67214-54-4

Upstream product

• 18951-85-4 (R)-citronellic acid 
• 98-59-9 p-toluenesulfonyl chloride 
• 7540-51-4 (S)-3,7-dimethyl-6-octen-1-ol 
• 103057-51-8 hypochlorous acid 4-methylbenzene sulfonic anhydride 
• 106-22-9 Citronellol 
• 20425-48-3 methyl (R)-(+)-citronellate 
• 65620-73-7 ethyl (3R)-3,7-dimethyloct-6-enoate 
• 17882-43-8 (?)-trans-isopulegone 
• 7786-67-6 isopulegol 
• 2385-77-5 (R)-Citronellal 

Downstream Products

• 110109-85-8 (R)-[(3,7-dimethyloct-6-en-1-yl)sulfonyl]benzene 
• 10340-84-8 (R)-8-bromo-2,6-dimethyloct-2-ene 
• 86414-33-7 (6S,10S)-(+)-2,6,10-trimethyldodec-2-ene 
• 254435-60-4 (6S)-2,6-dimethyl-2-hexadecene 
• 646-31-1 tetracosane 
• 230966-14-0 (6S)-2,6-dimethyl-2-icosene 
• 87106-39-6 4,8-dimethyldecanal dimethylacetal 
• 118195-59-8 (S)-4-methyloctyl tosylate 
• 340006-35-1 (S)-4-methyl-1-phenylsulfonyloctane 
• 340006-36-2 (5S,8RS)-5-methyl-8-phenylsulfonylheptacosane 
• 185745-67-9 ((S)-9-Methyl-tridecylsulfanyl)-benzene 
• 185745-69-1 ((S)-9-Methyl-tridecane-1-sulfonyl)-benzene 
• 185745-65-7 Toluene-4-sulfonic acid (S)-9-methyl-tridecyl ester 
• 185745-74-8 ((3R,13S)-3,13-Dimethyl-heptadecane-5-sulfonyl)-benzene 

Relevant academic research and scientific papers

Synthesis and biological evaluation of chemical tools for the study of Dolichol Linked Oligosaccharide Diphosphatase (DLODP)

Citronellyl- and solanesyl-based dolichol linked oligosaccharide (DLO) analogs were synthesized and tested along with undecaprenyl compounds for their ability to inhibit the release of [3H]OSP from [3H]DLO by mammalian liver DLO diphosphatase activity. Solanesyl (C45) and undecaprenyl (C55) compounds were 50–500 fold more potent than their citronellyl (C10)-based counterparts, indicating that the alkyl chain length is important for activity. The relative potency of the compounds within the citronellyl series was different to that of the solanesyl series with citronellyl diphosphate being 2 and 3 fold more potent than citronellyl-PP-GlcNAc2and citronellyl-PP-GlcNAc, respectively; whereas solanesyl-PP-GlcNAc and solanesyl-PP-GlcNAc2were 4 and 8 fold more potent, respectively, than solanesyl diphosphate. Undecaprenyl-PP-GlcNAc and bacterial Lipid II were 8 fold more potent than undecaprenyl diphosphate at inhibiting the DLODP assay. Therefore, at least for the more hydrophobic compounds, diphosphodiesters are more potent inhibitors of the DLODP assay than diphosphomonoesters. These results suggest that DLO rather than dolichyl diphosphate might be a preferred substrate for the DLODP activity.

Structure-Odor Activity Studies on Monoterpenoid Mercaptans Synthesized by Changing the Structural Motifs of the Key Food Odorant 1-p-Menthene-8-thiol

1-p-Menthene-8-thiol (1) has been discovered as the key odorant in grapefruit juice several decades ago and contributes to the overall odor of the fruit with an extremely low odor threshold of 0.000034 ng/L in air. This value is among the lowest odor thresholds ever reported for a food odorant. To check whether modifications in the structure of 1 would lead to changes in odor threshold and odor quality, 34 mercapto-containing p-menthane and 1-p-menthene derivatives as well as several aromatic and open-chain mercapto monoterpenoids were synthesized. Eighteen of them are reported for the first time in the literature, and their odor thresholds and odor qualities as well as analytical data are supplied. A comparison of the sensory data with those of 1 showed that hydrogenation of the double bond led to a clear increase in the odor threshold. Furthermore, moving the mercapto group into the ring always resulted in higher odor thresholds compared to thiols with a mercapto group in the side chains. Although all tertiary thiols always exhibited low odor thresholds, none of the 31 compounds reached the extremely low threshold of 1. Also, none of the synthesized mercapto monoterpenoids showed a similar odor quality resembling grapefruit. Although the saturated and aromatic analogues exhibited similar scents as 1, the aromas of the majority of the other compounds were described as sulfury, rubber-like, burned, soapy, or even mushroom-like. NMR and MS data as well as retention indices of the 23 newly reported sulfur-containing compounds might aid in future research to identify terpene-derived mercaptans possibly present in trace levels in foods.

Pheromone synthesis. Part 256: Synthesis of the four stereoisomers of 5,11-dimethylpentacosane, a new sex pheromone component of the male Galleria mellonella (L.), with high stereochemical purities as determined by the derivatization-HPLC analysis of the eight stereoisomers of 5,11-dimethyl-8-pentacosanol

Abstract All the four stereoisomers of 5,11-dimethylpentacosane (>96.8% purity) were synthesized via the stereoisomers of 5,11-dimethyl-8-pentacosanol, whose stereoisomeric compositions could be determined precisely by their low temperature HPLC analysis after derivatization. 5,11-Dimethyl-8-pentacosanol was prepared by a Grignard reaction between 3-methylheptylmagnesium bromide and 4-methyloctadecanal, both of which were prepared from the commercially available enantiomers of citronellal (97-98% ee). Alternatively, (R)-3-methyl-1-heptanol could be prepared from methyl (R)-3-hydroxybutanoate (100% ee). Pd/C-catalyzed hydrogenation of a 5-methyl-1-alkene caused partial racemaization at C-5.

PRODUCTION METHOD OF 4,8-DIMETHYLDECANAL

PROBLEM TO BE SOLVED: To provide a method of producing a mixture of (4R,8S)-4,8-dimethyldecanal and (4R,8R)-4,8-dimethyldecanal effective as pheromones for rust-red flour beetles and confused flour beetles, practically in a high yield through a small number of steps. SOLUTION: A method of producing a mixture of (4R,8S)-4,8-dimethyldecanal and (4R,8R)-4,8-dimethyldecanal includes a first step of tosylating (S)-citronellol to obtain a tosylate, a second step of reacting the tosylate with a Grignard reagent to obtain an alkene, a third step of epoxidating the alkene to obtain an epoxide, and a fourth step of cleaving the epoxide with a periodic acid to obtain 4,8-dimethyldecanal. COPYRIGHT: (C)2015,JPOandINPIT

Synthesis of all the stereoisomers of 6-methyl-2-octadecanone, 14-methyl-2-octadecanone, and 6,14-dimethyl-2-octadecanone, sex pheromone components of the Lyclene dharma dharma moth, from the enantiomers of citronellal

The enantiomers of citronellal were converted to all the stereoisomers of 6-methyl-2-octadecanone, 14-methyl-2-octadecanone, and 6,14-dimethyl-2- octadecanone, the female-produced sex pheromone components of the Lyclene dharma dharma moth. Three wellestablished procedures, the Wittig reaction, alkylation of alkynes, and acetoacetic ester synthesis, were employed for the carbon-carbon bond formation to connect the building blocks.

Total synthesis of a cuticular hydrocarbon from the cane beetle Antitrogus parvulus: Confirmation of the relative stereochemistry

The stereoselective reaction of an allyl bromide with an aldehyde mediated by a low valency bismuth species was the key reaction in stereoselective syntheses of (4S,6R,8R,10S,16S)- and (4S,6R,8R,10S,16R)-4,6,8,10,16- pentamethyldocosanes. 13C N

Aliphatic C-H to C-C conversion: Synthesis of (-)-cameroonan-7α-ol

In the course of a synthesis of the tricyclic sesquiterpene (-)- cameroonan-7α-ol from the acyclic (〈)-citronellal, seven aliphatic C-H bonds were converted to C-C bonds, and three rings and four new stereogenic centers were established. 2011 American Chemical Society.

Liposomal circular dichroism. assignment of remote stereocenters in plakinic acids K and L from a plakortis-xestospongia sponge association

"Figure Presented" Two new ωtu-phenyl polyketide peroxides, plakinic acids K and L, were isolated from a two-sponge association of Plakortis halichondroides and Xestospongia deweerdtae. The absolute configurations of the remote dimethyl-branched stereocenters in plakinic acid K were assigned by degradation of plakinic acid K to a long-chain naphthamide and analysis by liposomal circular dichroism (L-CD) and comparison with synthetic standards.

Composition of the cloacal gland secretion of tuatara, Sphenodon punctatus

The lipophilic content of the cloacal gland secretion of the tuatara (Sphenodon punctatus) was investigated. GC/EI-MS Analysis of CH2Cl2 extracts of the secretions revealed triacylglycerols as major glandular constituents. Twelve major medium-chain fatty acids were found to be conjugated to glycerol in different combinations, resulting in complex mixtures. These acids were identified by transesterification and subsequent derivatization of natural samples, and their structures were verified by synthesis. The natural glycerides contain predominantly three of the following acids: octanoic (A), (E)- and (Z)-oct-4-enoic (B and C, resp.), (4E,6Z)-octa-4,6-dienoic (tuataric acid;D), (R)-2,6-dimethylheptanoic (E), (R)-2,6-dimethylhept-5-enoic (F), (Z)-dec-4-enoic (G), (4Z,7Z)-deca-4,7-dienoic (H), (R)-3,7-dimethyloct-6-enoic (I), (R)-4,8-dimethylnon-7-enoic (J), (2R,6S)-2,6,10-trimethylundec-9-enoic (K), and (2R,5E)-2,6,10-trimethylundeca-5,9-dienoic acids (L). Several additional acids, occurring in trace amounts only, were tentatively identified by MS. The elucidation of the absolute configuration of the acids was performed by GC on chiral phases. Individual tuatara show specific mixtures of glycerides with up to 100 components. The individual mixtures may permit individual recognition because the bouquets seem to be stable over years.

Synthesis of all the six components of the female-produced contact sex pheromone of the German cockroach, Blattella germanica (L.)

All of the following six components of the female sex pheromone of the German cockroach, Blattella germanica (L.) were synthesized: (3S,11S)-3,11-dimethyl-2-nonacosanone (1), its 29-hydroxy derivative 2, its 29-oxo derivative 3, (3S,11S)-3,11-dimethyl-2-heptacosanone (4), its 27-hydroxy derivative 5, and its 27-oxo derivative 6. Both the enantiomers of citronellal were employed as the chiral sources and Wacker oxidation was employed for the introduction of the carbonyl group at C-2.