503-06-0

Basic information

• Product Name: phytomonic acid
• Synonyms: phytomonic acid;Cyclopropanedecanoic acid, 2-hexyl-;IJKRDVKGCQRKBI-UHFFFAOYSA-N
• CAS NO: 503-06-0
• Molecular Formula: C₁₉H₃₆O₂
• Molecular Weight: 296.49
• Mol File: 503-06-0.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 408.7°Cat760mmHg
• Flash Point: 180°C
• Appearance: /
• Density: 0.923g/cm³
• Vapor Pressure: 8E-08mmHg at 25°C
• Refractive Index: 1.47
• CAS DataBase Reference: phytomonic acid(CAS DataBase Reference)
• NIST Chemistry Reference: phytomonic acid(503-06-0)
• EPA Substance Registry System: phytomonic acid(503-06-0)

Safety Data

• Hazardous Substances Data: 503-06-0(Hazardous Substances Data)

Usage

Description

Phytomonic acid, also known as 11,12-methyleneoctadecanoic acid, is a saturated fatty acid predominantly found in gram-negative bacteria, L. arabinosus, as well as in protozoa and the seed oil of B. coccineus (Connaraceae). It features a unique cyclopropane ring structure, which exhibits properties similar to a double bond, potentially playing a role in regulating cell membrane fluidity.

Uses

Used in Pharmaceutical Applications:
Phytomonic acid is used as a bioactive compound for its potential therapeutic properties. Its unique cyclopropane ring structure may contribute to its ability to interact with cellular components, making it a candidate for further research and development in the pharmaceutical industry.
Used in Biomedical Research:
Phytomonic acid is used as a subject of study in biomedical research to better understand its interactions with cell membranes and its potential role in regulating cell membrane fluidity. This knowledge could lead to the development of new treatments for various medical conditions.
Used in Microbiology:
Phytomonic acid is used as a marker for the identification and classification of gram-negative bacteria, L. arabinosus, and other organisms where it is found. This can aid in the study of these organisms and their roles in various ecosystems.
Used in Plant Science:
Phytomonic acid is used as a component in the study of seed oils, particularly in the seed oil of B. coccineus (Connaraceae). Understanding the role of phytomonic acid in these plants can provide insights into their biological functions and potential applications in agriculture or the development of bioactive compounds.

InChI:InChI=1/C19H36O2/c1-2-3-4-10-13-17-16-18(17)14-11-8-6-5-7-9-12-15-19(20)21/h17-18H,2-16H2,1H3,(H,20,21)

Upstream product

• 506-17-2 cis-vaccenic acid 
• 252009-75-9 (1R,2S)-2-hexyl-1-(10'-hydroxydec-1'-yl)cyclopropane 
• 112418-57-2 methyl (Z)-10-(2-hexylcyclopropan-1-yl)decanoate 
• 2345-68-8 ((1R,2S)-2-Hydroxymethyl-cyclopropyl)-methanol 
• 21406-61-1 pentyltriphenylphosphonium bromide 
• 133494-56-1 cis-(1R,2S)-1-butyryloxymethyl-2-hydroxymethylcyclopropane 
• 133494-60-7 (1R,2S)-1-butyroyloxymethyl-2-formylcyclopropane 
• 106137-57-9 (1R,2R)-1-<(Z)-hex-1-enyl>-2-hydroxymethylcyclopropane 
• 133494-61-8 (1R,2R)-1-butyryloxymethyl-2-<(Z)-hex-1-enyl>cyclopropane 
• 55695-91-5 <9-((tetrahydro-2H-pyran-2-yl)oxy)nonyl>triphenylphosphonium bromide 
• 252009-68-0 (1R,2S)-2-hexylcyclopropane-1-carbaldehyde 
• 252009-90-8 (1R,2S)-2-hexyl-1-hydroxymethylcyclopropane 
• 252009-73-7 (1'Z,1R,2S)-2-hexyl-1-(10'-hydroxydec-1'-en-1'-yl)cyclopropane 
• 252009-74-8 (1R,2S)-2-hexyl-1-[[(10'-tetrahydropyranyl)oxy]dec-1'-yl]cyclopropane 

Relevant articles and documents

Synthesis of Cyclopropane Fatty Acids by C(sp3)?C(sp3) Cross-Coupling Reaction and Formal Synthesis of α-Mycolic Acid

An iterative Ni-catalyzed C(sp3)?C(sp3) cross-coupling reaction of a novel cis-cyclopropane containing bifunctional building blocks with alkyl halides and alkyl Grignard reagents enabled the introduction of a cyclopropane ring into the desired position(s) of saturated carbon frameworks, providing a straightforward synthetic route to cyclopropane fatty acids. The present method creates a direct route for the construction of saturated carbon frameworks, and can avoid the tedious multistep operations based on unsaturated functional group manipulations that are often employed in conventional synthetic routes. This method could be applicable to the synthesis of trans-cyclopropane fatty acids and enantioenriched cyclopropane fatty acids. Formal synthesis of α-mycolic acid was achieved by the C(sp3)?C(sp3) cross-coupling reaction of cyclopropane-containing bifunctional building blocks. (Figure presented.).

Total syntheses of cis-cyclopropane fatty acids: Dihydromalvalic acid, dihydrosterculic acid, lactobacillic acid, and 9,10-methylenehexadecanoic acid

cis-Cyclopropane fatty acids (cis-CFAs) are widespread constituents of the seed oils of subtropical plants, membrane components of bacteria and protozoa, and the fats and phospholipids of animals. We describe a systematic approach to the synthesis of enan

The synthesis of both enantiomers of lactobacillic acid and mycolic acid analogues

(11R, 12S)-Lactobacillic acid (1) has been prepared either from D- mannitol by asymmetric cyclopropanation or from cis-cyclopropane-1, 2- dimethanol by enzymatic desymmetrisation. The syntheses of (l1S 12R)- lactobacillic acid (2) and (1R, 2S) 1- (3'-methoxycarbonylpropyl)-2- octadecylcyclopropane (26) and related analogues (27 and 28) have also been achieved.