(+)-Norrangiformic acid

(+)-Norrangiformic acid

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(+)-Norrangiformic acid
Category Others
Catalog number BBF-05107
CAS 26534-85-0
Molecular Weight 372.5
Molecular Formula C20H36O6

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Specification

Synonyms 1,2,3-Heptadecanetricarboxylic acid, threo- (8CI)
IUPAC Name (2S,3S)-heptadecane-1,2,3-tricarboxylic acid
Canonical SMILES CCCCCCCCCCCCCCC(C(CC(=O)O)C(=O)O)C(=O)O
InChI InChI=1S/C20H36O6/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16(19(23)24)17(20(25)26)15-18(21)22/h16-17H,2-15H2,1H3,(H,21,22)(H,23,24)(H,25,26)/t16-,17-/m0/s1
InChI Key YBZIIVKQVVKTTD-IRXDYDNUSA-N

Properties

Boiling Point 461.5±25.0°C (Predicted)
Melting Point 118°C
Density 1.085±0.06 g/cm3 (Predicted)

Reference Reading

1. Brønsted Acid-Catalyzed Carbonyl-Olefin Metathesis: Synthesis of Phenanthrenes via Phosphomolybdic Acid as a Catalyst
Yi Chen, Di Liu, Rui Wang, Li Xu, Jingyao Tan, Mao Shu, Lingfeng Tian, Yuan Jin, Xiaoke Zhang, Zhihua Lin J Org Chem. 2022 Jan 7;87(1):351-362. doi: 10.1021/acs.joc.1c02385. Epub 2021 Dec 20.
Compared with the impressive achievements of catalytic carbonyl-olefin metathesis (CCOM) mediated by Lewis acid catalysts, exploration of the CCOM through Brønsted acid-catalyzed approaches remains quite challenging. Herein, we disclose a synthetic protocol for the construction of a valuable polycycle scaffold through the CCOM with the inexpensive, nontoxic phosphomolybdic acid as a catalyst. The current annulations could realize carbonyl-olefin, carbonyl-alcohol, and acetal-alcohol in situ CCOM reactions and feature mild reaction conditions, simple manipulation, and scalability, making this strategy a promising alternative to the Lewis acid-catalyzed COM reaction.
2. Response mechanisms to acid stress of acid-resistant bacteria and biotechnological applications in the food industry
Junnan Xu, Li Guo, Ning Zhao, Xuemei Meng, Jie Zhang, Tieru Wang, Xinyuan Wei, Mingtao Fan Crit Rev Biotechnol. 2023 Mar;43(2):258-274. doi: 10.1080/07388551.2021.2025335. Epub 2022 Feb 3.
Acid-resistant bacteria are more and more widely used in industrial production due to their unique acid-resistant properties. In order to survive in various acidic environments, acid-resistant bacteria have developed diverse protective mechanisms such as sensing acid stress and signal transduction, maintaining intracellular pH homeostasis by controlling the flow of H+, protecting and repairing biological macromolecules, metabolic modification, and cross-protection. Acid-resistant bacteria have broad biotechnological application prospects in the food field. The production of fermented foods with high acidity and acidophilic enzymes are the main applications of this kind of bacteria in the food industry. Their acid resistance modules can also be used to construct acid-resistant recombinant engineering strains for special purposes. However, they can also cause negative effects on foods, such as spoilage and toxicity. Herein, the aim of this paper is to summarize the research progress of molecular mechanisms against acid stress of acid-resistant bacteria. Moreover, their effects on the food industry were also discussed. It is useful to lay a foundation for broadening our understanding of the physiological metabolism of acid-resistant bacteria and better serving the food industry.
3. Ipso Nitration of Aryl Boronic Acids Using Fuming Nitric Acid
James I Murray, Maria V Silva Elipe, Kyle D Baucom, Derek B Brown, Kyle Quasdorf, Seb Caille J Org Chem. 2022 Feb 18;87(4):1977-1985. doi: 10.1021/acs.joc.1c00886. Epub 2021 Jun 8.
The ipso nitration of aryl boronic acid derivatives has been developed using fuming nitric acid as the nitrating agent. This facile procedure provides efficient and chemoselective access to a variety of aromatic nitro compounds. While several activating agents and nitro sources have been reported in the literature for this synthetically useful transformation, this report demonstrates that these processes likely generate a common active reagent, anhydrous HNO3. Kinetic and mechanistic studies have revealed that the reaction order in HNO3 is >2 and indicate that the ·NO2 radical is the active species.

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