150024-70-7

Basic information

• Product Name: METHYL 3-HYDROXYTRIDECANOATE
• Synonyms: 3-HYDROXY C13:0 METHYL ESTER;METHYL 3-HYDROXYTRIDECANOATE
• CAS NO: 150024-70-7
• Molecular Formula: C₁₄H₂₈O₃
• Molecular Weight: 244.37
• Mol File: 150024-70-7.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 343.6±15.0 °C(Predicted)
• Appearance: /
• Density: 0.936±0.06 g/cm3(Predicted)
• PKA: 13.91±0.20(Predicted)
• CAS DataBase Reference: METHYL 3-HYDROXYTRIDECANOATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 3-HYDROXYTRIDECANOATE(150024-70-7)
• EPA Substance Registry System: METHYL 3-HYDROXYTRIDECANOATE(150024-70-7)

Safety Data

• Hazardous Substances Data: 150024-70-7(Hazardous Substances Data)

Usage

Description

Methyl 3-hydroxytridecanoate, also known as 3-hydroxy Tridecanoic acid methyl ester, is a hydroxylated fatty acid methyl ester and a major fatty acid component found in A. lipolytica and A. glycerini. It is characterized by the presence of a hydroxyl group, which contributes to its unique chemical properties and potential applications.

Uses

Used in Pheromone Synthesis:
Methyl 3-hydroxytridecanoate is used as a key component in the synthesis of components of the female sex pheromone of the painted apple moth (T. anartoides). Its unique structure and properties make it a valuable precursor in the production of these biologically active compounds, which are used for pest control and monitoring purposes in the agricultural industry.
Used in Chemical Research:
Due to its unique structure and properties, methyl 3-hydroxytridecanoate can be used as a starting material or intermediate in the synthesis of various chemical compounds, particularly those with potential applications in the pharmaceutical, cosmetic, and fragrance industries. Its hydroxyl group can be further modified or functionalized to create a wide range of derivatives with diverse properties and uses.
Used in Biotechnology:
Methyl 3-hydroxytridecanoate, being a major fatty acid component of certain microorganisms, can be utilized in biotechnological applications, such as the production of biofuels, bioplastics, and other bio-based materials. Its unique properties may also make it suitable for use in the development of novel biocatalysts or as a component in the design of advanced biomaterials.

Upstream product

• 67-56-1 methanol 
• 87900-05-8 methyl 3-ketotridecanoate 
• 2855-19-8 Decyl-oxiran 
• 201230-82-2 carbon monoxide 
• 6175-49-1 dodecan-2-one 

Relevant articles and documents

Structure of the unusual Sinorhizobium fredii HH103 lipopolysaccharide and its role in symbiosis

Rhizobia are soil bacteria that form important symbiotic associations with legumes, and rhizobial surface polysaccharides, such as K-antigen polysaccharide (KPS) and lipopolysaccharide (LPS), might be important for symbiosis. Previously, we obtained a mutant of Sinorhizobium fredii HH103, rkpA, that does not produce KPS, a homopolysaccharide of a pseudaminic acid derivative, but whose LPS electrophoretic profile was indistinguishable from that of the WT strain. We also previously demonstrated that the HH103 rkpLMNOPQ operon is responsible for 5-acetamido-3,5,7,9-tetradeoxy-7-(3-hydroxybutyramido)-L-glyc-ero-L-manno-nonulosonic acid [Pse5NAc7(3OHBu)] production and is involved in HH103 KPS and LPS biosynthesis and that an HH103 rkpM mutant cannot produce KPS and displays an altered LPS structure. Here, we analyzed the LPS structure of HH103 rkpA, focusing on the carbohydrate portion, and found that it contains a highly heterogeneous lipid A and a peculiar core oligosaccharide composed of an unusually high number of hexuronic acids containing b-configured Pse5NAc7(3OHBu). This pseudaminic acid derivative, in its a-configuration, was the only structural component of the S. fredii HH103 KPS and, to the best of our knowledge, has never been reported from any other rhizobial LPS. We also show that Pse5NAc7(3OHBu) is the complete or partial epitope for a mAb, NB6-228.22, that can recognize the HH103 LPS, but not those of most of the S. fredii strains tested here. We also show that the LPS from HH103 rkpM is identical to that of HH103 rkpA but devoid of any Pse5NAc7(3OHBu) residues. Notably, this rkpM mutant was severely impaired in symbiosis with its host, Macroptilium atropurpureum.

Synthesis of the four components of the female sex pheromone of the painted apple moth, Teia anartoides.

Four pheromone components of the female painted apple moth (Teia anartoides), an Australian insect pest, were synthesized. These were (Z)-6-henicosen-11-one (1), (6Z, 8E)-6,8-henicosadien-11-one (2), (Z)-cis-9,10-epoxy-6-henicosene (3), and (Z)-cis-9,10-epoxy-6-icosene (4). 2-Dodecanone was converted to 1 and 2, and both the enantiomers of 3 and 4 were synthesized from the enantiomers of 4-tert-butyldimethylsilyloxy-cis-2,3-epoxy-1-butanol.