (alkenyl)pentamethyl phosphoric triamides: Useful synthons for the stereoselective synthesis of 9-oxo- and 10-hydroxy-2(E)-decenoic acids, important components of queen substance and royal jelly of honeybee Apis mellifera
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Lithiated anions derived from (alkenyl)pentamethyl phosphoric triamides as homoenolate equivalents are used in the reaction with halogenated acetal and ketal giving regioselectively the γ-alkylation adducts. Chemoselective acidic hydrolysis of the enephosphoramide moiety in the presence of acetal or ketal groups leads to expected carbonyl products, key intermediates in the synthesis of natural compounds. The synthetic potential of the presented strategy is illustrated by stereoselective synthesis of two pheromones namely, 9-oxo-2(E)-decenoic acid 1 from queen substance and 10-hydroxy-2(E)-decenoic acid 2 from royal jelly of honeybee Apis mellifera.
- Olszewski, Tomasz K.,Bomont, Catherine,Coutrot, Philippe,Grison, Claude
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supporting information; experimental part
p. 2354 - 2358
(2010/10/19)
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- Method for the preparation of unsaturated hydroxy fatty acids and their esters, their use in pharmaceutical and/or cosmetic preparations
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A method of preparing unsaturated hydroxy fatty acids and esters thereof corresponding to general formula (Id): wherein n=1 to 4, m=2 to 16, R1═OH, Cl, Br, OR3 in which R3 is a straight or branched alkyl, alkenyl or alkynyl radical of 1 to 16 carbons or glycerol esters, optionally substituted by one or more atoms selected from the group consisting of carbon, nitrogen, sulfur and halogens, R2═H, SiR′1R′2R′3 in which R′1, R′2 and R′3 can be identical or different from each other and are a straight or branched alkyl, alkenyl or alkynyl radical of 1 to 16 carbons or glycerol esters, optionally substituted by one or more atoms selected from the group consisting of carbon, nitrogen, sulfur and halogens, or R2═C—Ar3 with Ar representing an aryl radical optionally substituted by one or more atoms selected from the group consisting of carbon, nitrogen, sulfur and halogens, or R2=the tetrahydropyranyl of formula: is disclosed.
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- Method for the preparation of an alkynyl compound
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A novel and efficient method is proposed for the synthetic preparation of a long-chain alkynyl compound in a one-pot reaction without isolating the intermediate from the reaction mixture. The inventive method comprises the steps of: (a) a Grignard coupling reaction of an ω-halogeno-1-alkynyl magnesium halide compound of the general formula X1 MgC C(CH2)n X2, in which X1 is a halogen atom, X2 is an atom of Br or I and n is 3 to 10, and a Grignard reagent of the general formula RMgX1, in which R is a group selected from the class consisting of alkyl groups, alkenyl groups, alkynyl groups, alkapolyenyl groups, aryl groups and hydrocarbon groups having protected hydroxy group to give an intermediate compound of the general formula X1 MgC C(CH2)n R; (b) subjecting the intermediate compound to a reaction with a reactant selected from the class consisting of C2 -synthons, C1 -synthons and chlorosilane compounds having reactivity with the intermediate compound at the X1 Mg-terminal; and (c) hydrolyzing the reaction product obtained in step (b).
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- Synthesis of (E)-9-oxo-2-decenoic acid and (E)-10-hydroxy-2-decenoic acid
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Syntheses of (E)-9-oxo-decenoic acid (III), queen's substance and (E)-10-hydroxy-2-decenoic acid (V), a componenet of royal jelly and a bee pheromone, have been accomplished through a common intermediate (I).
- Trehen, I R,Vig, Rakesh,Singh, Vasundhara,Sharma, Sushma,Kad, G L
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p. 257 - 259
(2007/10/02)
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- A Short Synthesis of Royal Jelly Acid
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3-Bromopropanal acetal (I) is coupled with the Grignard reagent from 5-bromo-1-tetrahydropyranyloxypentane (II) to obtain 8-tetrahydropyranyloxy-1-octanal diethyl acetal (III).III on acid hydrolysis followed by Knoevenagel condensation with malonic acid affords the title compound (V).
- Kulkarni, S. M.,Mamdapur, V. R.
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p. 460 - 461
(2007/10/02)
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- Mechanism of Formation of α,β-Unsaturated Esters in the Reaction of Ethyl Mercaptoacetate Dianion with Carbonyl Compounds
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Dianion derived fron ethyl mercaptoacetate undergoes aldol type reaction with a carbonyl compounds to give an adduct, which exhibited low diastereoselectivity.However, the adducts obtained by the reaction with a variety of aldehydes were subsequently treated with ethyl chloroformate in the presence of trivalent phosphorus compound to give (E)-isomers of α,β-unsaturated esters in high yields with greater than 85percent stereoselectivity regardless of the stereochemistry of the diastereomers of the adducts.The stereochemical mechanism and application of this reaction were studied in detail.
- Matsui, Syuichi
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p. 426 - 434
(2007/10/02)
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- A NEW ROUTE FOR THE SYNTHESIS OF 10-HYDROXYDEC-2E-ENOIC AND DEC-2E-ENEDIOIC ACIDS
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A new simple route for the synthesis of 10-hydroxydec-2E-enoic and dec-2E-enedioic acids from cycloocta-1Z,5Z-diene has been developed.
- Odinokov, V. N.,Ishmuratov, G. Yu.,Tolstikov, G. A.
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p. 658 - 660
(2007/10/02)
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- A NOVEL SYNTHESIS OF ROYAL JELLY ACIDS AND QUEEN SUBSTANCE BY THE FIVE CARBON HOMOLOGATION USING β-VINYL-β-PROPIOLACTONE
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10-Hydroxy-(E)-2-decenoic acid, (E)-2-decenedioic acid (Royal jelly acids), and 9-oxo-(E)-2-decenoic acid (queen substance) were synthesized via 10-hydroxy-3-decenoic acid and 9,9-ethylenedioxy-3-decenoic acid, respectively, prepared easily by the regioselective ring-opening reaction of β-vinyl-β-propiolactone with Grignard reagents in the presence of copper(I) catalyst.
- Fujisawa, Tamotsu,Sato, Toshio,Itoh, Toshiyuki
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p. 219 - 220
(2007/10/02)
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