DMSO : 250 mg/mL (2497.00 mM; Need ultrasonic)
198.5±0.0 °C at 760 mmHg
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provides coniferyl ferulate(CAS#:565-63-9) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate
Up to 35% of (R)-methyl 2-methylbutanoate (M2MB) was observed in a beverage fermented with shiitake. As M2MB naturally occurs typically in high excesses of the (S)-enantiomer, the origin of the (R)-ester was elucidated by stable isotope labeled precursor-feeding studies. (R)-2-Methylbutanoic acid was identified as the main precursor in the substrate wort. Trace amounts of (R)-M2MB were produced by transformation of unsaturated secondary metabolites (tiglic aldehyde and tiglic acid) derived from l-isoleucine. Surprisingly, shiitake esterified (R)-2-methylbutanoic acid faster to (R)-M2MB than the corresponding (S)-enantiomer. Concurrently, spontaneous non-enantioselective degradation of M2MB occurred in shiitake. This explains diverse enantiomeric ratios of M2MB and different enantiomeric ratios of 2-methylbutanoic acid and M2MB in the beverage. As the odor threshold values of (R)-and (S)-M2MB differ significantly, these findings are of high relevance for the overall flavor of the fermented beverage and elucidate the discrepancy of enantiomeric ratios of 2-alkyl-branched acids and esters reported in nature.
(R)-2-Methylbutanoic acid (PubChem CID: 6950479); (R)-Methyl 2-methylbutanoate; (S)-2-Methylbutanoic acid (PubChem CID: 448893); 2-Methylbutanal (PubChem CID: 7284); 2-Methylbutanoic acid; 2-Methylbutanoic acid (PubChem CID: 8314); 2-Methylbutanol (PubChem CID: 8723); Beverage; Ethyl tiglate (PubChem CID: 5281163); Fermentation; Methyl 2-methylbutanoate (PubChem CID: 13357); Methyl tiglate (PubChem CID: 5323652); Odor threshold; Pathway; Shiitake; Tiglic acid (PubChem CID: 125468); Tiglic aldehyde (PubChem CID: 5321950); l-Isoleucine.
Enantiomeric ratios of 2-methylbutanoic acid and its methyl ester: Elucidation of novel biogenetic pathways towards (R)-methyl 2-methylbutanoate in a beverage fermented with shiitake
Yanyan Zhang 1, Marco Alexander Fraatz 2, Florian Birk 3, Marina Rigling 4, Andreas Hammer 5, Holger Zorn 6
2018 Nov 15
Derivatives of 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acid (chrysanthemic acid) are classic natural pyrethroids discovered in pyrethrum plants and show insecticidal activity. Chrysanthemic acid, with two asymmetric carbons, has four possible stereoisomers, and most natural pyrethroids have the (1R,3R)-trans configuration. Interestingly, chrysanthemic acid-related structures are also found in insect sex pheromones; carboxylic esters of (1R,3R)-trans-(2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropyl)methanol (chrysanthemyl alcohol) have been reported from two mealybug species. In the present study, another ester of chrysanthemyl alcohol was discovered from the striped mealybug, Ferrisia virgata (Cockerell), as its pheromone. By means of gas chromatography-mass spectrometry, nuclear magnetic resonance spectrometry, and high-performance liquid chromatography analyses using a chiral stationary phase column and authentic standards, the pheromone was identified as (1S,3R)-(-)-cis-chrysanthemyl tiglate. The (1S,3R)-enantiomer strongly attracted adult males in a greenhouse trapping bioassay, whereas the other enantiomers showed only weak activity. The cis configuration of the chrysanthemic acid-related structure appears to be relatively scarce in nature, and this is the first example reported from arthropods.
Chrysanthemic acid (chrysanthemum acid); Chrysanthemyl alcohol (chrysanthemol); Ferrisia virgata; Pyrethroids; Sex pheromone.
Jun Tabata 1, Ryoko T Ichiki 2
An efficient synthetic route for ipomoeassin F and its tiglate-modified analogues was developed. The route features late-stage conformation-controlled highly regioselective esterification of the glucose diol in the disaccharide core. The results from the NCI-60 cell line screens of ipomoeassin F were reported for the first time. Moreover, two new C-3-cinnamoyl-Glcp analogues (2 and 3) were prepared. Their in-house cytotoxicity data convey an important message that both identity and positioning of the two α,β-unsaturated esters are crucial. They are not interchangeable.
Synergistic Contribution of Tiglate and Cinnamate to Cytotoxicity of Ipomoeassin F
Guanghui Zong 1, Lucas Whisenhunt 1, Zhijian Hu 1, Wei Q Shi 1
2017 May 5